2-Nitrobenzenesulfonamide

Base Information

• Chemical Name: 2-Nitrobenzenesulfonamide
• CAS No.: 5455-59-4
• Molecular Formula: C6H6N2O4S
• Molecular Weight: 202.191
• Hs Code.: 29350090
• European Community (EC) Number: 625-668-6
• NSC Number: 629275,23381
• DSSTox Substance ID: DTXSID30202974
• Nikkaji Number: J236.633I
• ChEMBL ID: CHEMBL361396
• Mol file: 5455-59-4.mol

Synonyms:2-Nitrobenzenesulfonamide;5455-59-4;2-Nitro-benzenesulfonamide;2-nitrobenzene-1-sulfonamide;2-Nitrobenzenesulphonamide;MFCD00009807;NSC629275;nitrobenzenesulfonamide;NSC23381;2-nitrophenylsulfonamide;o-nitrobenzenesulfonylamide;2-nitrobenzene-sulfonamide;SCHEMBL370668;CHEMBL361396;SCHEMBL7256089;2-Nitrobenzenesulfonamide, 98%;AMY5016;DTXSID30202974;1-nitro-2-(sulfinatoamino)benzene;2-NITROPHENYL SULFONYLAMINE;BCP25648;NSC 23381;NSC-23381;AKOS000200557;CS-W008096;HY-W008096;NSC-629275;PS-6117;SB37611;NCGC00338999-01;2-(Hydroxy(oxido)amino)benzenesulfonamide;BP-12501;SY058096;FT-0613180;N0705;EN300-15720;AB01099064-03;A830240;J-510172;Z45415562

Chemical Property of 2-Nitrobenzenesulfonamide

Chemical Property:

• Appearance/Colour: yellow to light brown crystalline powder
• Vapor Pressure: 3.18E-07mmHg at 25°C
• Melting Point: 189-194 °C
• Refractive Index: 1.611
• Boiling Point: 418.8 °C at 760 mmHg
• PKA: 9.24±0.60(Predicted)
• Flash Point: 207.1 °C
• PSA: 114.36000
• Density: 1.552 g/cm³
• LogP: 2.54650
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO, Methanol (Slightly, Heated, Sonicated)
• Water Solubility.: Slightly soluble in water.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 202.00482785
• Heavy Atom Count: 13
• Complexity: 289

Purity/Quality:

99%, ^*data from raw suppliers

2-Nitro-benzenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)[N+](=O)[O-])S(=O)(=O)N
• Uses: 2-Nitro-benzenesulfonamide is a carbonic anhydrase inhibitor.

Technology Process of 2-Nitrobenzenesulfonamide

There total 8 articles about 2-Nitrobenzenesulfonamide 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: 100.0%

2-Nitrobenzenesulfonyl chloride (1694-92-4) → 2-Nitrobenzenesulfonamide (5455-59-4)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/acs.joc.8b01156

Reference yield: 87.0%

aniline (62-53-3) + 4-nitro-1-(o-nitrobenzenesulfonyl)imidazole → 2-Nitrobenzenesulfonamide (5455-59-4) + 1H-4(5)-nitroimidazole (3034-38-6) + 1-phenyl-4-nitro-1H-imidazole (41384-83-2)

Guidance literature:

In methanol; water; at 65 - 70 ℃; for 2h;

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[5-(N-benzyl-formimidoylamino)-4-(2-nitro-benzenesulfonylaminocarbonyl)-imidazol-1-yl]-tetrahydro-furan-3-yl ester; compound with benzylamine → 2-Nitrobenzenesulfonamide (5455-59-4) + 2',3',5'-tri-O-acetyl-1-benzylinosine

Guidance literature:

With trifluoroacetic acid; In acetonitrile; at 80 ℃;

DOI:10.1016/j.tetlet.2005.05.137

upstream raw materials:

2-Nitrobenzenesulfonyl chloride

aniline

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[1-(2-nitro-benzenesulfonyl)-6-oxo-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester

2-Chloronitrobenzene

Downstream raw materials:

acetoacetyl-(2-nitro-benzenesulfonyl)-amine

2-nitro-benzenesulfonic acid-(trichlorophosphoranyliden-amide)

2-AMINOBENZENESULFONAMIDE

ethyl ((2-nitrophenyl)sulfonyl)carbamate

Refernces

Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes

10.1021/acs.orglett.9b02819

The research explores an efficient method for synthesizing chiral heterocycles using a rhodium-catalyzed asymmetric ring opening reaction (ARO) of oxabicyclic alkenes. The study aims to address the challenges associated with using primary amines as nucleophiles in ARO reactions, which typically result in low yields and enantioselectivities. 2-nitrobenzenesulfonamide plays a crucial role as a pronucleophile in the rhodium-catalyzed asymmetric ring-opening reaction (ARO) of oxabicyclic alkenes. Specifically, it serves as a surrogate for primary amines, which traditionally face challenges such as low yields and enantioselectivities in ARO reactions. The 2-nitrobenzenesulfonamide derivatives of amino acids, such as alanine (2m), phenylalanine (2a), and valine (2o), are used to explore the ring-opening of oxabicyclic alkenes. These derivatives enable the formation of hydroxyesters and, subsequently, oxazinones through lactonization, demonstrating a high degree of enantioselectivity. The study concluded that the use of molecular sieves was crucial for driving the lactonization to completion, and the pairwise combination of chiral catalysts and nucleophiles allowed for the predictable and highly enantioselective synthesis of novel oxazinones and hydroxyesters.

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