Dipropyl succinate - ≥95% , CAS No.925-15-5

CAS: 925-15-5 Cat. No.: D1073067 Formula: C₁₀H₁₈O₄ Molecular Weight: 202.25 EC Number: EINECS213-114-2

GRADE & PURITY ≥95%

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Specifications

Specifications & Purity

≥95%

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CCCOC(=O)CCC(=O)OCCC
• IUPAC Name: dipropyl butanedioate
• InChIKey: SZHZCPHKDJWHNG-UHFFFAOYSA-N
• INCHI: 1S/C10H18O4/c1-3-7-13-9(11)5-6-10(12)14-8-4-2/h3-8H2,1-2H3
• Molecular Weight: 202.25

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Dicarboxylic acids and derivatives Carboxylic acid esters Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid ester - Dicarboxylic acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• 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

Chemical and Physical Properties

• Molecular Weight: 202.250 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 202.121 Da
• Monoisotopic Mass: 202.121 Da
• Topological Polar Surface Area: 52.600 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 157.000
• 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 antibody/assay protocols apply to this small-molecule reagent. For synthetic and processing workflows, see Reaction Conditions and Application notes provided in Reaction & Applications and Synthetic Utility.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet.

• General biochemical context (literature)

  • Dipropyl succinate itself has no intrinsic biological role; it is an aliphatic diester used in chemical synthesis and materials research.
  • Upon hydrolysis (chemical or enzymatic), it yields succinic acid and 1‑propanol. Succinic acid is a central metabolite in the tricarboxylic acid (TCA) cycle, linking carbohydrate, lipid, and amino acid metabolism. 1‑Propanol is a simple primary alcohol that can be further oxidized metabolically in biological systems, though its occurrence is limited.
  • Biocatalysis: Lipases and esterases can catalyze selective hydrolysis/transesterification of dialkyl succinates, enabling kinetic resolutions or chemoenzymatic routes to succinate derivatives under mild conditions.

• Use constraints

  • This product is designated For research use only. No medical, diagnostic, or therapeutic applications are implied.

Buffer Applications

Dipropyl succinate is not a buffering agent and is not typically used to prepare aqueous buffer systems. If your work requires succinate-buffered systems (pH ~5.0–6.5), use sodium/potassium salts of succinic acid (succinate buffer) rather than hydrophobic dialkyl esters. See Reaction & Applications for relevant non-buffer uses of this ester.

Green Alternatives

• Context

  • Dialkyl succinates are generally considered more benign than chlorinated solvents and some polar aprotics; they are often derived from bio-based succinic acid. However, choice of alkyl group impacts volatility, biodegradability, and process energy.

• Comparisons (literature/general)

  • Dimethyl/diethyl succinate: lower viscosity and boiling points; widely cited as greener solvent/reactant options due to better biodegradability data and availability from bio‑routes.
  • 2‑MeTHF and CPME (as reaction media): greener ether solvents compared with THF/MTBE; if using dipropyl succinate only as a solvent, these may reduce energy for removal and improve safety (lower peroxide risk than THF but still monitor for peroxides in ethers).
  • Propylene carbonate/ethyl lactate: high-boiling, biodegradable, and low-toxicity media for certain reactions and cleaning applications.

• Trade‑offs

  • Higher alkyl succinates (e.g., dipropyl) provide slower evaporation and sometimes improved solvency but at the cost of higher energy input for removal and potentially slower biodegradation versus methyl/ethyl analogs.
  • Enzymatic transesterifications in greener media (e.g., 2‑MeTHF or supercritical CO2) can replace strong acid catalysts, reducing waste.

• Practical guidance

  • If your process uses dipropyl succinate only as an inert medium, evaluate dimethyl/diethyl succinate or bio-derived esters for improved lifecycle metrics.
  • Retain dipropyl succinate where its higher boiling point or solvency profile is essential to product quality or selectivity.

Pharmaceutical Uses

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

• General formulation context (literature/general)

  • Aliphatic diesters of dicarboxylic acids can function as plasticizers or processing aids in polymeric excipients and film coatings; selection depends on compatibility, volatility, and toxicological profile.
  • Dipropyl succinate is not a commonly cited pharmacopeial excipient. Where succinate chemistry is required in drug product manufacturing, salts of succinic acid or specific succinate esters (validated for safety) are typically chosen.
  • Any use in pharmaceutical development would require full toxicological qualification, extractables/leachables assessment (if used with polymers), and compliance with ICH/compendial expectations.

No therapeutic claims are made. This product is for research/laboratory use only.

Physical Properties

• Item-specific specs (from Product Data)

  • Appearance: 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.

• Literature/typical properties (for reference; not item specifications)

  • Physical state: typically a colorless to pale liquid ester at ambient temperature.
  • Odor: faint, ester-like (literature, qualitative).
  • Solubility: low in water; miscible with many organic solvents (e.g., alcohols, ethers, esters, hydrocarbons) (literature, qualitative).
  • Volatility: lower than the corresponding methyl/ethyl succinates; higher than longer-chain succinate esters (literature trend).

• General chemistry notes

  • Polarity: moderately polar aprotic (due to two ester carbonyls) but overall hydrophobic from two n‑propyl chains.
  • Hydrogen-bonding: H‑bond acceptor (carbonyl oxygens); non-donor.
  • Thermal behavior: typical aliphatic diesters show good thermal stability under inert atmosphere; hydrolyze under strong acid/base, especially at elevated temperature.

For exact numeric BP/MP, density, refractive index, logP, or UV cut-off relevant to this SKU: Not specified for this item; refer to CoA/Spec Sheet.

Quality & Grades

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

• How to interpret grades for this class of product (general guidance)

  • Analytical or reagent grades typically control for acidity (acid number), water content (Karl Fischer), residual alcohol/acid, and GC purity. Low-UV or HPLC grades further control UV absorbance and trace impurities relevant to chromatographic detection.
  • Stabilizers: Aliphatic diesters generally do not require stabilizers; however, oxygen exclusion (argon headspace, as provided) limits oxidative byproduct formation and preserves baseline UV transparency.
  • Application-driven specifications: Polymer synthesis and materials R&D often require tight control of acid value and residual monofunctional alcohols; biocatalysis workflows may emphasize low metal/halogen residues and a narrow impurity profile.

• Documentation

  • For this SKU, definitive acceptance criteria (purity %, water, acidity, residual solvents, metals, UV cutoff) are Not specified for this item; refer to CoA/Spec Sheet.
  • Request the lot-specific CoA for method details (e.g., GC area %, KF, acid value) and any additional release tests.

Reaction & Applications

• Ester transformations (general/literature)

  • Hydrolysis/saponification: Base- or acid-catalyzed conversion to succinic acid or monoesters; useful for stepwise differentiation of termini in bifunctional synthesis.
  • Transesterification: Exchange with other alcohols under acid (e.g., H2SO4, p‑TsOH) or base (alkoxides) catalysis to access customized alkyl succinates; lipase-catalyzed variants enable mild, selective transformations.
  • Aminolysis: Reaction with primary amines to produce mono- or diamides; cyclization with ammonia or primary amines can lead to succinimide derivatives under dehydrating conditions.

• Reductive routes

  • Hydride reduction (e.g., LiAlH4) to 1,4‑butanediol via diol formation; partial reduction (DIBAL‑H, temperature control) can yield hemiacetal-like intermediates or aldehydes after workup (care required to avoid over‑reduction).
  • Catalytic hydrogenation/hydrogenolysis sequences can be employed en route to tetrahydrofuran (THF) or γ‑butyrolactone (GBL) via established succinate/semialdehyde pathways (literature).

• Polymer and materials chemistry

  • A monomeric diester feedstock for aliphatic polyester synthesis (polycondensation with diols/diols via transesterification) yielding biodegradable polyesters (literature context).
  • Acts as a reactive diluent or internal plasticizer in certain resin systems, modulating Tg and flexibility.

• Practical tips (general)

  • Maintain anhydrous, oxygen-limited conditions (argon, as supplied) for moisture- or oxidation-sensitive steps.
  • For selective mono-functionalization, employ controlled stoichiometry and stepwise protection (e.g., generate a monoester or half-amide first), or exploit enzymatic selectivity (lipases) at mild temperatures.
  • Monitor reactions by GC or 1H NMR; the methylene regions adjacent to carbonyls provide diagnostic shifts, and disappearance/appearance of alkoxy resonances track progress.

Reaction Conditions

The following are general literature guidelines for dialkyl succinate chemistry; adjust to your substrate, scale, and equipment. They are not item-specific specifications.

• Transesterification

  • Acid-catalyzed: 0.5–5 mol% p‑TsOH or H2SO4; 60–120 °C depending on alcohol; remove formed 1‑propanol (azeotropic distillation or N2 sweep) to drive equilibrium. Reaction times: 2–16 h. Use toluene, xylene, or neat conditions.
  • Base-catalyzed: 1–10 mol% sodium/potassium alkoxide in corresponding alcohol; 25–80 °C; 1–8 h. Exclude moisture/CO2.
  • Enzymatic: Lipase (e.g., CAL‑B, immobilized) 5–20 wt% relative to ester; 30–60 °C; solvent-free or in green solvents (2‑MeTHF, TBME); monitor by GC.

• Hydrolysis/saponification

  • Base: 1–2 equiv NaOH/KOH in aqueous alcohol (MeOH/EtOH/H2O); 20–60 °C; 1–6 h for mono‑ to di‑saponification; acidify to pH ~1 to isolate succinic acid.
  • Acid: Aqueous mineral acids (e.g., 1–3 M HCl); reflux; longer times relative to base hydrolysis.

• Aminolysis/amidation

  • Use 1.5–3.0 equiv amine with catalytic DMAP or stronger coupling (via diacid chloride from succinic acid with SOCl2/oxalyl chloride); 0–80 °C; 2–18 h.

• Reductions

  • LiAlH4 (1.5–3.0 equiv per ester) in dry THF/Et2O; 0 °C to reflux; 2–6 h; quench cautiously to afford 1,4‑butanediol (typical high yields reported in literature). DIBAL‑H at −78 to 0 °C enables partial reductions with careful control.

• Workup/monitoring

  • Monitor by GC-FID or 1H NMR; remove 1‑propanol formed in exchange/hydrolysis to shift equilibria; employ inert atmosphere (argon, as supplied) to minimize oxidative side products.

Safety & Handling

• Item-specific hazard 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.

• Storage conditions (from Product Data)

  • Store at 2–8 °C, under argon (argon charged).
  • Shipped on wet ice.

• General safety guidance for aliphatic diesters (literature/typical; defer to SDS)

  • Expected hazards: low to moderate acute toxicity; may cause skin/eye irritation and respiratory irritation upon vapor/aerosol exposure.
  • Incompatibilities: strong acids/bases (hydrolysis), strong oxidizers, and reactive alkali metals.
  • Combustibility: combustible organic liquid; keep away from ignition sources and hot surfaces.
  • PPE: safety glasses or face shield, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile); handle in a fume hood to minimize inhalation of vapors/aerosols.
  • Spill/first aid (overview): absorb small spills with inert material; for skin/eye contact, rinse with water for at least 15 minutes; seek medical attention if irritation persists. For inhalation, move to fresh air. For ingestion, rinse mouth; do not induce vomiting unless directed by medical personnel.

Always consult the product’s SDS for authoritative hazard, exposure limits, and emergency measures.

Solvent Selection

Dipropyl succinate is primarily a building block/reagent rather than a routine chromatography solvent; however, its solvency and polarity can be leveraged in synthesis and formulations.

• Polarity and miscibility (general chemistry)

  • Class: moderately polar aprotic ester; strong H‑bond acceptor, non-donor.
  • Miscibility: typically miscible with common organic solvents (alcohols, ethers, esters, ketones, chlorinated solvents, and many hydrocarbons); limited solubility in water.

• When to choose

  • As a high-boiling, moderately polar ester medium for transesterifications or biocatalytic esterifications where water content can be controlled.
  • As a compatibilizer/plasticizing co-solvent in polymer/dope solutions when a slower-evaporating ester is beneficial.

• Alternatives (selection logic)

  • Lower-boiling esters (ethyl acetate, methyl isobutyl acetate) for faster evaporation.
  • Higher-polarity aprotic solvents (DMF, DMSO) when solubilizing polar reagents; note these are more coordinating and less volatile.
  • Bio-based dialkyl succinates (dimethyl/diethyl succinate) if lower viscosity/boiling point is preferred.

Note: If your application primarily involves reaction chemistry, see Reaction & Applications and Reaction Conditions for solvent choice in those contexts.

Storage & Reconstitution

• Storage (from Product Data)

  • Temperature: 2–8 °C.
  • Atmosphere: Argon charged (store under inert gas; keep container tightly closed).
  • Shipping: Wet ice.

• General handling

  • Minimize headspace oxygen; reseal under argon or nitrogen after each use.
  • Keep away from moisture, strong acids/bases, and oxidizers to prevent hydrolysis/oxidation.
  • If solidification occurs at low temperature, gently warm to ambient and homogenize before use; no special reconstitution is required.

• Stability notes (general)

  • Aliphatic diesters are typically stable for extended periods when stored cool, dry, and inert. For long-term storage, consider amber glass to limit UV exposure and periodic GC check for alcohol/acid formation.

• Reconstitution

  • Not applicable; product is supplied ready-to-use. If dilution is needed, use dry, oxygen-free organic solvents compatible with your application (e.g., toluene, hexanes, EtOAc), and label secondary containers with preparation date and solvent.

Structure & Identity

Dipropyl succinate is the symmetrical di-n-propyl diester of succinic acid, featuring two terminal n-propyl groups connected through ester linkages to a central butane-1,4-dioate core.

• Item-specific identifiers (from Product Data)

  • CAS: 925-15-5
  • PubChem CID: 13549
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity (for reference; not item specifications)

  • Typical molecular formula (literature): C10H18O4
  • Typical molecular weight (literature): ~202.24 g/mol
  • Representative SMILES (literature): CCCOC(=O)CC(=O)OCCC (symmetrical di-n-propyl ester)

• Structural features (general chemistry)

  • Functional groups: two aliphatic ester moieties (–COO–) and two n-propyl substituents.
  • Backbone: a saturated four‑carbon succinate (butane‑1,4‑dioate) linker between the ester carbonyls.
  • 2D description: n‑propyl–O–C(=O)–CH2–CH2–C(=O)–O–n‑propyl; no rings, no stereocenters; fully aliphatic.

Synthetic Utility

• Functional group handles

  • Two ester carbonyls enable classic transformations: hydrolysis to diacid/monoacid, alcohol exchange (transesterification), reduction to diol, and conversion to acid chlorides (via diacid) followed by further derivatization.
  • Alpha‑position chemistry: The methylenes alpha to each carbonyl can be deprotonated with strong bases, enabling limited alkylation/acylation, though less reactive than malonates due to absence of a central activated methylene.

• Retrosynthetic value

  • As a succinic acid equivalent: Use aminolysis (→ diamides) or partial hydrolysis (→ monoester/acid) to build symmetrical/asymmetrical succinate derivatives.
  • Precursor to heterocycles: Through diamide formation and dehydration/cyclization, access succinimides and related imide scaffolds.

• Named/typical transformations (literature)

  • Fischer–Speier esterification (reverse direction for synthesis from succinic acid and 1‑propanol) and transesterifications (acid or base catalyzed).
  • LAH reductions to 1,4‑butanediol; subsequent intramolecular dehydration/hydrogenation sequences can yield THF under catalytic conditions.
  • Enzymatic lipase-catalyzed kinetic resolutions for selective mono-deprotection or alcohol exchange.

• Practical notes

  • Control water (molecular sieves, Dean–Stark) for equilibrium-driven steps.
  • For selective mono-functionalization, conduct stepwise reactions with stoichiometric control or employ immobilized lipases to exploit differential reactivity of the two ester ends.

Target Specificity

This product is a small-molecule chemical reagent and does not have biological target specificity (no antigen/epitope, clone, or isotype). Section not applicable.