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[ CAS No. 349-88-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 349-88-2
Chemical Structure| 349-88-2
Chemical Structure| 349-88-2
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Product Details of [ 349-88-2 ]

CAS No. :349-88-2 MDL No. :MFCD00007438
Formula : C6H4ClFO2S Boiling Point : -
Linear Structure Formula :- InChI Key :BFXHJFKKRGVUMU-UHFFFAOYSA-N
M.W : 194.61 Pubchem ID :9588
Synonyms :

Calculated chemistry of [ 349-88-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.48
TPSA : 42.52 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 2.04
Log Po/w (WLOGP) : 3.25
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 2.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.417 mg/ml ; 0.00214 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.535 mg/ml ; 0.00275 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.22
Solubility : 0.117 mg/ml ; 0.000601 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 349-88-2 ]

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

Application In Synthesis of [ 349-88-2 ]

* 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.

  • Upstream synthesis route of [ 349-88-2 ]
  • Downstream synthetic route of [ 349-88-2 ]

[ 349-88-2 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 349-88-2 ]
  • [ 371-42-6 ]
Reference: [1] Journal of Sulfur Chemistry, 2012, vol. 33, # 2, p. 179 - 185
[2] Synthetic Communications, 2012, vol. 42, # 16, p. 2432 - 2439
[3] Acta Chimica Academiae Scientiarum Hungaricae, 1954, vol. 4, p. 111,115
[4] Chemische Berichte, 1953, vol. 86, p. 172,180
[5] Collection of Czechoslovak Chemical Communications, 1975, vol. 40, # 3, p. 719 - 737
  • 2
  • [ 462-06-6 ]
  • [ 349-88-2 ]
  • [ 383-29-9 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 7, p. 1499 - 1501
[2] Chemische Berichte, 1953, vol. 86, p. 172,180
  • 3
  • [ 349-88-2 ]
  • [ 352-33-0 ]
  • [ 383-29-9 ]
  • [ 398-23-2 ]
  • [ 404-38-6 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 42, p. 7125 - 7128
  • 4
  • [ 371-42-6 ]
  • [ 349-88-2 ]
YieldReaction ConditionsOperation in experiment
95% With dihydrogen peroxide; titanium tetrachloride In water; acetonitrile at 25℃; for 0.0333333 h; General procedure: A mixture of thiol (1 mmol), 30percent H2O2 (3 mmol, 0.3 mL), and TiCl4 (1 mmol, 0.11 mL) was stirred in CH3CN at 25 °C for the time indicated in refPreviewPlaceHolderTable 1. A white solid, (TiO2) immediately precipitated. After completion of the reaction as indicated by TLC, the mixture was quenched by adding H2O (10 mL), extracted with EtOAc (4 .x. 5 mL), and the extract was dried over anhydrous MgSO4. The filtrate was evaporated under vacuum to afford the analytically pure product or chromatographed by passing through a short column of silica gel, and the products were identified by comparison of their 1H and 13C NMR spectra, and melting point with authentic samples prepared by known methods.
89% With N-chloro-succinimide; isopropyl alcohol In dichloromethane at 0 - 20℃; for 1 h; General procedure: To a stirred solution of the corresponding thiol 1 (1 eq) [1]a and isopropanol (CAS: 67-63-0) (2 eq) in dichloromethane [2] (0.15 M), N-bromosuccinimide (CAS: 128-08-5) or N-chlorosuccinimide (CAS: 128-09-6) (4 or 3.5 equiv) was added portion wise1b at rt (in the case of NBS) or 0 °C (in the case of NCS). The reaction mixture is stirred at rt until starting material was not visible by TLC (approx. 1 h). Then, the mixture was diluted with cold, saturated NaHCO3, and extracted with EtOAc (x4).1c The combined organic extracts were dried over anh. Na2SO4 and concentrated in vacuo to afford the crude material. Filtration on a SiO2 column or radial chromatography using mixtures of hexanes/ethyl acetate/acetone as eluents, yielded the pure sulfonyl halides 2 or 3.
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 24, p. 9287 - 9291
[2] Synlett, 2009, # 17, p. 2773 - 2776
[3] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 10, p. 3692 - 3695
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 2012, vol. 187, # 6, p. 769 - 775
[5] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5847 - 5850
[6] Tetrahedron Letters, 2012, vol. 53, # 3, p. 354 - 358
[7] Green Chemistry, 2014, vol. 16, # 6, p. 3125 - 3131
[8] Chemistry Letters, 1992, # 8, p. 1483 - 1486
[9] Tetrahedron Letters, 2010, vol. 51, # 2, p. 418 - 421
[10] Synthesis, 2012, vol. 2012, # 2, p. 316 - 322
[11] Tetrahedron Letters, 2017, vol. 58, # 23, p. 2244 - 2247
[12] Green Chemistry, 2017, vol. 19, # 9, p. 2286 - 2295
[13] Tetrahedron, 2012, vol. 68, # 25, p. 5095 - 5101
[14] Letters in Organic Chemistry, 2013, vol. 10, # 2, p. 111 - 117
[15] Journal of Sulfur Chemistry, 2013, vol. 34, # 4, p. 347 - 357
  • 5
  • [ 405-31-2 ]
  • [ 349-88-2 ]
Reference: [1] Synlett, 2009, # 17, p. 2773 - 2776
[2] Synthesis, 2012, vol. 2012, # 2, p. 316 - 322
[3] Journal of Sulfur Chemistry, 2013, vol. 34, # 4, p. 347 - 357
  • 6
  • [ 462-06-6 ]
  • [ 349-88-2 ]
Reference: [1] Angewandte Chemie, 1993, vol. 105, # 7, p. 1097 - 1099
[2] Journal of Organometallic Chemistry, 1994, vol. 475, # 1-2, p. 99 - 112
[3] Medicinal Chemistry Research, 2017, vol. 26, # 7, p. 1437 - 1458
[4] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, # 8, p. 1205 - 1214
[5] Journal of the American Chemical Society, 1940, vol. 62, p. 511,512
[6] Bulletin de la Societe Chimique de France, 1962, p. 1213 - 1218
[7] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 5, p. 1182 - 1192
[8] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 777 - 782
[9] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 19 - 32
[10] New Journal of Chemistry, 2014, vol. 38, # 12, p. 6193 - 6197
[11] Molecules, 2018, vol. 23, # 7,
  • 7
  • [ 1765-93-1 ]
  • [ 349-88-2 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10638 - 10641
  • 8
  • [ 459-45-0 ]
  • [ 349-88-2 ]
Reference: [1] ChemSusChem, 2017, vol. 10, # 1, p. 151 - 155
  • 9
  • [ 368-88-7 ]
  • [ 349-88-2 ]
Reference: [1] Synlett, 2011, # 18, p. 2671 - 2674
[2] Patent: WO2016/37591, 2016, A1, . Location in patent: Paragraph 00409
  • 10
  • [ 371-42-6 ]
  • [ 127-65-1 ]
  • [ 349-88-2 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 3051 - 3057
  • 11
  • [ 368-85-4 ]
  • [ 349-88-2 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1967, vol. 37, p. 149 - 155[2] Zhurnal Obshchei Khimii, 1967, vol. 37, # 1, p. 163 - 170
  • 12
  • [ 349-89-3 ]
  • [ 349-88-2 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1967, vol. 37, p. 149 - 155[2] Zhurnal Obshchei Khimii, 1967, vol. 37, # 1, p. 163 - 170
  • 13
  • [ 371-40-4 ]
  • [ 349-88-2 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 24 - 30
  • 14
  • [ 349-88-2 ]
  • [ 402-46-0 ]
Reference: [1] Liebigs Annales, 1997, # 1, p. 141 - 154
[2] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, # 8, p. 1205 - 1214
[3] Journal of the American Chemical Society, 1940, vol. 62, p. 511,512
[4] J. Gen. Chem. USSR (Engl. Transl.), 1967, vol. 37, p. 149 - 155[5] Zhurnal Obshchei Khimii, 1967, vol. 37, # 1, p. 163 - 170
[6] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 5, p. 1182 - 1192
[7] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 13, p. 1493 - 1498
[8] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 13, p. 1493 - 1498
[9] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 13, p. 1493 - 1498
[10] Patent: US5089499, 1992, A,
[11] Journal of Molecular Structure, 2014, vol. 1067, # 1, p. 43 - 51
[12] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4397 - 4406
[13] Molecules, 2018, vol. 23, # 7,
  • 15
  • [ 349-88-2 ]
  • [ 124-40-3 ]
  • [ 383-31-3 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In tetrahydrofuran; water at 20℃; for 0.333333 h; (1) 4-Fluoro-1-(N,N-dimethylaminosulfonyl)benzene To a solution of 4-fluorobenzenesulfonyl chloride (1.95 g, 10.0 mmol) in THF (40 mL) were added triethylamine (2.09 mL, 15.0 mmol) and 50percent aqueous dimethylamine solution (1.26 mL, 14.0 mmol) at room temperature, and the solution was stirred at the same temperature for 20 minutes. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 4-fluoro-1-(N,N-dimethylaminosulfonyl)benzene (2.03 g, 10.0 mmol).yield: quantitative
100% at 20℃; for 0.0833333 h; [00728] A mixture of 4-fluorobenzene-1 -sulfonyl chloride (2.0 g, 10.3 mmol), HNMe2 (2.0M in MeOH; 1 1 .0 mL, 22.0 mmol) and DCM (1 1 .0 mL) was stirred at rt for 5 min. DCM (30 mL) was added. The organic phase was washed with 1 M HCI (30 mL) and brine (30 mL), dried over MgSCv and filtered. The solvent was removed under reduced pressure to afford 4-fluoro-/V,/V- dimethylbenzenesulfonamide as a white solid (2.12 g, quant.). A mixture of 4-fluoro-/V,/V- dimethylbenzenesulfonamide (1 .50 g, 7.39 mmol), NaSMe (2.08 g, 29.7 mmol) and DMF (9.0 mL) was stirred at 170 °C in a sealed tube for 16 h. After cooling to rt, 1 M NaOH (40 mL) was added. The aqueous phase was washed with Et20 (2 χ 40 mL), acidified to pH <2 with 2 M HCI and then extracted with Et20 (3 χ 40 mL). The combined organic phase was dried over MgSCv and filtered. The solvent was removed under reduced pressure to afford 4-mercapto-/V,/V- dimethylbenzenesulfonamide as an orange oil (503 mg, 31 percent). H NMR (500 MHz, CDCI3) δ 7.67 - 7.58 (m, 2H), 7.43 - 7.35 (m, 2H), 3.67 (s, 1 H), 2.71 (s, 6H).
86% at 0℃; for 0.5 h; A cooled (0 0C) solution of 4-fluorobenzenesulfonyl chloride (2.00 g; 10.3 mmol) in THF (40 ml) is treated with a 2 M solution of dimethylamine in THF (1 1.3 ml; 22.6 mmol) and stirred at 0 0C for 30 minutes. The solvents were removed under reduced pressure, the residue taken up in EtOAc, the organic phase was washed with a saturated solution of NH4CI twice and with water. The organic phase was dried on MgSO4, filtered and the solvent removed under reduced pressure to afford the title compound (1.80 g, 86percent).
Reference: [1] Patent: EP1354882, 2003, A1, . Location in patent: Page/Page column 85
[2] Patent: WO2017/141049, 2017, A1, . Location in patent: Paragraph 00728
[3] Patent: WO2010/92043, 2010, A1, . Location in patent: Page/Page column 120
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7299 - 7317
[5] Patent: EP1757582, 2007, A1, . Location in patent: Page/Page column 31
  • 16
  • [ 349-88-2 ]
  • [ 506-59-2 ]
  • [ 383-31-3 ]
YieldReaction ConditionsOperation in experiment
50% With dmap In tetrahydrofuran at 20℃; Preparation of 4-fluoro-N,N-dimethyl-benzenesulfonamide
A solution of 4-fluorobenzenesulfonyl chloride (1.95 g, 10 mmol) and dimethylamine hydrochloric acid salt (978 mg, 12 mmol) in tetrahydrofuran (10 mL) was added to a solution of 4-dimethylaminopyridine (3.05 g, 25 mmol) in tetrahydrofuran (10 mL) dropwise at room temperature.
The resulting mixture was stirred at room temperature overnight and concentrated in vacuo.
The residue was purified by flash column (elution with 20percent ethyl acetate in petroleum ether) to afford 4-fluoro-N,N-dimethyl-benzenesulfonamide (1.02 g, 50percent) as a white solid.
The following sulfonamides were prepared in an analogous manner as described for 4-fluoro-N,N-dimethyl-benzenesulfonamide by the reaction of 4-fluorobenzenesulfonyl chloride with commercially available amines.
Reference: [1] Patent: US2010/125058, 2010, A1, . Location in patent: Page/Page column 31
[2] Patent: WO2005/18529, 2005, A2, . Location in patent: Page/Page column 49
[3] Patent: WO2005/18529, 2005, A2, . Location in patent: Page/Page column 49
  • 17
  • [ 110-18-9 ]
  • [ 349-88-2 ]
  • [ 383-31-3 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 18, p. 3502 - 3506
  • 18
  • [ 349-88-2 ]
  • [ 383-31-3 ]
Reference: [1] Patent: US4532240, 1985, A,
  • 19
  • [ 349-88-2 ]
  • [ 74-89-5 ]
  • [ 433-14-7 ]
Reference: [1] Nippon Kagaku Zasshi, 1955, vol. 76, p. 775,777[2] Chem.Abstr., 1957, p. 17793
[3] Patent: WO2007/31747, 2007, A1, . Location in patent: Page/Page column 42
[4] Patent: US2009/163534, 2009, A1, . Location in patent: Page/Page column 20-21
[5] Patent: US2003/208066, 2003, A1, . Location in patent: Page/Page column 26-27
[6] Organic Letters, 2016, vol. 18, # 9, p. 2280 - 2283
[7] Organic Letters, 2017, vol. 19, # 21, p. 5844 - 5847
[8] Chemical Communications, 2018, vol. 54, # 60, p. 8403 - 8406
  • 20
  • [ 824-75-9 ]
  • [ 349-88-2 ]
  • [ 433-14-7 ]
Reference: [1] Patent: US5877317, 1999, A,
  • 21
  • [ 349-88-2 ]
  • [ 824-80-6 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydrogencarbonate; sodium sulfite In water at 80℃; for 4 h; Take 250mL of mono vial,P-fluorobenzenesulfonyl chloride (48.5 mmol, 9.4 g, 1.0 equiv) was added,Sodium sulfite (97 mmol, 12.2 g, 2.0 equiv),Sodium bicarbonate (97 mmol, 8.1 g, 2.0 equiv)Add 60 mL of water,Equipped with reflux condenser,80 ° C for 4 h.The reaction ends,Dry water,Add methanol dissolved to filter,And then spin dry methanol to white solid 10.2g,Yield 99percent.
Reference: [1] Patent: CN107033046, 2017, A, . Location in patent: Paragraph 0192; 0193; 0194
[2] Chemistry - An Asian Journal, 2016, vol. 11, # 15, p. 2121 - 2125
[3] Acta Chemica Scandinavica, Series A: Physical and Inorganic Chemistry, 1976, vol. A30, # 8, p. 579 - 585
[4] European Journal of Medicinal Chemistry, 2007, vol. 42, # 6, p. 880 - 884
[5] Journal of Organic Chemistry, 1992, vol. 57, # 9, p. 2594 - 2599
[6] Patent: WO2007/66844, 2007, A1, . Location in patent: Page/Page column 13-14
[7] Tetrahedron Letters, 2012, vol. 53, # 33, p. 4347 - 4350
[8] Molecules, 2013, vol. 18, # 1, p. 97 - 113
[9] European Journal of Organic Chemistry, 2014, vol. 2014, # 15, p. 3196 - 3202
[10] Journal of Organic Chemistry, 2014, vol. 79, # 24, p. 12018 - 12032
[11] Journal of Chemical Research, 2014, vol. 38, # 11, p. 639 - 642
[12] Tetrahedron, 2014, vol. 70, # 47, p. 9107 - 9112
[13] Green Chemistry, 2015, vol. 17, # 3, p. 1395 - 1399
[14] Chemical Communications, 2015, vol. 51, # 29, p. 6418 - 6421
[15] Advanced Synthesis and Catalysis, 2015, vol. 357, # 9, p. 2050 - 2054
[16] Organic Letters, 2016, vol. 18, # 16, p. 4144 - 4147
[17] Organic Letters, 2018, vol. 20, # 17, p. 5353 - 5356
[18] Tetrahedron Letters, 2017, vol. 58, # 7, p. 690 - 693
[19] Chemical Communications, 2017, vol. 53, # 12, p. 2056 - 2059
[20] Angewandte Chemie - International Edition, 2017, vol. 56, # 16, p. 4447 - 4451[21] Angew. Chem., 2017, vol. 56, # 16, p. 4447 - 4451,5
[22] European Journal of Medicinal Chemistry, 2018, vol. 160, p. 120 - 132
[23] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7959 - 7963
  • 22
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  • [ 116649-85-5 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 10, p. 4842 - 4848
  • 23
  • [ 349-88-2 ]
  • [ 406233-31-6 ]
Reference: [1] Patent: CN106699614, 2017, A,
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