4333-56-6 Usage
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: 9783131484819D. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 4333-56-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,3 and 3 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4333-56:
(6*4)+(5*3)+(4*3)+(3*3)+(2*5)+(1*6)=76
76 % 10 = 6
So 4333-56-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H5Br/c4-3-1-2-3/h3H,1-2H2
4333-56-6Relevant articles and documents
Novel method for synthesizing cyclopropyl bromide
-
Paragraph 0003; 0010-0012, (2021/10/11)
The invention discloses a novel method for synthesizing cyclopropyl bromide. The method comprises the following steps: by taking bromoethylene as a raw material, carrying out denitrification cyclization reaction on the bromoethylene and diazomethane in a solvent under the action of a Pd(oAc)2 catalyst to obtain a cyclopropyl bromide crude product, and carrying out acid pickling, filtering layering and normal-pressure rectification to obtain a pure product with the content of 99% or more and the yield of 80% or more. The synthesis method has the advantages of mild conditions, few byproducts, high yield and environmental friendliness, and is more suitable for industrial amplification.
Synthetic method and process of halogenated cyclopropane
-
Paragraph 0014, (2021/03/31)
The invention discloses a synthetic method and process of halogenated cyclopropane. The synthesis method and process comprise the following two steps of: (1) reacting cyclopropylamine serving as a rawmaterial with halogenated metal salt in the presence of nitrosation reagents such as nitrous acid ester to obtain 1, 1-dihalogenated cyclopropane; and (2) carrying out metallization reaction on the 1, 1dihalogenated cyclopropane and an organic metal reagent, and hydrolyzing to obtain halogenated cyclopropane. The synthesis method and process have the advantages that toxic reagents causing environmental pollution are not used, the purity and yield of the obtained product are high, and the synthesis method and process are suitable for industrial production.
Decarboxylative Bromination of Sterically Hindered Carboxylic Acids with Hypervalent Iodine(III) Reagents
Kanazawa, Junichiro,Koyamada, Kenta,Miyamoto, Kazunori,Uchiyama, Masanobu,Watanabe, Ayumi
supporting information, p. 1328 - 1334 (2020/08/14)
Sterically hindered three-dimensional (3D) alkyl halides are promising precursors for various reactions; however, they are difficult to synthesize via conventional reactions. We present an efficient and practical method for decarboxylative bromination of sterically hindered 3D aliphatic carboxylic acids using commercially available (diacetoxyiodo)benzene and potassium bromide, one of the most stable and cheapest bromine sources in nature. The present method features a metal-free/Br2-free system, mild reaction conditions, one-pot operation under air at room temperature, wide functional group compatibility, and gram-scale synthetic capability. This highly efficient reaction cleanly converts a broad range of carboxylic acids, the most inexpensive and readily available sources of highly strained/naturally occurring/drug-related scaffolds, into the corresponding alkyl bromides in good to high yields.
