| Identification | More | [Name]
(Bromomethyl)cyclopropane | [CAS]
7051-34-5 | [Synonyms]
1-(BROMOMETHYL)CYCLOPROPANE
(BROMOMETHYL)CYCLOPROPANE
CYCLOPROPYLMETHYL BROMIDE
Cyclopropanemethyl bromide
CYCLOPROPYLMETYL BROMIDE
CyclopropylmethylBromide96%
Cyclopropyl bromo methane
Cyclopropane, (bromomethyl)-
Cyclopropylmethylbromid
CPMBr
Cyclopropylcarbinyl bromide
Bromo(cyclopropyl)methane | [EINECS(EC#)]
230-331-8 | [Molecular Formula]
C4H7Br | [MDL Number]
MFCD00001306 | [Molecular Weight]
135 | [MOL File]
7051-34-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to yellow liquid | [Melting point ]
87-90 °C | [Boiling point ]
105-107 °C(lit.)
| [density ]
1.392 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.457(lit.)
| [Fp ]
107 °F
| [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid | [color ]
Clear colorless to slightly colored | [Specific Gravity]
1.392 | [Stability:]
Stable. Flammable. Incompatible with strong bases, strong oxidizing agents. | [Water Solubility ]
Not miscible in water. | [Detection Methods]
GC | [BRN ]
605296 | [InChIKey]
AEILLAXRDHDKDY-UHFFFAOYSA-N | [CAS DataBase Reference]
7051-34-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Cyclopropane, (bromomethyl)-(7051-34-5) |
| Questions And Answer | Back Directory | [Uses]
(Bromomethyl)cyclopropane is used in the synthesis of 1,4-dienes by iron-catalyzed cross-coupling with alkenyl Grignard reagents.
| [Description]
(Bromomethyl) cyclopropane is a cyclopropane derivative. It can be used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1, 4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.
|
| Safety Data | Back Directory | [Hazard Codes ]
Xi,F,Xn | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S16:Keep away from sources of ignition-No smoking .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29035990 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to yellow liquid | [Synthesis Reference(s)]
Tetrahedron Letters, 13, p. 2135, 1972 DOI: 10.1016/S0040-4039(01)84787-0 | [General Description]
The coupling reaction of (bromomethyl)cyclopropane with phenylmagnesium bromide was studied. | [Synthesis]
Example 1 (control experiment): 1250 mL of dimethylformamide (DMF) was added to the reaction vessel under nitrogen protection, followed by 280.8 g of triphenylphosphine. 70 g of hydroxymethylcyclopropane was added with stirring and the reaction was carried out at room temperature for 30 minutes. After cooling the reaction solution to -10°C, 158.3 g of bromine (102% of the theoretical amount) was slowly added dropwise over a period of 4 hours. Upon completion of the reaction, the reaction mixture was purified by distillation to afford bromomethylcyclopropane in 77.5% yield (based on theoretical values) with a product purity of >97%, which contained 0.6% open-chain haloalkanes. | [References]
[1] Patent: US6008420, 1999, A
[2] Patent: US2016/355452, 2016, A1. Location in patent: Paragraph 0062; 0063
[3] Synthetic Communications, 1996, vol. 26, # 6, p. 1109 - 1115
[4] Journal of the Chemical Society, Chemical Communications, 1982, # 18, p. 1037 - 1039
[5] European Journal of Medicinal Chemistry, 1980, vol. 15, # 6, p. 571 - 573 |
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