Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
2-benzoyl-4,5-dichloropyridazin-3(2H)-one
A
4,5-dichloro-2H-pyridazin-3-one
B
benzoic acid anhydride
Conditions | Yield |
---|---|
With zinc(II) chloride In acetonitrile for 7h; Heating; | A n/a B 97% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In toluene at 40℃; for 0.5h; | 92% |
sodium benzoate
benzoyl chloride
A
benzoic acid anhydride
B
benzoic acid
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With aluminum oxide In acetonitrile at 85 - 115℃; for 7h; Concentration; Temperature; Large scale; | 91% |
methanesulfonyl chloride
benzoic acid
A
Benzoesaeure-methansulfonsaeure-anhydrid
B
benzoic acid anhydride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; | A 90% B 20% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
Phenylcarbonyloxy(pyridine-2-thione)
A
2,2'-dipyridyldisulphide
B
C12H9NO2S
C
S-(pyridin-2-yl) pyridine-2-thiosulfonate
D
benzoic acid anhydride
Conditions | Yield |
---|---|
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% |
N,N'carbonyldi<2(3H)-benzoxazolethione>
benzoic acid
A
3-benzoyl-2(3H)-benzoxazolethione
B
benzoic acid anhydride
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one In pyridine for 2h; Ambient temperature; | A 88% B n/a |
disodium terephthalate
benzoyl chloride
A
C22H14O6
B
benzoic acid anhydride
C
benzoic acid
Conditions | Yield |
---|---|
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 | Yield |
---|---|
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃; Rate constant; | A 12% B 88% |
di(p-anisyl)tellurium dibenzoate
A
di(p-methoxyphenyl)tellurium dichloride
B
benzoic acid anhydride
Conditions | Yield |
---|---|
With benzoyl chloride In chloroform Heating; | A 87% B 79% |
di(p-anisyl)tellurium dibenzoate
benzoyl chloride
A
di(p-methoxyphenyl)tellurium dichloride
B
benzoic acid anhydride
Conditions | Yield |
---|---|
In chloroform Heating; | A 87% B 79% |
sodium malonate
benzoyl chloride
A
benzoic acid anhydride
B
benzoic acid
Conditions | Yield |
---|---|
With Pyridine 1-oxide hydrochloride In dichloromethane; water at 18℃; Rate constant; | A 13% B 87% |
benzoic acid anhydride
Conditions | Yield |
---|---|
With water; scandium tris(trifluoromethanesulfonate) In benzene at 120℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; | 86.9% |
Conditions | Yield |
---|---|
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h; | A 86% B 10% |
ethanol
benzoic acid
A
benzoic acid ethyl ester
B
benzoic acid anhydride
Conditions | Yield |
---|---|
With magnesium chloride at 40℃; for 36h; | A 85% B n/a |
Conditions | Yield |
---|---|
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% |
disodium isophthalate
benzoyl chloride
A
benzoic acid anhydride
B
benzoic acid
Conditions | Yield |
---|---|
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% |
A
benzoic acid phenyl ester
B
o-benzoyloxybenzoic acid
C
benzoic acid anhydride
Conditions | Yield |
---|---|
In various solvent(s) at 235℃; for 1.33333h; | A 82.1% B 6.3% C 1.5% |
C,N-diphenylnitrone
A
benzaldehyde
B
benzoic acid anhydride
C
benzoic acid
D
trans-azobenzene
Conditions | Yield |
---|---|
With potassium In tetrahydrofuran for 16h; Product distribution; Mechanism; exclusion of O2, various conditions; | A 42% B 8% C 47% D 82% |
Conditions | Yield |
---|---|
With diphenyl diselenide; dihydrogen peroxide In acetonitrile at 25℃; for 24h; Reagent/catalyst; Temperature; Solvent; Concentration; Green chemistry; | 82% |
2-methoxy-phenol
benzoic acid
A
2-methoxyphenyl benzoate
B
benzoic acid anhydride
Conditions | Yield |
---|---|
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h; | A 81% B 14% |
benzoic acid
1-ethoxyacetylene
A
(1-ethoxy)vinyl benzoate
B
benzoic acid anhydride
Conditions | Yield |
---|---|
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In toluene at 40℃; for 15h; | A 80% B 5% |
disodium azelainate
benzoyl chloride
A
benzoic acid anhydride
B
benzoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 | Yield |
---|---|
With 1-[bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene | 100% |
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% |
isocyanoacetic acid methyl ester
benzoic acid anhydride
methyl 5-phenyl-4-oxazolecarboxylate
Conditions | Yield |
---|---|
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 |
methyl 4,6-O-benzylidene-3-deoxy-3-iodo-α-D-glucopyranoside
benzoic acid anhydride
methyl 2-O-benzoyl-4,6-O-benzylidene-3-deoxy-3-iodo-α-D-glucopyranoside
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane for 2h; Heating; | 100% |
With triethylamine; dmap In dichloromethane |
methyl (3R)-<3-(2)H>-4-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside
benzoic acid anhydride
methyl (3R)-<3-(2)H>-2,4-di-O-benzoyl-6-bromo-3,6-dideoxy-α-D-ribo-hexopyranoside
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane for 2h; Heating; | 100% |
N2-amino-N3-benzyloxycarbonylaminopyridine
benzoic acid anhydride
(2-Benzoylamino-pyridin-3-yl)-carbamic acid benzyl ester
Conditions | Yield |
---|---|
With pyridine Ambient temperature; overnight; | 100% |
cis-2-(iodomethyl)-3-hydroxytetrahydrofuran
benzoic acid anhydride
cis-2-(iodomethyl)-3-benzoxytetrahydrofuran
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran Ambient temperature; | 100% |
benzoic acid anhydride
C12H12F16O4Te
1,1,2,2-tetrafluoroethyl benzoate
Conditions | Yield |
---|---|
at 80 - 120℃; | 100% |
benzoic acid anhydride
C12H12F16O4Te
A
1,1,2,2-tetrafluoroethyl benzoate
B
C20H16F8O6Te
Conditions | Yield |
---|---|
at 20℃; for 24h; Yields of byproduct given; | A n/a B 100% |
benzoic acid anhydride
C12H12F16O4Te
A
1,1,2,2-tetrafluoroethyl benzoate
B
C16H14F12O5Te
Conditions | Yield |
---|---|
at 20℃; for 2h; ether as solvent;; Yields of byproduct given; | A n/a B 100% |
benzoic acid anhydride
Conditions | Yield |
---|---|
With dmap In dichloromethane for 2h; | 100% |
(1S,2R,5S)-(+)-menthol
benzoic acid anhydride
(2R,5S)-2-isopropyl-5-methyl-cyclohexyl benzoate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
benzoic acid anhydride
2-(trimethylsilyl)ethyl 3-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside
Conditions | Yield |
---|---|
With pyridine for 2h; Ambient temperature; | 100% |
benzoic acid anhydride
2'-deoxy-2'-fluorocytidine
N4-benzoyl-2-deoxy-2-fluorocytidine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; | 100% |
In N,N-dimethyl-formamide at 20℃; | 100% |
In N,N-dimethyl-formamide | 92% |
Conditions | Yield |
---|---|
ytterbium(III) chloride In tetrahydrofuran Acylation; | 100% |
With ytterbium(III) chloride In tetrahydrofuran | 100% |
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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