Methyl 1-bromocyclohexanecarboxylate

Base Information

• Chemical Name: Methyl 1-bromocyclohexanecarboxylate
• CAS No.: 3196-23-4
• Molecular Formula: C8H13BrO2
• Molecular Weight: 221.094
• European Community (EC) Number: 628-309-1
• DSSTox Substance ID: DTXSID60393248
• Nikkaji Number: J2.844.201G
• Mol file: 3196-23-4.mol

Synonyms:Methyl 1-bromocyclohexanecarboxylate;3196-23-4;methyl 1-bromocyclohexane-1-carboxylate;methyl 1-bromocyclohexanoate;SCHEMBL1604408;DTXSID60393248;RNWRVPVPLQMTAP-UHFFFAOYSA-N;methyl 1-bromocyclohexane carboxylate;MFCD00134214;AKOS015913649;DS-6297;Methyl 1-bromocyclohexanecarboxylate, 97%;CS-0150908;1-Bromocyclohexanecarboxylic acid methyl ester;1-Bromo-cyclohexanecarboxylic acid methyl ester;D81969;EN300-134099;A875755;J-018578

Chemical Property of Methyl 1-bromocyclohexanecarboxylate

Chemical Property:

• Vapor Pressure: 0.105mmHg at 25°C
• Melting Point: 115-116 °C at 19 mmHg(lit.)
• Refractive Index: n20/D 1.493(lit.)
• Boiling Point: 221.9 °C at 760 mmHg
• Flash Point: 105.6 °C
• PSA: 26.30000
• Density: 1.409 g/cm³
• LogP: 2.25720
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 220.00989
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 1-bromocyclohexanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CCCCC1)Br
• 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.

Technology Process of Methyl 1-bromocyclohexanecarboxylate

There total 15 articles about Methyl 1-bromocyclohexanecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cyclohexanorthocarboxylic acid trimethyl ester (51354-80-4) → methyl 1-bromocyclohexanecarboxylate (3196-23-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminium tert-butylate / 185 °C

2: bromine

With bromine; aluminum tri-tert-butoxide;

DOI:10.1021/ja01622a040

Reference yield:

dimethoxymethylene-cyclohexane (344259-58-1) → methyl 1-bromocyclohexanecarboxylate (3196-23-4)

Guidance literature:

With bromine;

DOI:10.1021/ja01622a040

Reference yield:

1-Acetoxy-cyclohexylcyanid (32379-37-6) → methyl 1-bromocyclohexanecarboxylate (3196-23-4)

Guidance literature:

Multi-step reaction with 6 steps

1: pyrex-glass / 500 °C

2: palladium/SrCO₃; diethyl ether; acetic acid anhydride / Hydrogenation

3: HCl; diethyl ether

5: aluminium tert-butylate / 185 °C

6: bromine

With hydrogenchloride; Pd/SrCO₃; diethyl ether; bromine; acetic anhydride; aluminum tri-tert-butoxide;

DOI:10.1021/ja01622a040

upstream raw materials:

dimethoxymethylene-cyclohexane

methanol

cyclohexanylcarbonyl chloride

bis(methylthio)methylene cyclohexane

Downstream raw materials:

methyl cyclohex-1-ene-1-carboxylate

1-(1-Hydroxy-1-methylethyl)cyclohexancarbonsaeure-methylester

methyl 1-(cyclohexylcarbonyl)cyclohexanecarboxylate

methyl 1-(cyclopentylcarbonyl)cyclohexanecarboxylate

Refernces

• 1、 Nikiforova,Baibarodskikh,Kirillov,Dmitriev,Zverev. "Reformatsky Reaction of 1-Aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones with Methyl 1-Bromocyclohexanecarboxylate". . p. 2074 - 2078. Retrieved 2021/02/09.
• 2、 Bourke, David G.,Collins, David J.. "Synthesis and some reactions of 1-(trimethoxymethyl)cyclohexene". . p. 1287 - 1291. Retrieved 2007/10/03.