Cyclobutyl bromide Chemical Properties

Boiling point:

108 °C(lit.)

Density 

1.434 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.479(lit.)

Flash point:

72 °F

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless

Water Solubility 

Insoluble

Sensitive 

Light Sensitive

BRN 

1900415

InChI

InChI=1S/C4H7Br/c5-4-2-1-3-4/h4H,1-3H2

InChIKey

KXVUSQIDCZRUKF-UHFFFAOYSA-N

SMILES

C1(Br)CCC1

CAS DataBase Reference

4399-47-7(CAS DataBase Reference)

NIST Chemistry Reference

Cyclobutyl bromide(4399-47-7)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

10-36/37/38-20/21/22

Safety Statements 

26-36-36/37/39-16

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

F 

8

HazardClass 

3

PackingGroup 

II

HS Code 

29038900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Cyclobutyl bromide Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Cyclobutyl bromide is a cyclopentyl compound that has an hydroxyl group. It is a potent inhibitor of the CB2 receptor, which is primarily expressed on cells of the immune system. Cyclobutyl bromide has been shown to inhibit the uptake of uv light and also has anti-inflammatory properties. Studies have confirmed that this drug inhibits the production of cytokines and chemokines in chronic bronchitis patients, as well as other inflammatory diseases such as rheumatoid arthritis.

Synthesis

The general procedure for the synthesis of cyclobutyl bromide and bromomethyl cyclopropane using hydroxymethyl cyclopropane as a starting material was as follows: first, a stirrer and thermometer were assembled on a 30 mL three-necked flask. 0.36 g (5.0 mmol) of hydroxymethylcyclopropane and 5 mL of chloroform were added to the flask, and the mixture was subsequently cooled to 10 °C with stirring. Then, 2.77 g (6.5 mmol) of a 19% hydrogen bromide/1,4-dioxane solution was slowly added dropwise. After the dropwise addition, the reaction mixture was heated to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction mixture was analyzed by gas chromatography (GC) to afford cyclobutyl bromide and bromomethyl cyclopropane in 74% overall yield. In addition, the reaction produced bromocyclobutane (9% yield) and 4-bromo-1-butene (2% yield) as isomers.

References

[1] Patent: JP2017/14124, 2017, A. Location in patent: Paragraph 0033
[2] European Journal of Medicinal Chemistry, 1980, vol. 15, # 6, p. 571 - 573
[3] Patent: JP5979791, 2016, B2. Location in patent: Paragraph 0036-0038; 0042-0052

Cyclobutyl bromide(4399-47-7)Related Product Information

• ISOBUTANE
• Potassium bromide
• tert-Butyl methyl ether
• Sodium bromate
• Benzyl bromide
• Bromocyclopentane
• Tetrabutylammonium bromide
• Sodium bromide
• Hydrogen bromide
• Ethidium bromide
• Rocuronium bromide
• Cyclopropane
• butyl rubber
• 1-Bromobutane
• Allyl bromide
• n-Butane
• 1,2,5,6,9,10-Hexabromocyclododecane
• Phosphorus tribromide