Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

242403

Sigma-Aldrich

(Bromomethyl)cyclopropane

97%

Synonym(s):

Cyclopropylmethyl bromide

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C3H5CH2Br
CAS Number:
7051-34-5
Molecular Weight:
135.00
Beilstein:
605296
EC Number:
230-331-8
MDL number:
MFCD00001306
UNSPSC Code:
12352100
PubChem Substance ID:
24854557
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.457 (lit.)

bp

105-107 °C (lit.)

density

1.392 g/mL at 25 °C (lit.)

functional group

bromo

SMILES string

BrCC1CC1

InChI

1S/C4H7Br/c5-3-4-1-2-4/h4H,1-3H2

InChI key

AEILLAXRDHDKDY-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

The coupling reaction of (bromomethyl)cyclopropane with phenylmagnesium bromide was studied.

Application

(Bromomethyl)cyclopropane was used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.

accessory

Product No.
Description
Pricing

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

105.8 °F

Flash Point(C)

41 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Robin B Bedford et al.
Chemical communications (Cambridge, England), (33)(33), 4161-4163 (2005-08-16)
Mixtures of iron(III) chloride and appropriate amine ligands are active catalysts for the coupling of aryl Grignard reagents with primary and secondary alkyl halide substrates bearing beta-hydrogens, under mild and simple reaction conditions.
Subramaniam Ananthan et al.
Journal of medicinal chemistry, 47(6), 1400-1412 (2004-03-05)
A series of pyridomorphinans derived from naloxone, oxymorphone, and hydromorphone (7a-k) were synthesized and evaluated for binding affinity at the opioid delta, micro, and kappa receptors in brain membranes using radioligand binding assays and for functional activity in vitro using
Yong-Jin Wu et al.
Bioorganic & medicinal chemistry letters, 14(8), 1991-1995 (2004-03-31)
(S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide ((S)-2) was identified as a potent and efficacious KCNQ2 opener. This compound demonstrated significant activity in reducing neuronal hyperexcitability in rat hippocampal slices, and the inhibition mediated by (S)-2 was reversed by the KCNQ blocker linopirdine.
Iron-catalyzed cross-coupling of alkyl halides with alkenyl grignard reagents.
Amandine Guérinot et al.
Angewandte Chemie (International ed. in English), 46(34), 6521-6524 (2007-07-28)
Ning Xi et al.
Bioorganic & medicinal chemistry letters, 14(2), 377-381 (2003-12-31)
A novel series of piperazines appended to a succinamide backbone were synthesized and found to have a high affinity for the melanocortin-4 receptor (IC(50)s ranging from <0.1 to 200 nM). Both agonists and antagonists of MC4R were prepared by modifying

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service