869-50-1

Basic information

• Product Name: 3-Chloro-1,2-diacetoxypropane
• Synonyms: 1,2-Diacetoxy-3-chloropropane;3-Chloro-1,2-diacetoxypropane
• CAS NO: 869-50-1
• Molecular Formula: C₇H₁₁ClO₄
• Molecular Weight: 194.63
• Mol File: 869-50-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 279.11°C (rough estimate)
• Flash Point: 99.2°C
• Appearance: /
• Density: 1.1990
• Vapor Pressure: 0.0294mmHg at 25°C
• Refractive Index: 1.4407 (estimate)
• CAS DataBase Reference: 3-Chloro-1,2-diacetoxypropane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-1,2-diacetoxypropane(869-50-1)
• EPA Substance Registry System: 3-Chloro-1,2-diacetoxypropane(869-50-1)

Safety Data

• Hazardous Substances Data: 869-50-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H11ClO4/c1-5(9)11-4-7(3-8)12-6(2)10/h7H,3-4H2,1-2H3

Upstream product

• 102-76-1 triacetylglycerol 
• 556-52-5 oxiranyl-methanol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 96-24-2 3-monochloro-1,2-propanediol 
• 64-19-7 acetic acid 
• 56-81-5 glycerol 
• 106-89-8 epichlorohydrin 
• 108-05-4 vinyl acetate 
• 108-22-5 Isopropenyl acetate 
• 24573-30-6 3-chloro-2-hydroxy-1-propyl acetate 
• 75-05-8 acetonitrile 
• 93713-40-7 Glycerin-monoacetat 
• 2156-73-2 2-acetoxy-2-methylbutyryl chloride 

Downstream Products

• 52829-30-8 7-chloro-1-(2,3-dihydroxy-propyl)-5-(2-fluoro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 60827-45-4 (S)-3-chloropropan-1,2-diol 

Relevant articles and documents

Diol-Ritter Reaction: Regio- And Stereoselective Synthesis of Protected Vicinal Aminoalcohols and Mechanistic Aspects of Diol Monoester Disproportionation

The well-known epoxide-Ritter reaction generally affords oxazolines with poor to average regioselectivity. Herein, a mechanism-based study of the less known diol-Ritter reaction has provided a highly regioselective procedure for the synthesis of 1-vic-amido-2-esters from either terminal epoxides or 1,2-diols via Lewis acid-catalyzed monoesterification. When treated with a stoichiometric Lewis acid catalyst (BF3), these diol monoesters form dioxonium cation intermediates that are ring-opened with nitrile nucleophiles to form nitrilium intermediates, which undergo rapid and irreversible hydration to give the desired amidoesters. Diester byproduct formation is irreversible and appears to occur through disproportionation of diol monoester. With chiral epoxide starting materials, the formation of amidoester occurs with retention of configuration and no apparent erosion of optical purity as determined by single-crystal X-ray analyses and chiral chromatography, respectively. The direct access to chiral vic-amidoesters is especially practical with regard to the synthesis of antibacterial oxazolidinone analogues of the Zyvox antimicrobial family.

Heterogeneous acidic and eco-friendly reagents for mild and convenient conversion of epoxides to 1,2-diacetates

A highly regioselective ring-opening of epoxides with acetic anhydride in the presence of hydrated disodium hydrogen phosphate and sodium hydrogen sulfate as efficient and eco-friendly reagents is described. The reactions are clean and lead to 1,2-diacetates in high to excellent yields.

One-pot catalytic conversion of epoxides to 1,2-diacetates with hydride transferring agents in acetic anhydride

Direct transformation of structurally different epoxides to the corresponding 1,2-diacetates was studied with catalytic amounts of NaBH 4, LiAlH4, CaH2, and NaH. The reactions were carried out in refluxing acetic anhydride within 1.5-2.5h to give vic-diacetates in good to excellent yields. Conversion of R-(+)-styrene oxide to S-(+)-1,2-diacetoxy-1-phenylethane was carried out with good yield and stereospecificity with the NaBH4/Ac2O system at 0°C.