5433-23-8

Basic information

• Product Name: 2-bromocyclohexyl 4-methylbenzenesulfonate
• CAS NO: 5433-23-8
• Molecular Formula: C₁₃H₁₇BrO₃S
• Molecular Weight: 333.2413
• Mol File: 5433-23-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 430.5°C at 760 mmHg
• Flash Point: 214.1°C
• Density: 1.47g/cm³
• Vapor Pressure: 3.25E-07mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: 2-bromocyclohexyl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromocyclohexyl 4-methylbenzenesulfonate(5433-23-8)
• EPA Substance Registry System: 2-bromocyclohexyl 4-methylbenzenesulfonate(5433-23-8)

Safety Data

• Hazardous Substances Data: 5433-23-8(Hazardous Substances Data)

Upstream product

• 592-76-7 1-Heptene 
• 10534-59-5 tetrabutylammonium acetate 
• 7182-86-7 tetrabutylammonium p-toluenesulfonate 
• 110-83-8 cyclohexene 
• 13149-97-8 Mercury(II) toluene-p-sulphonate 
• 2425-33-4 cis-2-bromocyclohexanol 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant articles and documents

BROMO- AND IODOFUNCTIONALIZATION OF OLEFINS BY MEANS OF THE MERCURY(II) SALT-HALOGEN COMBINATION

Mercury(II) salts (fluoride, chloride, bromide, formate, acetate, trifluoroacetate, propionate, benzoate, nitrate, methanesulphonate, toluene-p-sulphonate, thiocyanate, and toluene-p-sulphinate) reacted with monoolefines and bromine or iodine to give 1,2-bifunctionalized products resulting from the addition of the halogen and the mercury(II) salt anion selectively.The addition was regiospecific for styrene and for 3,3-dimethylbut-1-ene affording Markownikoff type products, respectively.In the case of hex-1-ene both regioisomers were obtained.For cyclic alkenes trans-1,2-derivatives were stereoselectively obtained.Cycloocta-1,5-diene gave the monoaddition products.Buta-1,3-diene underwent mainly 1,2-addition and allylic derivatives gave the corresponding 1,2,3-trifunctionalized compounds.A possible ionic mechanism is proposed to explain the obtained addition products.

PARTICIPATION OF SULFONATE IONS IN THE ELECTROPHILIC ADDITION OF HALOGENS TO OLEFINS

The reactions of ethylene, 1-heptene, cyclohexene, and styrene with chlorine and bromine in methylene chloride and chloroform in the presence of tetrabutylammonium p-toluenesulfonate and tetrabutylammonium methanesulfonate were investigated.In all cases the 2-halogenoalkyl esters of the sulfonic acids were obtained with comparable yields in addition to the 1,2-dihalides.The addition of chlorine and bromine to cyclohexene and also of bromine to 1-heptene in acetic acid in the presence of lithium p-nitrobenzenesulfonate leads to 2-halogenoalkyl esters of the sulfonicacids and acetic acid in addition to the 1,2-dihalides.These data indicate concurrent combination of the sulfonate anions at the concluding stage of AdE reactions.The mechanistic aspects and consequences of this effect are discussed.