598-09-4

Basic information

• Product Name: 2-(Chloromethyl)-2-methyloxirane
• Synonyms: e-methylchloridepropane;β-methylepichlorohydrin(MECH);2-(CHLOROMETHYL)-2-METHYLOXIRANE;BETA-METHYL EPICHLOROHYDRIN;2-methylepichlorohydrin;Methyl epichlorohydrin;1-Chloro-2,3-epoxy-2-methylpropane;3-Chloro-1,2-epoxy-2-methylpropane
• CAS NO: 598-09-4
• Molecular Formula: C₄H₇ClO
• Molecular Weight: 106.55
• EINECS: 209-916-7
• Product Categories: Industrial/Fine Chemicals;Methyl Halides;Methyl Halides;Ring Systems
• Mol File: 598-09-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 60°C (40 mmHg)
• Flash Point: 30°C(lit.)
• Appearance: /
• Density: 1.1011
• Vapor Pressure: 17.1mmHg at 25°C
• Refractive Index: 1.4320-1.4360
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-(Chloromethyl)-2-methyloxirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Chloromethyl)-2-methyloxirane(598-09-4)
• EPA Substance Registry System: 2-(Chloromethyl)-2-methyloxirane(598-09-4)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3265
• HazardClass: 8/3
• PackingGroup: II
• Hazardous Substances Data: 598-09-4(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to pale yellow liquid

Uses

2-(Chloromethyl)-2-methyloxirane is an important organic chemical raw material and intermediate, mainly used in the preparation of tris(β-methylglycerol) isocyanurate and a polyester resin.

InChI:InChI=1/C4H7ClO/c1-4(2-5)3-6-4/h2-3H2,1H3

Upstream product

• 597-32-0 1,3-dichloro-2-methyl-propan-2-ol 
• 42151-64-4 2,3-dichloro-2-methyl-propan-1-ol 
• 563-47-3 3-Chloro-2-methylpropene 
• 66466-56-6 1-bromo-3-chloro-2-methyl-2-propanol 
• 79-21-0 peracetic acid 
• 186581-53-3 diazomethane 
• 78-95-5 chloroacetone 

Downstream Products

• 597-33-1 3-chloro-2-methyl-propane-1,2-diol 
• 1449410-52-9 1,3-bis((2,4-dimethoxybenzyl)amino)-2-methylpropan-2-ol 
• 1318734-96-1 2-[(4-bromophenoxy)methyl]-2-methyloxirane 

Relevant articles and documents

Ti-rich TS-1: A highly active catalyst for epoxidation of methallyl chloride to 2-methyl epichlorohydrin

Ti-rich TS-1 showed high catalytic activity and H2O2 efficiency for epoxidation of methallyl chloride (MAC). Unexpectedly, it was much more active in tert-butyl alcohol (TBA) solvent than in methanol and acetonitrile partially because TBA increased the adsorption amount of MAC in the channel of Ti-rich TS-1, and consequently enhanced the MAC concentration around the Ti sites. By optimizing reaction conditions, the MAC conversion reached 85.4% with epoxide selectivity of 96.7%, which could be maintained by regenerating the catalyst by calcination. Addition of alkali or salt into the reaction system or impregnation of these materials on the Ti-rich TS-1 led to a drastic decrease in activity. In combination with NH3-TPD and diffuse reflectance UV-vis spectroscopy results, it was found that active Ti-OOH (η2) intermediates were formed for framework tetrahedral Ti species with moderately strong Br?nsted acidity. This indicates that an Eley-Rideal-type reaction mechanism probably dominated the MAC epoxidation over Ti-rich TS-1.

Optimization of the technological parameters of epoxidation of methallyl chloride by hydrogen peroxide over TS-1 catalyst

The influence of the technological parameters on the course of epoxidation of methallyl chloride by a 30 wt % hydrogen peroxide over the titanium silicalite TS-1 catalyst has been investigated. The effects of temperature, molar ratio of methallyl chloride to hydrogen peroxide, concentrations of methanol (solvent) and TS-1 catalyst, and reaction time were determined. The optimisation of the technological parameters of methallyl chloride epoxidation was performed by the application of a statistical experimental design method based on a rotatable uniform design. The epoxidation process was described by using the following functions: the selectivity of transformation to 2-methylepichlorohydrin in relation to methallyl chloride consumed, the selectivity of transformation to organic compounds in relation to hydrogen peroxide consumed, the conversions of methallyl chloride and hydrogen peroxide.

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides

The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.

Ti-rich TS-1: A highly active catalyst for epoxidation of methallyl chloride to 2-methyl epichlorohydrin

Ti-rich TS-1 showed high catalytic activity and H2O2 efficiency for epoxidation of methallyl chloride (MAC). Unexpectedly, it was much more active in tert-butyl alcohol (TBA) solvent than in methanol and acetonitrile partially because TBA increased the adsorption amount of MAC in the channel of Ti-rich TS-1, and consequently enhanced the MAC concentration around the Ti sites. By optimizing reaction conditions, the MAC conversion reached 85.4% with epoxide selectivity of 96.7%, which could be maintained by regenerating the catalyst by calcination. Addition of alkali or salt into the reaction system or impregnation of these materials on the Ti-rich TS-1 led to a drastic decrease in activity. In combination with NH3-TPD and diffuse reflectance UV-vis spectroscopy results, it was found that active Ti-OOH (η2) intermediates were formed for framework tetrahedral Ti species with moderately strong Br?nsted acidity. This indicates that an Eley-Rideal-type reaction mechanism probably dominated the MAC epoxidation over Ti-rich TS-1.