N-Hydroxybenzamide

Base Information

• Chemical Name: N-Hydroxybenzamide
• CAS No.: 495-18-1
• Deprecated CAS: 1005-00-1
• Molecular Formula: C7H7 N O2
• Molecular Weight: 137.138
• Hs Code.: 29280090
• European Community (EC) Number: 207-797-6
• NSC Number: 147248,3136
• UNII: K8YW73872D
• DSSTox Substance ID: DTXSID7025421
• Nikkaji Number: J1.560A
• Wikidata: Q27093030
• Pharos Ligand ID: 3BN2D2QH8BGT
• Metabolomics Workbench ID: 146541
• ChEMBL ID: CHEMBL16300
• Mol file: 495-18-1.mol

Synonyms:benzhydroxamic acid;benzhydroxamic acid, calcium salt (2:1);benzhydroxamic acid, monopotassium salt;benzhydroxamic acid, monosodium salt;benzohydroxamic acid

Chemical Property of N-Hydroxybenzamide

Chemical Property:

• Appearance/Colour: brownish crystalline powder
• Melting Point: 126-130 ºC
• Refractive Index: 1.5030 (estimate)
• Boiling Point: 327.1 °C at 760 mmHg
• PKA: pK1: 8.89(0) (20°C)
• Flash Point: 201 °C
• PSA: 49.33000
• Density: 1.237 g/cm³
• LogP: 1.19650
• Storage Temp.: 0-6°C
• Solubility.: Soluble in alcohol. Slightly soluble in ether. Insoluble in benz
• Water Solubility.: 22 g/L (6 ºC)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 119

Purity/Quality:

99.9% ^*data from raw suppliers

Benzohydroxamic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 68-40-20/21/22
• Safety Statements: 45-36/37-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NO
• Uses: Benzhydroxamic acid is used as precursor in the synthesis of novel mono-anionic and di-anionic hydroxamato complexes by reacting with BiPh3 and Bi(O(t)Bu)3, which has anti-bacterial activity against helicobacter pylori. It is used in the photometric determination of trace amounts of vanadium in alloy steels by making mixed-ligand vanadium chelates with ammonium thiocyanate. It is also involved in the palladium catalyzed synthesis of benzisoxazolones. Benzhydroxamic acid may be employed for the Pd-catalyzed synthesis of benzisoxazolones.

Technology Process of N-Hydroxybenzamide

There total 112 articles about N-Hydroxybenzamide 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: 98.3%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) → Benzohydroxamic acid (495-18-1)

Guidance literature:

benzoic acid methyl ester; With hydroxylamine hydrochloride; sodium hydroxide; at 40 - 50 ℃; for 4h;

With sulfuric acid; at 10 ℃;

Reference yield: 97.0%

benzaldehyde (100-52-7) → Benzohydroxamic acid (495-18-1)

Guidance literature:

With polymer-bound N-hydroxybenzenesulfonamide; sodium methylate; In tetrahydrofuran; methanol; at 20 ℃; for 7h;

DOI:10.1021/jo061018g

Reference yield: 91.0%

benzoic acid ethyl ester (93-89-0,99341-95-4) → Benzohydroxamic acid (495-18-1)

Guidance literature:

With hydroxylamine hydrochloride; potassium hydroxide; In methanol; Reagent/catalyst; Concentration;

upstream raw materials:

phenyl benzyl ketone

piloty's acid

tetrachloromethane

N-(benzoyloxy)benzamide

Downstream raw materials:

O-Phenylcarbamyl benzohydroxamic acid

N-benzoyl-O-diphenylacetyl-hydroxylamine

N-(benzoyloxy)benzamide

benzoic acid ethyl ester

Refernces

• 1、 Di Fiore, Anna,Maresca, Alfonso,Supuran, Claudiu T.,De Simone, Giuseppina. "Hydroxamate represents a versatile zinc binding group for the development of new carbonic anhydrase inhibitors". . p. 8838 - 8840. Retrieved 2012.
• 2、 Hegarty, Anthony F.,Mullane, Maria. "Large Stereoelectronic Effect in 1,3-Dehydrohalogenation to form a 1,3-Dipole". . p. 229 - 230. Retrieved 1984.
• 3、 Orth, Elisa S.,Da Silva, Pedro L. F.,Mello, Renata S.,Bunton, Clifford A.,Milagre, Humberto M. S.,Eberlin, Marcos N.,Fiedler, Haidi D.,Nome, Faruk. "Suicide nucleophilic attack: Reactions of benzohydroxamate anion with bis(2,4-dinitrophenyl) phosphate". . p. 5011 - 5016. Retrieved 2009.
• 4、 Nikitas, Nikolaos F.,Apostolopoulou, Mary K.,Skolia, Elpida,Tsoukaki, Anna,Kokotos, Christoforos G.. "Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters". . p. 7915 - 7922. Retrieved 2021/05/03.
• 5、 Zuo, Youpeng,He, Xinwei,Tang, Qiang,Hu, Wangcheng,Zhou, Tongtong,Hu, Wenbo,Shang, Yongjia. "Palladium-Catalyzed 5-exo-dig Cyclization Cascade, Sequential Amination/Etherification for Stereoselective Construction of 3-Methyleneindolinones". . p. 2117 - 2123. Retrieved 2020/12/22.