6-Bromo-1-hexene Chemical Properties

Melting point:

-102.35°C (estimate)

Boiling point:

47-51 °C/16 mmHg (lit.)

Density 

1.22 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4652(lit.)

Flash point:

126 °F

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear slightly yellow

Specific Gravity

1.217

Water Solubility 

Not miscible in water.

BRN 

506203

Stability:

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

InChIKey

RIMXEJYJXDBLIE-UHFFFAOYSA-N

CAS DataBase Reference

2695-47-8(CAS DataBase Reference)

NIST Chemistry Reference

1-Hexene, 6-bromo-(2695-47-8)

EPA Substance Registry System

1-Hexene, 6-bromo- (2695-47-8)

Safety Information

Hazard Codes 

Xi,F,T

Risk Statements 

10-36/37/38-61

Safety Statements 

26-36-37/39-16-45-53

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

8

Hazard Note 

Flammable/Irritant

TSCA 

T

HazardClass 

3.2

PackingGroup 

III

HS Code 

29039990

MSDS

• Language:English Provider:6-Bromo-1-hexene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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6-Bromo-1-hexene Usage And Synthesis

Chemical Properties

colourless liquid

Uses

6-Bromo-1-hexene was used in the preparation of epoxide, 6-bromo-1,2-epoxyhexane. It was also used in a simple, direct preparation of 4-alkenylbenzonitriles via anionic reduced forms of terephthalonitrile in liquid ammonia.

Synthesis Reference(s)

Synthesis, p. 885, 1984 DOI: 10.1055/s-1984-31010

General Description

Reaction of 6-bromo-1-hexene with Mg to form Grignard compounds has been investigated. The thermal chemistry of 6-bromo-1-hexene on Ni (100) surface has been studied under ultrahigh vacuum conditions by X-ray photoelectron spectroscopy and temperature-programmed desorption.

Synthesis

General method: To a stirred solution of 1,6-dibromohexane (1 eq.) in anhydrous tetrahydrofuran (THF, 0.1 M) was added potassium tert-butoxide (tert-BuOK, 1.15 eq.) in batches over a period of 30 min under argon protection. The reaction mixture was stirred under reflux conditions for 16 h before being cooled to room temperature and subsequently quenched with deionized water. The resulting mixture was diluted with diethyl ether and the organic and aqueous layers were separated. The aqueous layer was extracted several times with diethyl ether, all organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel fast column chromatography with petroleum ether as eluent to obtain the target product 6-bromo-1-hexene. 2.3.1 Synthesis of 6-bromo-1-hexene 6-Bromo-1-hexene was synthesized from 1,6-dibromohexane (8.1 g, 33.6 mmol) according to the general method described above. Yield: 4.3 g (79% yield) as a colorless oil. Thin layer chromatography (TLC) Rf value: 0.71 (100% hexane unfolding, potassium permanganate solution color development). 1H NMR (CDCl3, 500MHz, ppm): δ5.79 (ddt, J = 17.0, 10.2, 6.7Hz, 1H), 5.02 (ddd, J = 17.1, 3.5, 1.6Hz, 1H), 4.97 (ddt, J = 10.2, 2.2, 1.2 Hz, 1H), 3.41 (t, J = 6.8 Hz , 2H), 2.13 - 2.05 (m, 2H), 1.92 - 1.83 (m, 2H), 1.54 (tt, J = 9.3, 6.6 Hz, 2H). 13C NMR (CDCl3, 126MHz, ppm): δ 138.27, 115.14, 33.87, 32.95, 32.29, 27.48.

References

[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4047 - 4057
[2] Synthetic Communications, 2001, vol. 31, # 9, p. 1367 - 1371
[3] Synthesis, 1984, # 10, p. 885
[4] Journal of the American Chemical Society, 1992, vol. 114, # 8, p. 3044 - 3051
[5] Chemistry - A European Journal, 2013, vol. 19, # 3, p. 1002 - 1012

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