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Chemical Structure| 1623-93-4 Chemical Structure| 1623-93-4
Chemical Structure| 1623-93-4

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Biphenyl-4-sulfonyl chloride is an inhibitor of HDAC and it has synthetic applications in palladium-catalyzed desulfitative C-arylation.

Synonyms: p-Phenylbenzenesulfonyl chloride; Biphenyl-4-sulfonyl chloride; p-Biphenylsulfonyl chloride

4.5 *For Research Use Only !

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Product Details of 4-Biphenylsulfonyl chloride

CAS No. :1623-93-4
Formula : C12H9ClO2S
M.W : 252.72
SMILES Code : O=S(C1=CC=C(C2=CC=CC=C2)C=C1)(Cl)=O
Synonyms :
p-Phenylbenzenesulfonyl chloride; Biphenyl-4-sulfonyl chloride; p-Biphenylsulfonyl chloride
MDL No. :MFCD00078658
InChI Key :ALBQXDHCMLLQMB-UHFFFAOYSA-N
Pubchem ID :74192

Safety of 4-Biphenylsulfonyl chloride

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310
Class:8
UN#:3261
Packing Group:

Application In Synthesis of 4-Biphenylsulfonyl chloride

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1623-93-4 ]

[ 1623-93-4 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 1623-93-4 ]
  • [ 21344-90-1 ]
  • [ 376349-50-7 ]
YieldReaction ConditionsOperation in experiment
295A N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl][1,1'-biphenyl]-4-sulfonamide The title compound was prepared from <strong>[21344-90-1]4-(2-chlorophenyl)-1,3-thiazol-2-amine</strong> and 4-phenylbenzenesulfonyl chloride as described in the synthetic METHOD B to give a white solid (31.8 mg) with purity >90percent. MS (pos) m/z 427.1.
  • 3
  • [ 5683-33-0 ]
  • [ 1623-93-4 ]
  • [ 33084-49-0 ]
  • N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenyisulfonamide [ No CAS ]
  • [ 166964-10-9 ]
YieldReaction ConditionsOperation in experiment
60% In pyridine; (b) N-(4-Biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-dimethyl-aminopyridine (5 mg) was added, and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1 N HCl (2*50 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography using 8:2, hexanes/ethyl acetate, to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenyisulfonamide.
  • 4
  • [ 1623-93-4 ]
  • [ 37663-44-8 ]
  • C24H23NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With pyridine; at 80℃; The compound 3H-spiro [isobenzofuran- 1 ,4?-piperidine] hydrochloride (10mg, 0.O44mmol) and sulfonyl chloride (12mg, 0.O47mmol) were combined in pyridine (0.5m1) and stirred at 80 °C overnight, The solvent was removed and the residue was purified by preparative TLC to afford 14 mg of compound V:148 (mle=406[M+H]j, Yield: 78percent.
  • 5
  • [ 1623-93-4 ]
  • [ 145901-11-7 ]
  • N-(1H-pyrrolo[2,3-b]pyridin-6-yl)[1,1'-biphenyl]-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.6% With pyridine; at 20℃; for 2h; Pyridine (10 ml) to <strong>[145901-11-7]1H-pyrrolo[2,3-b]pyridin-6-amine</strong>(266 mg, 2 mmol) in a mixed solution was added [1,1'-biphenyl]-4-sulfonyl chloride It was added (500 mg, 2 mmol) and stirred for 2 hours at room temperature. The reaction mixture was concentrated and the residue was purified by graph silica gel (ethyl acetate: petroleum ether = 1: 2) to afford the title compound as a white solid (500 mg, 71.6% yield).
  • 6
  • [ 1623-93-4 ]
  • [ 25602-68-0 ]
  • 8-(biphenyl-4-ylsulfonyl)-8-azabicyclo[3.2.1]octan-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With dmap; triethylamine; In dichloromethane; for 24h; A 50 mL round bottom flask was charged with <strong>[25602-68-0]nortropinone hydrochloride</strong> (0.808 g, 5.00 mmol, 1.00 equiv.), dichloromethane (25 mL, c = 0.2 M), 4-biphenyl sulfonyl chloride (1.27 g, 5.00 mmol, 1.00 equiv.), triethylamine (2.0 g, 2.8 mL, 20 mmol, 4.0 equiv.) and 4- dimethylamino pyridine (61 mg, 0.50 mmol, 0.10 equiv.) were added. After 24 h the reaction mixture was diluted with dichloromethane (100 mL) and washed with 0.5 M HCI (150 mL). The aqueous layer was extracted with dichloromethane (3 chi 50 mL) and the combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane and ethyl acetate (90: 10 (v/v)) to afford nortropinone (4- biphenyl))sulfonamide 2q (1.12 g, 3.27 mmol, 65percent) as a colorless solid. R = 0.40 (ethyl acetate/dichloromethane, 10:90 (v/v)). (0337) [00179] NMR Spectroscopy: 1H NMR (500 MHz, CDC13, 23 °C, delta): 7.97 (d, J= 8.8 Hz, 2H), 7.74 (d, J= 8.8 Hz, 2H), 7.63 - 7.59 (m, 2H), 7.52 - 7.46 (m, 2H), 7.45 - 7.41 (m, 1H), 4.55 (tt, J= 3.9, 2.1 Hz, 2H), 2.83 (dd, J = 16.4, 4.6 Hz, 2H), 2.48 - 2.27 (m, 2H), 1.84 - 1.74 (m, 2H), 1.66 - 1.59 (m, 2H) ppm. 13C NMR (126 MHz, CDC13, 23°C, delta): delta 206.9, 146.2, 139.1, 138.4, 129.2, 128.8, 127.9 (d, J= 1.6 Hz), 127.4, 56.2, 50.4, 29.5 ppm. HRMS-ESI (m/z) calculated for Ci9Hi9SiN03Na [M+Na]+, 364.0978; found, 364.0981
  • 7
  • [ 1623-93-4 ]
  • [ 33084-49-0 ]
  • [ 166964-10-9 ]
YieldReaction ConditionsOperation in experiment
60% With dmap; In pyridine; ethyl acetate; (b) N-(4-Biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-Dimethylaminopyridine (5 mg) was added, and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1N HCl (2*50 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography using 8:2, hexanes/ethyl acetate, to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide.
  • 8
  • [ 1623-93-4 ]
  • [ 33084-49-0 ]
  • [ 166964-10-9 ]
YieldReaction ConditionsOperation in experiment
60% With dmap; In pyridine; ethyl acetate; (b) N-(4-Biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-Dimethylaminopyridine (5 mg) was added, and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1N HCl (2*50 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography using 8:2, hexanes/ethyl acetate, to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide.
60% With dmap; In pyridine; ethyl acetate; (a) N-(4-biphenylsulfonyl)-N-(4-Bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-(Dimethyl)aminopyridine (5 mg) was added and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1N HCl (2*50 ml) and the organic phase was dried: over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product which was purified by column chromatography using 8:2, hexanes/ethyl acetate to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-Bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide.
 

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