BENZENESULFOHYDROXAMIC ACID

Base Information

• Chemical Name: BENZENESULFOHYDROXAMIC ACID
• CAS No.: 599-71-3
• Molecular Formula: C6H7 N O3 S
• Molecular Weight: 173.192
• Hs Code.: 2935009090
• European Community (EC) Number: 209-973-8
• NSC Number: 45357
• UNII: C64L4UMH19
• DSSTox Substance ID: DTXSID4060521
• Nikkaji Number: J54.021H
• Wikipedia: Piloty%27s_acid
• Wikidata: Q27275238
• Pharos Ligand ID: 72JGZXVK2WVZ
• ChEMBL ID: CHEMBL55310
• Mol file: 599-71-3.mol

Synonyms:Benzenesulfohydroxamicacid; Hydroxylamine, N-(phenylsulfonyl)-; N-(Phenylsulfonyl)hydroxylamine;N-Hydroxybenzenesulfonamide; NSC 45357; Piloty's acid

Chemical Property of BENZENESULFOHYDROXAMIC ACID

Chemical Property:

• Appearance/Colour: white granular crystalline powder
• Vapor Pressure: 1.52E-05mmHg at 25°C
• Melting Point: 122-125 ºC
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 351.5 ºC at 760 mmHg
• PKA: 9.29(at 25℃)
• Flash Point: 166.4 ºC
• PSA: 74.78000
• Density: 1.431 g/cm³
• LogP: 1.82580
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 173.01466426
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

99.5% ^*data from raw suppliers

N-Hydroxybenzenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)NO
• Uses: Benzenesulfohydroxamic Acid can be used as HNO/NO- donor in biochemical model studies, In the Angeli-Rimini test for aldehydes.

Technology Process of BENZENESULFOHYDROXAMIC ACID

There total 6 articles about BENZENESULFOHYDROXAMIC ACID 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: 27.0%

benzenesulfonyl chloride (98-09-9) → piloty's acid (599-71-3)

Guidance literature:

With hydroxylamine hydrochloride; potassium carbonate; In methanol; water; Inert atmosphere; Cooling;

DOI:10.1021/ol9018198

Reference yield: 6.7%

benzenesulfonyl chloride (98-09-9) → piloty's acid (599-71-3) + benzenesulfonyl hydrazinium benzenesulfonate (127838-59-9)

Guidance literature:

With hydroxylamine hydrochloride; potassium carbonate; In methanol; water; at 0 ℃;

DOI:10.1016/S0040-4020(01)85786-0

Reference yield:

S-Nitrosoglutathione (57564-91-7) + sodium benzenesulfonate (873-55-2) → piloty's acid (599-71-3) + S-Phenylsulphonylglutathione (97512-84-0)

Guidance literature:

In aq. buffer; for 6h; pH=4; Kinetics; Darkness;

DOI:10.1016/j.tetlet.2013.08.011

upstream raw materials:

benzenesulfonyl chloride

ethanol

hydroxylamine

S-Nitrosoglutathione

Downstream raw materials:

N-hydroxy-N-piperidinomethyl-benzenesulfonamide

cinnamic acid N-hydroxylamide

Benzohydroxamic acid

p-tolyl-glyoxylohydroximic acid

Refernces

• 1、 Zhou, Yang,Cink, Ruth B.,Fejedelem, Zachary A.,Cather Simpson,Seed, Alexander J.,Sampson, Paul,Brasch, Nicola E.. "Development of Photoactivatable Nitroxyl (HNO) Donors Incorporating the (3-Hydroxy-2-naphthalenyl)methyl Phototrigger". . p. 1745 - 1755. Retrieved 2018/04/17.
• 2、 Banerjee, Ranjan,Bruce King. "Synthesis of cyclic hydroxamic acids through -NOH insertion of ketones". supporting information; experimental part. p. 4580 - 4583. Retrieved 2009/12/09.