4-Hexyloxyphenol

4-Hexyloxyphenol Property

Melting point:

45-47 °C (lit.)

Boiling point:

112 °C / 3mmHg

Density 

1.0010 (rough estimate)

refractive index 

1.5050 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

within almost transparency in Methanol

form 

powder to crystal

pka

10.36±0.15(Predicted)

color 

White to Light yellow to Light orange

BRN 

473079

CAS DataBase Reference

18979-55-0(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 4-(hexyloxy)- (18979-55-0)

Safety

Hazard Codes 

Xn,N,Xi

Risk Statements 

22-36/37/38-51/53

Safety Statements 

26-36-61-37/39

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

TSCA 

Yes

HazardClass 

9

HS Code 

29095000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H319Causes serious eye irritation

H335May cause respiratory irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

4-Hexyloxyphenol Chemical Properties,Usage,Production

Chemical Properties

light beige to brown crystalline solid

Uses

Intermediates of Liquid Crystals

Definition

ChEBI: 4-Hexyloxyphenol is an aromatic ether.

General Description

4-(Hexyloxy)phenol is a lead anti-melanoma agent against B16-F0 melanoma cells with minimal metabolism by rat liver P450 microsomal preparation.

Synthesis

The reaction of 1-(benzyloxy)-4-(hexyloxy)benzene (12.97 g) as raw material with 5% Pd/C (1.2 g) in 200 mL of 1:1 methanol/ethyl acetate solvent mixture was stirred under hydrogen atmosphere for 16 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) to confirm complete consumption of the raw materials. Upon completion of the reaction, the mixture was filtered through diatomaceous earth to remove the catalyst. Subsequently, the solvent in the filtrate was replaced with a 12% ethyl acetate/hexane mixture and filtered through a silica gel pad. Finally, the filtrate was concentrated to give 8.84 g of 4-(hexoxy)phenol. The product was detected by TLC with an Rf value of 0.21 (unfolding agent 10% ethyl acetate/hexane).1H NMR (CDCl3) data were as follows: δ 6.80-6.72 (m, 4H), 3.88 (t, 2H, J = 6.7Hz), 1.79-1.68 (m, 2H), 1.48-1.30 (m, 6H), 0.91-0.86 (m , 3H).

References

[1] Patent: WO2014/120995, 2014, A2. Location in patent: Page/Page column 100
[2] Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 20 - 35
[3] RSC Advances, 2015, vol. 5, # 127, p. 105066 - 105078