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Cyclopropyl bromide

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Cyclopropyl bromide Basic information

Product Name:
Cyclopropyl bromide
Synonyms:
  • bromo-cyclopropan
  • Cyclopropane, bromo-
  • CYCLOPROPYL BROMIDE
  • BROMOCYCLOPROPANE
  • Cyclopropylbromide,99%
  • Bromocyclopropane,99%
  • Cyclopropyl
  • Cyclopropyl bromide(CPB)
CAS:
4333-56-6
MF:
C3H5Br
MW:
120.98
EINECS:
224-375-7
Product Categories:
  • Pyridines
  • Alkyl
  • Building Blocks
  • Chemical Synthesis
  • Halogenated Hydrocarbons
  • Organic Building Blocks
  • Pharmaceutical Intermediates
  • Cyclopropanes
  • Simple 3-Membered Ring Compounds
  • Miscellaneous Reagents
  • 4333-56-6
Mol File:
4333-56-6.mol
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Cyclopropyl bromide Chemical Properties

Boiling point:
69 °C (lit.)
Density 
1.51 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.458(lit.)
Flash point:
20 °F
storage temp. 
2-8°C
solubility 
Chloroform (Sparingly), Methanol (Slightly)
form 
Liquid
Specific Gravity
1.510
color 
Clear colorless
Water Solubility 
immiscible
BRN 
1900287
CAS DataBase Reference
4333-56-6(CAS DataBase Reference)
NIST Chemistry Reference
Cyclopropyl bromide(4333-56-6)
EPA Substance Registry System
Cyclopropane, bromo- (4333-56-6)
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Safety Information

Hazard Codes 
F,Xi
Risk Statements 
11-36/37/38
Safety Statements 
16-26-36-37/39
RIDADR 
UN 1993 3/PG 2
WGK Germany 
3
8-19
Hazard Note 
Irritant
TSCA 
T
HazardClass 
3
PackingGroup 
II
HS Code 
29035990

MSDS

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Cyclopropyl bromide Usage And Synthesis

Description

Cyclopropyl bromide is also named as Bromocyclopropane. It is used in organic synthesis, for instance, for the formation of a Grignard Reagent, cyclopropyllithium. It is also used as an intermediate in the manufacture of pharmaceutical and agrochemical products.

Chemical Properties

Light yellow to clear colourless liquid, boiling point 67-69°C, refractive index (nD20) 1.4605, density (d420) 1.5120, flash point -6°C.

Uses

Bromocyclopropane is primarily used an intermediate in the manufacture of pharmaceutical and agrochemical products. It is also used in the production of cyclopropyl boric acid. It is used as an intermediate in organic synethesis.

Preparation

Bromocyclopropane has been prepared by the Hunsdiecker reaction by adding silver cyclopropanecarboxylate to bromine in dichlorodifluoromethane at ?29° (53% yield) or in tetrachloroethane at ?20° to ?25° (15–20% yield). Decomposition of the peroxide of cyclopropanecarboxylic acid in the presence of carbon tetrabromide gave bromocyclopropane in 43% yield. An attempt to prepare the bromide via the von Braun reaction was unsuccessful. Ten percent yields are reported for the photobromination of cyclopropane and the photochemical rearrangement of allyl bromide. Treatment of 1,1,3-tribromopropane with methyllithium prepared from methyl bromide furnishes a 60–65% yield of bromocyclopropane.

Application

Bromocyclopropane have anti-angiogenic effects that inhibits the growth of new blood vessels by interfering with the production of prostaglandins and nitric oxide, which are important for the formation of new blood vessels. Bromocyclopropane binds to cyclopropyl and hydrochloric acid, forming a hydrogen bond. It also forms a hydrogen bond with fatty acids and an a-type hydroxyl group.

References

Science of Synthesis: Houben-Weyl Methods of Molecular Transformation Vol. 7: Compounds of Group 13 and 2 (Al, Ga, In, Tl, Be…Ba), 2007, ISBN: 9783131484819
D. Seyferth, H. M. Cohen, The Stability of Cyclopropyllithium in diethyl ether and in tetrahydrofuran, Journal of Organometallic Chemistry, 1963, vol. 1, pp. 15-21
“Formal Nucleophilic Substitution of Bromocyclopropanes with Azoles”, Ryabchuk, P.; Rubina, M.; Xu, J.; Rubin, M. Org. Lett. 2012, 14, 1752.
“Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles”, Banning, J. E.; Gentillon, J.; Ryabchuk, P. G.; Prosser, A. R.; Rogers, A.; Edwards, A.; Holtzen, A.; Babkov, I.; Rubina, M.; Rubin, M. J. Org. Chem., 2013, 78, 7601.

Cyclopropyl bromide Preparation Products And Raw materials

Preparation Products

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