1,3-Propanediol - analytical standard , CAS No.504-63-2

CAS: 504-63-2 Cat. No.: P108207 Formula: C₃H₈O₂ Molecular Weight: 76.09 Beilstein Registry Number: 969155 EC Number: 207-997-3

GRADE & PURITY Analytical standard

Synonyms

2-Deoxyglycerol | HSDB 8263 | J-503943 | CAS-504-63-2 | DTXCID6021246 | 1,3-PROPANEDIOL | 1,3-propane-diol | propan-1,3-diol | (HOCH2)2CH2 | CHEBI:16109 | InChI=1/C3H8O2/c4-2-1-3-5/h4-5H,1-3H | 1,3-PROPANDIOL | propane 1.3-diol | 1.3-propanediol | C02457

Storage

Desiccated,Room temperature

Shipped In

Normal

Specifications

Synonyms

2-Deoxyglycerol | HSDB 8263 | J-503943 | CAS-504-63-2 | DTXCID6021246 | 1,3-PROPANEDIOL | 1,3-propane-diol | propan-1,3-diol | (HOCH2)2CH2 | CHEBI:16109 | InChI=1/C3H8O2/c4-2-1-3-5/h4-5H,1-3H | 1,3-PROPANDIOL | propane 1.3-diol | 1.3-propanediol | C02457

Specifications & Purity

analytical standard

Storage

Desiccated,Room temperature

Shipped In

Normal

Grade

Analytical standard

Names and Identifiers

Canonical Smiles

C(CO)CO

IUPAC Name

propane-1,3-diol

InChIKey

YPFDHNVEDLHUCE-UHFFFAOYSA-N

INCHI

1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2

Isomeric SMILES

C(CO)CO

WGK Germany

1

RTECS

TY2010000

Molecular Weight

76.09

Beilstein

969155

Reaxy-Rn

969155

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=969155&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Alcohols and polyols

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Not available
• Direct Parent: Primary alcohols
• Alternative Parents: Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Hydrocarbon derivative - Primary alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as primary alcohols. These are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• x_refractive_index: 1.44
• x_flash_point_drop_fahrenheit: 165 °F
• x_flash_point_drop_centigrade: 74 °C
• x_boil_point_char: 214°C
• x_melt_point_char: -27°C
• Molecular Weight: 76.090 g/mol
• XLogP3: -1.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 76.0524 Da
• Monoisotopic Mass: 76.0524 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 5
• Formal Charge: 0
• Complexity: 12.400
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No assay-specific protocols are provided for this small-molecule reagent.

General guidance for analytical standard use (not item-specific; follow your method SOPs):

• Preparation of stock solutions:
  • Use a calibrated balance and Class A volumetric glassware. If hygroscopicity is a concern, pre-dry material or correct for water using CoA data.
  • Choose a solvent compatible with your analytical method (e.g., water, methanol, acetonitrile). Verify solubility and stability.
• Calibration:
  • Prepare a series of calibrators by serial dilution; include quality controls and blanks per your QA plan.
  • Store standards in sealed containers, protected from moisture; label with preparation date and concentration.
• Chromatography notes:
  • For HPLC/LC–MS of small polyols, hydrophilic interaction chromatography (HILIC) or ion-exclusion aqueous methods are common. Derivatization (e.g., benzoylation, silylation for GC) can enhance retention/detection.

Item-specific tested applications, recommended dilutions, and positive controls: Not specified for this item; refer to CoA/Spec Sheet.

Biological Roles

Item-specific biological information: Not specified for this item; refer to CoA/Spec Sheet. The following is general background (literature; not item-specific):

• Microbial metabolism: 1,3-Propanediol is produced by certain bacteria (e.g., Klebsiella, Clostridium) via glycerol fermentation, with 3-hydroxypropionaldehyde as an intermediate. It can also be further metabolized by specialized pathways.
• Biochemical properties: As a small diol, it participates in extensive hydrogen-bonding networks and can act as a compatible solute/cosolvent in vitro, modulating protein stability and enzyme activity in a manner analogous to other polyols (effect is system-dependent).
• Toxicology/biocompatibility (general): Typically exhibits low acute toxicity and low volatility; however, osmotic effects and solvent interactions may impact cells or enzymes at higher concentrations. Use only in non-clinical, laboratory research contexts as directed.

Note: No medical, diagnostic, or therapeutic use is intended or implied for this product. For any biological experiments, determine suitable concentrations empirically and verify interference with assays (e.g., effects on enzyme-coupled reactions or spectrophotometric baselines).

Buffer Applications

1,3-Propanediol is not a buffering agent and does not provide a defined pH range or pKa couple suitable for classical buffer systems. Therefore, it is not typically used to prepare biological or analytical buffers.

Potential ancillary uses (general; not item-specific):

• Cosolvent/additive: Can be added to aqueous buffers to adjust polarity, viscosity, or cryoprotection properties, similar to other small polyols (effects are assay-dependent). Evaluate impacts on protein stability, enzyme rates, and spectral baselines.
• Sample preparation: May aid solubilization of polar organics or stabilize certain reagent concentrates for storage.

If a true buffer is needed, select a conventional buffering system (e.g., phosphate, Tris, HEPES, MOPS) with an appropriate pKa near the target pH. Validate compatibility if 1,3-propanediol is included as a cosolvent.

Green Alternatives

Context: 1,3-Propanediol (PDO) is increasingly available via bio-based fermentation routes (e.g., from glycerol or sugars), which can reduce greenhouse gas intensity and fossil resource use relative to petrochemical diols. The Product Data do not specify the production route or sustainability attributes for this item.

Green chemistry considerations (literature; not item-specific):

• Advantages of 1,3-PDO in polymers: Enables polyesters (e.g., PTT) with lower processing temperatures than some alternatives and favorable mechanical performance, potentially reducing energy demand during processing.
• Comparison to common diols:
  • Ethylene glycol (EG): Very common, highly toxic to mammals upon ingestion; petroleum-derived (though bio routes exist). Lower MW and higher volatility than PDO.
  • 1,2-Propanediol (propylene glycol, PG): Lower toxicity profile than EG, widely used as solvent/excipient; typically petro-derived (bio routes emerging).
  • Glycerol: Biogenic, nonvolatile, very high boiling point and viscosity; trihydric functionality may be undesirable for strictly difunctional polymer targets.

Illustrative comparison (literature attributes):

• Boiling point: glycerol > 1,3-PDO > PG > EG
• Volatility/worker exposure: lower for 1,3-PDO versus EG/PG due to higher BP.
• Renewable sourcing: feasible for 1,3-PDO and glycerol; item-specific provenance Not specified for this item; refer to CoA/Spec Sheet.

Greener practice tips:

• Use catalysis (Ti/Sn enzymes or organocatalysts) for esterifications to lower temperature and waste.
• Recycle excess diol and employ vacuum/energy-efficient separations.

Pharmaceutical Uses

Item-specific pharmacopeial status and excipient specifications: Not specified for this item; refer to CoA/Spec Sheet.

General formulation roles (literature; not item-specific):

• Cosolvent/humectant: Small diols are often used to enhance solubility of actives, control water activity, and modulate viscosity in non-clinical R&D formulations, preformulation studies, and process development.
• Process aid: Can serve as a high-boiling diluent or plasticizer in hot-melt processes, and as a reactant for polymeric excipients (e.g., polyester-based matrices) evaluated in dosage-form development.
• Compatibility: Miscible with water and many polar organics, which can be exploited to tune solvent systems; verify compatibility with actives and excipients experimentally (consider hydrogen bonding and potential for transesterification with reactive functional groups under processing conditions).

Regulatory note:

• This product is sold for research use only. No claims are made regarding compliance with pharmacopeial monographs (USP/EP/JP) or suitability for human or veterinary administration. For any work aimed at clinical development, procure excipient grade material with appropriate regulatory documentation.

Physical Properties

Item-specific physicochemical specifications (appearance, exact purity assay, water content, metals, stabilizers, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature properties for 1,3-propanediol (for reference; not item-specific):

• Typical molecular formula: C3H8O2; formula weight ~76.09 g/mol (literature)
• State at ambient conditions: colorless, viscous liquid; hygroscopic (literature)
• Boiling point: ~214–215 °C at 1 atm (literature)
• Melting point: approximately −26 to −27 °C (literature)
• Density: ~1.058–1.060 g/mL at 20 °C (literature)
• Refractive index: n20 D ~1.438–1.440 (literature)
• Vapor pressure: very low at room temperature (literature)
• Solubility: miscible with water; soluble in polar organic solvents (alcohols, glycols); limited solubility in nonpolar solvents (literature)
• LogP (octanol/water): around −0.9 (indicative of high hydrophilicity; literature)
• pKa: alcohol pKa typically ~15–16 for undissociated OH; conjugate acid pKa ~−2 to −3 (literature, context for acid/base chemistry)

Notes for laboratory use:

• Due to strong hydrogen bonding and low volatility, it exhibits high boiling point and low odor—beneficial for high-temperature condensations.
• Hygroscopicity can shift composition by water uptake; dry before moisture-sensitive applications (see Reaction Conditions). Always verify with the item’s CoA/SDS for authoritative values.

Quality and Grades

• Item-specific grade: Analytical standard (from Product Data).

Interpretation and implications:

• Analytical standard indicates the material is intended for use as a reference/calibration standard in analytical workflows (e.g., GC, HPLC, IC, spectroscopic quantitation). Such materials typically emphasize identity confirmation and assay traceability rather than process reagents.
• Benefits for analytical use:
  • High and well-characterized purity suitable for calibration curves and system suitability testing.
  • Often accompanied by a Certificate of Analysis (CoA) detailing identity confirmation (e.g., NMR/GC/MS), assay or purity methodology, uncertainty, and, where applicable, traceability to standards bodies or internal primary standards.
• Packaging/handling considerations for analytical standards:
  • Minimization of contamination and water uptake is critical for accurate gravimetric preparation of standards; the supplied storage recommendation (room temperature, desiccated) supports stability and constant composition.

What is not specified for this item:

• Specific assay value, residual solvents, water content, metals, stabilizers, and chromatographic suitability metrics: Not specified for this item; refer to CoA/Spec Sheet.

Practical tip:

• When preparing calibration solutions, record exact mass, temperature, and dilution solvent, and allow for complete mixing. For hygroscopic polyols like 1,3-propanediol, consider pre-drying or using a Karl Fischer result from the CoA to correct for water, if provided.

Reaction and Applications

Key roles (general; expand based on literature and common practice):

• Polymer building block: 1,3-Propanediol is a diol component for step-growth polymerizations. It is widely used in the synthesis of polyesters (e.g., poly(trimethylene terephthalate), PTT) by condensation with terephthalic acid/DMTA, and in polycarbonates or polyurethanes via reaction with phosgene/carbonates or diisocyanates.
• Esterification/transesterification: Reacts with carboxylic acids and esters to form mono- or diesters; acid catalysts (p-toluenesulfonic acid, sulfuric acid) or metal catalysts (Ti, Sn) accelerate transformations. Transesterification with dimethyl terephthalate is a classic route to PTT prepolymers.
• Urethane formation: Reaction with diisocyanates produces polyurethanes; catalysts such as dibutyltin dilaurate or tertiary amines are commonly employed.
• Functional group interconversion:
  • Selective protection/activation: Monotosylation/mesylation enables subsequent nucleophilic substitution to introduce functionality at the terminal carbon. Ditosylation affords difunctional linkers.
  • Oxidation to 3-hydroxypropanal/3-hydroxypropionic acid under controlled conditions (e.g., TEMPO or metal-catalyzed oxidations), or to malonic derivatives via further transformations.
  • Carbonate/sulfate formation to generate leaving groups for intramolecular cyclizations.
• Linker chemistry: Serves as a flexible C3 spacer in multistep synthesis and materials surface modification (e.g., creating hydrophilic termini or PEG-like segments).

Practical tips:

• Drying: Remove water by azeotropic distillation with toluene or by vacuum heating over molecular sieves or drying agents before moisture-sensitive steps.
• Viscosity: At room temperature it is viscous; mild heating (40–60 °C) can facilitate mixing and mass transfer.
• Workup: Excess diol can often be removed under high vacuum at elevated temperature or by extraction with water depending on product polarity.

Reaction Conditions

General/literature guidance for common transformations of 1,3-propanediol (not item-specific; optimize per substrate and scale):

• Esterification/transesterification:
  • Catalysts: p-TsOH (0.5–5 mol%), H2SO4 (caution), Ti(OBu)4 or Sn(Oct)2 (100–1000 ppm for polycondensations).
  • Conditions: 120–200 °C with removal of water/methanol; employ Dean–Stark or apply vacuum in later stages to drive equilibrium. Nitrogen sweep recommended.
• Urethane formation (with diisocyanates):
  • Catalysts: DBTDL (10–1000 ppm), tertiary amines.
  • Conditions: 25–80 °C in dry aprotic solvent (e.g., toluene, THF) or bulk; strictly anhydrous to suppress urea/biuret side products.
• Sulfonylation (mesylate/tosylate formation):
  • Reagents: MsCl or TsCl, base (triethylamine, pyridine), catalytic DMAP.
  • Conditions: 0–25 °C in DCM/THF; protect one OH if selective mono-activation is required.
• Nucleophilic substitutions of sulfonates:
  • Nucleophiles: NaN3, NaI, thiolates, CN−.
  • Conditions: Polar aprotic solvent (DMF/DMSO/MeCN), 25–80 °C; monitor for elimination at higher temperatures.
• Oxidations:
  • To 3-hydroxypropanal/acid: TEMPO/bleach or catalytic Ru/Co systems; 0–25 °C to limit overoxidation. Periodate-based glycol cleavage possible under specific conditions.

Drying and handling:

• Dry the diol over 3 Å molecular sieves or by rotary evaporation under high vacuum at 50–70 °C. Karl Fischer titration is recommended if water content critically affects stoichiometry.

Workup/purification:

• Excess diol removal via aqueous extraction (for hydrophobic products) or by high-vacuum stripping. For polymerizations, stepwise temperature/vacuum ramps improve molecular weight build.

These are general ranges; consult primary literature and scale-appropriate safety assessments.

Safety and Handling

Item-specific hazard classifications (GHS, signal word, H/P statements, pictograms): Not specified for this item; refer to the SDS for authoritative safety information.

General safety profile for 1,3-propanediol (literature; not item-specific):

• Hazard overview: Low acute toxicity relative to many solvents; may cause eye/skin irritation on contact and discomfort if inhaled as mist or ingested in quantity.
• Flammability: Combustible at elevated temperatures; high flash point compared to lower alcohols due to low volatility. Avoid ignition sources during heating and distillation.
• Reactive incompatibilities: Strong oxidizers (e.g., chromates, permanganates, nitric acid), strong acids/bases under dehydrating conditions, acyl halides, isocyanates, and acid anhydrides (will react to form esters/urethanes). Generate heat on mixing with acids/bases.

PPE and handling practices:

• Wear safety glasses or chemical splash goggles, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a well-ventilated area; local exhaust recommended during heating or aerosol-generating operations.
• Spill response: Contain with inert absorbent; wash residue with water and mild detergent. Prevent entry into drains if large quantities are involved.
• First aid (general guidance):
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing. Seek medical attention for persistent irritation.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; get medical advice.

Always consult and follow the product-specific SDS and institutional safety protocols.

Solvent Selection

Applicability: 1,3-Propanediol is primarily a reagent/monomer rather than a general-purpose chromatographic solvent. It can function as a high-boiling, highly polar protic medium but is seldom chosen as the primary solvent for routine synthesis or separations.

General solvent characteristics (literature; not item-specific):

• Polarity/proticity: Strongly hydrogen-bonding, polar protic diol; dielectric constant expected to be high compared to monohydric alcohols of similar size.
• Miscibility: Miscible with water and many polar organics (alcohols, glycols); limited miscibility with nonpolar hydrocarbons.
• Volatility: Very low; useful where solvent loss must be minimized at elevated temperatures.

When to consider 1,3-propanediol as a medium:

• As a reaction medium for high-temperature condensations or transesterifications when removal by vacuum is acceptable.
• As a cosolvent/hydrogen-bond donor to enhance solubility of polar substrates or adjust viscosity in specialized formulations.

Alternatives for common laboratory tasks:

• For extractions or general synthesis: methanol, ethanol, isopropanol (protic, more volatile); DMSO, DMF (polar aprotic) when aprotic polarity is needed; ethylene glycol or glycerol when higher boiling points/viscosities are desired.

Notes:

• Because it is hygroscopic, solvent selection for water-sensitive chemistry should include pre-drying of the diol or use of an alternative anhydrous solvent.

Storage and Reconstitution

• Item-specific storage (from Product Data): Room temperature, desiccated. Shipped at ambient conditions (Normal).
• Physical handling: 1,3-Propanediol is hygroscopic and viscous. Keep container tightly closed with an effective seal. Store with a desiccant in a dry cabinet. Minimize headspace or purge with dry inert gas if extended storage is anticipated to limit moisture uptake.
• Light sensitivity: Not strongly light-sensitive, but opaque or amber containers are good practice for long-term storage.
• Freeze/thaw: Not applicable; liquid at room temperature with a melting point well below 0 °C (literature). Avoid freezing aqueous solutions in rigid containers to prevent breakage.
• Reconstitution: Not required (neat liquid). For solution preparation, use dry, compatible solvents (e.g., water, methanol, acetonitrile) according to your method. Mix thoroughly; mild warming (30–40 °C) may reduce viscosity and aid dissolution or dispensing.
• Stability considerations:
  • Avoid prolonged exposure to strong oxidizers or acids/bases.
  • For analytical standards, prepare single-use aliquots of stock solutions when feasible to maintain accuracy; store sealed to prevent evaporation or moisture ingress.

For any specific shelf-life, assay, or impurity limits: Not specified for this item; refer to CoA/Spec Sheet and the product SDS.

Structure and Identity

A small, linear aliphatic diol featuring two primary alcohol groups at the 1- and 3-positions.

• Item-specific identifiers (from Product Data):
  • SKU: P108207
  • Product name: 1,3-Propanediol
  • CAS: 504-63-2
  • PubChem CID: 10442
  • InChIKey: 443258 (as provided)
  • Grade: Analytical standard
• Item-specific SMILES, molecular formula, and molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Literature structural identifiers (for reference; not item-specific):
  • Common name(s): 1,3-propanediol; trimethylene glycol
  • Molecular formula (literature): C3H8O2
  • Molecular weight (literature): 76.09 g/mol
  • SMILES (literature): OCCCO (equivalently, HOCH2CH2CH2OH)
• Structural features (general description):
  • Linear C3 skeleton with terminal primary hydroxyl groups at C1 and C3.
  • Functional groups: two primary alcohols (–CH2OH), capable of hydrogen bonding (donor and acceptor) and typical alcohol reactivity (esterification, etherification, oxidation).
  • No rings, no stereocenters, no heteroatoms other than oxygen.
  • 2D depiction in words: HO–CH2–CH2–CH2–OH, with hydroxyls at each terminus of a three-carbon chain.

Synthetic Utility

Functional handles and transformations (general; literature-based):

• Bifunctional C3 synthon: Two terminal primary alcohols enable symmetric difunctionalization or selective monofunctionalization, making 1,3-propanediol a versatile spacer in small-molecule and materials synthesis.
• Ester/amide derivatives: Acid-catalyzed esterification to mono-/diesters; carboxyl activation or mixed anhydrides can improve selectivity. Carbonates (e.g., with phosgene surrogates) provide activated leaving groups.
• Sulfonate activation: Conversion to mesylates/tosylates affords excellent leaving groups for SN2 substitutions, enabling installation of azides, halides, thiols, or cyanides at terminal carbons.
• Oxidation chemistry: Controlled oxidation furnishes 3-hydroxypropanal or 3-hydroxypropionic acid; further manipulation gives acrylic derivatives. Strong oxidants can lead to C–C cleavage (glycol cleavage) under harsh conditions.
• Polymer chemistry: Central to step-growth synthesis—polyesters (with diacids/diesters), polycarbonates (with carbonates), and polyurethanes (with diisocyanates). Chain extenders and crosslinkers can be incorporated via partial substitution.
• Protecting group strategies: Temporary protection of one OH (e.g., silyl ethers, tetrahydropyranyl ethers) allows orthogonal elaboration; cyclic carbonates/sulfates enable intramolecular selectivity.

Strategic value in retrosynthesis:

• Serves as a ready-made C3 linker to bridge functional motifs while preserving terminal reactivity.
• Provides access to amphiphilic constructs when combined with hydrophobic chains or ionic headgroups.

Practical notes:

• Achieving mono- versus di-functionalization often requires stoichiometric control and protecting groups. Removal of excess diol post-reaction may require high vacuum at elevated temperature or aqueous workups exploiting its hydrophilicity.

Target Specificity

Not applicable. This product is a small-molecule chemical (1,3-propanediol) and not a biological affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.

Item-specific target data: Not specified for this item; refer to CoA/Spec Sheet if any application-specific validation is provided.

Frequently Asked Questions

What does analytical standard mean?

analytical standard is a defined analytical purity tier suitable for quantitative analytical methods. It specifies a minimum assay percentage, controlled limits on common impurities (water, heavy metals, residue on ignition), and lot-to-lot consistency. analytical standard is one of several purity tiers — choose based on the sensitivity and regulatory requirements of your method.

How should this product be stored?

Store at room temperature, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 504-63-2, the molecular formula is C3H8O2, and the molecular weight is 76.09 g/mol. InChIKey YPFDHNVEDLHUCE-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.