5-Hexen-1-ol Property

Melting point:

<-20°C

Boiling point:

78-80 °C/25 mmHg (lit.)

Density 

0.834 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.435(lit.)

FEMA 

4351 | 5-HEXENOL

Flash point:

117 °F

storage temp. 

Sealed in dry,2-8°C

solubility 

18.6g/l

form 

Liquid

pka

15.17±0.10(Predicted)

color 

Clear colorless

Specific Gravity

0.846

Odor

green

PH

7 (H2O)

Odor Type

green

Water Solubility 

Miscible with water.

JECFA Number

1623

BRN 

1236458

Stability:

Volatile

InChIKey

UIZVMOZAXAMASY-UHFFFAOYSA-N

LogP

1.50

CAS DataBase Reference

821-41-0(CAS DataBase Reference)

EPA Substance Registry System

5-Hexen-1-ol (821-41-0)

Safety

Hazard Codes 

F

Risk Statements 

10

Safety Statements 

16-24/25

RIDADR 

UN 1987 3/PG 3

WGK Germany 

1

F 

9

Hazard Note 

Flammable

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29052290

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

5-Hexen-1-ol Chemical Properties,Usage,Production

Background

Enol is an important fine chemical, such as isophytol, folyl alcohol, etc. It can be further used as a critical intermediate for synthesizing medicines, pesticides, essences, spices and the like with high economic added values. It has a large market demand. 5-Hexen-1-ol is a common organic synthesis and medical intermediate and an essential raw material for chemical engineering and medicine.

Chemical Properties

Clear, colorless liquid with a green aroma.

Uses

5-Hexen-1-ol is used in cyclization to a tetrahydropyran by phenylselenoetherification. It is also used as a building block in synthetic chemistry. Further, it is used to prepare 6-bromo-hex-1-ene by reaction with phosphorus tribromide.

Preparation

5-hexen-1-ol may be prepared from 2-(chloromethyl)tetrahydropyran according to the literature procedure for the preparation of 4-penten-1-ol (Brooks, L. A.; Snyder, H. R. Org. Synth. Coll. Vol. III 1955, 698).

Application

5-Hexen-1-ol is used as a food flavouring agent and as a raw material in organic synthesis for cyclisation to other compounds such as tetrahydropyran via phenylselenide etherification.

Aroma threshold values

Medium strength odor; recommend smelling in a 10.00% solution or less

Synthesis

6-bromo-1-hexene is used as a raw material, and tetrabutylammonium bromide is used as a catalyst. In an acetonitrile solvent, it is heated to react with potassium acetate. The mixed solution is then cooled to room temperature (18-25°C), the reaction solution is concentrated under reduced pressure, and then water is added to dissolve; methyl tert-butyl ether is added and stirred to separate the layers, the water layer is extracted once with methyl tert-butyl ether, the organic phases are combined and filtered, and the filtrate is concentrated under reduced pressure. The concentrated solution begins to hydrolyze, and 15% alkaline aqueous solution and methanol are added to the concentrated solution. The mixture is stirred at room temperature to dissolve each other; after the hydrolysis is completed, the methanol is concentrated under reduced pressure. After concentration to dryness, the system begins to separate into layers, with an upper organic phase and a lower aqueous phase. The aqueous phase is extracted twice with dichloromethane, and the combined organic phases are concentrated under reduced pressure to obtain 5-Hexen-1-ol.