Benzoic anhydride Property

Melting point:

38-42 °C(lit.)

Boiling point:

360 °C

Density 

1.199 g/mL at 25 °C(lit.)

refractive index 

nD15 1.57665

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

0.01g/l (experimental)

form 

Crystals or Crystalline Powder

color 

White to almost white

Water Solubility 

0.01 g/L

Sensitive 

Moisture Sensitive

Merck 

14,1092

BRN 

516726

InChIKey

CHIHQLCVLOXUJW-UHFFFAOYSA-N

CAS DataBase Reference

93-97-0(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, anhydride(93-97-0)

EPA Substance Registry System

Benzoic anhydride (93-97-0)

Safety

Hazard Codes 

Xi

Risk Statements 

37/38-41-36/37/38

Safety Statements 

26-39-37/39

WGK Germany 

3

F 

10-21

TSCA 

Yes

HS Code 

29163900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H318Causes serious eye damage

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P314Get medical advice/attention if you feel unwell.

Benzoic anhydride Chemical Properties,Usage,Production

Chemical Properties

white to almost white crystals or crystalline

Uses

Benzoic anhydride is used as a benzoylating agent in the manufacture of pharmaceuticals, dyes and intermediates. It serves as an arylation agent in the Heck reaction. It is also used to get benzoic acid through dehydration. Further, it is used to prepare furan-2-yl-phenyl-methanone, which is similar to Friedel-Crafts acylation reaction. In addition to this, it is used for the synthesis of carboxylic esters and lactones.

Uses

Benzoic Anhydride is the more active analogue of benzoic acid formed via dehydration. Benzoic Anhydride is used in the synthesis of a wide range of organic compounds including some dyes. Benzoic Anhyd ride is also used as an arylation agent in the Heck reaction.

Uses

In organic syntheses, as benzoylating agent in the manufacture of pharmaceuticals, dyes, and intermediates.

Definition

ChEBI: Benzoic anhydride is an acyclic carboxylic anhydride. It is functionally related to a benzoic acid.

Preparation

To a flask containing 14.0 gm (0.1 mole) of benzoyl chloride and equipped with a stirrer is added 40 ml of dry dioxane and it is cooled to 5°C.Then 10 ml (0.1 mole) of dry pyridine is rapidly added at 5-10°C followed by 1.0 ml (0.056 mole) of water. After stirring for 10-15 min at 0-5°C, the reaction mixture is then poured into a mixture of 75 ml of cone, hydrochloric acid, 75 gm of cracked ice, and 350 ml of water. The product is filtered, washed first for 1 min with a cold 5% solution of sodium bicarbonate and then with water. The product is dried to afford 11.0 gm (97%), m.p. 43°C (recrystallized from a mixture of ether-petroleum ether).

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 35, p. 1262, 1987 DOI: 10.1248/cpb.35.1262
Tetrahedron Letters, 26, p. 1503, 1985 DOI: 10.1016/S0040-4039(00)98536-8

General Description

Benzoic anhydride undergoes Friedel-Crafts acylation reaction with benzene over various ion-exchanged heteropoly acids to yield benzophenone.

Purification Methods

Free it from benzoic acid by washing with NaHCO3, then water, and drying. Crystallise it from *benzene (0.5mL/g) by adding just enough pet ether (b 40-60o) to cause cloudiness, then cool in ice. It can be distilled at 210-220o/20mm. [Beilstein 19 IV 550.]