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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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 |
GHS Pictogram: |
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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: | Ⅱ |
* 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.
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |