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.)

Flash point:

158 °F

storage temp. 

Inert atmosphere,2-8°C

form 

Liquid

pka

15.05±0.10(Predicted)

Specific Gravity

0.880

color 

Colorless to pale yellow

Water Solubility 

Slightly miscible with water.

BRN 

1739774

InChI

InChI=1S/C6H10O/c1-2-3-4-5-6-7/h1,7H,3-6H2

InChIKey

GOQJMMHTSOQIEI-UHFFFAOYSA-N

SMILES

C(O)CCCC#C

CAS DataBase Reference

928-90-5(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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-HEXYN-1-OL Usage And Synthesis

Chemical Properties

Clear pale yellow liquid

Uses

5-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

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

5-HEXYN-1-OL(928-90-5)Related Product Information

• alfaprostol
• 5,7-DODECADIYNE-1,12-DIOL
• METHYL 5-HEXYNOATE
• 5-HEXYN-1-OL
• 5,8,11-EICOSATRIYNOIC ACID
• 5,7-OCTADECADIYNOIC ACID
• 5-HEXYNOIC ACID
• 5,7-EICOSADIYNOIC ACID
• 2-HEXANOL
• 2-Aminocyclohexanol
• 2,5-DIMETHYLCYCLOHEXANOL
• 3-HEXANETHIOL
• 5-METHYL-1-HEXANOL
• (1R)-(-)-Menthyl acetate
• 4-HEXYN-3-OL
• 2,4-DIMETHYLCYCLOHEXANOL
• 1,4-Dimethylcyclohexanol
• 5-HEXYN-3-OL,5-HEXYN-3-OL, 98+%,Ethyl propargyl carbinol~1-Hexyn-4-ol,1-Hexyn-4-ol