Benzoic anhydride

Base Information

• Chemical Name: Benzoic anhydride
• CAS No.: 93-97-0
• Molecular Formula: C14H10O3
• Molecular Weight: 226.232
• Hs Code.: 29163900
• European Community (EC) Number: 202-291-1
• NSC Number: 37116
• UNII: 9K7X34FOV2
• DSSTox Substance ID: DTXSID1029122
• Nikkaji Number: J4.689B
• Wikipedia: Benzoic_anhydride
• Wikidata: Q11567424
• Metabolomics Workbench ID: 56015
• ChEMBL ID: CHEMBL3185530
• Mol file: 93-97-0.mol

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

Chemical Property of Benzoic anhydride

Chemical Property:

• Appearance/Colour: white to almost white crystals or crystalline
• Vapor Pressure: 2.29E-05mmHg at 25°C
• Melting Point: 38-42 °C(lit.)
• Refractive Index: 1.589
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 168.4 °C
• PSA: 43.37000
• Density: 1.211 g/cm³
• LogP: 2.68380
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Solubility.: 0.01g/l (experimental)
• Water Solubility.: 0.01 g/L
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 226.062994177
• Heavy Atom Count: 17
• Complexity: 245

Purity/Quality:

99% ^*data from raw suppliers

BenzoicAnhydride(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• Safety Statements: 26-39-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Acid Anhydrides, Other
• Canonical SMILES: C1=CC=C(C=C1)C(=O)OC(=O)C2=CC=CC=C2
• Uses: Benzoic 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. In organic syntheses, as benzoylating agent in the manufacture of pharmaceuticals, dyes, and intermediates. Benzoic 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.

Technology Process of Benzoic anhydride

There total 336 articles about Benzoic anhydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-benzoyl-4,5-dichloropyridazin-3(2H)-one (155164-66-2) → 4,5-dichloro-2H-pyridazin-3-one (932-22-9) + benzoic acid anhydride (93-97-0)

Guidance literature:

With zinc(II) chloride; In acetonitrile; for 7h; Heating;

DOI:10.1081/SCC-200048939

Reference yield: 79.0%

N-(acetyloxy)-N-(((4-(methyloxy)phenyl)methyl)oxy)benzamide (139259-91-9) → benzaldehyde (100-52-7) + benzoic acid anhydride (93-97-0) + benzoic acid (65-85-0,8013-63-6) + 4-Methoxybenzyl alcohol (105-13-5)

Guidance literature:

With sulfuric acid; water-d2; In [D₃]acetonitrile; at 34.9 ℃; Rate constant; Mechanism; Product distribution; other O-(p-substituted benzyl) N-acetoxybenzohydroxamates; var. conc. of sulfuric acid;

Reference yield: 68.0%

N-(acetyloxy)-N-(((4-methylphenyl)methyl)oxy)benzamide (139259-94-2) → 4-Methylbenzyl alcohol (589-18-4) + Benzohydroxamic acid (495-18-1) + 4-methylbenzyl benzoate (38418-10-9) + benzaldehyde (100-52-7) + benzoic acid anhydride (93-97-0) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With sulfuric acid; water-d2; In [D₃]acetonitrile; at 34.9 ℃; Rate constant; var. conc. of sulfuric acid;

upstream raw materials:

pyridine

acetic anhydride

benzoic acid

acetamide

Downstream raw materials:

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside

benzoic acid methyl ester

2-diazo-acetophenone

N-benzoylpiperidine

Refernces

• 1、 Yadav,Naik, Suguna S.. "Clay-supported liquid-liquid-solid phase transfer catalysis: Synthesis of benzoic anhydride". . p. 141 - 146. Retrieved 2000.
• 2、 Kaspera, Rüdiger,Cape, Jonathan L.,Faraldos, Juan A.,Ketchum, Raymond E.B.,Croteau, Rodney B.. "Synthesis and in vitro evaluation of taxol oxetane ring D precursors". . p. 2017 - 2019. Retrieved 2010.
• 3、 Chen, Xiangyang,Houk, Kendall N.,Mo, Jia-Nan,Su, Junqi,Umanzor, Alexander,Zhang, Zheng,Zhao, Jiannan. "Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow". supporting information. . Retrieved 2022/01/06.
• 4、 Fan, Qinghua,Pan, Yixiao,Walsh, Patrick J.,Xu, Jianbin,Xu, Lijin,Xu, Xin,Yu, Zexin,Zhao, Haoqiang. "Rh(I)-Catalyzed Direct C6?H Arylation of 2-Pyridones with Aryl Carboxylic Acids". supporting information. p. 3995 - 4001. Retrieved 2021/07/02.