242403
(Bromomethyl)cyclopropane
97%
Synonym(s):
Cyclopropylmethyl bromide
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About This Item
Linear Formula:
C3H5CH2Br
CAS Number:
Molecular Weight:
135.00
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
230-331-8
Beilstein/REAXYS Number:
605296
MDL number:
Product Name
(Bromomethyl)cyclopropane, 97%
InChI key
AEILLAXRDHDKDY-UHFFFAOYSA-N
InChI
1S/C4H7Br/c5-3-4-1-2-4/h4H,1-3H2
SMILES string
BrCC1CC1
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
Quality Level
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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.
General description
The coupling reaction of (bromomethyl)cyclopropane with phenylmagnesium bromide was studied.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
105.8 °F
flash_point_c
41 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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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
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.
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)
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.
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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