3D Mol Similar

6-Bromo-1-hexene

: Iupac Name：6-bromohex-1-ene; CAS No.: 2695-47-8; Molecular Weight：163.058; Modify Date.: 2022-11-29 09:50; Introduction:
colourless liquid
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1. Names and Identifiers

: 1.1 Name; 6-Bromo-1-hexene; 1.2 Synonyms; 1-Bromo-5-hexene 1-Bromohex-5-ene 1-Hexene, 6-bromo- 1-Hexene,6-bromo- 5-HEXEN-1-YL BROMIDE 5-Hexenyl bromide 6-BROMOHEX-1-ENE 6-Bromohexene BROMO(6-)-1-HEXENE; View all

1.3 CAS No.: 2695-47-8

1.4 CID: 75906

1.5 EINECS(EC#): 220-267-9

1.6 Molecular Formula: C6H11Br (isomer)

1.7 Inchi: InChI=1S/C6H11Br/c1-2-3-4-5-6-7/h2H,1,3-6H2

1.8 InChIkey: RIMXEJYJXDBLIE-UHFFFAOYSA-N

1.9 Canonical Smiles: C=CCCCCBr

1.10 Isomers Smiles: C=CCCCCBr

2. Properties

2.1 Density: 1.217

2.1 Melting point: -102.35°C (estimate)

2.1 Boiling point: 47-51℃ (16 mmHg)

2.1 Refractive index: n20/D 1.4652(lit.)

2.1 Flash Point: 52℃

2.1 Precise Quality: 162.00400

2.1 PSA: 0.00000

2.1 logP: 2.73760

2.1 Appearance: Clear slightly yellow Liquid

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: colourless liquid

2.4 Color/Form: Clear slightly yellow

2.5 Water Solubility: Not miscible in water.

2.6 Stability: Stable. Incompatible with strong oxidizing agents, strong bases. Flammable.

2.7 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 Methods of Manufacturing: General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product. 2.3.1 6-Bromo-1-hexene 3 The title compound was synthesized from 1, 6-dibromohexane (8.1 g, 33.6 mmol) following the above protocol. Yield: 4.3 g (79percent), colorless oil. Rf: 0.71 (n-hexane 100percent, visualized with KMnO4 solution). 1H NMR (CDCl3, 500 MHz, ppm): δ 5.79 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 (ddd, J = 17.1, 3.5, 1.6 Hz, 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, 126 MHz, ppm): δ 138.27, 115.14, 33.87, 32.95, 32.29, 27.48.Reference Example 4; View all

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R10;R36/37/38

4.1 Safety Statements: S16;S26;S37/39

4.1 Packing Group: III

4.1 Hazard Class: 3.2

4.1 Hazard Declaration: H226-H315-H319-H335-H360D

4.1 RIDADR: UN 1993

4.1 Caution Statement: P201-P261-P305 + P351 + P338-P308 + P313

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H226 Flammable liquid and vapour H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

7. Synthesis Route

2695-47-8Total: 2 Synthesis Route

592-42-7 28 Suppliers

4558-27-4 2 Suppliers

2695-47-8 141 Suppliers

Literatures:
Golmow Zhurnal Obshchei Khimii, 1952 , vol. 22, p. 2132,2135;engl.Ausg.S.2187
Yield: null

592-42-7 28 Suppliers

10035-10-6 107 Suppliers

4558-27-4 2 Suppliers

2695-47-8 141 Suppliers

Literatures:
Golmow Zhurnal Obshchei Khimii, 1952 , vol. 22, p. 2132,2135;engl.Ausg.S.2187
Yield: null

8. Other Information

8.0 Usage: 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.

8.1 Storage Conditions: General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product. 2.3.1 6-Bromo-1-hexene 3 The title compound was synthesized from 1, 6-dibromohexane (8.1 g, 33.6 mmol) following the above protocol. Yield: 4.3 g (79percent), colorless oil. Rf: 0.71 (n-hexane 100percent, visualized with KMnO4 solution). 1H NMR (CDCl3, 500 MHz, ppm): δ 5.79 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 (ddd, J = 17.1, 3.5, 1.6 Hz, 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, 126 MHz, ppm): δ 138.27, 115.14, 33.87, 32.95, 32.29, 27.48.Reference Example 4; View all

8.2 Manufacturing Info: 1-Hexene, 6-bromo-: ACTIVE

9. Computational chemical data

Molecular Weight: 163.058g/mol
Molecular Formula: C₆H₁₁Br
Compound Is Canonicalized: True
XLogP3-AA: 2.8
Exact Mass: 162.00441
Monoisotopic Mass: 162.00441
Complexity: 41.4
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 0
Heavy Atom Count: 7
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgAAAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGABAAAABSACAAAAAAAAAAACAACBCAAAAAAAgAAAIAAAAACgAAAIAAQAAAAAAgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

What is the background and overview of 6-Bromo-1-hexene? Jan 27 2021
6-Bromo-1-hexene is an organic intermediate that can be prepared from 1-hexene-6-ol through bromination reaction. It has been reported in the literature that it can be used to prepare N-methyl-5-hexen..

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