3141-41-1

Basic information

• Product Name: α-Methylbenzylidene dichloride
• Synonyms: 1,1-Dichloro-1-phenylethane;α-Methylbenzylidene dichloride
• CAS NO: 3141-41-1
• Molecular Formula: C₈H₈Cl₂
• Molecular Weight: 175.06
• Mol File: 3141-41-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: α-Methylbenzylidene dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: α-Methylbenzylidene dichloride(3141-41-1)
• EPA Substance Registry System: α-Methylbenzylidene dichloride(3141-41-1)

Safety Data

• Hazardous Substances Data: 3141-41-1(Hazardous Substances Data)

Usage

General Description

1,1-Dichloroethylbenzene consists of a benzene ring attached to an ethyl group, where both carbon atoms of the ethyl group are substituted with chlorine atoms. This dichloroethylbenzene is a colorless liquid that is used in various industrial applications. It can be employed as a chemical intermediate in the synthesis of other compounds. The dichloroethyl group makes the molecule reactive, and it can participate in different chemical reactions, contributing to its versatility in organic synthesis.

Upstream product

• 536-74-3 phenylacetylene 
• 100-41-4 ethylbenzene 
• 10026-13-8 phosphorus pentachloride 
• 98-86-2 acetophenone 
• 13283-01-7 tungsten(VI) chloride 
• 7782-50-5 chlorine 
• 2492-30-0 acetophenone semicarbazone 
• 512-22-1 2,4,6-trimethyl-2,4,6-triphenyl-[1,3,5]trithiane 

Downstream Products

• 4160-92-3 3-methyl-3-phenylpentanedioic acid 
• 18905-76-5 2-acetyl-3-phenylbut-2-enoic acid ethyl ester 
• 28025-83-4 bis(diethoxythiophosphorylthio)methyl(phenyl)methane 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 

Relevant articles and documents

A crystallographic and spectroscopic study on the reactions of WCl 6 with carbonyl compounds

WCl6, 1, reacted with two equivalents of HC(O)NR2 (R = Me, Et) in CH2Cl2 to afford the W(vi) oxo-derivatives WOCl4(OCHNR2) (R = Me, 2a; R = Et, 2b) as main products. The hexachlorotungstate(v) salts [{OC-N(Me)CH2CH2CH 2}2(μ-H)][WCl6], 3, and [PhNHC(Me)N(Ph)C(O) Me][WCl6], 4, were isolated in moderate yields from the 1:2 molar reactions of 1 with N-methyl-2-pyrrolidone (in CH2Cl2) and acetanilide (in CDCl3), respectively. The additions of two equivalents of ketones/aldehydes to 1/CH2Cl2 yielded the complexes WOCl4[OC(R)(R′)] (R = Me, R′ = Ph, 5a; R = R′ = Ph, 5b; R = R′ = Me, 5c; R = R′ = Et, 5d; R = H, R′ = 2-Me-C6H4, 5e) and equimolar amounts of C(R)(R′)Cl2. Analogously, WOCl3[κ2- {1,2-C6H4(O)(CHO)}], 5f, and 1,2-C6H 4(OH)(CHCl2) were obtained from 1 and salicylaldehyde. The 1:1 reaction of 1 with acetone in CH2Cl2 resulted in the clean formation of WOCl4 and 2,2-dichloropropane. Compounds 5a,b,f were isolated as crystalline solids, whereas 5c,d,e could be detected by solution NMR only. The interaction of 1/CH2Cl2 with isatin, in a 1:1 molar ratio, revealed to be a new, convenient route for the synthesis of 3,3-dichloro-2,3-dihydro-1H-indol-2-one, 6. The 1:1 reactions of 1 with R′OCH(R)CO2Me (R = H, R′ = Me; R = Me, R′ = H) in a chlorinated solvent afforded the tungsten(v) adducts WCl 4[κ2-OCH(R)CO2Me] (R = H, 7a; R = Me, 7b). 1/CH2Cl2 reacted sluggishly with equimolar quantities of trans-(CO2Et)CHCH(CO2Et) and CH2(CO 2Me)2 to give, respectively, the W(iv) derivatives WCl4[κ2-CH2(CO2Me) 2], 8a, and [WCl4-κ2-{trans-(CO 2Et)CHCH (CO2Et)}]n, 8b, in about 70% yields. The molecular structures of 2a, 3, 4, 5a, 5f, 7a and 7b were ascertained by X-ray diffraction studies.

Method for chlorinating ketones

In a process for chlorinating ketones which, apart from the carbonyl group, are inert in respect of triarylphosphine dichlorides, except for cyclopropyl methyl ketone, in which the ketones are reacted with a chlorinating agent in the presence of triarylphosphine oxides, the amount of triarylphosphine oxide is from 0.1 to 10 mol %, based on the amount of ketone. The ketones preferably have a least one CH-acid proton in the α position to the carbonyl group.

AN EFFECTIVE CHLORINATING AGENT BENZYLTRIMETHYLAMMONIUM TETRACHLOROIODATE, BENZYLIC CHLORINATION OF ALKYLAROMATIC COMPOUNDS

The reaction of alkylaromatic compounds with benzyltrimethylammonium tetrachloroiodate in carbon tetrachloride in the presence of AIBN under reflux for several hours gave α-chloro-substituted compounds in fairly good yields.