EN300-93915

Product Information

EN300-93915 is 3-(4-Chlorophenyl)pentanedioic acid, also known as 3-(4-chlorophenyl)glutaric acid. Its central carbon carries a para-chlorophenyl group, a hydrogen atom and two identical CH2COOH arms. This arrangement provides a symmetrical starting material for routes that require selective modification of one end of the carbon chain.

The free diacid is achiral because C3 has two identical substituents. Converting only one of the two equivalent carboxyl groups into an ester or amide makes the two arms nonequivalent, so C3 becomes stereogenic. This desymmetrization does not itself guarantee an enantiomerically enriched product: a chiral catalyst, resolving agent or another source of stereochemical control is required.

3-(4-Chlorophenyl)pentanedioic acid Structure and Chemical Identifiers

The compound is registered under CAS 35271-74-0. The following identifiers describe the neutral diacid:

• Molecular formula: C11H11ClO4
• Molecular weight: 242.66 g/mol
• MDL number: MFCD00190249
• SMILES: OC(=O)CC(CC(=O)O)c1ccc(Cl)cc1
• InChIKey: URXVLIVRJJNJII-UHFFFAOYSA-N

The chlorine occupies the para position on the phenyl ring, while the aryl substituent is attached to C3 of the pentanedioic acid chain. Both features matter when distinguishing this compound from positional isomers. Its cyclic anhydride, monoesters and monoamides are separate substances with different formulas and should not be matched to the free acid solely by a shared glutaric acid name.

Applications of 3-(4-Chlorophenyl)pentanedioic acid

A documented application is the synthesis of baclofen through derivatives of the diacid. Published work describes optical resolution of the corresponding glutaramic acid, which contains one carboxylic acid group and one primary amide. Formation of diastereomeric salts with (S)-α-phenylethylamine enables separation of the enantiomers, followed by Hofmann degradation of the resolved amide to obtain (R)-baclofen.

A complementary approach first converts the diacid into its cyclic anhydride. Patent literature reports enantioselective alcoholysis of this anhydride with a chiral catalyst to give a monoester. Subsequent transformations use the differentiated acid and ester groups to access baclofen enantiomers through Curtius or Hofmann rearrangement sequences.

These routes illustrate two distinct uses of the symmetrical precursor: resolution separates enantiomers after the arms have been differentiated, whereas asymmetric anhydride opening establishes stereochemical bias during that differentiation. Selecting a route therefore requires attention to the intermediate being isolated and the stereochemical outcome of the subsequent steps.

3-(4-Chlorophenyl)pentanedioic acid Supply and Availability from EnamineStore

Use product code EN300-93915 when requesting this compound from EnamineStore, and confirm current ordering details directly with the supplier. For route development, request the product specification and, where available, a batch-specific CoA to assess whether the material meets the requirements of the planned synthesis. Consult the current SDS for handling and storage guidance. Any use as an analytical reference standard requires separate confirmation of the material's qualification for that purpose.