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Cyclobutyl bromide

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CAS:4399-47-7
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Cyclobutyl bromide Basic information
Product Name:Cyclobutyl bromide
Synonyms:BROMOCYCLOBUTANE;CYCLOBUTYL BROMIDE;Cyclobutylbromide,96%;Bromocyclobutane,95%;Cyclobutyl bromide, pure, 97%;Cyclobutane, bromo-;Cyclobutane,bromo-;Cyclobutyl bromide, 97%, pure
CAS:4399-47-7
MF:C4H7Br
MW:135
EINECS:224-530-9
Product Categories:Pyridines ,Halogenated Heterocycles;Cyclobutanes & Cyclobutenes;Simple 4-Membered Ring Compounds;Cycloalkanes
Mol File:4399-47-7.mol
Cyclobutyl bromide Structure
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.)
Fp 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
InChIInChI=1S/C4H7Br/c5-4-2-1-3-4/h4H,1-3H2
InChIKeyKXVUSQIDCZRUKF-UHFFFAOYSA-N
SMILESC1(Br)CCC1
CAS DataBase Reference4399-47-7(CAS DataBase Reference)
NIST Chemistry ReferenceCyclobutyl 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
8
HazardClass 3
PackingGroup II
HS Code 29038900
Storage Class3 - Flammable liquids
Hazard ClassificationsEye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Cyclobutyl bromide Usage And Synthesis
Chemical PropertiesCLEAR COLOURLESS LIQUID
UsesCyclobutyl 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
Cyclopropyl carbinol

2516-33-8

Cyclobutyl bromide

4399-47-7

(Bromomethyl)cyclopropane

7051-34-5

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
Tag: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

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