101980-41-0|2-Bromo-1-isopropyl-4-nitrobenzene| Ambeed

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Quality Control of [ 101980-41-0 ] Purity: 97% SDS Specification

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Product Details of [ 101980-41-0 ]

CAS No. :	101980-41-0
Formula :	C₉H₁₀BrNO₂
M.W :	244.09
SMILES Code :	O=[N+](C1=CC=C(C(C)C)C(Br)=C1)[O-]
MDL No. :	MFCD12024309
Boiling Point :	No data available
InChI Key :	QMWKRZOLOPHTIM-UHFFFAOYSA-N
Pubchem ID :	21531621

Safety of [ 101980-41-0 ]

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

Computational Chemistry of [ 101980-41-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	57.54
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.	2.23
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	3.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.48
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.	3.37
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	1.3
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.79

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.81
Solubility	0.0376 mg/ml ; 0.000154 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.	-4.22
Solubility	0.0148 mg/ml ; 0.0000605 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	-3.46
Solubility	0.0848 mg/ml ; 0.000348 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.	-5.25 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)	2.05

Application In Synthesis of [ 101980-41-0 ]

* 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 [ 101980-41-0 ]

[ 101980-41-0 ] Synthesis Path-Downstream 1~22

1
[ 1817-47-6 ]
[ 101980-41-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With iron(III) chloride; bromine; at 40.0℃; for 3.0h;	A solution of p-nitrocumene (X) (50 g, 0.300 mol, GC purity: 99.1 %) and iron(III) chloride was heated to 40C and bromine (59.92 g, 0.375 mol) was added dropwise over a period of 3 hours. The reaction mixture was poured into 120 ml of water, sodium hydrogensulphite (40% strength in water, 20.81 g, 0.078 mol) was added dropwise and the mixture was extracted with 100 ml of chlorobenzene. After phase separation, the chlorobenzene phase was washed with 100 ml of 5% strength aqueous HC1. Removal of the chlorobenzene under reduced pressure gave 2-bromo-l-isopropyl-4-nitrobenzene (74.05 g, 96.9 GC-% by area, 98% of theory) as a yellow oil. 1H-NMR (600 MHz, CDC13): delta = 8.41 (d, 1H), 8.14 (dd, 1H), 7.45 (d, 1H), 3.45 (heptet, 1H), 1.29 (d, 3H), 1.27 (d, 3H) ppm. GC-MS: m/ez = 245 [M+].
18%	With sulfuric acid; bromine; silver sulfate; In water; at 20.0℃; for 2.0h;	Bromine (0.32 mL) was added drop wise over 5 min to a reaction mixture containing 4-nitroisopropylbenzene (1.0 g, 6.06 mmol), silver sulfate (1.04 g, 3.33 mmol), and concentrated sulfuric acid (5.5 mL) in water (0.61 mL) at room temperature under constant stirring. The reaction mixture was stirred for 2 h, and poured on ether (200 mL). The ether layer was separated, washed with brine (2 X 50 mL), dried (Na2SO4), filtered, concentrated, and purified on a flash chromatography (SiO2, hexanes) to afford the title compound as a pale yellow liquid (1.15 g, 18%). [0239] 1H NMR (500 MHz, DMSO-J6): delta 1.23 (d, J= 6.9 Hz, 6H), 3.31-3.37 (m, IH), 7.68 (d, J = 8.7 Hz, IH), 8.20 (dd, J = 8.6, 2.4 Hz, IH), 8.37 (d, J= 2.4 Hz, IH)
	With sulfuric acid; bromine; silver sulfate; at 20.0℃;	Example 28 3-((3-carbamoyl-7-(2,4-dimethoxypyrimidin-5-yl)-6-isopropylquinolin-4-yl)amino)-5- cvclopentylbenzoic acid a) 2-bromo-1-isopropyl-4-nitrobenzene. To a mixture of 1-isopropyl-4-nitrobenzene (1 .0 g, 6.02 mmol), silver sulfate (1 .04 g, 3.01 mmol), concentrated sulphuric acid (5.5 mL) and water (0.61 mL) was added bromine (0.964 g, 6.02 mmol) dropwise at ambient temperature. After the addition, the mixture was stirred for 2 h at ambient temperature, then poured into dilute sodium hydrogensulfite solution (10%, 30 mL). The mixture was extracted with ethyl acetate (30 mL x 3) and dried over Na2S04. The solvent was removed under vacuum to provide the title compound (1.5 g) used crude in the next step.

23.1 g

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; for 3.0h;

1-Isopropyl-4-nitrobenzene (15 g) was added to sulfuric acid (26.7 g), 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (13.8 g) was added at 0C, and the mixture was then stirred for three hours. The reaction solution was poured into ice water and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium thiosulfate solution and an aqueous sodium bicarbonate solution and then concentrated under reduced pressure to give the target compound (23.1 g).

References: [1]Patent: WO2013/160387,2013,A1 .Location in patent: Page/Page column 22-23.
[2]Patent: WO2009/55674,2009,A1 .Location in patent: Page/Page column 68.
[3]Journal of the Chemical Society,1952,p. 4443,4445.
[4]Patent: WO2013/96151,2013,A1 .Location in patent: Page/Page column 93.
[5]Patent: EP3312172,2018,A1 .Location in patent: Paragraph 0313; 0314.

2
[ 101980-41-0 ]
[ 112299-61-3 ]

Yield	Reaction Conditions	Operation in experiment
3 g	With iron; acetic acid; In methanol; at 20.0℃; for 4.0h;	b) 3-bromo-4-isopropylaniline. 2-Bromo-1-isopropyl-4-nitrobenzene (5.86 g, 24.2 mmol) was dissolved in methanol (50 mL) and acetic acid (50 mL). Iron powder (6.78 g, 121 mmol) was added batchwise. The mixture was stirred for 4 h at room temperature and the reaction was monitored by TLC (ethyl acetate/petroleum ether 1 :5). After the starting material was consumed completely, the mixture was filtered. Methanol was removed by evaporation. The residue was neutralized with aqueous ammonia (100 mL) and extracted with ethyl acetate (100 mL x 3). The extracts were washed with brine, dried (Na2S04), and evaporated under reduced pressure. The crude product was purified by chromatography (silica gel, 2-10% ethyl acetate/petroleum ether) to give the title compound (3.0 g, 58%). LCMS (ES+) m/e 214 [M+H]+.
	With platinum on activated charcoal; hydrogen; zinc dibromide; In methanol; water; at 20.0℃; under 3750.38 Torr;Autoclave; Inert atmosphere;	2- Bromo-l-isopropyl-4-nitrobenzene (XI) (20 g, 78.1 mmol, 95.8 GC% by area), methanol (400 ml), platinum on carbon (5% of platinum, poisoned with sulphur, moist with water) (1.0 g, 0.090 mmol) and zinc dibromide (265 mg, 1.18 mmol) were placed in a 600 ml autoclave. The autoclave was subsequently flushed with nitrogen and pressurized to 5 bar with hydrogen at room temperature. The contents of the autoclave were filtered through Celite, washed with methanol and the solvent was distilled off under reduced pressure. 3-Bromo-4- isopropylaniline (17.4 g, 94.5 LC-% by area, 97.7 GC-% by area, >99 % of theory) was obtained as a brown oil. 3- Bromo-4-isopropylaniline of the formula (VII) -NMR (600 MHz, (CDCI3): delta = 7.04 (d, 1H), 6.89 (d, 1H), 6.61 (dd, 1H), 3.56 (br s, 2H), 3.25 (heptet, 1H), 1.19 (s, 3H), 1.18 (s, 3H) ppm. GC-MS: m/e = 213 [M+].
18 g	With ammonium chloride; zinc; In ethanol; water; at 40.0℃; for 1.0h;	2-Bromo-1-isopropyl-4-nitrobenzene (22.2 g) and ammonium chloride (58.4 g) were added to a mixed solvent of ethanol (445 mL) and water (445 mL). Zinc powder (35.7 g) was gradually added so that the temperature of the reaction solution did not exceed 40C, after which the mixture was stirred for one hour. The insoluble matter was filtered off through celite, and the filtrate was washed with ethanol and concentrated to about 500 mL under reduced pressure. The residue was extracted with ethyl acetate twice. The combined organic layers were washed with saturated saline and then dried over sodium sulfate. The drying agent was removed by filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography to give the target compound (18 g).

References: [1]Journal of the Chemical Society,1952,p. 4443,4445.
[2]Patent: WO2013/96151,2013,A1 .Location in patent: Page/Page column 93; 94.
[3]Patent: WO2013/160387,2013,A1 .Location in patent: Page/Page column 23.
[4]Patent: EP3312172,2018,A1 .Location in patent: Paragraph 0313; 0315.

4
[ 1147014-68-3 ]
[ 101980-41-0 ]
[ 1147014-94-5 ]