1005-91-0

Basic information

• Product Name: 2-(chloromethyl)-2-phenyloxirane
• Synonyms: 2-(Chloromethyl)-2-phenyloxirane; Oxirane, 2-(chloromethyl)-2-phenyl-
• CAS NO: 1005-91-0
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.6202
• Mol File: 1005-91-0.mol

Chemical Properties

• Boiling Point: 256.4°C at 760 mmHg
• Flash Point: 73.5°C
• Density: 1.21g/cm³
• Vapor Pressure: 0.0248mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 2-(chloromethyl)-2-phenyloxirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(chloromethyl)-2-phenyloxirane(1005-91-0)
• EPA Substance Registry System: 2-(chloromethyl)-2-phenyloxirane(1005-91-0)

Safety Data

• Hazardous Substances Data: 1005-91-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(chloromethyl)-2-phenyloxirane is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form new chemical entities with potential therapeutic applications.
Used in Chemical Production:
In the chemical industry, 2-(chloromethyl)-2-phenyloxirane is used as a precursor for the production of resins and polymers, contributing to the development of materials with specific properties for diverse applications.
Used as a Stabilizer:
2-(chloromethyl)-2-phenyloxirane is employed as a stabilizer in certain chemical formulations to prevent unwanted reactions or degradation, thereby enhancing the stability and shelf life of products.
Safety Considerations:
Given that styrene oxide has been identified as carcinogenic in animal studies, it is crucial to handle and store 2-(chloromethyl)-2-phenyloxirane with care to minimize exposure and potential health hazards. Precautionary measures should be implemented during its use in various applications to ensure safety.

Upstream product

• 593-71-5 Chloroiodomethane 
• 98-88-4 benzoyl chloride 
• 532-27-4 1-chloroacetophenone 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 591-51-5 phenyllithium 
• 87234-28-4 1,3-dichloro-2-hydroxy-2-phenylpropane 
• 563-79-1 2,3-Dimethyl-2-butene 
• 136749-73-0 3-(chloromethyl)-3-phenyl-1,2-dioxetane 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 60-29-7 diethyl ether 

Downstream Products

• 856432-35-4 (1R*,5S*)-2-oxo-5-phenyl-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid t-butyl ester 
• 1441288-41-0 5-fluoromethyl-3,5-diphenyloxazolidin-2-thione 
• 1441288-39-6 5-fluoromethyl-5-phenyl-3-tosyloxazolidin-2-one 
• 1441288-37-4 3-[3,5-bis(trifluoromethyl)phenyl]-5-fluoromethyl-5-phenyloxazolidin-2-one 
• 1441288-35-2 5-fluoromethyl-3-(3-nitrophenyl)-5-phenyloxazolidin-2-one 
• 1441288-30-7 3-(4-bromophenyl)-5-fluoromethyl-5-phenyloxazolidin-2-one 
• 1441288-26-1 5-fluoromethyl-3-(4-methylphenyl)-5-phenyloxazolidin-2-one 
• 1441288-04-5 5-fluoromethyl-3,5-diphenyloxazolidin-2-one 
• 1441287-98-4 1,3-difluoro-2-phenylpropan-2-yl N-(4-bromophenylcarbamate) 
• 1441287-96-2 1,3-difluoro-2-phenylpropan-2-yl N-(4-methylphenylcarbamate) 
• 1441287-78-0 1,3-difluoro-2-phenylpropan-2-yl N-phenylcarbamate 
• 876-43-7 1,3-difluoro-2-phenylpropan-2-ol 
• 141248-89-7 2-hydroxymethyl-2-phenyloxirane 
• 191479-39-7 3-chloro-2-phenyl-1,2-propanediol 

Relevant articles and documents

Facile one-pot transformation of carboxylic acid chlorides into 2-substituted allyl alcohols

The reaction of carboxylic acid chlorides (1) with chloromethyl-lithium generated in situ (1:2 molar ratio) in the presence of lithium iodide leads, after hydrolysis, to the corresponding homologated 2-substituted allyl alcohols (2).

Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates

The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).

Asymmetric Desymmetrization via Metal-Free C?F Bond Activation: Synthesis of 3,5-Diaryl-5-fluoromethyloxazolidin-2-ones with Quaternary Carbon Centers

We disclose the first asymmetric activation of a non-activated aliphatic C?F bond in which a conceptually new desymmetrization of 1,3-difluorides by silicon-induced selective C?F bond scission is a key step. The combination of a cinchona alkaloid based ch

CiF bond activation of unactivated aliphatic fluorides: Synthesis of fluoromethyl-3,5-diaryl-2-oxazolidinones by desymmetrization of 2-aryl-1,3-difluoropropan-2-ols

How to lose fluorine: Biologically relevant oxazolidinones 1 were synthesized through the desymmetrization of unactivated aliphatic difluorides by Si-induced catalytic CiF bond-cleavage using BSA/CsF (BSA=bis(trimethylsilyl) acetamide). The direct transfo

An improved method for the addition reactions of 1,3-dichloroacetone with combined organolithium-cerium trichloride reagents

Alkyl-, phenyl- and alkynyllithium reagents in combination with anhydrous cerium(III) chloride underwent addition reactions with 1,3-dichloroacetone in a very efficient manner. The addition products are versatile precursors for 2-substituted epichlorohydrins and glycidols. Fluconazole, a potent antifungal agent, was thus synthesized in 67% yield by addition of 1,3-dichloroacetone to 2,4-difluorophenyllithium in the presence of cerium(III) chloride, followed by substitution of the chlorine atoms with 1,2,4-triazole.

Reactions of 2-substituted epichlorohydrins

2-Substituted epichlorohydrins have been synthesized by starting with 1,2-dichloro acetone and various alkyl and aryl halides via dichlorohydrins followed by cyclization. The reactive 2-substituted epichlorohydrins were subjected to nucleophilic attacking of azide and cyanide ions to afford corresponding β-azido alcohols and α,β-unsaturated nitriles.

Facile One-pot Transformation of Carboxylic Acid Chlorides into 2-Substituted Allyl Alcohols or Epichlorohydrins

Treatment of carboxylic acid chlorides (1) with chloromethyl-lithium generated in-situ (1:2 molar ratio) in the presence of lithium iodide leads, after hydrolysis, to the corresponding homologated 2-substituted allyl alcohols (2).When the same reaction is carried out using iodide-free butyl-lithium, instead of methyl-lithium-lithium iodide, the corresponding 2-substituted epichlorohydrines (5) are formed.

Synthesis and Alkali-Metal Complexing Abilities of Crown Ether Tertiary Alcohols

Twenty-three crown ethers with a hydroxyl and an alkyl or aryl group linked directly to the central carbon of a three-carbon bridge were synthesized in one-step reactions of glycol and bisphenol dianions with substituted 2-(chloromethyl)oxiranes.Crown ether tertiary alcohols with methyl, n-decyl, n-tetradecyl, phenyl, and p-(n-decyl)phenyl substituents and four ring sizes are prepared.The effect of substituent on Na+ and K+ complexation is assessed by the picrate extraction method for closely related tertiary crown ether alcohols with 16-crown-5 and 15-crown-5-rings.

Synthesis and pharmacological study of aryloxypropanolamines substituted on carbon 2

In a series of aryloxypropanolamines, substitution on carbon 2 by alkyl, aryl or aralkyl groups lowers the β-blocking activity. This effect increases with the size of the substituent.