39150-45-3|4-Amino-3,5-dibromobenzenesulfonamide| Ambeed

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Quality Control of [ 39150-45-3 ] Purity: 97% SDS Specification

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Product Details of [ 39150-45-3 ]

CAS No. :	39150-45-3
Formula :	C₆H₆Br₂N₂O₂S
M.W :	330.00
SMILES Code :	O=S(C1=CC(Br)=C(N)C(Br)=C1)(N)=O
MDL No. :	MFCD00014783
InChI Key :	DLXJPWSYRLLYSV-UHFFFAOYSA-N
Pubchem ID :	3084733

Safety of [ 39150-45-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Computational Chemistry of [ 39150-45-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	57.24
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	94.56 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.39
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.19
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.53
Log P_o/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.	1.24
Log P_o/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	0.7
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.41

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.91
Solubility	0.405 mg/ml ; 0.00123 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.77
Solubility	0.558 mg/ml ; 0.00169 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	-3.28
Solubility	0.172 mg/ml ; 0.000522 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.	-7.47 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	1.0 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<0.0
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)	2.06

Application In Synthesis of [ 39150-45-3 ]

* 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 [ 39150-45-3 ]

[ 39150-45-3 ] Synthesis Path-Downstream 1~30

1
[ 39150-45-3 ]
[ 608-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In water; at 170℃; for 3.0h;	To a mixture of 50.0 g sulfanilamide, 850 mL water and 200 mL 48% HBr solution, 90.0 g sodium perborate was added at 85 C. The mixture was stirred at 80-85 C for 30 min and then was cooled to room temperature and filtered. The residue was washed to be neutral by water. The solid was desulfonated by reacting with 70% sulfuric acid solution for 3 h under reflux. Crude product was obtained by steam distillation and further purified by recrystallization in ethanol. 1H NMR (500 MHz, CDCl3, delta in ppm): 7.35-7.40 (d, 2H, Ar-Hm), 6.5 (t, 1H, Ar-Hp).

References: [1]Organic Syntheses,1944,vol. 24,p. 48.
[2]Monatshefte fur Chemie,1915,vol. 36,p. 132.
[3]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1989,vol. 28,p. 472 - 476.
[4]Journal of Molecular Catalysis A: Chemical,2014,vol. 390,p. 76 - 82.

2
[ 39150-45-3 ]
3,5,3',5'-tetrabromo-4,4'-azo-bis-benzenesulfonic acid diamide [ No CAS ]

References: [1]Gazzetta Chimica Italiana,1949,vol. 79,p. 186,189, 190.

3
[ 53297-69-1 ]
[ 39150-45-3 ]

References: [1]Gazzetta Chimica Italiana,1948,vol. 78,p. 275,280.
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 2187 - 2196.

4
(4-amino-3,5-dibromo-benzenesulfonyl)-urea [ No CAS ]
[ 39150-45-3 ]

References: [1]Archiv der Pharmazie,1956,vol. 289,p. 39,45.

5
[ 39150-45-3 ]
[ 108-24-7 ]
[ 15018-96-9 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2386.

6
[ 39150-45-3 ]
[ 108-24-7 ]
4-acetylamino-3,5-dibromo-benzenesulfonic acid amide [ No CAS ]
4-acetylamino-3,5-dibromo-benzenesulfonic acid acetylamide [ No CAS ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2386.

7
[ 39150-45-3 ]
[ 108-24-7 ]
4-acetylamino-3,5-dibromo-benzenesulfonic acid acetylamide [ No CAS ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2386.

8
[ 39150-45-3 ]
[ 108-24-7 ]
3,5-dibromo-4-diacetylamino-benzenesulfonic acid acetylamide [ No CAS ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2386.

9
[ 63-74-1 ]
[ 39150-45-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With hydrogen bromide; dihydrogen peroxide; at 20℃; for 5.0h;	Sulfanilamide (0.43g, 0.0025mol) was stirred in 15mL of 6N halogen acid (0.08mol) at room temperature, and 2mL of 30% hydrogen peroxide (0.02mol) was slowly added. After 5h, the product was filtered and recrystallized from ethanol. White solid. Yield: 62%. 1H NMR (DMSO-d6, 400MHz): delta 7.79 (s, 2H, ArH), 7.26 (s, 2H, SO2NH2), 6.11 (s, 2H, NH2). 13C NMR (DMSO-d6, 100MHz): delta 145.8, 132.7, 129.5, 106.1.
	With sodium perborate; hydrogen bromide; at 80 - 90℃;	To a mixture of 50.0 g sulfanilamide, 850 mL water and 200 mL 48% HBr solution, 90.0 g sodium perborate was added at 85 C. The mixture was stirred at 80-85 C for 30 min and then was cooled to room temperature and filtered. The residue was washed to be neutral by water. The solid was desulfonated by reacting with 70% sulfuric acid solution for 3 h under reflux. Crude product was obtained by steam distillation and further purified by recrystallization in ethanol. 1H NMR (500 MHz, CDCl3, delta in ppm): 7.35-7.40 (d, 2H, Ar-Hm), 6.5 (t, 1H, Ar-Hp).

References: [1]Green Chemistry,2011,vol. 13,p. 2187 - 2196.
[2]European Journal of Medicinal Chemistry,2016,vol. 124,p. 229 - 236.
[3]Analytical Chemistry,1984,vol. 56,p. 2157 - 2160.
[4]Organic Syntheses,1955,vol. Coll. Vol. III,p. 262.
[5]Gazzetta Chimica Italiana,1948,vol. 78,p. 275,280.
[6]Monatshefte fur Chemie,1915,vol. 36,p. 132.
[7]Archiv der Pharmazie,1943,vol. 281,p. 193,200.
[8]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1989,vol. 28,p. 472 - 476.
[9]Journal of Molecular Catalysis A: Chemical,2014,vol. 390,p. 76 - 82.

10
[ 7726-95-6 ]
[ 64-19-7 ]
[ 63-74-1 ]
[ 39150-45-3 ]

References: [1]Monatshefte fur Chemie,1915,vol. 36,p. 132.

12
[ 7664-93-9 ]
[ 39150-45-3 ]
[ 608-30-0 ]

References: [1]Monatshefte fur Chemie,1915,vol. 36,p. 132.

13
[ 7664-93-9 ]
[ 39150-45-3 ]
[ 608-30-0 ]
[ 147-82-0 ]

References: [1]Archiv der Pharmazie,1943,vol. 281,p. 193,200.

14
2-amino-5-sulfamoyl-phenylmercury ⁽¹⁺⁾-chloride [ No CAS ]
[ 39150-45-3 ]

References: [1]Annali di Chimica Applicata,1949,vol. 39,p. 621,625.

15
[ 89-83-8 ]
[ 39150-45-3 ]
5-Methyl-2-(1-methylethyl)-1,4-benzochinon-4-[(4-amino-3,5-dibromphenyl)imin] [ No CAS ]
5-Methyl-2-(1-methylethyl)-1,4-benzochinon-4-[(4-amino-2,6-dibromphenyl)imin] [ No CAS ]

References: [1]Pharmazie,2000,vol. 55,p. 781 - 782.

16
[ 614-76-6 ]
[ 39150-45-3 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2187 - 2196.

17
[ 547742-79-0 ]
[ 39150-45-3 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2187 - 2196.

18
[ 615-36-1 ]
[ 39150-45-3 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2187 - 2196.

19
[ 88963-75-1 ]
[ 39150-45-3 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 2187 - 2196.

20
[ 39150-45-3 ]
[ 608-21-9 ]

References: [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1989,vol. 28,p. 472 - 476.

21
[ 39150-45-3 ]
[ 39234-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	In chlorosulfonic acid; dichloromethane;	EXAMPLE 10 4-Amino-3,5-dibromobenzenesulfonylchloride A solution of 15 g. of <strong>[39150-45-3]4-amino-3,5-dibromobenzenesulfonamide</strong> in 45 ml. of chlorosulfonic acid is heated on a steam bath at 95 C. for two hours. The reaction mixture is cooled and poured onto 400 ml. of ice/water mixture. The resultant precipitate is filtered, dissolved in methylene chloride, and the methylene chloride solution is dried, filtered and evaporated to dryness, affording 4-amino-3,5-dibromobenzenesulfonylchloride, m.p. 153-155 C.

References: [1]Patent: US3987199,1976,A .

22
[ 39150-45-3 ]
[ 340187-66-8 ]