26473-48-3

Basic information

• Product Name: 2-Mercaptobutyric acid
• Synonyms: (S)-3-BROMOBUTANOIC ACID;2-Mercaptobutanoic acid;2-Mercaptobutyric acid;Butanoic acid, 2-Mercapto-;(3S)-3-BroMobutanoic acid;(S)-2-mercaptobutanoic acid
• CAS NO: 26473-48-3
• Molecular Formula: C₄H₈O₂S
• Molecular Weight: 120.17
• Mol File: 26473-48-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 224 °C
• Flash Point: 89 °C
• Appearance: /
• Density: 1.159
• Vapor Pressure: 0.034mmHg at 25°C
• Refractive Index: 1.491
• PKA: pK1:3.53(0) (25°C)
• CAS DataBase Reference: 2-Mercaptobutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mercaptobutyric acid(26473-48-3)
• EPA Substance Registry System: 2-Mercaptobutyric acid(26473-48-3)

Safety Data

• Hazardous Substances Data: 26473-48-3(Hazardous Substances Data)

Usage

General Description

2-Mercaptobutyric acid, also known as 2-MBA, is a naturally occurring compound found in various foods and beverages, especially in certain types of cheese. It is a colorless liquid with a strong, unpleasant odor, and is commonly used as a flavoring agent and preservative in the food industry. 2-MBA is also a key component in the synthesis of cysteine, an important amino acid. Additionally, it has potential applications in the production of pharmaceuticals, agrochemicals, and other industrial processes. The compound is classified as a hazardous substance and precautions should be taken when handling it due to its irritant and corrosive properties.

InChI:InChI=1/C4H8O2S/c1-2-3(7)4(5)6/h3,7H,2H2,1H3,(H,5,6)

Upstream product

• 80-58-0 2-Bromobutyric acid 
• 1762-69-2 5-Aethyl-pseudothiohydantoin 
• 51475-58-2 2-ethoxythiocarbonylmercapto-butyric acid 
• 90114-01-5 (+/-)-2,5-diethyl-3,4-dithia-adipic acid 
• 64-19-7 acetic acid 
• 1217740-06-1 C₁₁H₁₂O₃S 

Downstream Products

• 1986-34-1 5-ethyl-3-phenyl-2-thioxothiazolidin-4-one 
• 147131-44-0 1-{4-[N-methyl-N-ethylmercaptoacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride 

Relevant articles and documents

O-to-S Substitution Enables Dovetailing Conflicting Cyclizability, Polymerizability, and Recyclability: Dithiolactone vs. Dilactone

Developing chemically recyclable polymers represents a greener alternative to landfill and incineration and offers a closed-loop strategy toward a circular materials economy. However, the synthesis of chemically recyclable polymers is still plagued with certain fundamental limitations, including trade-offs between the monomer's cyclizability and polymerizability, as well as between polymer's depolymerizability and properties. Here we describe the subtle O-to-S substitution, dithiolactone monomers derived from abundant feedstock α-amino acids can demonstrate appealing chemical properties different from those of dilactone, including accelerated ring closure, augmented kinetics polymerizability, high depolymerizability and selectivity, and thus constitute a unique class of polythioester materials exhibiting controlled molecular weight (up to 100.5 kDa), atactic yet high crystallinity, structurally diversity, and chemical recyclability. These polythioesters well addresses the formidable challenges of developing chemically recyclable polymers by having an unusual set of desired properties, including easy-to-make monomer from ubiquitous feedstock, and high polymerizability, crystallinity and precise tunability of physicochemical performance, as well as high depolymerizability and selectivity. Computational studies explain why O-to-S modification of polymer backbone enables dovetailing desirable, but conflicting, performance into one polymer structure.

Asymmetric synthesis of the four diastereoisomers of a novel non-steroidal farnesoid X receptor (FXR) agonist: Role of the chirality on the biological activity

An asymmetric synthetic strategy was designed for the preparation of the four possible diastereoisomers of 3,6-dimethyl-1-(2-methylphenyl)-4-(4- phenoxyphenyl)-4,8-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-7-one, a non-steroidal FXR agonist, we recently discovered following a virtual screening approach. The results obtained from an AlphaScreen assay clearly demonstrated that only the isomer endowed with 4R,6S absolute configuration is responsible for the biological activity. A deep investigation of the different putative binding modes adopted by these enantiomerically pure ligands using computational modeling studies confirmed the enantioselectivity of FXR towards this class of molecules.

2-Mercaptoaldehyde dimers and 2,5-dihydrothiophenes from 1,3-oxathiolan-5-ones

Representative 1,3-oxathiolan-5-ones (6), prepared from 2-mercaptoacids, have been reduced to 2-mercaptoaldehydes 1 with diisobutylaluminum hydride.The aldehydes 1, which appear to exist in several dimeric forms, react with vinyltriphenylphosphonium bromide to give 2,5-dihydrothiophenes.