Home Cart Sign in  
Chemical Structure| 402-46-0 Chemical Structure| 402-46-0
Chemical Structure| 402-46-0

4-Fluorobenzenesulfonamide

CAS No.: 402-46-0

4.5 *For Research Use Only !

Cat. No.: A415842 Purity: 98%

Change View

Size Price

US Stock

Global Stock

In Stock
10g łÇÿ¶ÊÊ Inquiry Inquiry
25g łËʶÊÊ Inquiry Inquiry
100g łòď¶ÊÊ Inquiry Inquiry
500g ł§§Ê¶ÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 10g

    łÇÿ¶ÊÊ

  • 25g

    łËʶÊÊ

  • 100g

    łòď¶ÊÊ

  • 500g

    ł§§Ê¶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Alternative Products

Product Details of [ 402-46-0 ]

CAS No. :402-46-0
Formula : C6H6FNO2S
M.W : 175.18
SMILES Code : NS(=O)(=O)C1=CC=C(F)C=C1
MDL No. :MFCD00025384
InChI Key :LFLSATHZMYYIAQ-UHFFFAOYSA-N
Pubchem ID :120231

Safety of [ 402-46-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P301+P312+P330-P305+P351+P338

Calculated chemistry of [ 402-46-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 37.39
TPSA ?

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

68.54 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.01
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

0.71
Log Po/w (WLOGP)?

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

1.97
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.

0.73
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

0.41
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.97

Water Solubility

Log S (ESOL):?

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

-1.71
Solubility 3.41 mg/ml ; 0.0195 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.

-1.73
Solubility 3.28 mg/ml ; 0.0187 mol/l
Class?

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

Very 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

-2.24
Solubility 1.01 mg/ml ; 0.00577 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

Yes
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.

-6.86 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

1.0
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

0.0 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)

1.8

Application In Synthesis of [ 402-46-0 ]

* 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 [ 402-46-0 ]

[ 402-46-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 402-46-0 ]
  • [ 5497-76-7 ]
  • (S)-1-(4-sulfamoylphenyl)pyrrolidine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With caesium carbonate; In dimethyl sulfoxide; at 168℃;Inert atmosphere; A round bottom flask was charged with 4-fluorobenzenesulfonamide (945 mg, 5.4 mmol), L-proline-t-butyl ester HCl (1.24 g, 6 mmol), and cesium carbonate (4.2 g, 12 mmol) and suspended in 10 ml anhydrous DMSO. The mixture was placed in a preheated oil bath and equipped with a condenser, and heated under nitrogen at 168 oC overnight. HPLC analysis of the mixture indicated complete conversion of the benzenesulfonamide starting material. The mixture was transferred to an Erlenmeyer flask, the reaction pot was diluted with 2 ml of concentrated HCl, and added to the mixture in the Erlenmeyer flask and allowed to stir. The aqueous was then extracted with ethyl acetate (3 x 50 ml), and the combined extracts were washed with water (3 x 15 ml). The volatiles were then removed under vacuum, and 1.24 g of crude material was obtained. The desired intermediate was isolated using MPLC, utilizing a 0 to 60% gradient of acetone in DCM, affording 0.56 g (41%):1H NMR (300 MHz, DMSO-d6)d ppm 7.58 (d, J= 9.0 Hz, 2H), 6.98 (s, 2H), 6.54 (d, J= 9.0 Hz, 2H), 4.28 (d, J= 8.4 Hz, 1H), 2.35-2.22 (m, 2H), 2.04-1.96 (m, 2H).
  • 2
  • [ 402-46-0 ]
  • [ 5497-76-7 ]
  • C15H22N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In dimethyl sulfoxide; at 168℃;Inert atmosphere; A round bottom flaskwas charged with 4-fluorobenzenesulfonamide (945 mg, 5.4 mmol), L-proline-t-butyl ester HCl(1.24 g, 6 mmol), and cesium carbonate (4.2 g, 12 mmol) and suspended in 10 mL anhydrousDMSO. The mixture was placed in a preheated oil bath and equipped with a condenser, and10 heated under nitrogen at 168 C overnight. HPLC analysis of the mixture indicated completeconversion of the benzenesulfonamide starting material. The mixture was transferred to anErlenmeyer flask, the reaction pot was diluted with 2 mL of concentrated HCl, and added to themixture in the Erlenmeyer flask and allowed to stir. The aqueous was then extracted with ethylacetate (3 x 50 mL ), and the combined extracts were washed with water (3 x 15 mL ). The15 volatiles were then removed under vacuum, and 1.24 g of crude material was obtained. Thedesired intermediate was isolated using MPLC, utilizing a 0 to 60% gradient of acetone in DCM,affording 35 (0.56 g, 41 %): 1H NMR (300 MHz, DMSO-d6) 8 ppm 7.58 (d, J= 9.0 Hz, 2H), 6.98(s, 2H), 6.54 (d, J= 9.0 Hz, 2H), 4.28 (d, J= 8.4 Hz, 1H), 2.35-2.22 (m, 2H), 2.04-1.96 (m, 2H).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 402-46-0 ]

Fluorinated Building Blocks

Chemical Structure| 1524-40-9

A755791 [1524-40-9]

3-Fluorobenzenesulfonamide

Similarity: 0.98

Chemical Structure| 108966-71-8

A155827 [108966-71-8]

3,4-Difluorobenzenesulfonamide

Similarity: 0.95

Chemical Structure| 30058-40-3

A110731 [30058-40-3]

2-Fluorobenzenesulfonamide

Similarity: 0.91

Chemical Structure| 13656-60-5

A400217 [13656-60-5]

2,4-Difluorobenzenesulfonamide

Similarity: 0.90

Chemical Structure| 433-14-7

A696388 [433-14-7]

4-Fluoro-N-methylbenzenesulfonamide

Similarity: 0.88

Aryls

Chemical Structure| 1524-40-9

A755791 [1524-40-9]

3-Fluorobenzenesulfonamide

Similarity: 0.98

Chemical Structure| 108966-71-8

A155827 [108966-71-8]

3,4-Difluorobenzenesulfonamide

Similarity: 0.95

Chemical Structure| 30058-40-3

A110731 [30058-40-3]

2-Fluorobenzenesulfonamide

Similarity: 0.91

Chemical Structure| 13656-60-5

A400217 [13656-60-5]

2,4-Difluorobenzenesulfonamide

Similarity: 0.90

Chemical Structure| 433-14-7

A696388 [433-14-7]

4-Fluoro-N-methylbenzenesulfonamide

Similarity: 0.88

Amines

Chemical Structure| 1524-40-9

A755791 [1524-40-9]

3-Fluorobenzenesulfonamide

Similarity: 0.98

Chemical Structure| 108966-71-8

A155827 [108966-71-8]

3,4-Difluorobenzenesulfonamide

Similarity: 0.95

Chemical Structure| 30058-40-3

A110731 [30058-40-3]

2-Fluorobenzenesulfonamide

Similarity: 0.91

Chemical Structure| 13656-60-5

A400217 [13656-60-5]

2,4-Difluorobenzenesulfonamide

Similarity: 0.90

Chemical Structure| 433-14-7

A696388 [433-14-7]

4-Fluoro-N-methylbenzenesulfonamide

Similarity: 0.88

Sulfamides

Chemical Structure| 1524-40-9

A755791 [1524-40-9]

3-Fluorobenzenesulfonamide

Similarity: 0.98

Chemical Structure| 108966-71-8

A155827 [108966-71-8]

3,4-Difluorobenzenesulfonamide

Similarity: 0.95

Chemical Structure| 30058-40-3

A110731 [30058-40-3]

2-Fluorobenzenesulfonamide

Similarity: 0.91

Chemical Structure| 13656-60-5

A400217 [13656-60-5]

2,4-Difluorobenzenesulfonamide

Similarity: 0.90

Chemical Structure| 433-14-7

A696388 [433-14-7]

4-Fluoro-N-methylbenzenesulfonamide

Similarity: 0.88