1623-93-4

Basic information

• Product Name: 4-BIPHENYLSULFONYL CHLORIDE
• Synonyms: SALOR-INT L301086-1EA;4-PHENYLBENZENESULFONYL CHLORIDE;4-BIPHENYLSULFONYL CHLORIDE;4-BIPHENYLSULPHONYL CHLORIDE;BIPHENYL-4-SULFONYL CHLORIDE;[1,1'-biphenyl]-4-sulphonyl chloride;Biphenyl-4-sulphonyl chloride;4-Biphenylsulfonyl chloride, 98+%
• CAS NO: 1623-93-4
• Molecular Formula: C₁₂H₉ClO₂S
• Molecular Weight: 252.72
• EINECS: 216-609-1
• Product Categories: Phenyls & Phenyl-Het;Sulphonyl Chlorides;Phenyls & Phenyl-Het;Sulphonyl Chlorides;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 1623-93-4.mol
• Article Data: 19

Chemical Properties

• Melting Point: 103-108 °C(lit.)
• Boiling Point: 200-205°C 6mm
• Flash Point: 200-205°C/6mm
• Appearance: White/Crystalline Powder
• Density: 1.32 g/cm³
• Vapor Pressure: 1.7E-05mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 2694373
• CAS DataBase Reference: 4-BIPHENYLSULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BIPHENYLSULFONYL CHLORIDE(1623-93-4)
• EPA Substance Registry System: 4-BIPHENYLSULFONYL CHLORIDE(1623-93-4)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1623-93-4(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

Different sources of media describe the Uses of 1623-93-4 differently. You can refer to the following data:
1. Reactant for:? ;Preparation of anilinopyrimidinesulfonamides as potential anticancer agents1? ;Synthesis of inhibitors of the hypoxia inducible factor pathway2? ;Preparation of hydroxy-sulfonyl-piperidinyl butyramides as HDAC inhibitors and potential antitumors3? ;Palladium-catalyzed desulfitative C-arylation4
2. It is a reactant for preparation of anilinopyrimidinesulfonamides as potential anticancer agents, synthesis of inhibitors of the hypoxia inducible factor pathway. It participates in the preparation of hydroxy-sulfonyl-piperidinyl butyramides as HDAC inhibitors and potential antitumors and is also involved in palladium-catalyzed desulfitative C-arylation.

InChI:InChI=1/C12H9ClO2S/c13-16(14,15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H

Synthetic route

4-biphenylmonosulfonic acid (2113-68-0) → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide at 80℃; for 2h;	80%
With P,P-dichlorophenylphosphine oxide at 90℃; for 24h;
With trichlorophosphate Yield given;

4-Aminobiphenyl (92-67-1) → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
Stage #1: 4-phenylalanine With hydrogenchloride; acetic acid; sodium nitrite In water; acetonitrile at 0 - 5℃; Stage #2: With sulfur dioxide; copper dichloride In water; acetonitrile at 20℃; for 16h;	80%

biphenyl-4-sulphonic acid potassium salt → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate at 130℃; for 3h;	77.3%

biphenyl (92-52-4) → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
With chlorosulfonic acid; thionyl chloride for 168h; Ambient temperature;	43%
With chlorosulfonic acid at 5 - 65℃;
With chlorosulfonic acid In chloroform at 20℃; for 0.75h;
Multi-step reaction with 2 steps 1: chlorosulfonic acid / chloroform / 1.5 h / Inert atmosphere; Cooling with ice 2: thionyl chloride; N,N-dimethyl-formamide / 2 h / 80 °C View Scheme

potassium salt of/the/ dibenzenesulfonic acid-(4) → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
With phosphorus pentachloride

4-bromo-1,1'-biphenyl (92-66-0) → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
Stage #1: 4-bromo-1,1'-biphenyl With iodine; magnesium In tetrahydrofuran for 1h; Heating; Stage #2: With sulfur dioxide In tetrahydrofuran at -40℃; for 0.5h; Stage #3: With sulfuryl dichloride In tetrahydrofuran at -40 - 20℃;

biphenyl (92-52-4) + C6H4Cl2, C12H9Cl, HCl → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ClSO3H / CHCl3 / 20 °C 2: SOCl2 / dimethylformamide / Heating View Scheme

biphenyl (92-52-4) + trans-PdPh(I)(PEt2Ph)2 → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid / 1 h / 80 °C 2: phosphorus oxychloride View Scheme

biphenyl (92-52-4) + methyldibenzothiophene, ethyldibenzothiophene, H2S,others → 4-diphenylsulfonyl chloride (1623-93-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 0.5 h 2: phenylphosphonic dichloride / 24 h / 90 °C View Scheme

1-(4-chlorophenyl)-N3,N3-dimethylpropane-1,3-diamine (885672-69-5) + 4-diphenylsulfonyl chloride (1623-93-4) → N-[1-(4-chlorophenyl)-3-dimethylaminopropyl]-4-phenyl-benzenesulfonamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 18h;	100%

4-diphenylsulfonyl chloride (1623-93-4) + 1-amino-2-propene (107-11-9) → N-allyl-[1,1'-biphenyl]-4-sulfonamide (1136711-00-6)

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 3h;	100%

(R)-phenylglycine (875-74-1) + 4-diphenylsulfonyl chloride (1623-93-4) → N-(biphenyl-4-sulfonyl)-D-phenylglycine (193808-16-1)

Conditions	Yield
With sodium hydroxide In diethyl ether at 20℃; for 16h;	99%

4-diphenylsulfonyl chloride (1623-93-4) + L-proline methyl ester monohydrochloride (2133-40-6) → methyl (S)-1-([1,1’-biphenyl]-4-ylsulfonyl)pyrrolidine-2-carboxylate

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at 20℃; for 5h; Inert atmosphere;	98%

1,3-benzodioxol-5-ylmethyl amine (2620-50-0) + 4-diphenylsulfonyl chloride (1623-93-4) → N-(1,3-benzodioxol-5-ylmethyl)-4-diphenylsulfonamide

Conditions	Yield
With triethylamine In dichloromethane for 4h; Reflux;	98%

4-diphenylsulfonyl chloride (1623-93-4) → 4-biphenylthiol (19813-90-2)

Conditions	Yield
With tris(2-carboxyethyl)phosphine In 1,4-dioxane; water for 6h; Heating;	96%
With triphenylphosphine In 1,4-dioxane; water for 16h; Heating;	84%

N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-aminobenzamide (1365699-34-8) + 4-diphenylsulfonyl chloride (1623-93-4) → 4β-[4'-(biphenyl-4-sulfonamido)benzamide]podophyllotoxin (1365699-51-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	96%

1,2,3,4-Tetrahydro-quinoline-3-carboxylic acid methyl ester (177198-62-8, 177198-64-0, 177202-62-9) + 4-diphenylsulfonyl chloride (1623-93-4) → (±)-methyl 1-([1,1'-biphenyl]-4-ylsulfonyl)-1,2,3,4-tetrahydroquinoline-3-carboxylate

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In chloroform for 16h; Inert atmosphere; Reflux;	96%

4-diphenylsulfonyl chloride (1623-93-4) + (1R,2R,3S,5S)-(5Z)-7-(2-amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)-hept-5-enoic acid methyl ester (197069-37-7) → methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-biphenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate (120632-50-0)

Conditions	Yield
With triethylamine In dichloromethane for 1h; Ambient temperature;	95.3%

8-amino quinoline (578-66-5) + 4-diphenylsulfonyl chloride (1623-93-4) → N-(quinolin-8-yl)-[1,1’-biphenyl]-4-sulfonamide

Conditions	Yield
With pyridine at 0 - 20℃;	95%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	77%
With triethylamine In dichloromethane at 0 - 20℃;	70%

4-diphenylsulfonyl chloride (1623-93-4) + 4β-amino-4-deoxypodophyllotoxin (155252-35-0) → 4β-[biphenyl-4-sulfonamido]podophyllotoxin (1365699-73-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	95%

C14H21N5O2 + 4-diphenylsulfonyl chloride (1623-93-4) → C26H29N5O4S (1401318-33-9)

Conditions	Yield
In dichloromethane Inert atmosphere;	95%

1-acetoxy-1-phenylethene (2206-94-2) + 4-diphenylsulfonyl chloride (1623-93-4) → 2-([1,1′-biphenyl]-4-ylsulfonyl)-1-phenylethan-1-one (130188-81-7)

Conditions	Yield
With fac-Ir(ppy)3 In dichloromethane at 20℃; Inert atmosphere; Irradiation;	95%

4-diphenylsulfonyl chloride (1623-93-4) + copper(l) cyanide → 4-cyano-1,1'-biphenyl (2920-38-9)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); copper acetylacetonate; sodium carbonate In 1,4-dioxane at 130℃; for 24h; Sealed tube; Air;	93%

4-diphenylsulfonyl chloride (1623-93-4) + D-phenylalanine methyl ester hydrochloride (13033-84-6) → methyl ([1,1'-biphenyl]-4-ylsulfonyl)-D-phenylalaninate

Conditions	Yield
With pyridine at 130℃; for 0.2h; Microwave irradiation;	93%

4-diphenylsulfonyl chloride (1623-93-4) + 4-(4-bromo-phenyl)-1-nicotinoyl semicarbazide (824420-41-9) → biphenyl-4-sulfonic acid (4-bromophenyl)-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-yl)amide

Conditions	Yield
With polymer-supported 1,3,2-diazaphosphorinane derivative In acetonitrile at 150℃; for 0.333333h; microwave irradiation;	92%

benzyl 7-amino-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (1016265-90-9) + 4-diphenylsulfonyl chloride (1623-93-4) → benzyl-7-([(4-biphenyl)sulfonyl]amino)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Conditions	Yield
With pyridine In dichloromethane at 20℃;	92%

1-ethenyl-2-pyrrolidinone (88-12-0) + 4-diphenylsulfonyl chloride (1623-93-4) → (E)-1-(2-(biphenyl-4-ylsulfonyl)vinyl)pyrrolidin-2-one (1429936-59-3)

Conditions	Yield
With sodium dihydrogenphosphate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In acetonitrile at 20℃; for 8h; Inert atmosphere; Irradiation;	92%

5-hydroxypentylamine (2508-29-4) + 4-diphenylsulfonyl chloride (1623-93-4) → biphenyl-4-sulfonic acid-(5-hydroxypentyl)amide

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2h;	91%

4-diphenylsulfonyl chloride (1623-93-4) + D-phenylalanine tert-butyl ester (3081-28-5, 6404-30-4, 16367-71-8, 16874-17-2) → C25H27NO4S (1469273-31-1)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;	91%

4-diphenylsulfonyl chloride (1623-93-4) + 2-allyl-4-methyl-phenylamine (59816-83-0) → C22H21NO2S

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 16h;	91%

C9H9Cl2N3OS (438012-15-8) + 4-diphenylsulfonyl chloride (1623-93-4) → biphenyl-4-sulfonic acid (3,4-dichloro-phenyl)-(5-methyl-[1,3,4]oxadiazol-2-yl)-amide

Conditions	Yield
With polymer-supported 1,3,2-diazaphosphorinane derivative at 150℃; for 0.333333h; microwave irradiation;	90%

4-diphenylsulfonyl chloride (1623-93-4) + 5-aminopentanoic acid (660-88-8) → 5-(biphenyl-4-sulfonylamino)pentanoic acid

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2h;	90%

2-allyl-phenylamine (32704-22-6) + 4-diphenylsulfonyl chloride (1623-93-4) → C21H19NO2S

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 16h;	90%
With pyridine In chloroform at 0 - 20℃;

2-allyl-5-methylaniline (477983-48-5) + 4-diphenylsulfonyl chloride (1623-93-4) → C22H21NO2S

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 16h;	90%

4-diphenylsulfonyl chloride (1623-93-4) + N-benzyl-2-(pyridin-3-ylcarbonyl)hydrazinecarbothioamide (211572-59-7) → biphenyl-4-sulfonic acid benzyl-(5-pyridin-3-yl-[1,3,4]thiadiazol-2-yl)-amide

Conditions	Yield
With polymer-supported 1,3,2-diazaphosphorinane derivative at 150℃; for 0.333333h; microwave irradiation;	89%

4-Aminobutanol (13325-10-5) + 4-diphenylsulfonyl chloride (1623-93-4) → biphenyl-4-sulfonic acid-(4-hydroxybutyl)amide (871113-50-7)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2h;	89%
With pyridine In dichloromethane at 20℃; for 2h;

4-diphenylsulfonyl chloride (1623-93-4) + leelamine (1446-61-3) → C32H39NO2S

Conditions	Yield
With triethylamine In dichloromethane at 0 - 23℃;	89%

4-diphenylsulfonyl chloride (1623-93-4) + 3-(4-(aminomethyl)benzyl)-7-ethyl-1H-purine-2,6(3H,7H)-dione trifluoroacetic acid salt → N-(4-((7-ethyl-2,6-dioxo-1H-purin-3(2H,6H,7H)-yl)methyl)benzyl)-[1,1′-biphenyl]-4-sulfonamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 12h;	89%

4-diphenylsulfonyl chloride (1623-93-4) + (S)-N-(5,6-dihydroxybenzo[d]thiazol-2-yl)pyrrolidine-2-carboxamide hydrobromide → (S)-1-([1,1'-biphenyl]-4-ylsulfonyl)-N-(5,6-dihydroxybenzo[d]thiazol-2-yl)pyrrolidine-2-carboxamide

Conditions	Yield
With pyridine In acetonitrile for 14h;	89%

Upstream product

• 92-52-4 biphenyl 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 92-67-1 4-phenylalanine 
• 2113-68-0 4-biphenylmonosulfonic acid 

Downstream Products

• 111711-84-3 1-(Biphenyl-4-sulfonyl)-5-isopropoxy-pyrrolidin-2-one 
• 120632-50-0 methyl (5Z)-7-((1R,2R,3S,5S)-2-(p-biphenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoate 
• 115206-11-6 (Z)-7-[(1S,2R,3R,4R)-3-(Biphenyl-4-sulfonylamino)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester 
• 32337-50-1 Biphenyl-4-sulfonic acid m-tolyl ester 
• 166964-10-9 N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 
• 378238-21-2 (S)-N-(biphenyl-4-sulfonyl)proline 

Relevant articles and documents

POTENTIAL HYPOGLYCEMIC SULFONYLUREAS.

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Fragment-Based Design, Synthesis, and Biological Evaluation of 1-Substituted-indole-2-carboxylic Acids as Selective Mcl-1 Inhibitors

Based on a known selective Mcl-1 inhibitor, 6-chloro-3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-1H-indole-2-carboxylic acid, we applied a fragment-based approach to obtain new molecules that extended into the p1 pocket of the BH3 groove and then exhibited binding selectivity for the Mcl-1 over the Bcl-2 protein. After we deconstructed the 1H-indole-2-carboxylic acid from the parental molecule, a benzenesulfonyl was substituted at the 1-position to adopt a geometry preferred for accessing the p1 pocket according to the binding mode of the parental molecule identified by X-ray crystallography. A linear relationship between the free energy of ligand binding (ΔG) and the count of non-hydrogen heavy atoms (HAC) was maintained during the molecular growing to occupy the p1 pocket. Finally, we not only obtained compound 12 with a 7.5-fold selectivity to Mcl-1 (Ki = 0.48 μM by fluorescence polarization) over Bcl-2 (Ki = 3.6 μM), but also provided evidence that additional occupation of the p1 pocket is more favorable for Mcl-1 than for Bcl-2 binding, and contributes more to Mcl-1 inhibition than occupation of the p2 pocket. Compound 12 exhibited a selective killing ability on Mcl-1-dependent cancer cells.

Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides

A series of arene and heteroarene sulfonamides were prepared in one vessel from aryl and heteroaryl bromides via conversion into the corresponding Grignard reagents using either magnesium or isopropylmagnesium chloride and subsequent reaction with sulfur dioxide, sulfuryl chloride, and an amine.