(Bromomethyl)cyclopropane
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(Bromomethyl)cyclopropane
structure -
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CAS No:
7051-34-5
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Formula:
C4H7Br
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Chemical Name:
(Bromomethyl)cyclopropane
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Synonyms:
Cyclopropane,(bromomethyl)-;(Bromomethyl)cyclopropane;Cyclopropylmethyl bromide;Cyclopropanemethyl bromide;Cyclopropylcarbinyl bromide;1-(Bromomethyl)cyclopropane;(Bromo)(cyclopropyl)methane
- Categories:
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CAS No:
Characteristics
0
1.7
Clear colorless to slightly colored Liquid
1.433 g/cm3 @ Temp: 26.5 °C
87-90 °C
101.5-102.0 °C @ Press: 627 Torr
107 °F
1.475-1.479
Not miscible in water.
0-6°C
Safety Information
Ⅲ
3
UN 1993 3/PG 3
3
10-36/37/38-22
23-24/25-37/39-26-16-36/37/39
Xi,F,Xn
Irritant
Stable. Flammable. Incompatible with strong bases, strong oxidizing agents.
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
H226
|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 75 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(Bromomethyl)cyclopropane Use and Manufacturing
Into a clean, dry reactor equipped with a stirrer and under nitrogen are successively loaded 4.63 kg of DMF (5.1 eqV) and then 4.53 kg of triphenylphosphite. 2.34 kg of bromine is then introduced while maintaining the temperature at less than 12° C. The stirring speed is regulated according to the fluidity of the reaction medium. When casting ends, a very thick medium with a yellow solid suspension is obtained.10063] The set point of the jacket is then adjusted to —12° C. and then 0.96 kg of cyclopropylmethanol is introduced in such a way as not to exceed a temperature of —5° C. On completion of the addition the whole is allowed to return slowly to room temperature. The set point of the jacket is then adjusted to 64° C. for distillation, which is carried out at a pressure of 13 mbar by collecting the first 24 to 30° C. fraction at the top of the colunm, then the second 30 to 40° C. fraction (partial reflux). Two fractions, Fl (1.38 kg) and F2 (293 g), are collected. The two fractions, after washing with carbonated water and then drying by means of CaC12, lead to a final product 2a (mass 1.316 kg) having a GC relative purity of 98.7percent with a yield of 73percent.General procedure: Tetramethyl haloenamines 2a, 3 or 4 (1.1 equiv) were added at 0 °C to a solution of cyclopropyl carbinol in dry dichloromethane, then left at room temperature for 30 min. The cyclopropyl halides were quickly distilled under vacuum (bath temperature 60 °C) to avoid the formation of cyclobutyl and homoallylic halides. The halides were identical to authentic samples.A stirrer and a thermometer were attached to a 30 mL three-necked flask, and 0.36 g (5.0 mmol) of (hydroxymethyl) cyclopropane and 5 mL of chloroform were added, followed by cooling to 10 ° C. with stirring. Next, 2.77 g (6.5 mmol) of 19percent hydrogen bromide / 1, 4-dioxane solution was added dropwise, and then the reaction solution was heated to room temperature and stirring was continued for 2 hours. GC analysis was carried out on the obtained reaction solution, whereby the target compound (bromomethyl) cyclopropane was obtained in a yield of 74percent. In this reaction, bromocyclobutane as an isomer was produced in a yield of 9percent, and 4-bromo-1-butene was produced in a yield of 2percent, respectively.
Used as pharmaceutical intermediate
Computed Properties
Molecular Weight:135.00
XLogP3:1.7
Rotatable Bond Count:1
Exact Mass:133.97311
Monoisotopic Mass:133.97311
Heavy Atom Count:5
Complexity:30.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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