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Chemical Structure| 97-09-6 Chemical Structure| 97-09-6

Structure of 97-09-6

Chemical Structure| 97-09-6

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Product Details of [ 97-09-6 ]

CAS No. :97-09-6
Formula : C6H5ClN2O4S
M.W : 236.63
SMILES Code : O=S(C1=CC=C(Cl)C([N+]([O-])=O)=C1)(N)=O
MDL No. :MFCD00035783
Boiling Point : No data available
InChI Key :SPZGXONNVLTQDE-UHFFFAOYSA-N
Pubchem ID :7324

Safety of [ 97-09-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 97-09-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 51.27
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

114.36 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.77
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.66
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.98
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.12
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.41
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.37

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.91
Solubility 2.92 mg/ml ; 0.0124 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.64
Solubility 0.545 mg/ml ; 0.0023 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.97
Solubility 2.55 mg/ml ; 0.0108 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.27 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.29

Application In Synthesis of [ 97-09-6 ]

* 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 [ 97-09-6 ]

[ 97-09-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 97-08-5 ]
  • [ 97-09-6 ]
YieldReaction ConditionsOperation in experiment
93.7% Add 200g of water to a clean three-necked bottle, 2-nitrochlorobenzene-4-sulfonyl chloride wet product 80g(mass fraction 61.2%), converted into 2-nitrochlorobenzene-4-sulfonyl chloride 49g,And 1g of Turkish red oil as a wetting agent,Stirring and stirring for 30 minutes, then adding 40 g of solid ammonium chloride and stirring for 15 minutes.Adding a 20% aqueous solution of sodium hydroxide,Adjusting the pH of the system raises the pH of the feed to 7-9, thenWarming up to 30-55 C to maintain the ammoniation reaction,During the reaction, the sodium hydroxide aqueous solution with a mass fraction of 20% is used to maintain the pH of the ammoniated solution of the system between 7-9.Until the end of the ammoniation reaction is complete, cooling causes the product to precipitate completely and filter.The filter cake is washed twice with cold water, and the wet product is dried at 95 C.Obtained 42 g of 2-nitrochlorobenzene-4-sulfonamide as an ammoniated product, the yield was 93.7%.The purity is over 99%.
80.7% With ammonia; In 1,4-dioxane; at 20℃; for 1h; To a solution of (7.5 g, 29.3 mmol) of 4-chloro-3-nitrobenzenesulfonyl chloride in dioxane 150 ml was bubbled NH3 s for one hour. The reaction was stirred until completion, then filtered, rinsed with dioxane and concentrated. The resulting solid was suspended in distilled water, filtered and dried. Yield 5.6 g, 23.7 mmol (80.7%). IH NMR (400 MHz3 DMSO-D6) delta ppm 7.75 (s, 2 H) 8.01 (d, J=8.40 Hz, 1 H) 8.07 (dd, J=8.40, 2.15 Hz, 1 H) 8.45 (d, J=2.15 Hz, 1 H).
66% With ammonium hydroxide; In water; isopropyl alcohol; at -40 - -20℃; for 0.5h; 1L three bottles were added 350mL water,250 mL isopropanol,47 g of aqueous ammonia (0. 69 mol, 3 eq), cooled with stirring to -40 C, and a solution of 58 g (0.23 mol, 1eq) dissolved in 100 ml of 3-nitro-4-chlorobenzenesulfonyl chloride was added dropwise, keeping the temperature <-20 C. After the dropping insulation 0. 5h, TLC detection (PE/EA-5/1) no raw materials, add hydrochloric acid to adjust the pH = 1-2, keep the temperature <-20 C, adjust the temperature after recovery, remove isopropyl alcohol, filter, and dry cake washed with EA dissolved after filter and dry to gave 3-nitro-4-chlorobenzenesulfonamide, pale yellow crystals 36g, yield 66%
With ammonium hydroxide; In diethyl ether; at 20℃; for 4h; 4-Chloro-3-nitrobenzenesulfonylchloride (1081.7 mg, 4.14 mmol) dissolved in diethyl ether and ammonia solution (25%, 6 mL) was added to mixture and stirred at rt for 4h. Reaction mixture poured into water and extracted with ethyl acetate. Organic layer was dried, filtered and evaporated. The crude 1 (955.2 mg, 97.3% yield) was used in the next step without purification [1]. Mp 174.5-175.8 C, (175-176 C [2]). CAS # 97-09-6

  • 2
  • [ 97-08-5 ]
  • ammonium carbonate [ No CAS ]
  • [ 97-09-6 ]
  • 3
  • [ 121-18-6 ]
  • [ 97-09-6 ]
  • 4
  • [ 1336-21-6 ]
  • [ 97-08-5 ]
  • [ 97-09-6 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; EXAMPLE 1C 4'-chloro-3'-nitrobenzenesulfonamide A 0 C. solution of 4-chloro-3-nitrobenzenesulfonyl chloride (12.8 g, 50.0 mmol) in diethyl ether (1 L) was slowly treated with 0 C. concentrated NH4OH (50 mL) and stirred for 30 minutes. The organic layer was dried (MgSO4), filtered, and concentrated to provide the desired product of sufficient purity for subsequent use.
  • 5
  • concentrated NH40H [ No CAS ]
  • [ 97-08-5 ]
  • [ 97-09-6 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; Example 1C 4-chloro-3-nitrobenzenesulfonamide A 0 C. solution of 4-chloro-3-nitrobenzenesulfonyl chloride (12.8 g, 50.0 mmol) in diethyl ether (1 L) was slowly treated with 0 C. concentrated NH40H (50 mL) and stirred for 30 minutes. The organic layer was dried (MgSO4), filtered, and concentrated to provide the desired product of sufficient purity for subsequent use.
 

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