3196-23-4

Basic information

• Product Name: METHYL 1-BROMOCYCLOHEXANECARBOXYLATE
• Synonyms: LABOTEST-BB LT00160081;METHYL 1-BROMOCYCLOHEXANECARBOXYLATE;METHYL 1-BROMOCYCLOHEXANECARBOXYLATE, 97 %;Methyl 1-broMocyclohexanecarboxylate 97%;1-Bromocyclohexanecarboxylic acid methyl ester
• CAS NO: 3196-23-4
• Molecular Formula: C₈H₁₃BrO₂
• Molecular Weight: 221.09
• Product Categories: C8 to C9;Carbonyl Compounds;Esters
• Mol File: 3196-23-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 115-116 °C19 mm Hg(lit.)
• Flash Point: 222 °F
• Appearance: /
• Density: 1.39 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.105mmHg at 25°C
• Refractive Index: n20/D 1.493(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 1-BROMOCYCLOHEXANECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 1-BROMOCYCLOHEXANECARBOXYLATE(3196-23-4)
• EPA Substance Registry System: METHYL 1-BROMOCYCLOHEXANECARBOXYLATE(3196-23-4)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3196-23-4(Hazardous Substances Data)

Usage

Uses

Methyl 1-bromocyclohexanecarboxylate may be used in the improved method of preparation of methyl 3-oxo-1-cyclohexene-1-carboxylate. It may be used in the Reformatsky synthesis of 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones.

General Description

Methyl 1-bromocyclohexanecarboxylate reacts with zinc and substituted chalcones to yield the corresponding spiro-3,4-dihydropyran-2-one derivatives, 3-aryl-5-aryl-2-oxaspiro[5.5]undec-3-en-1-ones. Reformatsky reaction of methyl 1-bromocyclohexanecarboxylate with 2-aryl-2-oxoacetaldehyde is reported. Methyl 1-bromocyclohexanecarboxylate reacts with zinc and amides or methylamides of 3-aryl-2-cyanopropenoic acids to yield 5-aryl-1,3-dioxo-2-azaspiro[5.5]undecane-4-carbonitriles or 5-aryl-2-methyl-1,3-dioxo-2-azaspiro[5.5]undecane-4-carbonitriles.

InChI:InChI=1/C8H13BrO2/c1-11-7(10)8(9)5-3-2-4-6-8/h2-6H2,1H3

Upstream product

• 98-89-5 Cyclohexanecarboxylic acid 
• 32379-37-6 1-Acetoxy-cyclohexylcyanid 
• 108-94-1 cyclohexanone 
• 51354-80-4 cyclohexanorthocarboxylic acid trimethyl ester 
• 67-56-1 methanol 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 344259-58-1 dimethoxymethylene-cyclohexane 
• 1855-63-6 cyclohex-1-enecarbonitrile 
• 766-05-2 cyclohexane carbonitrile 
• 94052-40-1 methyl cyclohexanecarboximidate hydrochloride 
• 90675-94-8 α-bromocyclohexanecarboxaldehyde dimethylacetal 
• 55106-50-8 (1-Bromo-cyclohexyl)-oxo-acetonitrile 
• 40920-15-8 bis(methylthio)methylene cyclohexane 

Downstream Products

• 1012050-24-6 C₁₇H₃₃NO₃ 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 40195-48-0 methyl 1-(cyclohexylcarbonyl)cyclohexanecarboxylate 
• 911717-61-8 1-[(4-phenylpyridin-2-yl)amino]cyclohexanecarboxylic acid 

Relevant articles and documents

Reaction of methyl 1-bromocycloalkanecarboxylates with zinc and benzoin

The Reformatsky reagents derived from methyl 1-bromocyclohexane-or 1-bromocyclopentanecarboxylate and zinc add to benzoin to afford the corresponding 4-hydroxy-3,4-diphenyl-2-oxaspiro[4.5]decan-1-one and 4-hydroxy-3,4-diphenyl-2-oxaspiro[4.4]nonan-1-one.

Iridium(I)-catalyzed vinylic C-H borylation of 1-cycloalkenecarboxylates with bis(pinacolato)diboron

Ir(i)-catalyzed C-H borylation of 1-cycloalkenecarboxylic derivatives with bis(pinacolato)diboron affords various alkenylboronates with functional groups in excellent yields. This reaction was also used in a one-pot borylation/Suzuki-Miyaura cross-coupling procedure.

Preparation of 2,2-Dihalocarboxylic Acid Methyl Esters by Oxidation-Chlorination of 2-(1-Haloalkyl)-4-methyl-1,3-dioxolanes with Trichloroisocyanuric Acid

Methyl 2,2-dichloro or 2-bromo-2-chloro carboxylates were obtained in excellent yields by oxidation-chlorination of 2-(1-haloalkyl)-4-methyl-1,3-dioxolanes with trichloroisocyanuric acid.