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Benzoic anhydride

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Name

Benzoic anhydride

EINECS 202-291-1
CAS No. 93-97-0 Density 1.211 g/cm3
PSA 43.37000 LogP 2.68380
Solubility water: 0.01 g/L Melting Point 38-42 °C(lit.)
Formula C14H10O3 Boiling Point 360 °C at 760 mmHg
Molecular Weight 226.232 Flash Point 168.4 °C
Transport Information N/A Appearance white to almost white crystals or crystalline
Safety 26-39-37/39 Risk Codes 37/38-41-36/37/38
Molecular Structure Molecular Structure of 93-97-0 (Benzoic anhydride) Hazard Symbols IrritantXi
Synonyms

Benzoicacid, anhydride (9CI);Benzoic anhydride (8CI);Benzoylbenzoate;NSC 37116;Benzoic anhydride;

Article Data 391

Benzoic anhydride Synthetic route

98-88-4

benzoyl chloride

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In toluene for 3h; Heating;99%
With pyridine; 1,1,1-trichloro-3,3,3-trifluoro-propan-2-one; water In toluene for 0.5h; Ambient temperature;97%
With water; triethylamine In acetone at 20℃; for 1h;97%
65-85-0

benzoic acid

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 0.5h;99%
With 2,6-dimethylpyridine; tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide; N,N-dimethyl-formamide at 25 - 30℃; for 12h; Inert atmosphere; Photolysis;99%
With thionyl chloride In dichloromethane at 22 - 25℃; for 1h;98.6%
582-25-2

Potassium benzoate

98-88-4

benzoyl chloride

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In chloroform at 20℃; for 2h; Acylation;98%
With 1,4-diaza-bicyclo[2.2.2]octane for 0.1h;98%
155164-66-2

2-benzoyl-4,5-dichloropyridazin-3(2H)-one

A

932-22-9

4,5-dichloro-2H-pyridazin-3-one

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With zinc(II) chloride In acetonitrile for 7h; Heating;A n/a
B 97%
582-25-2

Potassium benzoate

65-85-0

benzoic acid

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
Stage #1: benzoic acid With trichloroisocyanuric acid; triphenylphosphine In dichloromethane at 0 - 20℃;
Stage #2: Potassium benzoate In dichloromethane at 20℃; for 0.833333h; Reagent/catalyst; Solvent; Time;
95%
553-72-0

zinc benzoate

98-88-4

benzoyl chloride

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
In toluene at 40℃; for 0.5h;92%
532-32-1

sodium benzoate

98-88-4

benzoyl chloride

A

93-97-0

benzoic acid anhydride

B

65-85-0

benzoic acid

Conditions
ConditionsYield
Pyridine 1-oxide hydrochloride In dichloromethane; water at 22℃; Kinetics; Rate constant; Thermodynamic data; mechanism, effect of agitation, influence of ionic strength, other org. solvents, other temperatures;A 91.8%
B n/a
In dichloromethane; water Thermodynamic data; influence of ionic strength;
98-88-4

benzoyl chloride

65-85-0

benzoic acid

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
cobalt(II) chloride In dichloromethane; acetonitrile at 40℃; various acid chlorides, other carboxylic acids;91%
cobalt(II) chloride In dichloromethane; acetonitrile at 40℃;91%
With Fe/SWCNTs at 20℃; for 1.41667h;90%
55-21-0

benzamide

65-85-0

benzoic acid

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With aluminum oxide In acetonitrile at 85 - 115℃; for 7h; Concentration; Temperature; Large scale;91%
124-63-0

methanesulfonyl chloride

65-85-0

benzoic acid

A

26926-35-2

Benzoesaeure-methansulfonsaeure-anhydrid

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;A 90%
B 20%

Benzoic anhydride Specification

The Benzoic anhydride is an organic compound with the formula C14H10O3. The IUPAC name of this chemical is benzoyl benzoate. With the CAS registry number 93-97-0, it is also named as phenylcarbonyl benzoate. The product's categories are 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. Besides, it is a white to almost white crystal or crystalline, which should be stored in a closed cool and dry palce. It is a major industrial chemical widely used for preparing acetate esters, e.g. cellulose acetate.

Physical properties about Benzoic anhydride are: (1)ACD/LogP: 2.738; (2)ACD/LogD (pH 5.5): 2.74; (3)ACD/LogD (pH 7.4): 2.74; (4)ACD/BCF (pH 5.5): 70.94; (5)ACD/BCF (pH 7.4): 70.94; (6)ACD/KOC (pH 5.5): 735.32; (7)ACD/KOC (pH 7.4): 735.32; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.59; (11)Molar Refractivity: 62.992 cm3; (12)Molar Volume: 186.741 cm3; (13)Polarizability: 24.972 10-24cm3; (14)Surface Tension: 48.5200004577637 dyne/cm; (15)Density: 1.211 g/cm3; (16)Flash Point: 168.44 °C; (17)Enthalpy of Vaporization: 60.566 kJ/mol; (18)Boiling Point: 360 °C at 760 mmHg
 

Preparation of Benzoic anhydride: Benzoic anhydride is mainly produced by the carbonylation of methyl acetate. Maleic anhydride is produced by the oxidation of benzene or butane. Laboratory routes emphasize the dehydration of the corresponding acids. The conditions vary from acid to acid, but phosphorus pentoxide is a common dehydrating agent:
2 CH3COOH + P4O10 → CH3C(O)OC(O)CH3 + "(HO)2P4O9"

Uses of Benzoic anhydride: it can be used to produce furan-2-yl-phenyl-methanone by heating. This reaction is a kind of Friedel-Crafts acylation. It will need  solvent CH2Cl2. The yield is about 80%.

When you are using this chemical, please be cautious about it as the following:
It is risk of serious damage to eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(=O)c1ccccc1)c2ccccc2
(2)InChI: InChI=1/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H
(3)InChIKey: CHIHQLCVLOXUJW-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H
(5)Std. InChIKey: CHIHQLCVLOXUJW-UHFFFAOYSA-N

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