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Cyclopropyl bromide

CAS No.
4333-56-6
Chemical Name:
Cyclopropyl bromide
Synonyms
BROMOCYCLOPROPANE;Cyclopropyl;NSC 89692;BromocycL;bromo-cyclopropan;1-Bromocyclopropane;CYCLOPROPYL BROMIDE;Cyclopropyl bromine;Cyclopropane, bromo-;Bromocyclopropane>
CBNumber:
CB8421267
Molecular Formula:
C3H5Br
Molecular Weight:
120.98
MDL Number:
MFCD00001271
MOL File:
4333-56-6.mol
MSDS File:
SDS
Last updated:2023-12-25 17:47:29

Cyclopropyl bromide 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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS02
Signal word  Danger
Hazard statements  H225
Precautionary statements  P210-P233-P240-P241-P242-P243
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
NFPA 704
4
2 0

Cyclopropyl bromide price More Price(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C117307 Bromocyclopropane 99% 4333-56-6 5g $79.9 2024-03-01 Buy
Sigma-Aldrich C117307 Bromocyclopropane 99% 4333-56-6 25g $170 2024-03-01 Buy
TCI Chemical C1067 Bromocyclopropane >98.0%(GC) 4333-56-6 5g $50 2024-03-01 Buy
TCI Chemical C1067 Bromocyclopropane >98.0%(GC) 4333-56-6 25g $145 2024-03-01 Buy
Alfa Aesar A14996 Bromocyclopropane, 99% 4333-56-6 10g $60.65 2024-03-01 Buy
Product number Packaging Price Buy
C117307 5g $79.9 Buy
C117307 25g $170 Buy
C1067 5g $50 Buy
C1067 25g $145 Buy
A14996 10g $60.65 Buy

Cyclopropyl bromide Chemical Properties,Uses,Production

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.

1759-53-1
4333-56-6
Synthesis of Cyclopropyl bromide from Cyclopropanecarboxylic acid
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View Lastest Price from Cyclopropyl bromide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Cyclopropyl bromide pictures 2023-12-26 Cyclopropyl bromide
4333-56-6
US $100.00-1.00 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
Cyclopropyl bromide pictures 2023-09-27 Cyclopropyl bromide
4333-56-6
US $0.00-0.00 / kg 1kg 99% 100tons Hebei Yanxi Chemical Co., Ltd.
 Cyclopropyl bromide pictures 2023-03-06 Cyclopropyl bromide
4333-56-6
US $200.60 / KG 1KG 99% 5000kg Hebei Guanlang Biotechnology Co,.LTD
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