(Bromomethyl)cyclopropane Chemical Properties

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.)

Flash point:

107 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

Specific Gravity

1.392

color 

Clear colorless to slightly colored

Water Solubility 

Not miscible in water.

BRN 

605296

Stability:

Stable. Flammable. Incompatible with strong bases, strong oxidizing agents.

InChIKey

AEILLAXRDHDKDY-UHFFFAOYSA-N

CAS DataBase Reference

7051-34-5(CAS DataBase Reference)

NIST Chemistry Reference

Cyclopropane, (bromomethyl)-(7051-34-5)

Safety Information

Hazard Codes 

Xi,F,Xn

Risk Statements 

10-36/37/38-22

Safety Statements 

23-24/25-37/39-26-16-36/37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

3

PackingGroup 

III

HS Code 

29035990

MSDS

• Language:English Provider:1-(Bromomethyl)cyclopropane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(Bromomethyl)cyclopropane Usage And Synthesis

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.

Chemical Properties

Colorless to yellow liquid

Uses

(Bromomethyl)cyclopropane was 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.

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

(Bromomethyl)cyclopropane(7051-34-5)Related Product Information

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