Benzoic anhydride

Benzoic anhydride Basic information
Product Name:Benzoic anhydride
Synonyms:BENZOIC ANHYDRIDE pure;BENZOIC ANHYDRIDE, TECH., 90%;BenzoicAnhydride,~98%;BenzoicAnhydride99%;Phenyl anhydride;Banzoyl benzoate;Dibenzoic acid anhydride;Dibenzoic anhydride
CAS:93-97-0
MF:C14H10O3
MW:226.23
EINECS:202-291-1
Product Categories:Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Reagents for Oligosaccharide Synthesis;Carboxylic Acid Anhydrides;Carbonyl Compounds;Organic Building Blocks;bc0001;93-97-0
Mol File:93-97-0.mol
Benzoic anhydride Structure
Benzoic anhydride Chemical Properties
Melting point 38-42 °C(lit.)
Boiling point 360 °C
density 1.199 g/mL at 25 °C(lit.)
refractive index nD15 1.57665
Fp >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
InChIKeyCHIHQLCVLOXUJW-UHFFFAOYSA-N
CAS DataBase Reference93-97-0(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, anhydride(93-97-0)
EPA Substance Registry SystemBenzoic anhydride (93-97-0)
Safety Information
Hazard Codes Xi
Risk Statements 37/38-41-36/37/38
Safety Statements 26-39-37/39
WGK Germany 3
10-21
TSCA Yes
HS Code 29163900
MSDS Information
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Benzoic anhydride Usage And Synthesis
Chemical Propertieswhite to almost white crystals or crystalline
UsesBenzoic 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.
UsesIn organic syntheses, as benzoylating agent in the manufacture of pharmaceuticals, dyes, and intermediates.
UsesBenzoic 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.
PreparationTo 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).
Preparation of Benzoic Anhydride
DefinitionChEBI: Benzoic anhydride is an acyclic carboxylic anhydride. It is functionally related to a benzoic acid.
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 DescriptionBenzoic anhydride undergoes Friedel-Crafts acylation reaction with benzene over various ion-exchanged heteropoly acids to yield benzophenone.
Purification MethodsFree 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.]
2,2-Dimethoxy-2-phenylacetophenone 2-Iodobenzoic acid 4-Hydroxybenzoic acid Acetic anhydride Maleic anhydride 4-Aminobenzoic acid Di-tert-butyl dicarbonate Benzoin Succinic anhydride Phthalic anhydride Glutaric anhydride 1,8-Naphthalic anhydride BENZOIN COMPOUND TINCTURE Benzoic acid Anthranilic acid Estradiol benzoate Benzyl benzoate BENZOICACID

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