15410-44-3

Usage

General Description

2,3-Butanediol,1,4-dibromo-, (2R,3R)- is a chemical compound with the molecular formula C4H8Br2O2. It is a derivative of butanediol, containing bromine atoms at positions 1 and 4 on the molecule. The (2R,3R) designation indicates the stereochemistry of the compound, with the bromine atoms oriented in a specific configuration. This chemical is often used in organic synthesis and as a reagent in various reactions. It may also have applications in pharmaceuticals and other industries due to its unique structure and properties.

Upstream product

• 2418-52-2 D-threitol 
• 564-00-1 (R,R)-butane-1,2:3,4-bisoxide 
• 299-70-7 threo-1,4-dibromo-2,3-butanediol 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 73744-64-6 (+)-(2R,3R)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-dibromobutane 

Downstream Products

• 1947-62-2 treosulfan 
• 299-74-1 treosulfan 

Relevant academic research and scientific papers

Kinetic resolution of d,l-1,2-diols catalyzed by amine-phosphinite bifunctional organocatalysis derived from quinidine

Racemic C2-symmetric 1,2-diols were kinetically resolved by the acylation reaction catalyzed by the phosphinite derivative of quinidine to afford the corresponding monoacylated product with good to high enantioselectivities.

In vitro metabolism of chloroprene: Species differences, epoxide stereochemistry and a de-chlorination pathway

Chloroprene (1) was metabolized by liver microsomes from Sprague-Dawley rats, Fischer 344 rats, B6C3F1 mice, and humans to the monoepoxides, (1-chloro-ethenyl)oxirane (5a/5b), and 2-chloro-2-ethenyloxirane (4a/4b). The formation of 4a/4b was inferred from the identification of their degradation products. With male Sprague-Dawley and Fischer 344 rat liver microsomes, there was a ca. 3:2 preference for the formation of (R)-(1-chloroethenyl)oxirane (5a) compared to the (S)-enantiomer (5b). A smaller but distinct enantioselectivity in the formation of (S)-(1-chloro-ethenyl)oxirane occurred with liver microsomes from male mouse (R:S, 0.90:1) or male human (R:S, 0.86:1). 2-Chloro-2-ethenyloxirane was very unstable in the presence of the microsomal mixture and was rapidly converted to 1-hydroxybut-3-en-2-one (11) and 1-chlorobut-3-en-2-one (12). An additional rearrangement pathway of 2-chloro-2-ethenyloxirane gave rise to 2-chlorobut-3-en-1-al (14) and 2-chlorobut-2-en-1-al (15). Further reductive metabolism of these metabolites occurred to form 1-hydroxybutan-2-one (17) and 1-chlorobutan-2-one (18). In the absence of an epoxide hydrolase inhibitor, the microsomal incubations converted (1-chloroethenyl)oxirane to 3-chlorobut-3-ene-1,2-diol (21a/21b). When microsomal incubations were supplemented with glutathione, 1-hydroxybut-3-en-2-one was not detected because of its rapid conjugation with this thiol scavenger.