3477-94-9

Basic information

• Product Name: 1-Benzoyloxy-3-chloropropan-2-ol
• Synonyms: 1-Benzoyloxy-3-chloropropan-2-ol;3-Chloro-2-hydroxypropyl=benzoate;Benzoic acid 2-hydroxy-3-chloropropyl ester;Benzoic acid 3-chloro-2-hydroxypropyl ester;U-27574
• CAS NO: 3477-94-9
• Molecular Formula: C₁₀H₁₁ClO₃
• Molecular Weight: 214.66
• Mol File: 3477-94-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 308.11°C (rough estimate)
• Flash Point: 167.5°C
• Appearance: /
• Density: 1.2413 (rough estimate)
• Vapor Pressure: 1.32E-05mmHg at 25°C
• Refractive Index: 1.5390 (estimate)
• PKA: 12.89±0.20(Predicted)
• CAS DataBase Reference: 1-Benzoyloxy-3-chloropropan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzoyloxy-3-chloropropan-2-ol(3477-94-9)
• EPA Substance Registry System: 1-Benzoyloxy-3-chloropropan-2-ol(3477-94-9)

Safety Data

• Hazardous Substances Data: 3477-94-9(Hazardous Substances Data)

Usage

General Description

1-Benzoyloxy-3-chloropropan-2-ol is a chemical compound with the molecular formula C10H11ClO3. It is a white, crystalline solid that is used in the synthesis of various organic compounds. The compound is a derivative of propan-2-ol and contains a benzoyloxy group and a chlorine atom. It is commonly used as a reagent in organic synthesis and can undergo various chemical reactions to form new compounds. The compound is also known for its mild narcotic effects and has been used in medicinal and pharmacological research. Additionally, it is important to handle this chemical with caution as it may be hazardous if not used properly.

InChI:InChI=1/C10H11ClO3/c11-6-9(12)7-14-10(13)8-4-2-1-3-5-8/h1-5,9,12H,6-7H2

Upstream product

• 36236-72-3 4-chloromethyl-2-phenyl[1,3]dioxolane 
• 98-88-4 benzoyl chloride 
• 96-24-2 3-monochloro-1,2-propanediol 
• 98760-25-9 oxiran-2-ylmethyl benzoate 
• 2463-45-8 4-chloromethyl-[1,3]dioxolan-2-one 
• 100-58-3 phenylmagnesium bromide 
• 100-51-6 benzyl alcohol 
• 65-85-0 benzoic acid 
• 106-89-8 epichlorohydrin 

Downstream Products

• 27933-26-2 1-benzoyloxy-3-chloropropan-2-one 
• 32604-68-5 1,2-Dibenzoyloxy-3-chlor-propan 
• 128733-47-1 3-diethylamino-2-hydroxypropyl benzoate 
• 130277-95-1 1-chloro-3-benzoyloxy-2-chloromethoxypropane 

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.

A Modified Synthesis of Oxetan-3-ol

Abstract: A highly regioselective ring opening reaction of terminal epoxides with 2-bromobenzoic acid catalyzed by tetrabutylammonium bromide was accomplished. The procedure is operationally simple and practical for the synthesis of a series of β-hydroxy esters. Using this protocol, oxetan-3-ol could be prepared efficiently in a good yield.

Regioselectivity of the acidolysis of 2-(chloromethyl)oxirane with aromatic acids in the presence of organic bases

Regioselectivity of the reaction of 2-(chloromethyl)oxirane with aromatic acids in the presence of tertiary amines and tetraalkylammonium halides has been studied. Opening of the oxirane ring follows simultaneously SN2 and borderline SN2 mechanisms. The regioselectivity of the acidolysis of substituted oxiranes is determined by acid-base properties of the reactants and catalysts and steric factor. The regioselectivity increases as the contribution of the SN2 mechanism increases.