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93-97-0

Basic Information
CAS No.: 93-97-0
Name: Benzoicacid, 1,1'-anhydride
Molecular Structure:
Molecular Structure of 93-97-0 (Benzoicacid, 1,1'-anhydride)
Formula: C14H10O3
Molecular Weight: 226.23
Synonyms: Benzoicacid, anhydride (9CI);Benzoic anhydride (8CI);Benzoylbenzoate;NSC 37116;Benzoic anhydride;
EINECS: 202-291-1
Density: 1.211 g/cm3
Melting Point: 38-42 °C(lit.)
Boiling Point: 360 °C at 760 mmHg
Flash Point: 168.4 °C
Solubility: water: 0.01 g/L
Appearance: white to almost white crystals or crystalline
Hazard Symbols: IrritantXi
Risk Codes: 37/38-41-36/37/38
Safety: 26-39-37/39
Transport Information:
PSA: 43.37000
LogP: 2.68380
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%
591-50-4

iodobenzene

201230-82-2

carbon monoxide

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With 1,3-bis-(diphenylphosphino)propane; water; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 20 - 115℃; under 760.051 Torr; for 6h; Inert atmosphere; Autoclave;90%
100-51-6

benzyl alcohol

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetrabutyl phosphonium bromide In water; chlorobenzene at 80℃; for 2.5h; Reagent/catalyst; Solvent; Temperature; Sealed tube;90%
Multi-step reaction with 2 steps
1: trichloroisocyanuric acid / dichloromethane / 20 °C / Inert atmosphere
2: triethylamine / 1 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: trichloroisocyanuric acid / dichloromethane / 20 °C / Inert atmosphere
2: triethylamine; water / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
22574-12-5

Phenylcarbonyloxy(pyridine-2-thione)

A

2127-03-9

2,2'-dipyridyldisulphide

B

127878-49-3

C12H9NO2S

C

127878-50-6

S-(pyridin-2-yl) pyridine-2-thiosulfonate

D

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
In chloroform-d1 at -27℃; for 0.25h; Irradiation;A 22%
B 13%
C 20%
D 88%
In dichloromethane at 0 - 5℃; for 0.5h; Product distribution; Irradiation; other solvent (CDCl3), temperature (-27 deg C), time (5 min); also other acyl derivatives investigated;A n/a
B 11%
C n/a
D 84%
In dichloromethane at -27℃; for 0.0833333h; Irradiation;A n/a
B 21%
C n/a
D 84%
91292-18-1

N,N'carbonyldi<2(3H)-benzoxazolethione>

65-85-0

benzoic acid

A

33388-23-7

3-benzoyl-2(3H)-benzoxazolethione

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one In pyridine for 2h; Ambient temperature;A 88%
B n/a
10028-70-3

disodium terephthalate

98-88-4

benzoyl chloride

A

114833-01-1

C22H14O6

B

93-97-0

benzoic acid anhydride

C

65-85-0

benzoic acid

Conditions
ConditionsYield
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃; Rate constant;A 88%
B 1%
C 11%
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃;A 88%
B 1%
C 11%
Conditions
ConditionsYield
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃; Rate constant;A 12%
B 88%
57857-69-9

di(p-anisyl)tellurium dibenzoate

A

4456-36-4

di(p-methoxyphenyl)tellurium dichloride

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With benzoyl chloride In chloroform Heating;A 87%
B 79%
57857-69-9

di(p-anisyl)tellurium dibenzoate

98-88-4

benzoyl chloride

A

4456-36-4

di(p-methoxyphenyl)tellurium dichloride

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
In chloroform Heating;A 87%
B 79%
141-95-7

sodium malonate

98-88-4

benzoyl chloride

A

93-97-0

benzoic acid anhydride

B

65-85-0

benzoic acid

Conditions
ConditionsYield
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃; Rate constant;A 13%
B 87%

1-(benzoyl)piperidine-2,6-dione

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With water; scandium tris(trifluoromethanesulfonate) In benzene at 120℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique;86.9%
672-13-9

2-hydroxy-5-methoxybenzaldehyde

65-85-0

benzoic acid

A

2-formyl-4-methoxyphenyl benzoate

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h;A 86%
B 10%
64-17-5

ethanol

65-85-0

benzoic acid

A

93-89-0

benzoic acid ethyl ester

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With magnesium chloride at 40℃; for 36h;A 85%
B n/a
100-52-7

benzaldehyde

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetrabutyl phosphonium bromide In chlorobenzene at 80℃; for 3h; Reagent/catalyst; Solvent; Temperature; Sealed tube;85%
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 2h; Catalytic behavior; Solvent; Reagent/catalyst;82%
With tert.-butylhydroperoxide; palladium diacetate In chlorobenzene at 140℃; for 2h;80%
98-88-4

benzoyl chloride

A

93-97-0

benzoic acid anhydride

B

65-85-0

benzoic acid

C

C22H14O6

Conditions
ConditionsYield
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃; Rate constant;A 1%
B 16%
C 83%
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃;A 1%
B 16%
C 83%
(C6H5CO2)2Cu

(C6H5CO2)2Cu

A

93-99-2

benzoic acid phenyl ester

B

4578-66-9

o-benzoyloxybenzoic acid

C

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
In various solvent(s) at 235℃; for 1.33333h;A 82.1%
B 6.3%
C 1.5%
201024-81-9

C,N-diphenylnitrone

A

100-52-7

benzaldehyde

B

93-97-0

benzoic acid anhydride

C

65-85-0

benzoic acid

D

17082-12-1

trans-azobenzene

Conditions
ConditionsYield
With potassium In tetrahydrofuran for 16h; Product distribution; Mechanism; exclusion of O2, various conditions;A 42%
B 8%
C 47%
D 82%
119-53-9

2-hydroxy-2-phenylacetophenone

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With diphenyl diselenide; dihydrogen peroxide In acetonitrile at 25℃; for 24h; Reagent/catalyst; Temperature; Solvent; Concentration; Green chemistry;82%
90-05-1

2-methoxy-phenol

65-85-0

benzoic acid

A

531-37-3

2-methoxyphenyl benzoate

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h;A 81%
B 14%
65-85-0

benzoic acid

927-80-0

1-ethoxyacetylene

A

38425-59-1

(1-ethoxy)vinyl benzoate

B

93-97-0

benzoic acid anhydride

Conditions
ConditionsYield
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In toluene at 40℃; for 15h;A 80%
B 5%
17265-13-3

disodium azelainate

98-88-4

benzoyl chloride

A

93-97-0

benzoic acid anhydride

B

65-85-0

benzoic acid

C

C16H20O5

D

C23H24O6

Conditions
ConditionsYield
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃; Rate constant;A 3%
B 8%
C 9%
D 80%
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃;A 3%
B 8%
C 9%
D 80%
100-66-3

methoxybenzene

93-97-0

benzoic acid anhydride

611-94-9

4-Methoxybenzophenone

Conditions
ConditionsYield
With gallium(III) trichloride; silver hexafluoroantimonate In 1,2-dichloro-ethane for 7h; Heating;100%
With trifluoroacetic acid at 20℃; for 1.5h; Friedel-Crafts Acylation;98%
With lithium perchlorate In nitromethane at 100℃; for 4h;97%
Conditions
ConditionsYield
With 1-[bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene100%
With 4-(1H,1H-perfluorotetradecyl)-C6F4-CH(SO2CF3)2 In toluene at 70℃; for 14h;99%
With 4-(dimethylamino)pyridine hydrochloride In toluene at 60℃; for 6h;98%
39687-95-1

isocyanoacetic acid methyl ester

93-97-0

benzoic acid anhydride

38061-18-6

methyl 5-phenyl-4-oxazolecarboxylate

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In tetrahydrofuran 1.) 5 deg C, 15 min, 2.) r.t., 30 min;100%
With P(MeNCH2CH2)3N for 2h;90%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran
90503-12-1

methyl 4,6-O-benzylidene-3-deoxy-3-iodo-α-D-glucopyranoside

93-97-0

benzoic acid anhydride

127244-71-7

methyl 2-O-benzoyl-4,6-O-benzylidene-3-deoxy-3-iodo-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 2h; Heating;100%
With triethylamine; dmap In dichloromethane
129090-81-9

methyl (3R)-<3-(2)H>-4-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside

93-97-0

benzoic acid anhydride

131129-47-0

methyl (3R)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 2h; Heating;100%
99314-92-8

N2-amino-N3-benzyloxycarbonylaminopyridine

93-97-0

benzoic acid anhydride

99314-94-0

(2-Benzoylamino-pyridin-3-yl)-carbamic acid benzyl ester

Conditions
ConditionsYield
With pyridine Ambient temperature; overnight;100%
100590-12-3

cis-2-(iodomethyl)-3-hydroxytetrahydrofuran

93-97-0

benzoic acid anhydride

109788-30-9, 109788-31-0

cis-2-(iodomethyl)-3-benzoxytetrahydrofuran

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran Ambient temperature;100%
93-97-0

benzoic acid anhydride

85878-21-3

C12H12F16O4Te

67103-71-3

1,1,2,2-tetrafluoroethyl benzoate

Conditions
ConditionsYield
at 80 - 120℃;100%
93-97-0

benzoic acid anhydride

85878-21-3

C12H12F16O4Te

A

67103-71-3

1,1,2,2-tetrafluoroethyl benzoate

B

107905-31-7

C20H16F8O6Te

Conditions
ConditionsYield
at 20℃; for 24h; Yields of byproduct given;A n/a
B 100%
93-97-0

benzoic acid anhydride

85878-21-3

C12H12F16O4Te

A

67103-71-3

1,1,2,2-tetrafluoroethyl benzoate

B

107905-28-2

C16H14F12O5Te

Conditions
ConditionsYield
at 20℃; for 2h; ether as solvent;; Yields of byproduct given;A n/a
B 100%
93-97-0

benzoic acid anhydride

17-<(tert-Butyldiphenylsilyl)oxy>-trans-3,4-dihydroxy-15,16-dihydro-11-methylcyclopentaphenanthrene

17-<(tert-Butyldiphenylsilyl)oxy>-trans-3,4-bis(benzoyloxy)-15,16-dihydro-11-methylcyclopentaphenanthrene

Conditions
ConditionsYield
With dmap In dichloromethane for 2h;100%
15356-60-2

(1S,2R,5S)-(+)-menthol

93-97-0

benzoic acid anhydride

58641-29-5

(2R,5S)-2-isopropyl-5-methyl-cyclohexyl benzoate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 50℃; for 1.66667h;100%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 92h;96%
With scandium tris(trifluoromethanesulfonate) In acetonitrile for 20h; Ambient temperature;95%
With 2,4,6-tris(2,2-bis(trifluoromethylsulfonyl)ethyl)benzene-1,3,5-triol at 70℃; for 3h; Inert atmosphere;93%
93-97-0

benzoic acid anhydride

100-51-6

benzyl alcohol

120-51-4

benzoic acid benzyl ester

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 50℃; for 0.833333h;100%
With bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.5h; Heating;98%
With tris(pentafluorophenyl)borate In neat (no solvent) at 20℃; for 0.166667h; Green chemistry;95%
91-16-7

1,2-dimethoxybenzene

93-97-0

benzoic acid anhydride

4038-14-6

3,4-dimethoxybenzophenone

Conditions
ConditionsYield
With silver perchlorate; niobium pentachloride In nitromethane at 80℃; for 7h; Friedel-Crafts acylation;100%
With trifluorormethanesulfonic acid; titanium(IV) chloride tris(trifluoromethanesulfonate) In acetonitrile for 12h; Ambient temperature;94%
Hf[N(SO2C8F17)2]4 In chlorobenzene at 110℃; for 2h;94%
93-97-0

benzoic acid anhydride

191924-37-5

2-(trimethylsilyl)ethyl 3-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside

2-(trimethylsilyl)ethyl 2-O-benzoyl-3-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside

Conditions
ConditionsYield
With pyridine for 2h; Ambient temperature;100%
93-97-0

benzoic acid anhydride

10212-20-1

2'-deoxy-2'-fluorocytidine

146954-76-9

N4-benzoyl-2-deoxy-2-fluorocytidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;100%
In N,N-dimethyl-formamide at 20℃;100%
In N,N-dimethyl-formamide92%
93-97-0

benzoic acid anhydride

4358-64-9

cis-1,4-anhydroerythritol

cis-3-benzoyloxy-4-hydroxytetrahydrofuran

Conditions
ConditionsYield
ytterbium(III) chloride In tetrahydrofuran Acylation;100%
With ytterbium(III) chloride In tetrahydrofuran100%
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    Product Name: Benzoic anhydride CAS: 93-97-0 MF: C14H10O3 MW: 226.23 EINECS: 202-291-1 Mol File: 93-97-0.mol Benzoic anhydride Structure Benzoic anhydride Chemical Properties Melting point 38-42 °C(lit.) Boiling point

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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