71183-36-3

Basic information

• Product Name: (3S)-3-bromo-2-oxobutanoic acid
• CAS NO: 71183-36-3
• Molecular Formula: C₄H₅BrO₃
• Molecular Weight: 180.9847
• Mol File: 71183-36-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 218.1°C at 760 mmHg
• Flash Point: 85.7°C
• Density: 1.812g/cm³
• Vapor Pressure: 0.0487mmHg at 25°C
• Refractive Index: 1.509
• CAS DataBase Reference: (3S)-3-bromo-2-oxobutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3-bromo-2-oxobutanoic acid(71183-36-3)
• EPA Substance Registry System: (3S)-3-bromo-2-oxobutanoic acid(71183-36-3)

Safety Data

• Hazardous Substances Data: 71183-36-3(Hazardous Substances Data)

Usage

Description

(3S)-3-bromo-2-oxobutanoic acid is a chiral chemical compound with the molecular formula C4H5BrO3. It is a derivative of butanoic acid, featuring a bromine atom and a ketone functional group attached to the third carbon of the carbon chain. The (3S) designation signifies the specific stereochemistry of the molecule, which is crucial for its potential applications and interactions.

Uses

Used in Organic Synthesis:
(3S)-3-bromo-2-oxobutanoic acid is utilized as an intermediate in organic synthesis for the production of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structural features, including the bromine atom and ketone group, make it a valuable building block for creating complex organic molecules.
Used in Biological Research:
Due to its structural characteristics, (3S)-3-bromo-2-oxobutanoic acid has potential biological activity, which can be explored in research for developing new drugs or understanding biological processes. Its chirality may also play a role in its interactions with biological systems, as stereochemistry often influences the efficacy and selectivity of compounds in biological contexts.
Used in Chemical Education:
(3S)-3-bromo-2-oxobutanoic acid can serve as an educational tool in teaching the principles of stereochemistry, organic synthesis, and the properties of functional groups. It provides a concrete example for students to learn about the importance of stereochemistry in chemical reactions and its implications in various fields.
Safety Considerations:
It is important to handle (3S)-3-bromo-2-oxobutanoic acid with care, as bromine-containing chemicals can be hazardous. Proper training, protective equipment, and a controlled environment are necessary when working with this compound to ensure safety and minimize potential risks.

Upstream product

• 600-18-0 2-Oxobutyric acid 

Downstream Products

• 343322-65-6 ethyl 5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxylate 

Relevant articles and documents

Multiple-step, one-pot synthesis of 2-substituted-3-phosphono-1-thia-4-aza-2-cyclohexene-5-carboxylates and their corresponding ethyl esters

The multiple-step, one-pot procedure for a series of 2-substituted-3-phosphono-1-thia-4-aza-2-cyclohexene-5-carboxylates, analogues of the natural, sulfur amino acid metabolite lanthionine ketimine (LK), its 5-ethyl ester (LKE) and 2-substituted LKEs is described. Initiating the synthesis with the Michaelis-Arbuzov preparation of α-ketophosphonates allows for a wide range of functional variation at the 2-position of the products. Nine new compounds were synthesized with overall yields range from 40 to 62%. In addition, the newly prepared 2-isopropyl-LK-P, 2-n-hexyl-LKE-P and 2-ethyl-LKE were shown to stimulate autophagy in cultured cells better than that of the parent compound, LKE.

HETEROCYCLIC DERIVATIVE AND USE THEREOF

The present invention aims to provide a compound having superior pharmacological action, physicochemical properties and the like and useful as an sGC activation drug, or an agent for the prophylaxis and/or treatment of diseases such as hypertension, ischemic cardiac disease, cardiac failure, kidney disease, arteriosclerotic disease, atrial fibrillation, pulmonary hypertension, diabetes, diabetic complications, metabolic syndrome, peripheral arterial obstruction, erectile dysfunction and the like. An sGC activation drug containing a compound represented by the formula (II): wherein each symbol is as defined in the specification, or a salt thereof, as an active ingredient.

Substituted 2-[(4-aminomethyl)phenoxy]-2-methylpropionic acid PPARα agonists. 1. Discovery of a novel series of potent HDLc raising agents

The peroxisome proliferator activated receptors PPARα, PPARγ, and PPARδ are ligand-activated transcription factors that play a key role in lipid homeostasis. The fibrates raise circulating levels of high-density lipoprotein cholesterol and lower levels of triglycerides in part through their activity as PPARα agonists; however, the low potency and restricted selectivity of the fibrates may limit their efficacy, and it would be desirable to develop more potent and selective PPARα agonists. Modification of the selective PPARδ agonist 1 (GW501516) so as to incorporate the 2-aryl-2-methylpropionic acid group of the fibrates led to a marked shift in potency and selectivity toward PPARα agonism. Optimization of the series gave 25a, which shows EC50 = 4 nM on PPARα and at least 500-fold selectivity versus PPARγ and PPARγ. Compound 25a (GW590735) has been progressed to clinical trials for the treatment of diseases of lipid imbalance.