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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:
605296
EC Number:
230-331-8
MDL number:
MFCD00001306
UNSPSC Code:
12352100
PubChem Substance ID:
24854557
NACRES:
NA.22
Pricing and availability is not currently available.

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

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General description

The coupling reaction of (bromomethyl)cyclopropane with phenylmagnesium bromide was studied[1].

Application

(Bromomethyl)cyclopropane was used as a synthetic building block for the introduction of the cyclopropylmethyl group[2][3][4]. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents[5].

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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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3790
STBJ9474
STBJ0834
STBG7254
STBF5089V

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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.
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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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