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5-HEXYN-1-OL

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CAS:928-90-5
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CAS:928-90-5
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Purity:98% Package:g-Kg Remarks:Light yellow liquid
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CAS:928-90-5
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  • 2019-07-06
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5-HEXYN-1-OL Basic information
Product Name:5-HEXYN-1-OL
Synonyms:1-Hydroxy-5-hexyne;5-hexyn-1-0l;6-Hydroxy-1-hexyne;Hex-5-yn-1-ol;5-HEXYN-1-OL;5-Hexyn-1-ol, 98 %;5-Hexyn-1-ol,97%;5-HEXYN-1-OL 98%
CAS:928-90-5
MF:C6H10O
MW:98.14
EINECS:
Product Categories:Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Organic Building Blocks;Terminal
Mol File:928-90-5.mol
5-HEXYN-1-OL Structure
5-HEXYN-1-OL Chemical Properties
Melting point -34°C (estimate)
Boiling point 73-75 °C/15 mmHg (lit.)
density 0.89 g/mL at 25 °C (lit.)
refractive index n20/D 1.450(lit.)
Fp 158 °F
storage temp. Inert atmosphere,2-8°C
pka15.05±0.10(Predicted)
form Liquid
color Colorless to pale yellow
Specific Gravity0.880
Water Solubility Slightly miscible with water.
BRN 1739774
InChIInChI=1S/C6H10O/c1-2-3-4-5-6-7/h1,7H,3-6H2
InChIKeyGOQJMMHTSOQIEI-UHFFFAOYSA-N
SMILESC(O)CCCC#C
CAS DataBase Reference928-90-5(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
PackingGroup III
HS Code 29052900
Storage Class10 - Combustible liquids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
5-HEXYN-1-OL Usage And Synthesis
Chemical PropertiesClear pale yellow liquid
Uses5-Hexyn-1-ol is used as starting material for the preparation of terminal alkynes and lactones containing terminal alykyne groups. It is also used in the synthesis of cinnoline-fused cyclic enediyne, llycopodium alkaloids, (+)-nankakurine A and (+)-nankakurine B and 7-benzoyloxy-3-(2-nitrophenylseleno)-1,5-cyclodecadiyne.
Synthesis
2-(CHLOROMETHYL)TETRAHYDROPYRAN

18420-41-2

5-HEXYN-1-OL

928-90-5

General procedure for the synthesis of 5-hexyn-1-ol from 2-(chloromethyl)tetrahydro-2H-pyran: A small amount of iron(III) nitrate hydrate IX was added as a catalyst to about 100 mL of liquid ammonia at -40 °C. Subsequently, sodium metal (85.3 g, 3.72 mol) was added in small portions. After confirming the formation of sodium amide by observing the change in color of the reaction mixture from dark blue to gray, the reaction was slowly added dropwise, which lasted for 5 hours, after which the reaction mixture was continued to be stirred for 3 hours. Upon completion of the reaction, the cold bath was removed and nitrogen was introduced to accelerate the evaporation of ammonia. Once the ammonia had largely evaporated, water was added slowly and dropwise at ambient temperature to quench the reaction. The reaction mixture was extracted with ether, all organic layers were combined and dried with anhydrous magnesium sulfate. The dried organic phase was filtered, the filtrate was concentrated under reduced pressure to remove the solvent, and the residue was purified by vacuum distillation to give 53.8 g (67% yield) of the target product 5-hexyn-1-ol as a colorless oil.

References[1] Tetrahedron Letters, 2005, vol. 46, # 38, p. 6449 - 6451
[2] Tetrahedron, 1986, vol. 42, # 7, p. 2017 - 2024
[3] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 3, p. 298 - 305
[4] Journal of the Chemical Society, 1952, p. 2873,2880
[5] Helvetica Chimica Acta, 1977, vol. 60, p. 1161 - 1174
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