| Identification | More | [Name]
6-Bromo-1-hexene | [CAS]
2695-47-8 | [Synonyms]
5-HEXEN-1-YL BROMIDE
6-BROMO-1-HEXENE
6-BROMOHEX-1-ENE
BROMO(6-)-1-HEXENE
1-Bromo-5-hexene
1-Bromohex-5-ene
1-Hexene,6-bromo-
5-Hexenyl bromide
6-bromo-1-hexen
6-Bromohexene
6-BROMO-1-HEXENE, STAB.
Bromo-1-hexene,6-
6-Bromo-1-hexene,tech.85%
6-Bromohex-1-ene 96%
6-Bromo-1-hexene, GC 98%
6-BROMO-1-HEXENE: TECH., 85%
6-BROMO-1-HEXENE 95+% GC | [EINECS(EC#)]
220-267-9 | [Molecular Formula]
C6H11Br | [MDL Number]
MFCD00000269 | [Molecular Weight]
163.06 | [MOL File]
2695-47-8.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless liquid | [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.)
| [Fp ]
126 °F
| [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid | [color ]
Clear slightly yellow | [Specific Gravity]
1.217 | [Stability:]
Stable. Incompatible with strong oxidizing agents, strong bases. Flammable. | [Water Solubility ]
Not miscible in water. | [BRN ]
506203 | [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]
2695-47-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,F | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking . | [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 |
| Hazard Information | Back Directory | [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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