4'-Nitro-4-biphenylsulfonic acid

Base Information

• Chemical Name: 4'-Nitro-4-biphenylsulfonic acid
• CAS No.: 91493-72-0
• Molecular Formula: C₁₂H₉NO₅S
• Molecular Weight: 279.273
• DSSTox Substance ID: DTXSID00699014
• Wikidata: Q82629669
• Mol file: 91493-72-0.mol

Synonyms:91493-72-0;4'-NITRO-4-BIPHENYLSULFONIC ACID;4'-nitrobiphenyl-4-sulfonic acid;SCHEMBL3612769;4-Nitro-4-biphenylsulfonic acid;DTXSID00699014;YTLRCQWMAYGBFQ-UHFFFAOYSA-N;4'-Nitro-biphenyl-4-sulfonic acid;AKOS015966320;4'-Nitro[1,1'-biphenyl]-4-sulfonic acid

Chemical Property of 4'-Nitro-4-biphenylsulfonic acid

Chemical Property:

• Melting Point: 149-150 °C
• PKA: -0.86±0.50(Predicted)
• Density: 1.474±0.06 g/cm3(Predicted)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 279.02014356
• Heavy Atom Count: 19
• Complexity: 408

Purity/Quality:

99%min ^*data from raw suppliers

4'-NITRO-4-BIPHENYLSULFONIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC=C(C=C2)S(=O)(=O)O)[N+](=O)[O-]

Technology Process of 4'-Nitro-4-biphenylsulfonic acid

There total 2 articles about 4'-Nitro-4-biphenylsulfonic 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: 61.0%

1-phenyl-4-nitrobenzene (92-93-3) → 4-nitrobiphenylsulfonic acid (91493-72-0)

Guidance literature:

With chlorosulfonic acid; In chloroform; at 20 - 60 ℃; for 6h;

Reference yield:

→ 4-nitrobiphenylsulfonic acid (91493-72-0)

Guidance literature:

With nitric acid;

Reference yield:

4-nitrobiphenylsulfonic acid (91493-72-0) → (S)-2-[4'-(3-Methoxy-benzoylamino)-biphenyl-4-sulfonylamino]-3-methyl-butyric acid

Guidance literature:

Multi-step reaction with 5 steps

1: SOCl₂ / Heating

2: NaHCO₃ / CH₂Cl₂

3: SnCl₂ / dimethylformamide

4: iPr₂EtN / CH₂Cl₂

5: TFA

With thionyl chloride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; tin(ll) chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.06.019

upstream raw materials:

1-phenyl-4-nitrobenzene

Downstream raw materials:

4'-nitrobiphenyl-4-sulfonyl chloride

N-({4'-[(1-benzofuran-2-ylcarbonyl)amino]-1,1'-biphenyl-4-yl}sulfonyl)glycine t-butyl ester

Refernces

• 1、 Wu, Junjun,Rush III, Thomas S.,Hotchandani, Rajeev,Du, Xuemei,Geck, Mary,Collins, Elisabeth,Xu, Zhang-Bao,Skotnicki, Jerry,Levin, Jeremy I.,Lovering, Frank E.. "Identification of potent and selective MMP-13 inhibitors". . p. 4105 - 4109. Retrieved 2007/10/03.
• 2、 O'Brien, Patrick M.,Ortwine, Daniel F.,Pavlovsky, Alexander G.,Picard, Joseph A.,Sliskovic, Drago R.,Roth, Bruce D.,Dyer, Richard D.,Johnson, Linda L.,Man, Chiu Fai,Hallak, Hussein. "Structure-activity relationships and pharmacokinetic analysis for a series of potent, systemically available biphenylsulfonamide matrix metalloproteinase inhibitors". . p. 156 - 166. Retrieved 2007/10/03.