13195-50-1|2-Bromo-5-nitrothiophene| Ambeed

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Quality Control of [ 13195-50-1 ] Purity: 97% (stabilized with Cu+HQ+MgO) SDS Specification

COA

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Product Details of [ 13195-50-1 ]

CAS No. :	13195-50-1
Formula :	C₄H₂BrNO₂S
M.W :	208.03
SMILES Code :	O=[N+](C1=CC=C(Br)S1)[O-]
MDL No. :	MFCD00022493
InChI Key :	ZPNFMDYBAQDFDY-UHFFFAOYSA-N
Pubchem ID :	83222

Safety of [ 13195-50-1 ]

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

Computational Chemistry of [ 13195-50-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	5
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	40.84
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	74.06 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.5
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	2.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.42
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.	1.39
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	1.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.86

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.23
Solubility	0.122 mg/ml ; 0.000585 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.	-4.0
Solubility	0.0207 mg/ml ; 0.0000996 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-1.91
Solubility	2.58 mg/ml ; 0.0124 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	Yes
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.	-5.59 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	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)	2.64

Application In Synthesis of [ 13195-50-1 ]

* 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 [ 13195-50-1 ]

[ 13195-50-1 ] Synthesis Path-Downstream 1~35

1
[ 123-75-1 ]
[ 13195-50-1 ]
[ 137687-16-2 ]

References: [1]Journal of the Chemical Society. Chemical communications,1994,p. 2057 - 2058.
[2]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 965 - 970.
[3]Journal of Organic Chemistry,2006,vol. 71,p. 5144 - 5150.
[4]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 971 - 975.

2
[ 110-89-4 ]
[ 13195-50-1 ]
[ 19991-84-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1982,p. 625 - 630.
[2]Journal of the Chemical Society. Chemical communications,1994,p. 1689 - 1690.
[3]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 965 - 970.
[4]Journal of Organic Chemistry,2006,vol. 71,p. 5144 - 5150.
[5]Journal of the Chemical Society. Perkin Transactions 2 (2001),2002,p. 971 - 975.
[6]International Journal of Chemical Kinetics,2011,vol. 43,p. 185 - 190.

3
[ 110-89-4 ]
[ 4298-52-6 ]
[ 13195-50-1 ]
1-[2-(5-nitrothien-2-yl)-1-(thien-2-yl)vinyl]piperidine [ No CAS ]

References: [1]European Journal of Organic Chemistry,2006,p. 405 - 413.

4
[ 878886-76-1 ]
[ 13195-50-1 ]
2-(5-methoxythien-2-ylethynyl)-5-nitrothiophene [ No CAS ]

References: [1]European Journal of Organic Chemistry,2006,p. 405 - 413.

5
[ 878886-78-3 ]
[ 13195-50-1 ]
2-(5-methoxythien-2-ylethynyl)-5-(5-nitrothienylethynyl)thiophene [ No CAS ]

References: [1]European Journal of Organic Chemistry,2006,p. 405 - 413.

6
[ 878886-80-7 ]
[ 13195-50-1 ]
C₂₃H₁₁NO₃S₄ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2006,p. 405 - 413.

7
[ 878886-82-9 ]
[ 13195-50-1 ]
C₂₉H₁₃NO₃S₅ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2006,p. 405 - 413.

8
[ 878886-84-1 ]
[ 13195-50-1 ]
C₃₅H₁₅NO₃S₆ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2006,p. 405 - 413.

9
[ 13195-50-1 ]
[ 171290-94-1 ]
[ 450358-65-3 ]
dimethyl 2,2'-[2-(2-methoxy-2-oxoethoxy)-4-(5''-nitro-2,2';5',2''-terthien-5-yl)phenyl]imino}diacetate [ No CAS ]

References: [1]Tetrahedron,2006,vol. 62,p. 684 - 690.

10
[ 13195-50-1 ]
[ 492-97-7 ]
[ 122845-17-4 ]

References: [1]Tetrahedron,2006,vol. 62,p. 684 - 690.

11
[ 13195-50-1 ]
[ 100-67-4 ]
[ 190966-67-7 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 5144 - 5150.

12
[ 888504-62-9 ]
[ 13195-50-1 ]
2-[5-(butylthio)thien-2-ylethynyl]-5-nitrothiophene [ No CAS ]

References: [1]Synthesis,2006,p. 1009 - 1015.

13
[ 888504-75-4 ]
[ 13195-50-1 ]
2-[5-(dodecylthio)thien-2-ylethynyl]-5-nitrothiophene [ No CAS ]

References: [1]Synthesis,2006,p. 1009 - 1015.

14
[ 892878-83-0 ]
[ 13195-50-1 ]
[ 892878-91-0 ]

References: [1]Synthesis,2006,p. 1325 - 1332.

15
[ 892878-82-9 ]
[ 13195-50-1 ]
[ 892878-86-3 ]

References: [1]Synthesis,2006,p. 1325 - 1332.

16
[ 888504-66-3 ]
[ 13195-50-1 ]
C₂₈H₃₁NO₂S₄ [ No CAS ]

References: [1]Synthesis,2006,p. 1009 - 1015.

17
[ 888504-69-6 ]
[ 13195-50-1 ]
C₃₄H₃₃NO₂S₅ [ No CAS ]

References: [1]Synthesis,2006,p. 1009 - 1015.

18
[ 888504-72-1 ]
[ 13195-50-1 ]
C₄₀H₃₅NO₂S₆ [ No CAS ]

References: [1]Synthesis,2006,p. 1009 - 1015.

19
[ 13195-50-1 ]
(5-formylthiophen-2-yl)boronic acid [ No CAS ]
[ 34683-86-8 ]

References: [1]Chemistry - A European Journal,2006,vol. 12,p. 667 - 675.

20
[ 13195-50-1 ]
[ 59016-93-2 ]
[ 1198096-24-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 20 - 60℃; for 2h;	A solution of compound 52ii (100 mg, 0.48 mmol), 52iii (73 mg, 0.48 mmol), and KOAc (190 mg, 1.92 mmol) in DMF (5 ml) was degassed thrice and PdCl2(drhopf) (36 mg, 0.048 mmol) added to it at rt under an argon atmosphere. The reaction mixture was heated at 6O0C for two hours, diluted with ethyl acetate (EA) and washed with brine. The organic layer was dried, concentrated, and the residue separated by column chromatography on silica gel employing as eluent EA/Hex (0 - 80percent) to yield 52i.

References: [1]Patent: WO2007/2931,2007,A2 .Location in patent: Page/Page column 131-132.

21
[ 13195-50-1 ]
[ 10602-04-7 ]
C₁₃H₉NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; In N,N-dimethyl-formamide; at 20 - 60℃; for 2h;	A solution of compound 59ii (200 mg, 0.96 mmol) and 59iii (127 mg, 0.96 mmol) in DMF (3 ml) was degassed thrice and PdCl2(dppf) (50 mg, 0.07 mmol) was added to it, EPO <DP n="135"/>followed by CuI (8.5 mg, 0.043 mmol) and TEA (0.27 ml, 1.92 mmol), at rt, under argon atmosphere and the reaction mixture was heated at 60 0C for two hours. The reaction mixture was diluted with EA, washed with brine, the organic layer separated, dried, and concentrated to yield a residue which was separated by column chromatography on silica gel employing as eluent EA\\Hex (0-70percent) to yield compound 5Si.

References: [1]Patent: WO2007/2931,2007,A2 .Location in patent: Page/Page column 133-134.

22
[ 13195-50-1 ]
[ 791594-90-6 ]
[ 959393-25-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; toluene; at 90℃;	Example 6B methyl flJR,2i')-2-f4-(5-ni<tauothien-2-yl')benzoyl]cvclopentanecarboxylate To an ambient slupiy of 6A (270 rng, 0.75 mmol), 2-brorno-5-nittauo-thiophene (156 mg, 0.75 mmol) and potassium fluoride (130 mg, 2,24 mmol) in dimethyoxyethane/toluene/ethanol/HiO (10/1/6/3 ratio, 3 mL) was added palladium tettauakis(triphenylphosphipie) (10 mg, 0 0086 mmol) in a single portion The reaction was heated at 90 0C overnight, cooled Io room iemperatipie, filtered through celite, washed with ethyl acetate, concent. aled and puiified by flash chromatography on SiO? column (0 - 5percent ethyl acetate in hexanes) to provide the title compound as yellow solid 1H NMR (500 MHz, DMSO-d6) delta ppm 1 .54-1 87 (m, 4H), 1 99-2 20 (m, 2H), 3 30 (m, IH), 3.57 (s, 3H), 4. 12 (m, 1 H), 7 ,84 (d, ./ = 4.27 Hz, 1 H), 8 ,01 (d, J = 8.54 Hz, 2H), 8 10 (d, J = 8 54 Hz, 2H), 8 23 (d, J = 427 Hz, IH); MS (DCl/NHj) m/z 360 [M+I-lf

References: [1]Patent: WO2007/137107,2007,A2 .Location in patent: Page/Page column 64.

23
[ 13195-50-1 ]
[ 910251-11-5 ]
[ 910251-46-6 ]