532440-88-3|2-Bromo-5-methoxy-4-methylaniline| Ambeed

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Quality Control of [ 532440-88-3 ] Purity: 98% SDS Specification

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Product Details of [ 532440-88-3 ]

CAS No. :	532440-88-3
Formula :	C₈H₁₀BrNO
M.W :	216.08
SMILES Code :	NC1=CC(OC)=C(C)C=C1Br
MDL No. :	MFCD11841053
Boiling Point :	No data available
InChI Key :	WGVJMLYQPNCPSD-UHFFFAOYSA-N
Pubchem ID :	21966452

Safety of [ 532440-88-3 ]

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

Computational Chemistry of [ 532440-88-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	50.0
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.17
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	2.27
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.36
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.	2.22
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	2.23
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.25

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.95
Solubility	0.244 mg/ml ; 0.00113 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.	-2.65
Solubility	0.487 mg/ml ; 0.00225 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	0.0835 mg/ml ; 0.000386 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.	-6.01 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	1.0 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)	1.44

Application In Synthesis of [ 532440-88-3 ]

* 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 [ 532440-88-3 ]

[ 532440-88-3 ] Synthesis Path-Downstream 1~10

1
[ 144-55-8 ]
[ 16452-01-0 ]
[ 532440-88-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetra-n-butylammonium tribromide; In hexane; dichloromethane; ethyl acetate;	g. 2-bromo-5-methoxy-4-methyl-aniline. To a solution of 3-methoxy-4-methyl-aniline (8.19 g, 59.71 mmol) in dichloromethane (200 mL), was added tetrabutylammonium tribromide (28.79 g, 59.71 mmol) and the reaction mixture was stirred at room temperature for 2.5 hrs. Aqueous NaHCO3 was added and the layers separated. The aqueous layer was further extracted with dichloromethane and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (20% ethyl acetate in hexane) to give 11.05 g of 2-bromo-5-methoxy-4-methyl-aniline (85% yield). 1H NMR (300 MHz; CDCl3): 2.09 (s, 3 H), 3.75 (s, 3 H), 3.95 (br s, 1 H), 6.27 (s, 1 H), 7.13 (s, 1 H).

References: [1]Patent: US2003/144329,2003,A1 .

2
[ 532440-88-3 ]
[ 79-30-1 ]
[ 532440-87-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium hydroxide; In dichloromethane;	f. N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide. To a biphasic mixture of <strong>[532440-88-3]2-bromo-5-methoxy-4-methyl-aniline</strong> (5.6 g, 25.96 mmol), 10% KOH (27 mL) and dichloromethane (30 mL), was added dropwise isobutyryl chloride (3 mL, 28.55 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 48 hrs. The layers were separated. The aqueous layer was further extracted with dichloromethane and the combined organics washed successively with water and brine, dried over MgSO4, filtered and evaporated to give 7.38 g of N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (99% yield). 1H NMR (300 MHz; CDCl3): 1.29 (d, J=6.9 Hz, 6 H), 2.14 (s, 3 H), 2.59 (m, 1 H), 3.84 (s, 3 H), 7.24 (s, 1 H), 7.66 (br s, 1 H), 8.07 (s, 1 H).

References: [1]Patent: US2003/144329,2003,A1 .

3
[ 16452-01-0 ]
[ 532440-88-3 ]

Yield	Reaction Conditions	Operation in experiment
7.85 g	With tetra-N-butylammonium tribromide; In chloroform; at 0℃; for 0.333333h;	Reference Production Example 79 (1473) A mixture of 6.85 g of 3-methoxy-4-methylaniline and 150 mL of chloroform was cooled to 0 C. and 26.5 g of tetrabutylammonium tribromide was added, followed by stirring at the same temperature for 20 minutes. To the reaction mixture, chloroform was added. The organic layer was washed with a sodium bicarbonate solution, an aqueous sodium sulfite solution, water, and a saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. (1474) The residue thus obtained was subjected to silica gel column chromatography to obtain 7.85 g of 2-bromo-5-methoxy-3-methylalanine. (1475) 1H-NMR (CDCl3) delta: 2.08 (3H, s), 3.76 (3H, s), 3.93 (2H, br s), 6.28 (1H, s), 7.12 (1H, s).

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1876 - 1891.
[2]Patent: US2016/150787,2016,A1 .Location in patent: Paragraph 1473-1475.

4
[ 532440-88-3 ]
1-bromo-2-chloro-4-methoxy-5-methylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 g	With hydrogenchloride; copper(I) bromide; sodium nitrite; In water; at 0 - 70℃; for 1.0h;	Reference Production Example 80 (1476) A mixture of 3.24 g of <strong>[532440-88-3]2-bromo-5-methoxy-3-methylaniline</strong> and 50 mL of concentrated hydrochloric acid was cooled to 0 C., and 10 ml of an aqueous solution of 1.14 g of sodium nitrite was added dropwise. Then, 1.78 g of copper(I) bromide was added, followed by stirring at 70 C. for 1 hour. After cooling, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.00 g of 1-bromo-2-chloro-4-methoxy-5-methylbenzene. (1477) 1H-NMR (CDCl3) delta: 2.15 (3H, s), 3.80 (3H, s), 6.88 (1H, s), 7.33 (1H, s).

References: [1]Patent: US2016/150787,2016,A1 .Location in patent: Paragraph 1476-1477.

5
[ 532440-88-3 ]
C₁₆H₂₁ClN₄O [ No CAS ]