Cyclopropyl bromide
- Product Name
- Cyclopropyl bromide
- CAS No.
- 4333-56-6
- Chemical Name
- Cyclopropyl bromide
- Synonyms
- BROMOCYCLOPROPANE;Cyclopropyl;BromocycL;NSC 89692;bromo-cyclopropan;1-Bromocyclopropane;CYCLOPROPYL BROMIDE;Cyclopropyl bromine;Cyclopropane, bromo-;Bromocyclopropane>
- CBNumber
- CB8421267
- Molecular Formula
- C3H5Br
- Formula Weight
- 120.98
- MOL File
- 4333-56-6.mol
Cyclopropyl bromide Property
- 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
- InChI
- InChI=1S/C3H5Br/c4-3-1-2-3/h3H,1-2H2
- InChIKey
- LKXYJYDRLBPHRS-UHFFFAOYSA-N
- SMILES
- C1(Br)CC1
- 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
- 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
- F
- 8-19
- Hazard Note
- Irritant
- TSCA
- T
- HazardClass
- 3
- PackingGroup
- II
- HS Code
- 29035990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H225Highly Flammable liquid and vapour
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233Keep container tightly closed.
P240Ground/bond container and receiving equipment.
P241Use explosion-proof electrical/ventilating/lighting/…/equipment.
P242Use only non-sparking tools.
P243Take precautionary measures against static discharge.
N-Bromosuccinimide Price
- Product number
- C117307
- Product name
- Bromocyclopropane
- Purity
- 99%
- Packaging
- 5g
- Price
- $82.4
- Updated
- 2025/07/31
- Product number
- C117307
- Product name
- Bromocyclopropane
- Purity
- 99%
- Packaging
- 25g
- Price
- $175
- Updated
- 2025/07/31
- Product number
- C1067
- Product name
- Bromocyclopropane
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $50
- Updated
- 2025/07/31
- Product number
- C1067
- Product name
- Bromocyclopropane
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $145
- Updated
- 2025/07/31
- Product number
- C1067
- Product name
- Bromocyclopropane
- Purity
- >98.0%(GC)
- Packaging
- 250g
- Price
- $849
- Updated
- 2025/07/31
Cyclopropyl bromide Chemical Properties,Usage,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.
Synthesis
1759-53-1
4333-56-6
(1) 179 g of 1,3-bromochloropropane was added to a three-necked flask, 29 g of potassium cyanide and 50 ml of water were added and heated and stirred until completely dissolved. Subsequently, 70 ml of ethanol solution was added and the mixture was stirred and refluxed for 2 hours. After completion of the reaction, it was cooled to room temperature and diluted with 300 ml of water to separate the oil and aqueous phases. The aqueous phase was extracted with 40 ml of chloroform, the organic phases were combined and dried with anhydrous calcium chloride. 316.9 g of hydrogen chloride was obtained. Chlorobutanenitrile 241.6 g was prepared by adding 100 ml of sodium hydroxide solution and stirring the reaction for 2 hours. Then 200 ml of water was added, cooled to about 10°C, 44 ml of concentrated sulfuric acid was added to acidify the reaction mixture, extracted with petroleum ether as an extractant, the organic phases were combined and dried with anhydrous sodium sulfate to obtain 330.1 g of cyclopropionic acid. (2) 324.8 g of cyclopropionic acid was added dropwise to a reaction flask with 48 g of mercuric oxide, 160 ml of a mixture of 1,1,2,2-tetrachloroethane and 64.4 g of liquid bromine, and stirred for 2 hours. After completion of the reaction, the mixture was cooled to 5°C, washed with tetrachloroethane and then dried with calcium chloride to give 419.15 g of bromocyclopropane.
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
Raw materials
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View Lastest Price from Cyclopropyl bromide manufacturers
- Product
- Bromocyclopropane 4333-56-6
- Price
- US $860.00/Kg
- Min. Order
- 0.100Kg
- Purity
- 99 %
- Supply Ability
- 5000 Kg
- Release date
- 2025-09-12
- Product
- Cyclopropyl bromide 4333-56-6
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-22
- Product
- Cyclopropyl bromide 4333-56-6
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100tons
- Release date
- 2023-09-27