| Identification | More | [Name]
Cyclobutyl bromide | [CAS]
4399-47-7 | [Synonyms]
BROMOCYCLOBUTANE
CYCLOBUTYL BROMIDE
Cyclobutane, bromo-
Cyclobutane,bromo-
Cyclobutylbromide,96%
Bromocyclobutane,95%
Cyclobutyl bromide, pure, 97%
Cyclobutyl halide
Cyclobutyl bromide, 97%, pure | [EINECS(EC#)]
224-530-9 | [Molecular Formula]
C4H7Br | [MDL Number]
MFCD00001317 | [Molecular Weight]
135 | [MOL File]
4399-47-7.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS LIQUID | [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. ]
0-6°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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
3
| [F ]
8 | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29038900 |
| Hazard Information | Back Directory | [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 |
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