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Sigma-Aldrich

Methyl 1-bromocyclohexanecarboxylate

97%

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About This Item

Linear Formula:
BrC6H10CO2CH3
CAS Number:
3196-23-4
Molecular Weight:
221.09
MDL number:
MFCD00134214
UNSPSC Code:
12352100
PubChem Substance ID:
24862285
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.493 (lit.)

bp

115-116 °C/19 mmHg (lit.)

density

1.39 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C1(Br)CCCCC1

InChI

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

InChI key

RNWRVPVPLQMTAP-UHFFFAOYSA-N

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.

Application

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.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

222.8 °F - closed cup

Flash Point(C)

106 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Improved preparation of methyl 3-oxo-1-cyclohexene-1-carboxylate and its use in the synthesis of substituted 1, 5-cyclodecadienes.
Lange GL and Otulakowski JA.
The Journal of Organic Chemistry, 47(26), 5093-5096 (1982)
Kirillov NF, et al.
Russ. J. Org. Chem., 40(7), 953-956 (2004)
Reformatsky Synthesis of 16-Aryl-15-oxadispiro [5.1. 5.3] hexadecane-7, 14-diones.
Kirillov NF and Shchepin VV.
Russ. J. Org. Chem., 37(9), 1223-1224 (2001)
Reaction of Reformatsky reagent prepared from methyl 1-bromocyclohexanecarboxylate and zinc with substituted chalcones.
Kirillov NF and Gavrilov AG.
Russ. J. Org. Chem., 44(7), 963-964 (2008)
Reaction of methyl 1-bromocyclohexanecarboxylate with zinc and 3-aryl-2-cyanopropenoic acids amides.
Kirillov NF, et al.
Russ. J. Gen. Chem., 82(7), 1228-1232 (2012)
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