52414-98-9|4-Bromo-2-methyl-1-nitrobenzene| Ambeed

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Quality Control of [ 52414-98-9 ] Purity: 97% SDS Specification

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Product Details of [ 52414-98-9 ]

CAS No. :	52414-98-9
Formula :	C₇H₆BrNO₂
M.W :	216.03
SMILES Code :	O=[N+](C1=CC=C(Br)C=C1C)[O-]
MDL No. :	MFCD00137824
Boiling Point :	No data available
InChI Key :	PAHAIHXVVJMZKU-UHFFFAOYSA-N
Pubchem ID :	81577

Safety of [ 52414-98-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 52414-98-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	47.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.82
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	3.53
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.67
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.	2.77
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	0.8
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.32

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.74
Solubility	0.0392 mg/ml ; 0.000182 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.	-4.18
Solubility	0.0144 mg/ml ; 0.0000666 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	-3.02
Solubility	0.204 mg/ml ; 0.000946 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.	-5.11 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<2.0
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 [ 52414-98-9 ]

* 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 [ 52414-98-9 ]

[ 52414-98-9 ] Synthesis Path-Downstream 1~35

1
[ 591-17-3 ]
[ 52414-98-9 ]
[ 40385-54-4 ]

References: [1]Bulletin de la Societe Chimique de France,1932,vol. <4> 51,p. 1416,1421.

2
[ 52414-98-9 ]
[ 1124-31-8 ]
(3-methyl-4-nitro-phenyl)-(3-nitro-phenyl)-ether [ No CAS ]

References: [1]Journal of the Chemical Society,1934,p. 52,54.

3
[ 52414-98-9 ]
[ 930-69-8 ]
[ 60326-45-6 ]

References: [1]Bulletin de la Societe Chimique de France,1932,vol. <4> 51,p. 1416,1421.

4
[ 52414-98-9 ]
[ 88070-23-9 ]

References: [1]Journal of the Chemical Society,1932,p. 1987.

5
[ 52414-98-9 ]
bis-(3-methyl-4-nitro-phenyl)-sulfide [ No CAS ]

References: [1]Journal of the Chemical Society,1934,p. 1140.

6
[ 52414-98-9 ]
bis-(3-methyl-4-nitro-phenyl)-disulfide [ No CAS ]

References: [1]Journal of the Chemical Society,1934,p. 1140.

7
[ 52414-98-9 ]
[ 583-75-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 2 wt% Pd/C; hydrogen; at 120℃; under 7500.75 Torr;	Examples 27 to 34 investigated the effect of carbon-supported large-particle palladium catalysts on the synthesis of halogenated aromatic amines by solvent-free hydrogenation of different halogenated aromatic nitro compounds. In a 500 ml reactor, 200 g of different halogenated aromatic nitro compounds were added, 2 g of a 2 wt% palladium catalyst containing a large particle size in Example 5, shutting down the reactor; first with nitrogen replacement reactor inside the air three times, and then replaced with hydrogen three times, And then heated to 120 C, and the hydrogen pressure rose to 1MPa, open stirring to 1000r/min; to maintain the reaction temperature and pressure until the end of the reaction; cooling cooling, remove the reactor liquid, filter separation The catalyst was used and the water in the filtrate was separated by phase separation to give the desired product Halogenated aromatic amine. The reaction product was analyzed by gas chromatography. The results are shown in Table 4.

References: [1]Justus Liebigs Annalen der Chemie,1875,vol. 177,p. 246.
[2]Justus Liebigs Annalen der Chemie,1875,vol. 177,p. 246.
[3]Patent: CN104163764,2016,B .Location in patent: Paragraph 0050-0053.

8
[ 611-05-2 ]
[ 52414-98-9 ]

Yield	Reaction Conditions	Operation in experiment
73%		Preparation of 4-bromo~2-methyI-1-nitro-benzene (102):[0190] To an ice cold solution of 10.0 g (65.7 mmol) 3-methyl-4-nitro-phenylamine in 200 niL acetone, was added 21 niL (197.2 mmol) 48% HBr. 4.54g (65.7 mmol) NaNO2 was dissolved in 20 mL water and was added dropwise to the amine solution at a rate to keep the temperature under 5 C. The mixture was stirred at this temperature for an additional 10 minutes then 1.5 g (10 mmol) solid CuBr was added portion-wise at a rate to keep the temperature under 15 C. The reaction was complete when no EPO <DP n="94"/>more nitrogen evaluated (about 15 minutes). The reaction mixture was evaporated to dryness; the residue was dissolved in a mixture of 500 mL water and 750 mL ethyl acetate. The organic phase was separated, washed with water (2x), saturated NaCl (2x) and was dried (Na2SO4). It was then evaporated to dryness to give the crude product as a yellow solid which was purified by filtering through 400 mL silica gel pad using toluene elution;Yield: 10.45g (73%);1H-NMR (CDCl3): delta (ppm) 7.87 (d, 1H, J=8.7Hz), 7.51-7.46 (m, 2H), 2.61 (s, 3H).
73%		To an ice cold solution of 10.0 g (65.7 mmol) 3-methyl-4-nitro-phenylamine in 200 mL acetone, was added 21 mL (197.2 mmol) 48% HBr. 4.54 g (65.7 mmol) NaNO2 was dissolved in 20 mL water and was added dropwise to the amine solution at a rate to keep the temperature under 5 C. The mixture was stirred at this temperature for an additional 10 minutes then 1.5 g (10 mmol) solid CuBr was added portion-wise at a rate to keep the temperature under 15 C. The reaction was complete when no more nitrogen evaluated (about 15 minutes). The reaction mixture was evaporated to dryness; the residue was dissolved in a mixture of 500 mL water and 750 mL ethyl acetate. The organic phase was separated, washed with water (2), saturated NaCl (2) and was dried (Na2SO4). It was then evaporated to dryness to give the crude product as a yellow solid which was purified by filtering through 400 mL silica gel pad using toluene elution; Yield: 10.45 g (73%); 1H-NMR (CDCl3): delta (ppm) 7.87 (d, 1H, J=8.7 Hz), 7.51-7.46 (m, 2H), 2.61 (s, 3H).
73%		To an ice cold solution of 10.0 g (65.7 mmol) 3-methyl-4-nitro-phenylamine in 200 mL acetone, was added 21 mL (197.2 mmol) 48% HBr. 4.54g (65.7 mmol) NaNO2 was dissolved in 20 mL water and was added dropwise to the amine solution at a rate to keep the temperature under 5 0C. The mixture was stirred at this temperature for an additional 10 <n="96"/>minutes then 1.5 g (10 mmol) solid CuBr was added portion- wise at a rate to keep the temperature under 15 0C. The reaction was complete when no more nitrogen evaluated (about 15 minutes). The reaction mixture was evaporated to dryness; the residue was dissolved in a mixture of 500 mL water and 750 mL ethyl acetate. The organic phase was separated, washed with water (2x), saturated NaCl (2x) and was dried (Na2SO4). It was then evaporated to dryness to give the crude product as a yellow solid which was purified by filtering through 400 mL silica gel pad using toluene elution;Yield: 10.45g (73%);1H-NMR (CDCl3): delta (ppm) 7.87 (d, IH, J=8.7Hz), 7.51-7.46 (m, 2H), 2.61 (s, 3H).

References: [1]Mendeleev Communications,2018,vol. 28,p. 261 - 263.
[2]Patent: WO2006/76529,2006,A1 .Location in patent: Page/Page column 92-93.
[3]Patent: US2007/32488,2007,A1 .Location in patent: Page/Page column 28-29.
[4]Patent: WO2008/8912,2008,A1 .Location in patent: Page/Page column 81; 94-95.
[5]Journal of the American Chemical Society,1948,vol. 70,p. 219.
[6]Journal of the Chemical Society,1929,p. 1255.

9
[ 583-75-5 ]
[ 52414-98-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dihydrogen peroxide; trifluoroacetic anhydride; In dichloromethane; at 0℃; for 1.58333h;Heating / reflux;	Example 37; 2-methoxy-N-(2-methyl-4-(1-(2-(methylamino)ethyl)piperidin-4-yl)phenyl)benzamide (199); Step 1 4-bromo-2-methyl-1 -nitrobenzene (193); [0383] To a mixture of H2O2 (3 95 ml, 64 5 mmol) in DCM (32 0 ml) cooled at O 0C was added TFAA (10 93 ml, 77 mmol) and the mixture was stirred for 5 minutes at that temperature then the ice bath was removed and a reflux condenser was installed and a solution of 4-bromo-2-methylaniline (3 g, 16 12 mmol) in DCM (6 4 ml) was added drop-wise over approx 30 minutes The reaction was heated at reflux for an additional hour then it it was cooled, washed with 30 mL of water then 30 mL of sat NaHCO3 and the organic layer was dried over MgSO4 and concentrated under vacuum The crude material was purified by flash to afford 193 (2 57 g, 1 1 9 mmol, 74%) 1H NMR (CDCI3) delta (ppm) 7 88 (d, J = 8 6 Hz, 1 H),7 53 (d, J = 2 2 Hz, 1 H), 7 49 (dd, J = 8 6, 2 2 Hz, 1 H), 2 60 (s, 3H)
	With sulfuric acid; dihydrogen peroxide; In hexane; water; acetic acid;	Step A: Preparation of 5-bromo-2-nitrotoluene A solution of 4-bromotoluidine (27.9 g, 150 mmoles) in glacial acetic acid (600 ml) is stirred while 30% hydrogen peroxide (180 ml) and concentrated sulfuric acid (12 ml) are added. The mixture is heated in an oil bath at 100. When the pot temperature reaches 65 the mixture darkens and there is a mild exotherm. The bath is removed and the temperature rises to 105. When the reaction subsides, the bath is replaced and reflux is maintained for two hours. The mixture is cooled and poured onto ice (1500 g). The product crystallizes slowly with scratching. Another liter of cold water is added and the product is filtered and washed. The damp solid is dissolved in hexane, filtered, dried and evaporated to a residue which crystallizes to give 14.3 g of 5-bromo-2-nitrotoluene, containing minor contaminants by tlc [silica gel-dichloromethane/hexane (3:7)] which were removed by column chromatography using the same solvent system. Final weight; 12.8 g.

References: [1]Patent: WO2008/104077,2008,A1 .Location in patent: Page/Page column 122.
[2]Journal of Organic Chemistry,1955,vol. 20,p. 1458.
[3]Patent: US4287201,1981,A .

10
[ 52414-98-9 ]
[ 4637-24-5 ]
[ 105205-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 145℃; for 2h;	Preparation of [(E)-2-(5-bromo-2-nitro-phenyl)-viny1]-dimethyI-amine (104): [0191] A mixture of 9.26 g (42.9 mmol) of compound 102, 14.3 mL (107.2 mmol) N,N-dimethylformamide dimethylacetal and 11 mL DMF was heated under a slow argon flow at 145 C (bath) for two hours. The reaction mixture was then evaporated to dryness. The dark pink product crystallized upon standing; MS: 271.01 & 273.01 (M+-H+); 1H-NMR (DMSO-d6): delta (ppm) 7.88 (d, 1H), 7.68 (dd, 1H), 7.58 (d, 1H), 7.05 (d, 1H), 5.59 (d, 1H), 2.90 (s, 6H).
	In N,N-dimethyl-formamide; at 145℃; for 2h;	Preparation of [(E)-2-(5-bromo-2-nitro-phenyl)-vinyl]-dimethyl-amine 7.4: A mixture of 9.26 g (42.9 mmol) of compound 7.2, 14.3 mL (107.2 mmol) N,N-dimethylformamide dimethylacetal 7.3 and 11 mL DMF was heated under a slow argon flow at 145 C. (bath) for two hours. The reaction mixture was then evaporated to dryness. The dark pink product crystallized upon standing; MS: 271.01 & 273.01 (M+H+); 1H-NMR (DMSO-d6): delta (ppm) 7.88 (d, 1H), 7.68 (dd, 1H), 7.58 (d, 1H), 7.05 (d, 1H), 5.59 (d, 1H), 2.90 (s, 6H).
	In N,N-dimethyl-formamide; at 145℃; for 2h;	A mixture of 9.26 g (42.9 mmol) of compound 4.2, 14.3 mL (107.2 mmol) N,N- dimethylformamide dimethylacetal 4.3 and 11 mL DMF was heated under a slow argon flow at 145 0C (bath) for two hours. The reaction mixture was then evaporated to dryness. The dark pink product crystallized upon standing; MS: 271.01 & 273.01 (M+H+); 1H-NMR (DMSO-de): delta (ppm) 7.88 (d, IH), 7.68 (dd, IH), 7.58 (d, IH), 7.05 (d, IH), 5.59 (d, IH), 2.90 (s, 6H).

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 5106 - 5110.
[2]Patent: WO2006/76529,2006,A1 .Location in patent: Page/Page column 92; 93.
[3]Patent: US2007/32488,2007,A1 .Location in patent: Page/Page column 28-29.
[4]Patent: WO2008/8912,2008,A1 .Location in patent: Page/Page column 81; 95.

11
[ 52414-98-9 ]
[ 35287-42-4 ]

References: [1]Journal of Heterocyclic Chemistry,1972,vol. 9,p. 119 - 122.

12
[ 52414-98-9 ]
[ 95-92-1 ]
[ 17403-17-7 ]

References: [1]Journal of the Chemical Society C: Organic,1968,p. 504 - 507.

13
[ 52414-98-9 ]
[ 10486-08-5 ]
[ 53258-92-7 ]

References: [1]Gazzetta Chimica Italiana,1973,vol. 103,p. 723 - 730.
[2]Gazzetta Chimica Italiana,1973,vol. 103,p. 723 - 730.

14
[ 591-17-3 ]
[ 7697-37-2 ]
[ 108-39-4 ]
[ 52414-98-9 ]
[ 52414-97-8 ]
[ 40385-54-4 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1934,vol. 53,p. 1011,1016, 1025.

15
[ 591-17-3 ]
[ 7697-37-2 ]
[ 52414-98-9 ]
[ 52414-97-8 ]
[ 40385-54-4 ]
[ 5411-53-0 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1934,vol. 53,p. 1011,1016, 1025.

19
m-bromo-toluene [ No CAS ]
[ 52414-98-9 ]

References: [1]Justus Liebigs Annalen der Chemie,1875,vol. 177,p. 246.

20
[ 64-17-5 ]
[ 52414-98-9 ]
Na₂S₂ [ No CAS ]
bis-(3-methyl-4-nitro-phenyl)-disulfide [ No CAS ]

References: [1]Journal of the Chemical Society,1934,p. 1140.

21
[ 52414-98-9 ]
[ 7732-18-5 ]
Na₂S₂ [ No CAS ]
[ 88070-23-9 ]
[ 583-75-5 ]

References: [1]Journal of the Chemical Society,1932,p. 1987.

22
[ 52414-98-9 ]
sodium-salt of 4-amino-3-methyl-thiophenol [ No CAS ]
[ 858843-42-2 ]

References: [1]Journal of the Chemical Society,1934,p. 1140.

23
[ 52414-98-9 ]
[ 108-59-8 ]
4-(5-bromo-2-nitro-phenyl)-3-oxo-butyric acid [ No CAS ]