Trifluoroacetic anhydride Property

Melting point:

-65 °C (lit.)

Boiling point:

39.5-40 °C (lit.)

Density 

1.511 g/mL at 20 °C (lit.)

vapor pressure 

6.28 psi ( 20 °C)

refractive index 

n20/D 1.3(lit.)

Flash point:

-26 °C

storage temp. 

2-8°C

solubility 

Miscible with benzene, dichloromethane, diethyl ether, dimethylformamide, terahydrofuran and acetonitrile.

form 

Liquid

pka

0.43[at 20 ℃]

Specific Gravity

1.487

color 

Clear

Water Solubility 

Hydrolysis

Sensitive 

Moisture Sensitive

BRN 

746197

Stability:

Stable, but moisture sensitive. Reacts with water to liberate hydrogen (flammable!). Incompatible with water, strong oxidizing agents.

LogP

0.79 at 25℃

CAS DataBase Reference

407-25-0(CAS DataBase Reference)

NIST Chemistry Reference

Acetic acid, trifluoro-, anhydride(407-25-0)

EPA Substance Registry System

Acetic acid, trifluoro-, anhydride (407-25-0)

Safety

Hazard Codes 

C,T

Risk Statements 

14-20-35-52/53-34-23/24/25

Safety Statements 

26-36/37/39-43-45-61-9-8-28A-27

RIDADR 

UN 3265 8/PG 1

WGK Germany 

2

RTECS 

AJ9800000

F 

3-10

Hazard Note 

Corrosive/Moisture Sensitive

TSCA 

T

HazardClass 

8

PackingGroup 

I

HS Code 

29159080

Toxicity

skn-rbt 500 mg/24H SEV 28ZPAK -,91,72

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

H332Harmful if inhaled

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

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.

Trifluoroacetic anhydride Chemical Properties,Usage,Production

Description

Trifluoroacetic acid anhydride (TFAA), a perfluoroacylated acylation reagent, forms stable, volatile derivatives with alcohols, amines, and phenols. 

Chemical Properties

Clear, colorless liquid

Uses

Used as analytical reagents, solvents, catalysts, dehydration condensing agent, protection agent of trifluoroacetylation of carboxyl and amino; used as Intermediate of fluorine fine chemicals, pharmaceutical, agrochemical.

Uses

Trifluoroacetic anhydride is used for the introduction of trifluoroacetyl group in organic synthesis. It is involved in the preparation of N- and O-trifluoroacetyl derivatives of a wide range of biologically active compounds for gas chromatography analysis. It plays an important role as desiccant for trifluoroacetic acid. It is also used in the oxidation of aldehydes to acids, esters, amides as well as in the protection of alcohols and amines. In addition, it is used as analytical reagents, solvents and dehydration condensing agent. It serves as an intermediate of fluorine fine chemicals, pharmaceuticals and agrochemicals.

Preparation

Trifluoroacetic anhydride is prepared by reaction of trifluoroacetyl chloride with an alkali metal or alkaline-earth metal salt of trifluoroacetic acid at approximately 50° C. 

Safety Profile

A severe skin and eye irritant.Explosive reaction with dimethyl sulfoxide; nitric acid +1,3,5-triazine (at 36°C); nitric acid + 1,3,5-triacetylhexahydro-1,3,5-triazine (at 30°C). Incompatiblewith lithium tetrahydroaluminate. When heated todecomposit

Purification Methods

Purification by distilling over KMnO4, as for the acid above, is EXTREMELY DANGEROUS due to the possiblility of EXPLOSION. It is best purified by distilling from P2O5 slowly, and collecting the fraction boiling at 39.5o. Store it in a dry atmosphere. Highly TOXIC vapour and attacks skin, work in an efficient fume hood. [Beilstein 2 IV 469.]