15540-81-5|1-Bromo-2,5-dimethyl-4-nitrobenzene| Ambeed

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Quality Control of [ 15540-81-5 ] Purity: 98% SDS Specification

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Product Details of [ 15540-81-5 ]

CAS No. :	15540-81-5
Formula :	C₈H₈BrNO₂
M.W :	230.06
SMILES Code :	O=[N+](C1=C(C)C=C(Br)C(C)=C1)[O-]
MDL No. :	MFCD01463298
Boiling Point :	No data available

Safety of [ 15540-81-5 ]

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

Computational Chemistry of [ 15540-81-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	52.9
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.	2.05
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	3.17
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.97
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.	3.08
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	1.26
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.51

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.57
Solubility	0.0623 mg/ml ; 0.000271 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.	-3.8
Solubility	0.0362 mg/ml ; 0.000157 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	-3.41
Solubility	0.0891 mg/ml ; 0.000387 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.	-5.45 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)	1.99

Application In Synthesis of [ 15540-81-5 ]

* 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 [ 15540-81-5 ]

[ 15540-81-5 ] Synthesis Path-Downstream 1~35

1
[ 15540-81-5 ]
[ 30273-40-6 ]

References: [1]Chemisches Zentralblatt,1913,vol. 84,p. 1108.

2
[ 553-94-6 ]
[ 15540-81-5 ]

Yield	Reaction Conditions	Operation in experiment
36.1%	With sulfuric acid; nitric acid; acetic acid; at 8 - 10℃; for 1.75h;	Example 4; 4-(2-Fluorophenyl)-7-methyl-6-(pyrimidin-5-yloxy)-9H-pyrido[3,4-b]indole-1- carboxamide; l-Bromo-2,5-dimethyl-4-nitrobenzene; To a slurry of 2-bromo-1,4-dimethylbenzene (10.13 g, 54.7 mmol) in acetic acid (44 mL) at 8 C (inner temperature) was added a solution of nitric acid (6 mL, 134 mmol) in sulfuric acid (22 mL, 413 mmol) over 45 min; temperature rose to 10 C. After 1 hr, the reaction mixture was poured into ice and stirred, filtered and washed with water to give a light yellow solid. This was triturated with EtOH (10 mL) to give the desired product (4.550 g, 19.78 mmol, 36.1% yield) as an off-white solid.

References: [1]Tetrahedron,1980,vol. 36,p. 3535 - 3542.
[2]Patent: WO2011/159857,2011,A1 .Location in patent: Page/Page column 68.
[3]Journal of the Indian Chemical Society,1935,vol. 12,p. 540.

3
[ 3460-29-5 ]
[ 15540-81-5 ]

Yield	Reaction Conditions	Operation in experiment
76%		Part A- Preparation of Copper (1) bromide solution A solution of copper(I) bromide (72.5 g, 505 mmol) in hydrochloric acid, 37% ( 150 mL) was heated to 80 C to obtain a clear solution. Part B- To a mixture of 2,5-dimethyl-4-nitroaniline (21 g, 126 mmol) in cone, hydrochloric acid, ( 1 50 mL), a saturated solution of sodium nitrite ( 1 7.5 g, 253 mmol) in water (20 mL) was added dropwise at 0 C and mixture was stirred for 30 min. After 30 min, above (Part-A) solution of copper (I) bromide (72.5 g, 505 mmol) was added dropwise at 0 C. After complete addition, mixture was heated to 80 C for 1 h. The reaction mixture was di luted with water, extracted with ethyl acetate. The organic layer was dried over anhydrous sodi um sulfate, concentrated under reduced pressure and purified by col umn chromatography (Hexane/EthylAcetate (8:2) to obtain l -bromo-2,5-dimethyl-4-nitrobenzene (22 g, 76 % yield).

References: [1]Patent: WO2018/211442,2018,A1 .Location in patent: Page/Page column 71-72.
[2]Recueil des Travaux Chimiques des Pays-Bas,1956,vol. 75,p. 1137,1138, 1149.

4
[ 15540-81-5 ]
[ 10486-08-5 ]
[ 53258-93-8 ]

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

8
diazotized 5-nitro-2-amino-p-xylene [ No CAS ]
[ 15540-81-5 ]

References: [1]Chemisches Zentralblatt,1913,vol. 84,p. 1108.

9
[ 553-94-6 ]
[ 7697-37-2 ]
[ 108-24-7 ]
SO₂ [ No CAS ]
[ 15540-81-5 ]

References: [1]Journal of the Indian Chemical Society,1935,vol. 12,p. 540.

10
[ 106-42-3 ]
[ 15540-81-5 ]

References: [1]Tetrahedron,1980,vol. 36,p. 3535 - 3542.

11
[ 15540-81-5 ]
[ 13711-31-4 ]

References: [1]Chemisches Zentralblatt,1913,vol. 84,p. 1108.

12
[ 675-20-7 ]
[ 15540-81-5 ]
[ 444002-66-8 ]

References: [1]Patent: WO2004/87646,2004,A2 .Location in patent: Page/Page column 108.
[2]Patent: WO2006/34789,2006,A1 .Location in patent: Page/Page column 37.

13
(1-benzo-2-thienyl)boronic acid [ No CAS ]
[ 15540-81-5 ]
[ 497-19-8 ]
4-(1-benzo-2-thienyl)-2,5-dimethyl-aniline [ No CAS ]
2-(2,5-dimethyl-4-nitrophenyl)-1-benzothiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene;	Preparation of 4-(1-benzo-2-thienyl)-2,5-dimethyl-aniline A mixture of <strong>[15540-81-5]1-bromo-2,5-dimethyl-4-nitrobenzene</strong> (3.6 g), (1-benzo-2-thienyl)boronic acid (3.6 g), tetrakis(triphenylphosphine)palladium (0.4 g) and aqueous sodium carbonate solution (2M) (17 ml) in ethanol (36 ml) and toluene (100 ml) is stirred at reflux for 18 h. Partial evaporation followed by extraction with ethyl acetate, drying of the organic phase and then re-evaporation gives 2-(2,5-dimethyl-4-nitrophenyl)-1-benzothiophene. 2-(2,5-Dimethyl-4-nitrophenyl)-1-benzothiophene is reduced according to the methods described above to give the title aniline.

References: [1]Patent: US2003/8884,2003,A1 .

14
[ 15540-81-5 ]
[ 97674-02-7 ]
[ 1202389-14-7 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 3 2,5-dimethyl-4-(3-methyrisoxazol-5-vl)anirine <n="32"/>Step 1: l-(2,5-dimethyl-4-nitrophenyl)ethanone[0080] To a mixture of l-Bromo-2,5-dimethyl-4-nitrobenzene (I g, 4.34 mmol) and tributyl(l-ethoxyvinyl)tin (1.88 g, 5.2 mmol) in DMF (20 mL), was added tetrakis(triphenylphospine) palladium (0) (250 mg, 5 % mmol). The reaction tube was sealed, the mixture was purged with N2 for 3 min and then heated at 900C under N2 for overnight. The reaction was cooled to room temperature and poured into aqueous HCl (IN, 100 mL). The mixture was stirred for 1 hour, and then extracted with ethyl acetate (3 x 100 mL). The organic extracts were combined, washed with brine and concentrated. The crude product was purified with silica gel chromatography (20 % ethyl acetate in hexanes) to afford l-(2,5-dimethyl-4-nitrophenyl)ethanone as a yellow solid.

References: [1]Patent: WO2009/158431,2009,A2 .Location in patent: Page/Page column 30-31.

15
[ 680596-79-6 ]
[ 15540-81-5 ]
[ 1202389-28-3 ]