112966-13-9

Basic information

• Product Name: (4S,5S)-2-CHLORO-4,5-DIME.-1,3,2-DIOXA- PHOSPHOLANE 2-OXIDE
• Synonyms: (4S,5S)-2-CHLORO-4,5-DIME.-1,3,2-DIOXA- PHOSPHOLANE 2-OXIDE;(4S,5S)-2-Chloro-4,5-dimethyl-1,3,2-dioxaphospholane 2-oxide
• CAS NO: 112966-13-9
• Molecular Formula: C₄H₈ClO₃P
• Molecular Weight: 170.531281
• Mol File: 112966-13-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 84-86 °C/0.2 mmHg(lit.)
• Flash Point: 56 °C
• Appearance: /
• Density: 1.3 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.440(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (4S,5S)-2-CHLORO-4,5-DIME.-1,3,2-DIOXA- PHOSPHOLANE 2-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-2-CHLORO-4,5-DIME.-1,3,2-DIOXA- PHOSPHOLANE 2-OXIDE(112966-13-9)
• EPA Substance Registry System: (4S,5S)-2-CHLORO-4,5-DIME.-1,3,2-DIOXA- PHOSPHOLANE 2-OXIDE(112966-13-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2920 8/PG 2
• Hazardous Substances Data: 112966-13-9(Hazardous Substances Data)

Usage

General Description

The chemical (4S,5S)-2-chloro-4,5-dime.-1,3,2-dioxa- phospholane 2-oxide, also known as chloramphenicol, is a broad-spectrum antibiotic used to treat various bacterial infections. It works by inhibiting bacterial protein synthesis, making it effective against a wide range of gram-positive and gram-negative bacteria. Chloramphenicol is commonly used in veterinary medicine to treat bacterial infections in animals, and occasionally in humans for specific illnesses. However, it is important to use caution when using chloramphenicol as it can cause serious side effects, including aplastic anemia, and it is considered a "drug of last resort" due to its potential for toxicity.

Upstream product

• 6982-25-8 d,l-2,3-butanediol 
• 1029272-42-1 (2R,3S)-2,3-butanediol 

Downstream Products

• 2365-02-8 racem-4,5-Dimethyl-2-<4-nitro-phenoxy>-1,3,2-dioxaphospholan-2-oxid 
• 2365-02-8 (4R,5R)-4,5-Dimethyl-2-(4-nitro-phenoxy)-[1,3,2]dioxaphospholane 2-oxide 
• 88853-17-2 (2S,4S,5R)-4,5-Dimethyl-2-phenoxy-[1,3,2]dioxaphospholane 2-oxide 
• 88853-18-3 (2R,4R,5S)-4,5-Dimethyl-2-phenoxy-[1,3,2]dioxaphospholane 2-oxide 

Relevant articles and documents

Chemistry of β-(phosphatoxy)alkyl and β-(acyloxy)alkyl radicals. Migration reactions: Scope and stereoselectivity of β-(phosphatoxy)alkyl rearrangement. Mechanism of β-(phosphatoxy)alkyl and β-(acyloxy)alkyl migration

An in depth study of the mechanism of the β-(phosphatoxy)alkyl radical migration is presented. Examples are presented which define the scope and limitations of the migration and show that, in certain cases, it is highly stereoselective. It is shown that phosphoranyl radicals are not intermediates in this rearrangement. A series of experiments with stereochemically-, 18O-, and deuterium-labeled probes indicate that the migration is intramolecular, proceeds through competing 1,2- and 2,3-pathways, and does not involve fragmentation to a cage pair followed by recombination. The deuterium-labeled probe is also applied to the β-(acyloxy)alkyl migration with the same result. The changing proportions of 1,2- and 2,3-shifts in going from the β-(phosphatoxy)alkyl to the β-(acyloxy)alkyl migration are discussed in terms of the conformational equilibria of the two different esters and the Curtin-Hammett principle.