Cas no 93-97-0 (Benzoic anhydride)

Benzoic anhydride structure
Benzoic anhydride structure
Product Name:Benzoic anhydride
CAS No:93-97-0
MF:C14H10O3
MW:226.227404117584
MDL:MFCD00003073
CID:34723
PubChem ID:7167
Update Time:2024-10-26

Benzoic anhydride Chemical and Physical Properties

Names and Identifiers

    • Benzoic anhydride
    • benzoyl benzoate
    • Benzoic acid, anhydride (9CI)
    • Benzoic anhydride (8CI)
    • Benzoyl anhydride
    • Bis(phenylcarbonyl)ether
    • NSC 37116
    • Benzoic anhydride,98%
    • MDL: MFCD00003073
    • Inchi: 1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H
    • InChI Key: CHIHQLCVLOXUJW-UHFFFAOYSA-N
    • SMILES: O=C(C1C=CC=CC=1)OC(C1C=CC=CC=1)=O
    • BRN: 516726

Computed Properties

  • Exact Mass: 226.06300
  • Monoisotopic Mass: 226.062994
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 4
  • Complexity: 245
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 3.2
  • Topological Polar Surface Area: 43.4

Experimental Properties

  • Color/Form: White prismatic crystals. Sensitive to moisture.
  • Density: 1.199?g/mL?at 25?°C(lit.)
  • Melting Point: 38-42?°C (lit.)
  • Boiling Point: 158°C/1mmHg(lit.)
  • Flash Point: Degrees Fahrenheit:235.4°F
    Degrees Celsius:113°C
  • Refractive Index: nD15 1.57665
  • Solubility: 0.01g/l (experimental)
  • Water Partition Coefficient: 0.01 g/L
  • PSA: 43.37000
  • LogP: 2.68380
  • Merck: 1092
  • Sensitiveness: Moisture Sensitive
  • FEMA: 2684
  • Solubility: Soluble in ethanol, chloroform, acetone, ethyl acetate, benzene, toluene, xylene, ether, glacial acetic acid and acetic anhydride, slightly soluble in petroleum ether, almost insoluble in water. It is stable in aqueous solution and cold alkaline solution.

Benzoic anhydride Security Information

  • Symbol: GHS05 GHS07
  • Prompt:warning
  • Signal Word:Danger
  • Hazard Statement: H315,H318,H335
  • Warning Statement: P261,P280,P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 37/38-41
  • Safety Instruction: S26-S39-S37/39
  • FLUKA BRAND F CODES:10-21
  • Hazardous Material Identification: Xi
  • Safety Term:5.1
  • Packing Group:I; II; III
  • Risk Phrases:R36/37/38
  • TSCA:Yes
  • Storage Condition:0-10°C

Benzoic anhydride Customs Data

  • HS CODE:4002191900
  • Customs Data:

    China Customs Code:

    4002191900

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Benzoic anhydride Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Oxygen ,  Ozone Solvents: Dichloromethane
Reference
Convenient synthesis of mixed anhydrides by the ozonolysis of oxazoles
Kashima, Choji; Hibi, Shigeki; Harada, Kazuo; Omote, Yoshimori, Journal of the Chemical Society, 1988, (3), 529-33

Production Method 2

Reaction Conditions
Reference
Usefulness of various solvents for the catalytic aldehyde synthesis from acid chlorides
Zetzsche, Fritz; Enderlin, Florian; Flutsch, Christian; Menzi, Ernest, Helvetica Chimica Acta, 1926, 9, 177-81

Production Method 3

Reaction Conditions
1.1 Reagents: tert-Butyl hydroperoxide Catalysts: Potassate(1-), aqua(nitrato-κO,κO′)bis[(2-pyridinecarboxylato-κN1,κO2)cuprate]bi… Solvents: Acetonitrile ;  20 min, 80 °C
Reference
Catalytic C-H Bond Activation and Knoevenagel Condensation Using Pyridine-2,3-Dicarboxylate-Based Metal-Organic Frameworks
Pandey, Rampal ; Singh, Durgesh; Thakur, Neha; Raj, Krishna K., ACS Omega, 2021, 6(20), 13240-13259

Production Method 4

Reaction Conditions
1.1 Reagents: Triethylamine ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  0 °C → 25 °C; 5 min, 25 °C
Reference
Acid anhydrides and the unexpected N,N-diethylamides derived from the reaction of carboxylic acids with Ph3P/I2/Et3N
Phakhodee, Wong; Duangkamol, Chuthamat; Wangngae, Sirilak; Pattarawarapan, Mookda, Tetrahedron Letters, 2016, 57(3), 325-328

Production Method 5

Reaction Conditions
1.1 Reagents: 2,6-Lutidine ,  Carbon tetrabromide Catalysts: Tris(2,2′-bipyridyl)ruthenium(II) chloride Solvents: Dimethylformamide ;  12 h, 25 - 30 °C
Reference
Synthesis of symmetric anhydrides using visible light-mediated photoredox catalysis
Konieczynska, Marlena D.; Dai, Chunhui; Stephenson, Corey R. J., Organic & Biomolecular Chemistry, 2012, 10(23), 4509-4511

Production Method 6

Reaction Conditions
1.1 Catalysts: Trichloroisocyanuric acid Solvents: Dichloromethane ;  1 - 2 min, rt; rt → 0 °C
1.2 0 °C
1.3 Reagents: Triethylamine ;  0 °C; rt
Reference
Anhydrides from aldehydes or alcohols via oxidative cross-coupling
Gaspa, Silvia; Amura, Ida; Porcheddu, Andrea; De Luca, Lidia, New Journal of Chemistry, 2017, 41(3), 931-939

Production Method 7

Reaction Conditions
1.1 Reagents: Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  5 min, 0 °C
1.2 Reagents: Triethylamine ;  5 min, 0 °C
1.3 Reagents: Benzylamine ;  0 °C → rt; 10 min, rt
Reference
Significance of reagent addition sequence in the amidation of carboxylic acids mediated by PPh3 and I2
Wangngae, Sirilak; Duangkamol, Chuthamat; Pattarawarapan, Mookda; Phakhodee, Wong, RSC Advances, 2015, 5(33), 25789-25793

Production Method 8

Reaction Conditions
1.1 Reagents: Triphosgene Catalysts: Dimethylformamide Solvents: Tetrahydrofuran ;  2.5 h, 50 °C; 0.5 h, 50 °C
Reference
An efficient method for preparation of acyl chlorides and symmetrical anhydrides from carboxylic acids with BTC/DMF
Chen, Zhiwei; Jiang, Ling; Su, Weike; Xu, Zhijun, Journal of the Chemical Society of Pakistan, 2012, 34(4), 1003-1006

Production Method 9

Reaction Conditions
1.1 Reagents: Pyridine ,  Methanesulfonyl chloride Solvents: Toluene ;  4 h, rt
1.2 Reagents: 1-Butyl-3-methylimidazolium hexafluorophosphate ,  1-(Carboxymethyl)-3-methylimidazolium tetrafluoroborate ;  30 min, rt
Reference
Carboxyl-functional ionic liquids as scavengers: case studies on benzyl chloride, amines, and methanesulfonyl chloride
Cai, Yueqin; Zhang, Ying; Peng, Yanqing; Lu, Feng; Huang, Xinglong; et al, Journal of Combinatorial Chemistry, 2006, 8(5), 636-638

Production Method 10

Reaction Conditions
1.1 Reagents: Thionyl chloride ,  Pyridine, 4-ethenyl-, polymer with diethenylbenzene and 1-ethenyl-4-ethylbenzene Solvents: Dichloromethane
Reference
Phase-managed organic synthesis. 3. Symmetrical anhydrides from carboxylic acids via polymer-assisted reaction
Fife, Wilmer K.; Zhang, Zhi Dong, Tetrahedron Letters, 1986, 27(41), 4937-40

Production Method 11

Reaction Conditions
1.1 Reagents: Divinylbenzene-4-vinylpyridine copolymer Solvents: Dichloromethane
Reference
Phase-managed organic synthesis. 2. A new polymer-assisted synthesis of acid anhydrides
Fife, Wilmer K.; et al, Tetrahedron Letters, 1986, 27(41), 4933-6

Production Method 12

Reaction Conditions
1.1 Reagents: Di-tert-butyl dicarbonate Catalysts: Magnesium chloride Solvents: Benzene ;  2 h, 100 °C
Reference
Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes
Deng, Xue-Zu; Chen, Zi-Yan; Song, Yang; Xue, Fei; Yamane, Motoki; et al, Journal of Organic Chemistry, 2021, 86(18), 12693-12704

Production Method 13

Reaction Conditions
1.1 Solvents: Toluene ;  100 atm, rt; 2 h, 260 - 270 °C
Reference
Transition Metal Catalyst-Free and Radical Initiator-Free Carbonylation of Aryl Iodides
Fukuoka, Shinsuke, Industrial & Engineering Chemistry Research, 2016, 55(17), 4830-4835

Production Method 14

Reaction Conditions
1.1 Reagents: Di-tert-butyl dicarbonate Catalysts: Magnesium chloride Solvents: Tetrahydrofuran ;  1.5 h, rt
Reference
Reaction of dicarbonates with carboxylic acids catalyzed by weak lewis acids: general method for the synthesis of anhydrides and esters
Bartoli, Giuseppe; Bosco, Marcella; Carlone, Armando; Dalpozzo, Renato; Marcantoni, Enrico; et al, Synthesis, 2007, (22), 3489-3496

Production Method 15

Reaction Conditions
1.1 Reagents: Potassium carbonate Catalysts: Benzyltriethylammonium chloride Solvents: Toluene ;  3 h, reflux
Reference
Reaction of chlorides of phosphoric, sulfonic, and carboxylic acids on solid potassium carbonate surface under PTC circumstances
Jaszay, Zsuzsa M.; Petnehazy, Imre; Toke, Laszlo, Heteroatom Chemistry, 2004, 15(6), 447-450

Production Method 16

Reaction Conditions
Reference
Deoxygenation of amine N-oxides or C-nitroso compounds by dialkyl sulfoxylates
Kagami, Hiroaki; Motoki, Shinichi, Journal of Organic Chemistry, 1978, 43(6), 1267-8

Production Method 17

Reaction Conditions
1.1 Reagents: Triethylamine ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  0 °C → rt; 20 min, rt
Reference
Ph3P-I2 mediated aryl esterification with a mechanistic insight
Phakhodee, Wong; Duangkamol, Chuthamat; Pattarawarapan, Mookda, Tetrahedron Letters, 2016, 57(19), 2087-2089

Production Method 18

Reaction Conditions
1.1 Reagents: Thionyl chloride Catalysts: Dimethylformamide Solvents: Toluene ;  rt → 70 °C; 1 h, 70 °C
1.2 Reagents: Pyridine Solvents: Toluene ;  0 °C
1.3 20 °C; 2 h, reflux
Reference
Organocatalytic Desymmetrisation of Fittig's Lactones: Deuterium as a Reporter Tag for Hidden Racemisation
Spranitz, Peter; Soregi, Petra; Botlik, Bence Bela; Berta, Mate; Soos, Tibor, Synthesis, 2019, 51(5), 1263-1272

Production Method 19

Reaction Conditions
1.1 Reagents: Di-tert-butyl dicarbonate Catalysts: Magnesium carbonate hydroxide Solvents: Tetrahydrofuran ;  25 °C; 24 h, 25 °C
Reference
Preparation of carboxylic acid anhydride by catalytic reaction of dihydrocarbyl dicarbonate and carboxylic acid, and preparation of carboxylic acid ester from the same and alcohol
, World Intellectual Property Organization, , ,

Production Method 20

Reaction Conditions
1.1 Reagents: Dabco ;  6 min, rt
Reference
An efficient and simple procedure for preparation of esters and anhydrides from acid chlorides in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) under solvent-free conditions
Hajipour, A. R.; Mazloumi, Gh., Synthetic Communications, 2002, 32(1), 23-30

Production Method 21

Reaction Conditions
1.1 Reagents: 1,1′-Oxalyldi(imidazole) Solvents: Acetonitrile
1.2 Reagents: Methanesulfonic acid Solvents: Acetonitrile
Reference
A convenient one-stage synthesis of carboxylic acid anhydrides using 1,1'-oxalyldiimidazole
Kitagawa, Tokujiro; Kuroda, Hiroko; Sasaki, Hideaki, Chemical & Pharmaceutical Bulletin, 1987, 35(3), 1262-5

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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:93-97-0)苯甲酸酐
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Quantity:25KG,200KG,1000KG/25KG,200KG,1000KG
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Suzhou Senfeida Chemical Co., Ltd
(CAS:93-97-0)Benzoic anhydride
sfd2962
Purity:99.9%
Quantity:200kg
Price ($):Inquiry
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