127413-59-6|1-(3-Bromo-5-nitrophenyl)ethanone| Ambeed

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Quality Control of [ 127413-59-6 ] Purity: 95% SDS Specification

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Product Details of [ 127413-59-6 ]

CAS No. :	127413-59-6
Formula :	C₈H₆BrNO₃
M.W :	244.04
SMILES Code :	CC(C1=CC([N+]([O-])=O)=CC(Br)=C1)=O
MDL No. :	MFCD20923634
InChI Key :	KMNMBNPBERMCLJ-UHFFFAOYSA-N
Pubchem ID :	182852

Safety of [ 127413-59-6 ]

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

Computational Chemistry of [ 127413-59-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	53.16
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	62.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.51
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	2.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.56
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.	1.33
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	0.69
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.64

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.9
Solubility	0.304 mg/ml ; 0.00125 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.	-3.08
Solubility	0.202 mg/ml ; 0.000828 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	-2.97
Solubility	0.26 mg/ml ; 0.00107 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	Yes
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.	-6.28 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)	2.1

Application In Synthesis of [ 127413-59-6 ]

* 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 [ 127413-59-6 ]

[ 127413-59-6 ] Synthesis Path-Downstream 1~35

1
[ 121-89-1 ]
[ 127413-59-6 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 239 - 240.
[2]Synlett,2013,vol. 24,p. 603 - 606.
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 1281 - 1297.

2
[ 7787-71-5 ]
[ 121-89-1 ]
[ 127413-59-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bromine; sodium sulfite; In 1,1,2-Trichloro-1,2,2-trifluoroethane;	EXAMPLE 15 A vigorously stirred mixture consisting of 2.5 ml (0.05 mole) of bromine trifluoride and 3.2 ml (0.056 mole) of bromine was added into an ice-water cooled three necked flask equipped with a magnetic stirrer and a condenser, containing a suspension of 36 gr (0.2 mole) 3-nitroacetophenone in 80 ml of freon 113. The addition was carried out dropwise with vigorous stirring while the temperature was kept under 20 C. After the addition was completed the crude reaction mixture was poured into a stirred icy 5% sodium sulfite solution. The organic layer was separated and the aqueous solution was extracted twice with 100 ml dichloromethane. The combined organic layer was washed with 5% sodium bicarbonate solution and successively with water. The organic phase was dried over anhydrous magnesium sulphate and the solvent evaporated. The residue was distilled under reduced pressure in order to get rid of unreacted substrate. The residue was recrystallized from toluene. 7.3 gr of 3-bromo-5-nitroacetophenone were obtained, 85% yield based on reacted substrate.

References: [1]Patent: US4954648,1990,A .

3
[ 1202036-18-7 ]
manganedioxide [ No CAS ]
[ 127413-59-6 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane;	b) 1-(3-Bromo-5-nitro-phenyl)-ethanone 1-(3-Bromo-5-nitro-phenyl)-ethanol (12.84 g, 52.2 mmol) was dissolved in dioxane (245 ml) and manganedioxide (31.8 g, 365 mmol) was added. The reaction was refluxed for 17 hrs. The reaction was filtered and solvent was removed under reduced pressure yielding the title compound as yellow solid. 1H-NMR (500 MHz, DMSO-d6): 8.64 (s, 1H), 8.58 (s, 1H), 8.53 (s, 1H), 2.70 (s, 3H); GC/MS: 243 [(M)+].

References: [1]Patent: US8338413,2012,B1 .

4
[ 127413-59-6 ]
[ 196929-78-9 ]
[ 1262859-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With titanium(IV) tetraethanolate; In tetrahydrofuran; for 2.5h;Reflux;	<strong>[127413-59-6]1-(3-Bromo-5-nitro-phenyl)-ethanone</strong> (11.6 g, 47.5 mmol), (R)-(+)-tert-butanesulfinamide (6.34 g, 52.3 mmol) and Ti(OEt)4 (24.64 ml, 119 mmol) were mixed in 62 ml THF and refluxed for 2.5 hrs. The reaction was cooled and carefully quenched by addition of ice and water. The white precipitate was filtered off and the aqueous mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure. The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as yellow oil. 1H-NMR (500 MHz, DMSO-d6): 8.58 (s, 1H), 8.55 (s, 1H), 8.43 (s, 1H), 2.79 (s, 3H), 1.24 (s, 9H); MS: 347 [(M+H)+]; [alpha]D=+54.5 (c=0.481% in chloroform).

References: [1]Patent: US2011/21520,2011,A1 .Location in patent: Page/Page column 49.

5
[ 1202036-18-7 ]
[ 127413-59-6 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese(IV) oxide; In 1,4-dioxane; for 17.0h;Reflux;	1-(3-Bromo-5-nitro-phenyl)-ethanol (12.84 g, 52.2 mmol) was dissolved in dioxane (245 ml) and manganedioxide (31.8 g, 365 mmol) was added. The reaction was refluxed for 17 hrs. The reaction was filtered and solvent was removed under reduced pressure yielding the title compound as yellow solid. 1H-NMR (500 MHz, DMSO-d6): 8.64. (s, 1H), 8.58 (s, 1H), 8.53 (s, 1H), 2.70 (s, 3H); GC/MS: 243 [(M)+].
	With manganese(IV) oxide; In 1,4-dioxane; for 17.0h;Reflux;	b) 1-(3-Bromo-5-nitro-phenyl)-ethanone 1-(3-Bromo-5-nitro-phenyl)-ethanol (12.84 g, 52.2 mmol) was dissolved in dioxane (245 ml) and manganedioxide (31.8 g, 365 mmol) was added. The reaction was refluxed for 17 hrs. The reaction was filtered and solvent was removed under reduced pressure yielding the title compound as yellow solid. 1H-NMR (500 MHz, DMSO-d6): 8.64 (s, 1H), 8.58 (s, 1H), 8.53 (s, 1H), 2.70 (s, 3H); GC/MS: 243 [(M)+].

References: [1]Patent: US2011/21520,2011,A1 .Location in patent: Page/Page column 49.
[2]Patent: US2012/172359,2012,A1 .Location in patent: Page/Page column 49.

6
Ti(OEt)4 [ No CAS ]
2-methyl-propane-2-sulfinic acid amide [ No CAS ]
[ 127413-59-6 ]
2-Methyl-propane-2-sulfinic acid [1-(3-bromo-5-nitro-phenyl)-eth-(E)-ylidene]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	c) 2-Methyl-propane-2-sulfinic acid [1-(3-bromo-5-nitro-phenyl)-eth-(E)-ylidene]-amide <strong>[127413-59-6]1-(3-Bromo-5-nitro-phenyl)-ethanone</strong> (11.6 g, 47.5 mmol), (R)-(+)-tert-butanesulfinamide (6.34 g, 52.3 mmol) and Ti(OEt)4 (24.64 ml, 119 mmol) were mixed in 62 ml THF and refluxed for 2.5 hrs. The reaction was cooled and carefully quenched by addition of ice and water. The white precipitate was filtered off and the aqueous mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure. The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as yellow oil. 1H-NMR (500 MHz, DMSO-d6): 8.58 (s, 1H), 8.55 (s, 1H), 8.43 (s, 1H), 2.79 (s, 3H), 1.24 (s, 9H); MS: 347 [(M+H)+]; [alpha]D=+54.5 (c=0.481% in chloroform).

References: [1]Patent: US8338413,2012,B1 .

7
[ 127413-59-6 ]
[ 1262859-19-7 ]

References: [1]Patent: US2012/172359,2012,A1 .

8
[ 127413-59-6 ]
[ 1262859-20-0 ]

References: [1]Patent: US2012/172359,2012,A1 .

9
[ 127413-59-6 ]
[ 1262859-23-3 ]

References: [1]Patent: US2012/172359,2012,A1 .

10
[ 127413-59-6 ]
[ 1262859-21-1 ]

References: [1]Patent: US2012/172359,2012,A1 .

11
[ 127413-59-6 ]
[ 1262859-24-4 ]

References: [1]Patent: US2012/172359,2012,A1 .

12
[ 127413-59-6 ]
[ 1262859-25-5 ]

References: [1]Patent: US2012/172359,2012,A1 .

13
[ 127413-59-6 ]
[ 1262859-29-9 ]

References: [1]Patent: US2012/172359,2012,A1 .

14
[ 127413-59-6 ]
[ 1262859-27-7 ]

References: [1]Patent: US2012/172359,2012,A1 .

15
[ 127413-59-6 ]
[ 1262859-31-3 ]

References: [1]Patent: US2012/172359,2012,A1 .

16
[ 127413-59-6 ]
[ 1262855-75-3 ]

References: [1]Patent: US2012/172359,2012,A1 .

17
[ 127413-59-6 ]
2-methyl-propane-2-sulfinic acid [(R)-(3-bromo-5-nitro-phenyl)-cyano-methyl-methyl]-amide [ No CAS ]

References: [1]Patent: US2012/172359,2012,A1 .

18
(S)-(-)-tert-butanesulfinamide [ No CAS ]
[ 127413-59-6 ]
2-Methyl-propane-2-sulfinic acid [1-(3-bromo-5-nitro-phenyl)-eth-(E)-ylidene]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		c) 2-Methyl-propane-2-sulfinic acid [1-(3-bromo-5-nitro-phenyl)-eth-(E)-ylidene]-amide <strong>[127413-59-6]1-(3-Bromo-5-nitro-phenyl)-ethanone</strong> (11.6 g, 47.5 mmol), (R)-(+)-tert-butanesulfinamide (6.34 g, 52.3 mmol) and Ti(OEt)4 (24.64 ml, 119 mmol) were mixed in 62 ml THF and refluxed for 2.5 hrs. The reaction was cooled and carefully quenched by addition of ice and water. The white precipitate was filtered off and the aqueous mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure. The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as yellow oil. 1H-NMR (500 MHz, DMSO-d6): 8.58 (s, 1H), 8.55 (s, 1H), 8.43 (s, 1H), 2.79 (s, 3H), 1.24 (s, 9H); MS: 347 [(M+H)+]; [alpha]D=+54.5 (c=0.481% in chloroform).

References: [1]Patent: US2012/172359,2012,A1 .Location in patent: Page/Page column 49.

19
[ 355134-13-3 ]
[ 127413-59-6 ]