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Cyclopropyl bromide

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CAS:4333-56-6
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Products Intro: Product Name:Bromocyclopropane
CAS:4333-56-6
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CAS:4333-56-6
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Cyclopropyl bromide manufacturers

  • Cyclopropyl bromide
  • Cyclopropyl bromide pictures
  • $100.00 / 1KG
  • 2023-12-26
  • CAS:4333-56-6
  • Min. Order: 1KG
  • Purity: 99%
  • Supply Ability: g-kg-tons, free sample is available
  • Cyclopropyl bromide
  • Cyclopropyl bromide pictures
  • $0.00 / 1kg
  • 2023-09-27
  • CAS:4333-56-6
  • Min. Order: 1kg
  • Purity: 99%
  • Supply Ability: 100tons
  • Cyclopropyl bromide
  •  Cyclopropyl bromide pictures
  • $200.60 / 1KG
  • 2023-03-06
  • CAS:4333-56-6
  • Min. Order: 1KG
  • Purity: 99%
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Cyclopropyl bromide Basic information
Product Name:Cyclopropyl bromide
Synonyms:bromo-cyclopropan;Cyclopropane, bromo-;CYCLOPROPYL BROMIDE;Cyclopropylbromide,99%;Bromocyclopropane,99%;Cyclopropyl bromide(CPB);1-Bromocyclopropane;Cyclopropyl Bromide / Bromocyclopropane (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;Miscellaneous Reagents;Pharmaceutical Intermediates;Cyclopropanes;Simple 3-Membered Ring Compounds;4333-56-6
Mol File:4333-56-6.mol
Cyclopropyl bromide Structure
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.)
Fp 20 °F
storage temp. 2-8°C
solubility Chloroform (Sparingly), Methanol (Slightly)
form Liquid
Specific Gravity1.510
color Clear colorless
Water Solubility immiscible
BRN 1900287
CAS DataBase Reference4333-56-6(CAS DataBase Reference)
NIST Chemistry ReferenceCyclopropyl bromide(4333-56-6)
EPA Substance Registry SystemCyclopropane, bromo- (4333-56-6)
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 Information
ProviderLanguage
Bromocyclopropane English
SigmaAldrich English
ACROS English
ALFA English
Cyclopropyl bromide Usage And Synthesis
DescriptionCyclopropyl 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 PropertiesLight yellow to clear colourless liquid, boiling point 67-69°C, refractive index (nD20) 1.4605, density (d420) 1.5120, flash point -6°C.
UsesBromocyclopropane 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.
PreparationBromocyclopropane 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.
ApplicationBromocyclopropane 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.
ReferencesScience 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.
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