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[ CAS No. 349-96-2 ] {[proInfo.proName]}

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Chemical Structure| 349-96-2
Chemical Structure| 349-96-2
Structure of 349-96-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 349-96-2 ]

CAS No. :349-96-2 MDL No. :MFCD00009637
Formula : C6H4FNO4S Boiling Point : -
Linear Structure Formula :- InChI Key :HRLAPUHJWRZEIC-UHFFFAOYSA-N
M.W : 205.16 Pubchem ID :188246
Synonyms :

Calculated chemistry of [ 349-96-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.6
TPSA : 88.34 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.93
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 2.75
Log Po/w (MLOGP) : 0.25
Log Po/w (SILICOS-IT) : -0.97
Consensus Log Po/w : 0.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.668 mg/ml ; 0.00326 mol/l
Class : Soluble
Log S (Ali) : -3.33
Solubility : 0.0968 mg/ml ; 0.000472 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.99
Solubility : 2.1 mg/ml ; 0.0103 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 349-96-2 ]

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 [ 349-96-2 ]

* 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 [ 349-96-2 ]
  • Downstream synthetic route of [ 349-96-2 ]

[ 349-96-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 349-96-2 ]
  • [ 73901-01-6 ]
YieldReaction ConditionsOperation in experiment
92% With trimethylsilylazide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 1 h; General procedure: To a solution of sulfonyl fluoride (0.5 mmol) in MeCN (1 mL) was added DBU(22 μL, 0.15 mmol, 0.3 eq) followed by TMSN3 (50 μL, 0.375 mmol, 0.75 eq). The resultant solutionwas stirred at room temperature for 15 min, then a further portion of TMSN3 (50 μL, 0.375 mmol, 0.75eq) was added. The solution was stirred for a further 45 min, filtered through a silica plug, eluting withEtOAc (50 mL) and volatiles removed under reduced pressure to yield the desired sulfonyl azide.
Reference: [1] Synlett, 2016, vol. 27, # 12, p. 1840 - 1843
  • 2
  • [ 98-74-8 ]
  • [ 349-96-2 ]
YieldReaction ConditionsOperation in experiment
94% With potassium fluoride; 18-crown-6 ether In acetonitrile for 24 h; To a solution of 4-nitrobenzene-1-sulfonyl chloride (20.0g, 90.2mmol) in 500mL CH3CN was added KF (26.0g, 451mmol) and 18-crown-6 (1.2g, 4.5mmol). After stirring for 24h, the reaction mixture was evaporated to dryness and EtOAc (600mL) was added. It was washed with H2O (300mL×3) and brine (300mL). The organic layer was dried over Na2SO4, filtered, and evaporated under vacuum to provide 9a (17.4g, 94percent) as a yellow solid, mp 76–77°C. Rf=0.63 (hexane/EtOAc=6/4). 1H NMR (400MHz, CDCl3): δ 8.47 (d, J=8.7Hz, 2H, aromatic), 8.25 (d, J=8.7Hz, 2H, aromatic); 13C NMR (100MHz, CDCl3): δ 151.8 (C), 138.2 (d, J=26.7Hz, C), 130.0 (CH), 124.9 (CH); 19F NMR (376 MHz, CDCl3): δ 65.1. IR (KBr): 3105, 2872, 1951, 1818, 1613, 1540, 1420, 1354, 1314, 1215cm−1. HRMS calcd for C6H5FNO4S (M+H)+ 205.9923, found 205.9918.
80% With potassium fluoride In acetone at 60℃; for 8 h; Reflux p-Nitrobenzenesulfonyl chloride (5.00 g, 22.6 mmol) and KF (3.39 g, 67.8 mmol) (1:3) were added into a 50 mL round bottom flask with 30 mL of acetone. The mixture was refluxed at 60 °C for 8 h. A light green solid (3.81 g, 82percent) was obtained after removing the solvent and sublimation under high vacuum at 80 °C. p-Nitrobenzenesulfonylfluoride (10.0 g, 45.2 mmol) was added under N2 to a 250 mL 3-necked flask. The flask was cooled to -60 °C and 30 mL of ammonia was condensed into the reactor. The mixture was allowed to slowly warm to 22 °C and stand for 8 h. The product was washed 3* with 20 mL of water to remove the NH4F. The solid, yellow product (7.55 g, 81percent) was obtained by drying under vacuum for 24 h at 22 °C. p-NO2PhSO2F: 19F NMR (CD3CN) δ 65.7(s); 1H NMR (CD3CN) δa 8.46 (2H, d), δb 8.27 (2H,d), Jab = 8 Hz. (Note: The 1H represent an aa'bb' spin system but it appears as a deceptively simple ab system with J/δ near 0.5. The δa,b for all compounds are taken as the midpoint of the second order doublets as an approximation as if it is a classic ab spin system. The Jab is assigned as that of a classic ab spin system.
No effort was made to analyze the spectra further.) p-NO2PhSO2NH2: 1H NMR (CD3CN) δa 8.34 (2H, d), δb 8.06 (2H,d), Jab = 11 Hz, δNH2 5.90 (2H,s).
Reference: [1] Tetrahedron, 2016, vol. 72, # 1, p. 58 - 68
[2] ACS Combinatorial Science, 2018, vol. 20, # 11, p. 672 - 680
[3] Journal of Fluorine Chemistry, 2013, vol. 145, p. 35 - 40
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 45, p. 9685 - 9695
[5] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11262 - 11270
[6] Journal of the Chemical Society, 1938, p. 887,893
[7] Journal of Organic Chemistry, 1972, vol. 37, p. 3549 - 3550
[8] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1919 - 1924
  • 3
  • [ 2937-05-5 ]
  • [ 349-96-2 ]
YieldReaction ConditionsOperation in experiment
72% With Selectfluor In water at 80℃; for 18 h; Schlenk technique In a clean, dry 10 ml Schlenk reaction tube,Followed by adding p-nitrobenzenesulfonyl hydrazide 54.3 mg,1-chloromethyl-4-fluoro-1,4-diazotized bicycles 2.2.2 octane bis (tetrafluoroborate) 123 mg,And using 2 ml of water as the reaction solvent,80 ° C for 18 hours. After completion of the reaction, the upper organic phase was extracted directly by the addition of ethyl acetateAfter drying, a small amount of petroleum ether and ethyl acetate (30: 1 by volume) were dissolved and separated by a short column of silica gel.34.7 mg of a white solid in 72percent yield.
Reference: [1] Patent: CN105198683, 2017, B, . Location in patent: Paragraph 0088; 0089; 0090
[2] Green Chemistry, 2016, vol. 18, # 5, p. 1224 - 1228
  • 4
  • [ 100-32-3 ]
  • [ 2613-27-6 ]
  • [ 349-96-2 ]
YieldReaction ConditionsOperation in experiment
6.73 g at 60 - 125℃; for 8 h; Sealed tube General procedure: A stainless steel cylinder was charged with 10.00 g(33.00 mmol) of 4-nitrophenyl disulfide (1a), 100 mL of R-113,150.0 g (1.030 mol) of AgF2, and 3 glass slides (25 cm 75 cm)containing a 100 nm coinage metal film (either Cu, Ag, or Au),which is approximately 1 106 g of Ag. The coinage metals werevapor deposited onto Cr-primed glass microscope slides underhigh vacuum conditions. The reaction cylinder was then sealed andheated to between 60 and 65 8C for 2 h, agitating intermittently.After the initial heating the temperature was raised and heldbetween 120 and 125 8C for 6 h, agitating intermittently. Once thissecond heating phase was completed, the cylinder was allowed tocool to room temperature. The CFC 113 was recovered by vacuumtransfer to avoid any loss. The contents of the cylinder wereextracted with chloroform, and the recovered silver salts (amixture of AgF2 and AgF) were washed 3 times in 50 mL each ofchloroform. The chloroform was then partitioned with a 10percent (byweight) solution of NaHCO3, and the aqueous layer was verified tobe alkaline using pH paper. The chloroform layer was reduced byrotary evaporation, and the resulting yellow oil was purified bycolumn chromatography (60-mesh silica gel eluted with 9:1hexane:benzene). All pure fractions of 4-nitro-pentafluorosulfa-nylbenzene (3a) were combined and crystallized in hexane. MultinuclearNMR was used to verify the identity of the crystals. Theyields of the experiments, performed in triplicate are presented inTable 1. The yields 3a from the individual experiments for thecopper film were 5.94 g, 5.81 g, and 6.73 g, respectively, while theyields of 3a for the three silver film experiments were 7.24 g,7.00 g, and 6.85 g, respectively. And finally, the yields of 3a fromthe three gold film experiments were 8.21 g, 7.88 g, and 7.88 g,respectively.
Reference: [1] Journal of Fluorine Chemistry, 2014, vol. 167, p. 203 - 210
  • 5
  • [ 15959-31-6 ]
  • [ 349-96-2 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 5, p. 1224 - 1228
  • 6
  • [ 6325-93-5 ]
  • [ 349-96-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 1909 - 1914[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 10, p. 2142 - 2147
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