13881-41-9

Usage

Uses

Used in Pharmaceutical Industry:
3-chloro-2-hydroxy-2-methyl-propanoic acid is used as a chiral building block for the synthesis of pharmaceutical intermediates, contributing to the development of new drugs with improved efficacy and selectivity. Its unique structure allows for the creation of enantiomerically pure compounds, which is crucial for the production of effective and safe medications.
Used in Chemical Industry:
In the chemical industry, 3-chloro-2-hydroxy-2-methyl-propanoic acid serves as a versatile building block for the synthesis of various agrochemicals and fine chemicals. Its reactivity and functional groups enable the production of a wide range of specialty chemicals, including herbicides, insecticides, and other bioactive compounds, enhancing crop protection and agricultural productivity.
Used in Organic Chemistry:
3-chloro-2-hydroxy-2-methyl-propanoic acid is utilized as a key intermediate in organic synthesis, allowing for the preparation of a diverse array of organic compounds. Its unique functional groups, such as the chloro and hydroxyl groups, facilitate various chemical reactions, enabling the synthesis of complex molecules with potential applications in materials science, pharmaceuticals, and other fields.

InChI:InChI=1/C4H7ClO3/c1-4(8,2-5)3(6)7/h8H,2H2,1H3,(H,6,7)

Upstream product

• 79-41-4 poly(methacrylic acid) 
• 33401-05-7 β-chloro-α-hydroxy-isobutyronitrile 
• 412013-31-1 1,6-dichloro-2,5-dimethyl-hex-3-yne-2,5-diol 
• 54051-00-2 α-acetoxy-β-chloro-isobutyric acid methyl ester 
• 563-47-3 3-Chloro-2-methylpropene 
• 7647-01-0 hydrogenchloride 
• 38649-35-3 rac-2-methyloxirane-2-carboxylic acid 
• 7732-18-5 water 
• 13898-47-0 hypochloric acid 
• 927203-28-9 3-bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione 
• 67-64-1 acetone 

Downstream Products

• 21620-60-0 2-methylglyceric acid 

Relevant academic research and scientific papers

Chiral nonsteroidal affinity ligands for the androgen receptor. 1. Bicalutamide analogues bearing electrophilic groups in the B aromatic ring

A series of chiral analogues of bicalutamide bearing electrophilic groups (isothiocyanate, N-chloroacetyl, and N-bromoacetyl) on aromatic ring B of the parent molecule were synthesized. These compounds were designed as affinity ligands for the androgen receptor (AR). We prepared the (R)- and (S)-optical isomers of these compounds as pure enantiomers. The AR binding affinities of these compounds were measured in a competitive binding assay with the radiolabeled high-affinity AR ligand, [3H]mibolerone. In accordance with our previous results for the enantiomers of bicalutamide, we found that all (R)-isomers demonstrated much higher binding affinity to the AR as compared to their corresponding (S)-isomers. The para-substituted affinity ligands in ring B bound the AR with higher affinities than the corresponding metasubstituted analogues. Oxidation of thioester affinity ligands to their sulfonyl analogues for the para-substituted compounds decreased AR binding affinities and similar modification increased binding affinities for corresponding meta-analogues. The least potent para-substituted sulfonyl compounds had higher AR binding affinities than the most potent meta- substituted sulfonyl compounds. Overall, the para-substituted unoxidized molecules demonstrated the highest AR binding affinity. Subsequent research using AR exchange assays and Scatchard analyses showed that the isothiocyanate affinity ligands (R)-7, (R)-9, and (R)-10 reported herein are the first specific chemoaffinity ligands for the AR.

SYNTHESIS OF HYDROXY CARBOXYLIC ACIDS BY THE OXIDATION OF α-OLEFINS WITH CONCENTRATED NITRIC ACID

The reaction of propene, 2-methylpropene, 3-chloro-1-propene, and 2-methyl-3-chloro-1-propene with concentrated nitric acid (initial weight fraction 98-91percent) leads to the corresponding α-hydroxy carboxylic acids. The key stage in the oxidation of the α-olefin to the hydroxy acid is its nitrosation, which is promoted by increase in the solvent polarity and in the nucleophilicity of the double bond in the olefin. The introduction of chlorine into the olefin molecule leads to some increase in the probability of nitration.