3,3-Diethoxy-1-propanol - ≥98% , CAS No.16777-87-0

CAS: 16777-87-0 Cat. No.: D472286 Formula: C₇H₁₆O₃ Peso molecolare: 148.2 Numero EC: 695-818-3

GRADE & PURITY ≥98%

Synonyms

3,3-Diethoxy-1-propanol, 98% | DTXSID30168369 | 3,3-Diethoxy-1-propanol | MFCD00074850 | 3,3-diethoxypropan-1-ol | SY029207 | 1-Propanol, 3,3-diethoxy- | 1-Propanol, 3,3-diethoxy-;3,3-Diethoxypropanol | 3-hydroxypropionaldehyde diethyl acetal | 3, 3-dieth

Storage

Room temperature

Panoramica

Description

3,3-Diethoxy-1-propanol was used in the synthesis of α-acetal-poly(ethylene glycol) via reaction with potassium napthalide and ethylene oxide inside an UniLab Glovebox.

Specifications

Sinonimi

3,3-Diethoxy-1-propanol, 98% | DTXSID30168369 | 3,3-Diethoxy-1-propanol | MFCD00074850 | 3,3-diethoxypropan-1-ol | SY029207 | 1-Propanol, 3,3-diethoxy- | 1-Propanol, 3,3-diethoxy-;3,3-Diethoxypropanol | 3-hydroxypropionaldehyde diethyl acetal | 3, 3-dieth

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Pubchem Sid: 488188069
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488188069
• Sorrisi canonici: CCOC(CCO)OCC
• IUPAC Name: 3,3-diethoxypropan-1-ol
• InChIKey: ASERXEZXVIJBRO-UHFFFAOYSA-N
• INCHI: 1S/C7H16O3/c1-3-9-7(5-6-8)10-4-2/h7-8H,3-6H2,1-2H3
• Isomeri SMILES: CCOC(CCO)OCC
• Peso molecolare: 148.2
• Reaxy-Rn: 1698608
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1698608&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Acetals
• Alternative Parents: Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Acetal - Hydrocarbon derivative - Primary alcohol - Alcohol - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as acetals. These are compounds having the structure R2C(OR')2 ( R' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R' groups.
• External Descriptors: Not available

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

Proprietà chimiche e fisiche

• Punto di ebollizione (°C): 90-93° C (lit.)
• Peso molecolare: 148.200 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 148.11 Da
• Monoisotopic Mass: 148.11 Da
• Topological Polar Surface Area: 38.700 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 59.900
• 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

Not applicable. No assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data.

• Practical usage guidance instead:
  • For acetal hydrolysis: prepare a dilute acid aqueous–organic mixture, add reagent at controlled temperature, monitor by TLC/GC/MS, then neutralize and isolate promptly to prevent over-reaction.
  • For alcohol derivatization: dry glassware/solvents, exclude strong acids, and verify completion by NMR/GC.

Refer to primary literature and internal SOPs for detailed reaction procedures.

Biological Roles

This product is a small organic synthetic intermediate (acetal–alcohol) and does not have established endogenous biological roles.

• Research use context:

  • May be employed to install protected aldehyde handles on small molecules, polymers, or surfaces for subsequent bioorthogonal conjugation (e.g., oxime or hydrazone formation after acetal hydrolysis). Such applications are chemical in nature and not biological functions per se.

• Metabolism/toxicity considerations (general):

  • Low-molecular-weight acetals can hydrolyze in strongly acidic aqueous environments to yield alcohols/aldehydes; biological matrices vary widely in pH/enzymatic content, but no specific metabolic pathways are assigned to this compound.

No medical, diagnostic, or therapeutic uses are claimed or supported. For any work involving biological systems, ensure complete removal of residual acids or catalysts after processing and conduct appropriate biocompatibility assessments independently.

Buffer Applications

Not typically used as a buffering agent. 3,3-Diethoxy-1-propanol is a synthetic building block rather than a buffering acid/base pair.

• Practical note:
  • If used in workflows that later contact buffers (e.g., after surface functionalization and acetal hydrolysis), thoroughly remove residual acids used for hydrolysis (dialysis, desalting, or repeated extractions) to avoid perturbing buffer pH.

Green Alternatives

• Solvent/process choices:

  • When conducting acetal hydrolysis or formation, consider aqueous ethanol or 2-MeTHF with catalytic acids over chlorinated solvents where feasible. Use solid acids (Amberlyst-15, sulfonated silica) to simplify workup and reduce aqueous acid waste.
  • For alcohol activation, favor organic carbonates (e.g., dimethyl/diethyl carbonate) as greener alkylating media when compatible, rather than halogenated reagents.

• Protecting-group strategy (contextual comparison; literature/general):

  • Diethyl acetals are relatively benign and form under azeotropic removal of water (EtOH/toluene). Alternatives include dimethyl acetal, cyclic acetals (1,3-dioxolanes from ethylene glycol), or acetonides; selection balances hydrolysis rate, stability window, and solvent footprint.

• Comparison snapshot (general):

  • Diethyl acetal vs cyclic acetals:
    • Stability: cyclic acetals often more robust to hydrolysis; diethyl acetals cleave faster under dilute acid.
    • Greenness: ethanol-derived acetals leverage a bio-based solvent; cyclic acetals often require diols/ketones with similar profiles.
    • Reversibility: diethyl acetals enable mild deprotection, reducing energy/input at end-of-life.

• Operational green tips:

  • Employ molecular sieves instead of Dean–Stark when possible to minimize energy use.
  • Recover and reuse ethanol and 2-MeTHF via distillation.
  • Choose catalytic rather than stoichiometric acid where compatible, and use buffered aqueous workups to limit salt loads.

Pharmaceutical Uses

No pharmacopeial monograph or excipient role is specified for this item; refer to CoA/Spec Sheet if an excipient grade is required.

• Context (general, non-clinical):
  • As a reagent, 3,3-diethoxy-1-propanol can be used in synthetic routes to small-molecule actives or intermediates where a masked aldehyde and a handle for diversification are advantageous.
  • Any use would be in the context of process development or research-scale synthesis, not as a formulated drug substance or clinical excipient.

Always verify and qualify material to internal specifications for GMP or clinical manufacturing; this catalog item is labeled “For research use only.”

Physical Properties

Item-specific physicochemical data were not provided.

• Product Data specifics:

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general expectations for this class (diethyl acetals of small alkanols; for context only, not item specifications):

  • Physical state: typically a colorless, low-to-moderate viscosity liquid for small acetal–alcohols.
  • Volatility: acetals of this size generally have moderate boiling points and appreciable vapor pressure; fractional distillation under reduced pressure is common for purification.
  • Polarity/solubility: polar protic due to the terminal –OH; miscible with many organic solvents (e.g., ethers, esters, chlorinated solvents, alcohols) and shows limited to moderate water miscibility depending on exact structure.
  • Refractive index/density: usually higher than hydrocarbons of similar size due to multiple heteroatoms.

To obtain exact numerical values (BP, MP, density, refractive index, water content, residual solvents, or UV cutoff) for this catalog item, please consult the CoA/Spec Sheet for SKU D472286. No numeric physical constants are claimed here for this specific lot/item.

Quality and Grades

• Item-specific grade/purity from Product Data: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades (general guidance):

  • Analytical/ACS grade: Tight specs for assay, water, and common impurities; suitable for analytical work and general synthesis.
  • Anhydrous/dry grade: Water content controlled to low ppm; critical for moisture-sensitive steps (e.g., acylations, organometallic chemistry). If required, verify Karl Fischer value on the CoA.
  • HPLC grade: Low UV-absorbing impurities; more relevant to solvents than to building-block reagents.

• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Acetals generally do not require polymerization inhibitors but benefit from neutral storage away from acids to prevent hydrolysis.

• What to check on receipt:

  • Assay/identity: GC, 1H/13C NMR consistent with an acetal (characteristic ethoxy –CH3 triplets and –CH2– quartets; acetal CH around 4–5 ppm) and a primary alcohol (–CH2OH near 3.4–3.8 ppm; OH broadened signal).
  • Water content: If low moisture is important to your application, verify KF on the CoA or dry before use.
  • Residual solvents/GC purity: Confirm meets your process requirements. If UV specs are needed (e.g., for photochemical work), request UV cutoff data specifically.

Reaction and Applications

3,3-Diethoxy-1-propanol serves as an acetal-protected aldehyde equivalent bearing a handle for further elaboration at the terminal primary alcohol.

• Protecting-group logic (literature/general):

  • The diethyl acetal masks the corresponding aldehyde (3-hydroxypropanal). Under aqueous acid, it hydrolyzes to the aldehyde, enabling two-stage sequences: build from the alcohol, then unmask the aldehyde for further carbonyl chemistry (e.g., reductive amination, aldol, Wittig).

• Representative synthetic applications:

  • Alcohol functionalization:
    • Tosylation/mesylation of the primary –CH2OH, followed by SN2 displacement (e.g., cyanide, azide, halide) to access diverse 3,3-diethoxypropyl derivatives.
    • Williamson ether synthesis to install alkyl/aryl ethers while retaining the acetal.
    • Mitsunobu coupling with acidic pronucleophiles to invert the terminal stereochemistry (where applicable).
  • Post-unmasking carbonyl chemistry: After acidolysis to 3-hydroxypropanal, perform Wittig/Julia–Kocienski olefinations, reductive aminations, or acylations at the aldehyde.
  • Orthogonal reactivity: The acetal is typically stable to many bases, mild nucleophiles, and neutral hydrogenation conditions, allowing selective transformations at the alcohol first.

• Synthesis planning tips:

  • Maintain neutral to basic conditions when modifying the alcohol to avoid acetal cleavage.
  • Control water activity in any acid-mediated step; employ Dean–Stark or molecular sieves during acetal exchange/transacetalizations.
  • For polymer/linker chemistry, the alcohol can be used to graft onto resins or surfaces; subsequent deprotection reveals an aldehyde-terminus for bioorthogonal ligations (e.g., oxime formation).

Reaction Conditions

General literature guidance for transformations of acetal–alcohols (not item-specific specifications):

• Acetal hydrolysis (to 3-hydroxypropanal equivalent):

  • Catalyst: dilute mineral acids (HCl, H2SO4) or organic acids (p-TsOH) in aqueous MeOH/THF/acetone; solid acids (Amberlyst-15) are effective.
  • Key variables: water content, temperature, and acidity. Maintain low temperatures for sensitive substrates; drive to completion by adjusting water equivalents.

• Alcohol activation and substitution:

  • Tosylation/mesylation: base (pyridine, Et3N) in DCM or MeCN at 0–25 °C; acetal typically survives under neutral/basic conditions.
  • Williamson ether synthesis: alkoxide nucleophiles in polar aprotic solvents (DMF, DMSO) with NaH/K2CO3; monitor to avoid any incidental acid formation.
  • Mitsunobu coupling: DIAD/DEAD and PPh3 in THF/DMF at 0–25 °C; the acetal is generally compatible.

• Oxidations of the primary alcohol:

  • TEMPO/bleach, PDC, Swern, Dess–Martin conditions can convert –CH2OH to the aldehyde/acid while typically preserving the acetal (absence of strong acids during workup is important).

• Purification:

  • Normal-phase silica gel at neutral to slightly basic conditions; pre-treat acidic silica or add a small amount of base (e.g., 0.1% Et3N) to protect acetals.

These are representative conditions from the literature; optimize on small scale and consult primary sources for substrates of interest.

Safety and Handling

• Product-specific hazard data (GHS/CLP) from Product Data:

  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification & pictograms: Not specified for this item; refer to SDS.

• General safety considerations for acetal–alcohols (literature/general guidance; defer to SDS for authoritative information):

  • Irritation/combustibility: Organic acetals and alcohols are typically flammable liquids and may cause eye/skin irritation. Handle away from ignition sources with proper ventilation.
  • Incompatibilities: Avoid strong acids (risk of acetal hydrolysis to the corresponding carbonyl compound) and strong oxidizers. Prolonged exposure to moisture plus acid catalysis accelerates hydrolysis.
  • Peroxide formation: Acetals are not classically peroxide-forming like ethers; nevertheless, routine peroxide testing is generally unnecessary. Alcoholic function does not promote dangerous peroxidation.
  • PPE: Safety glasses, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to control vapors.
  • First aid (overview):
    • Skin/eyes: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
    • Inhalation: Move to fresh air; support breathing as needed; seek medical attention if symptoms occur.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

Always consult the product-specific SDS for D472286 for definitive hazard classification, exposure limits, spill response, and firefighting media.

Solvent Selection

This product is a functionalized building block rather than a routine chromatography or reaction solvent.

• Polarity/solubility profile (general for acetal–alcohols):

  • Polarity: Moderately polar, protic (due to –OH) with significant organic solubility; hydrogen-bond donor and acceptor.
  • Miscibility: Typically miscible with many organic media (Et2O, THF, DCM, toluene, alcohols, esters). Water miscibility is limited to moderate; consult a small-scale partition test if aqueous processing is planned.

• When used as a reaction medium (less common):

  • The –OH and acetal functions can participate in side equilibria under acidic catalysis; therefore, inert solvents (DCM, toluene, EtOAc, MeCN, THF) are usually preferred when employing this reagent in synthesis.

• Selection tips for transformations involving this reagent:

  • Acid-catalyzed steps: Choose non-protic, non-nucleophilic solvents to minimize premature acetal hydrolysis (e.g., DCM or toluene with catalytic acid at controlled temperature and water activity).
  • Base-mediated steps (e.g., tosylation, Williamson ether syntheses): Polar aprotic solvents such as DMF, DMSO, or MeCN often enhance SN2 rates on the primary –CH2OH derivative.

For purification, normal-phase silica chromatography with gradients of hexanes/EtOAc or DCM/MeOH is typical; avoid strongly acidic silica when preserving the acetal.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Container and environment:
  • Store tightly sealed under an inert or dry atmosphere if possible to limit moisture ingress.
  • Keep away from acids and acidic vapors to prevent acetal hydrolysis during storage.
• Stability notes (general for acetals):
  • Stable under neutral/basic conditions and in dry environments. Prolonged exposure to moisture plus acid catalysis promotes hydrolysis.
• Before use:
  • If moisture sensitivity is critical, consider passing through a short plug of basic alumina/silica, or dry over molecular sieves (3 Å) briefly.
  • Warm to ambient temperature if stored cold; mix thoroughly to ensure homogeneity.

No reconstitution is required for this liquid reagent. For exact shelf-life, impurity limits, and water content applicable to your lot, consult the CoA/Spec Sheet for SKU D472286. The product is labeled For research use only.

Structure and Identity

3,3-Diethoxy-1-propanol is a bifunctional acetal–alcohol building block featuring a terminal primary alcohol and an acid-labile diethyl acetal at the 3-position.

• Item-specific identifiers (from Product Data):

  • SKU: D472286
  • CAS: 16777-87-0
  • CID: 140135
  • InChIKey: 13567 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (interpretation from the chemical name; general description):

  • Functional groups: primary alcohol (–CH2OH) and 1,1-diethoxy (acetal) moiety [–CH(OC2H5)2].
  • Backbone: three-carbon chain (propan-1-ol) with the acetal substituent at C-3.
  • Stereochemistry: none specified; the acetal center is typically achiral if substituents are identical (two ethoxy groups) and the remaining substituents are not stereogenic.
  • 2D description: HO–CH2–CH2–CH(–OEt)–OEt, where the terminal C1 bears –OH, C2 is methylene, and C3 bears two ethoxy substituents (diethyl acetal).

• Related identity notes (literature/general):

  • Often described as an acetal-protected 3-hydroxypropanal equivalent (the acetal hydrolyzes to the corresponding aldehyde under acid).

Synthetic Utility

Key reactivity stems from orthogonal functional groups:

• Primary alcohol (–CH2OH):

  • Readily protected (silyl ethers, carbonates), activated (tosylate/mesylate), or transformed via Mitsunobu and oxidation (to aldehyde/acid) under conditions that often spare the acetal.
  • Enables coupling to polymers/resins (carbonate/urethane linkages) or etherification for spacer installation.

• Diethyl acetal [–CH(OR)2]:

  • Stable under many basic and neutral conditions; cleavable under mild aqueous acid to reveal the corresponding aldehyde (3-hydroxypropanal).
  • Amenable to transacetalization with other alcohols under acid catalysis to tune protecting-group properties (e.g., switch to cyclic acetals for enhanced robustness).

• Strategic sequences (literature/general examples):

  • Functionalize the alcohol first (e.g., convert to azide → Staudinger or CuAAC elaboration), then hydrolyze the acetal to unlock aldehyde chemistry (e.g., oxime/hydrazone ligations, reductive amination).
  • Oxidize the primary alcohol to acid/ester while retaining the acetal (e.g., TEMPO/bleach, PDC, or Swern variants), then deprotect to dialdehyde/aldehyde–acid motifs for advanced building blocks.

• Selectivity tips:

  • Avoid strong Brønsted/Lewis acids if the acetal must be retained; buffer workups to neutral pH promptly.
  • Use drying agents or molecular sieves to limit hydrolysis during acid-catalyzed transformations involving other substrates.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and does not possess biological target specificity (no antigen/epitope, clone, or isotype). No item-specific targeting information is provided in the Product Data.