4-Trifluoromethylphenol Chemical Properties

Melting point:

45-47 °C(lit.)

Boiling point:

71.5-72 °C (8 mmHg)

Density 

1.3226 (estimate)

Flash point:

183 °F

storage temp. 

Store at <= 20°C.

Water Solubility 

Insoluble in water

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

pK1:8.675 (25°C)

form 

Crystals

color 

White to yellow-brown

BRN 

1637019

Stability:

Light Sensitive

InChI

1S/C7H5F3O/c8-7(9,10)5-1-3-6(11)4-2-5/h1-4,11H

InChIKey

BAYGVMXZJBFEMB-UHFFFAOYSA-N

SMILES

Oc1ccc(cc1)C(F)(F)F

CAS DataBase Reference

402-45-9(CAS DataBase Reference)

NIST Chemistry Reference

p-Hydroxybenzotrifluoride(402-45-9)

EPA Substance Registry System

4-(Trifluoromethyl)phenol (402-45-9)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41-36/37/38

Safety Statements 

26-39-24/25

RIDADR 

UN 2926 4.1/PG 2

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

PackingGroup 

Ⅱ

HS Code 

29081000

Storage Class

4.1B - Flammable solid hazardous materials

Hazard Classifications

Acute Tox. 3 Oral
Eye Dam. 1
Flam. Sol. 1
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:alpha,alpha,alpha-Trifluoro-p-cresol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Trifluoromethylphenol Usage And Synthesis

Preparation method

Chlorosilane and bromotrifluoromethane at-59℃form trifluoromethylsilane. Trifluoromethylsilane and benzoquinone in the presence of catalyst form 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-ketone which is reduced by zinc powder to p-trifluoromethylphenol with a yield of 71%. This method avoids the use of  hydrofluoric acid in the traditional process but  should be carried out under anhydrous conditions.If there were water trifluoromethyl silane would rapidly become silanol under the effect of water and alkali. The catalyst used in the reaction is alkali of which the strength has nothing to do with the catalytic activity. By now the role of catalyst is still unknown but the reaction can not proceed without catalyst.

Chemical Characteristics

Off-white crystal

Uses

For intermediate of medicine and pesticide.

Chemical Properties

White to yellowish-brown crystals

Uses

4-(Trifluoromethyl)phenol (4-hydroxybenzotrifluoride) was used in the synthesis of diaryl ether.

Uses

Intermediates of Liquid Crystals

Definition

ChEBI: 4-(trifluoromethyl)phenol is a member of the class of (trifluoromethyl)benzenes that is p-cresol in which the methyl group is perfluorinated. It is a metabolite of the drug fluoxetine. It has a role as a marine xenobiotic metabolite and a drug metabolite. It is a member of phenols and a member of (trifluoromethyl)benzenes. It is functionally related to a (trifluoromethyl)benzene and a p-cresol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2873, 1989 DOI: 10.1021/jo00273a020

General Description

4-(Trifluoromethyl)phenol molecule, bound at the active site of H61T (His-61→Thr) mutant, shows strong density.

Synthesis

Step 1: Pretreatment of strongly acidic cation exchange resin: put 10g of resin into a 1000mL beaker, soak and rinse the resin (macroporous strongly acidic styrene-based cation exchange resin, or strongly acidic 732 cation resin) with water, place it in an exchange column and soak the resin in hydrochloric acid with a concentration of 4-5% by mass for 2-4 hours, and then drain off the hydrochloric acid solution, and then rinse it to neutrality with clean water. The resin is then soaked in hydrochloric acid solution at a concentration of 4 to 4% by mass for 2 to 4 hours, then drained of the hydrochloric acid solution, and finally drenched with clean water until neutral.
Step 2: In a 100 mL three-necked flask, add 0.1 mol (16.1 g) of p-trifluoromethylaniline and 16.1 g of macroporous strongly acidic styrene-based cation exchange resin in turn, and then drop in a pre-configured aqueous sodium nitrite solution (0.1 mol, 6.9 g of sodium nitrite dissolved in 6 mL of deionized water) with stirring, and then mix and stir for 2 hours at 0 ??, and then carry out diazotization. After the reaction is completed, the mixture is filtered through 80-100 mesh sieve to separate the strongly acidic cation exchange resin; the filtrate is warmed to 95-100 ?? and hydrolyzed directly for 1 hour; after hydrolysis is completed, the water is removed by atmospheric distillation, and the fraction is collected at 71-72 ?? by reduced-pressure distillation (8 mmHg) to obtain the corresponding target product of p-(trifluoromethyl)phenol, with a yield of 90%; the separated cation The separated cation exchange resin needs to be regenerated and used, in the exchange column with a mass percentage concentration of 8% hydrochloric acid solution soaked for 2 hours, exhaust the hydrochloric acid solution, and finally washed with deionized water to pH = 4.5-6.5 can be recycled, according to the material ratio of the previous batch of material feeding for the next batch of synthesis reaction.

4-Trifluoromethylphenol(402-45-9)Related Product Information

• 4-Trifluoromethylphenylboronic acid
• p-Cresol
• alpha,alpha,alpha-Trifluoro-o-toluoyl chloride
• 2-(Trifluoromethyl)benzoic acid
• Diethylstilbestrol
• Xylenol
• o-Cresol
• 4-(Trifluoromethyl)cinnamic acid
• 4-(Trifluoromethyl)benzene-1-sulfonyl chloride
• Trifluoromethanesulfonic acid
• Cresol
• 4'-(Trifluoromethyl)acetophenone
• 3-Chloro-4-hydroxybenzotrifluoride
• Trifluoro-p-tolunitrile
• 3-Trifluoromethylphenol
• p-Trifluoromethoxy phenol
• 3-(Trifluoromethyl)benzaldehyde
• 4-Fluorophenol