4-Acetamidobenzenesulfonyl azide

Base Information

• Chemical Name: 4-Acetamidobenzenesulfonyl azide
• CAS No.: 2158-14-7
• Molecular Formula: C8H8N4O3S
• Molecular Weight: 240.243
• Hs Code.: 29350090
• DSSTox Substance ID: DTXSID10408598
• Nikkaji Number: J1.396.154I
• NSC Number: 82543
• Mol file: 2158-14-7.mol

Synonyms:4-Acetamidobenzenesulfonyl azide;2158-14-7;N-(4-azidosulfonylphenyl)acetamide;p-ABSA;4-acetamidophenylsulfonyl azide;4-acetamidobenzenesulphonyl azide;4-(acetylamino)benzenesulfonyl azide;4-acetamidobenzene-1-sulfonyl azide;MFCD00029626;NSC 82543;4-Acetamidophenylsulfonyl azide;N-(4-Azidosulfonylphenyl)acetamide;4-acetamidobenzenesulfonylazide;4-Acetamidobenzene sulfonyl azide;4-Acetamidophenyl sulphonyl azide;SCHEMBL25234;p-acetamidobenzensulfonyl azide;4-acetamidobenzenesulphonylazide;4-acetylaminobenzensulfonylazide;p-acetamidobenzenesulfonyl azide;4-acetamido benzenesulfonylazide;p-acetamidobenzenesulphonyl azide;4-Acetylaminobenzenesulfonylazide;p-acetamidobenzene sulfonyl azide;4-Acetamidobenzensesulfonyl azide;DTXSID10408598;NTMHWRHEGDRTPD-UHFFFAOYSA-N;4-acetylamino-benzenesulfonyl azide;4-acetylamino-benzenesulphonyl azide;BCP29216;NSC82543;4-(acetylamino)benzene sulfonylazide;NSC-82543;NS-00009;SY009104;A1786;BB 0263019;FT-0617376;NS00123086;EN300-86232;A815501;J-014157;J-514273;Butanedioic acid, 2,3-diacetyl-, 1,4-dimethyl ester;N-(4-azidosulfonylphenyl)acetamide pound>>4-acetamidobenzene-1-sulfonyl azide

Chemical Property of 4-Acetamidobenzenesulfonyl azide

Chemical Property:

• Appearance/Colour: white crystals
• Melting Point: 107-111 °C(lit.)
• PSA: 121.37000
• LogP: 2.25056
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 240.03171130
• Heavy Atom Count: 16
• Complexity: 400

Purity/Quality:

99% ^*data from raw suppliers

4-Acetamidobenzenesulfonyl azide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)S(=O)(=O)N=[N+]=[N-]
• Uses: 4-Acetamidobenzenesulfonyl azide is an important organic intermediate (building block) to synthetize substituted amidobenzene products. 4-Acetamidobenzenesulfonyl azide is used as a hydroazidation catalyst for facile preparation of organoazides. It is used as a reagent for synthesis of: monosaccharide-derived alcohols, a late-stage intermolecular C-H olefination, intramolecular isomuenchnone cycloaddition approach to antitumor agents, rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates and Suzuki-Miyaura cross coupling reaction. Hydroazidation Catalyst for Facile Preparation of OrganoazidesDiazo transfer agent.

Technology Process of 4-Acetamidobenzenesulfonyl azide

There total 5 articles about 4-Acetamidobenzenesulfonyl azide 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: 99.0%

p-acetylaminobenzenesulfonyl chloride (121-60-8) → 4-acetamidobenzenesulfonyl azide (2158-14-7)

Guidance literature:

With sodium azide; In acetone; at 25 ℃; for 48h; Inert atmosphere;

DOI:10.1039/c5cc05740j

Reference yield: 94.0%

N-acetylsulfanilic acid (121-62-0) → 4-acetamidobenzenesulfonyl azide (2158-14-7)

Guidance literature:

N-acetylsulfanilic acid; With trichloroisocyanuric acid; triphenylphosphine; In tetrahydrofuran; at 0 - 5 ℃;

With sodium azide; In tetrahydrofuran; at 5 - 20 ℃;

DOI:10.1080/17415993.2013.801476

Reference yield: 60.0%

→ 4-acetamidobenzenesulfonyl azide (2158-14-7)

Guidance literature:

upstream raw materials:

p-acetylaminobenzenesulfonyl chloride

N-acetylsulfanilic acid

Downstream raw materials:

p-acetylaminobenzenesulfonamide

dimethyl diazomethylphosphonate

trans-2-buten-1-yl diazoacetate

Diazo-acetic acid (Z)-but-2-enyl ester

Refernces

• 1、 Dabbagh,Teimouri. "Insertion reaction of azidosulfonyl azo dye with model alicyclic and heterocyclic compounds". . p. 1464 - 1470. Retrieved 2008.
• 2、 Drikermann, Denis,M??el, Robert S.,Al-Jammal, Walid K.,Vilotijevic, Ivan. "Synthesis of Allylboranes via Cu(I)-Catalyzed B-H Insertion of Vinyldiazoacetates into Phosphine-Borane Adducts". supporting information. p. 1091 - 1095. Retrieved 2020/02/15.
• 3、 -. "Microchannel synthesis method of aryl sulfonyl azide". Paragraph 0033-0034. . Retrieved 2019/07/04.