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242403

Sigma-Aldrich

(Bromomethyl)cyclopropane

97%

Synonym(s):

Cyclopropylmethyl bromide

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About This Item

Linear Formula:
C3H5CH2Br
CAS Number:
7051-34-5
Molecular Weight:
135.00
Beilstein/REAXYS Number:
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.)

SMILES string

BrCC1CC1

InChI

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

InChI key

AEILLAXRDHDKDY-UHFFFAOYSA-N

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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

signalword

Warning

hcodes

H226,H302

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

105.8 °F

flash_point_c

41 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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

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