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MilliporeSigma

441171

(Bromomethyl)cyclobutane

97%

Synonym(s):

Cyclobutylmethyl bromide

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$134.00

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$409.00

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About This Item

Linear Formula:
C4H7CH2Br
CAS Number:
17247-58-4
Molecular Weight:
149.03
NACRES:
NA.22
PubChem Substance ID:
24867336
UNSPSC Code:
12352100
MDL number:
MFCD00040960
Assay:
97%
Form:
liquid

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InChI

1S/C5H9Br/c6-4-5-2-1-3-5/h5H,1-4H2

SMILES string

BrCC1CCC1

InChI key

FLHFTXCMKFVKRP-UHFFFAOYSA-N

assay

97%

form

liquid

refractive index

n20/D 1.48 (lit.)

bp

123-124 °C (lit.)

density

1.326 g/mL at 25 °C (lit.)

functional group

bromo

Quality Level

100

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This Item
242403144711C106003
(Bromomethyl)cyclobutane 97%

Sigma-Aldrich

441171

(Bromomethyl)cyclobutane

(Bromomethyl)cyclopropane 97%

Sigma-Aldrich

242403

(Bromomethyl)cyclopropane

2-(Bromomethyl)benzonitrile ≥97%

Sigma-Aldrich

144711

2-(Bromomethyl)benzonitrile

(Bromomethyl)cyclohexane 99%

Sigma-Aldrich

C106003

(Bromomethyl)cyclohexane

assay

97%

assay

97%

assay

≥97%

assay

99%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

refractive index

n20/D 1.48 (lit.)

refractive index

n20/D 1.457 (lit.)

refractive index

-

refractive index

n20/D 1.492 (lit.)

form

liquid

form

liquid

form

solid

form

liquid

density

1.326 g/mL at 25 °C (lit.)

density

1.392 g/mL at 25 °C (lit.)

density

-

density

1.269 g/mL at 25 °C (lit.)

bp

123-124 °C (lit.)

bp

105-107 °C (lit.)

bp

-

bp

76-77 °C/26 mmHg (lit.)

General description

(Bromomethyl)cyclobutane (bromomethyl-cyclobutane) is an aryl fluorinated building block. Its reaction with various hydroxychromen-4-one derivatives in the presence of anhydrous K2CO3/dry acetone and Bu4N+I- (PTC) has been investigated.[1]

Application

(Bromomethyl)cyclobutane may be used in the synthesis of racemic 3-cyclobutylalanine[2] and 17-(cyclobutylmethyl)morphinan-3-ol (butorphan).[3]

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

105.8 °F - closed cup

flash_point_c

41 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL6314
STBG9302
STBD7854V
STBD0549V
S43184V

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Cyclopropylmethyl-and cyclobutylmethyllithium by an arene-catalyzed lithiation. Stability and reactivity.
Pe?afiel I, et al.
Tetrahedron, 66(16), 2928-2935 (2010)
Ao Zhang et al.
Journal of medicinal chemistry, 47(1), 165-174 (2003-12-30)
A series of 10-ketomorphinan analogues were synthesized, and their binding affinity at all three opioid receptors was investigated. In most cases, high affinity at micro and kappa receptors, and lower affinity at delta receptor was observed, resulting in good selectivity
Michael Decker et al.
Journal of medicinal chemistry, 53(1), 402-418 (2009-11-26)
The phenolic group of the potent mu and kappa opioid morphinan agonist/antagonists cyclorphan and butorphan was replaced by phenylamino and benzylamino groups including compounds with para-substituents in the benzene ring. These compounds are highly potent mu and kappa ligands, e.g.
Markus Nett et al.
Journal of medicinal chemistry, 52(19), 6163-6167 (2009-09-15)
The natural proteasome inhibitor salinosporamide A from the marine bacterium Salinispora tropica is a promising drug candidate for the treatment of multiple myeloma and mantle cell lymphoma. Using a comprehensive approach that combined chemical synthesis with metabolic engineering, we generated
Photochemical synthesis and antimicrobial studies of new chromen-4-one based vinyl ethers.
Yusuf M, et al.
Arabian Journal of Chemistry (2013)
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