3913-23-3|2-(Bromomethyl)-1-methoxy-4-nitrobenzene| Ambeed

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Structure of 3913-23-3

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Quality Control of [ 3913-23-3 ] Purity: 95% SDS Specification

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Product Details of [ 3913-23-3 ]

CAS No. :	3913-23-3
Formula :	C₈H₈BrNO₃
M.W :	246.06
SMILES Code :	COC1=C(CBr)C=C(C=C1)[N+]([O-])=O
MDL No. :	MFCD00007329
InChI Key :	JRHMPHMGOGMNDU-UHFFFAOYSA-N
Pubchem ID :	77516

Safety of [ 3913-23-3 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	3261
Packing Group:	Ⅱ

Computational Chemistry of [ 3913-23-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	54.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.92
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	2.28
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.35
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.	1.41
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	0.68
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.73

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.95
Solubility	0.279 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.	-3.07
Solubility	0.208 mg/ml ; 0.000845 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	-3.17
Solubility	0.167 mg/ml ; 0.000679 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.	-6.18 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	3.0 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)	1.87

Application In Synthesis of [ 3913-23-3 ]

* 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 [ 3913-23-3 ]

[ 3913-23-3 ] Synthesis Path-Downstream 1~35

1
[ 5804-49-9 ]
[ 3913-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; In carbon tetrabromide; acetonitrile;	13.9 g of carbon tetrabromide and then 8.9 g of triphenylphosphine are added in the course of 10 min to a solution of 5.2 g of <strong>[5804-49-9]2-methoxy-5-nitrophenylmethanol</strong> in 150 cm3 of acetonitrile. The mixture is stirred for 1 hour at a temperature close to 20 C. and then concentrated to dryness under reduced pressure (2.7 kPa) at 40 C. The crude product obtained is purified by chromatography on 25 g of silica (0.065-0.200 mm) contained in a column 4.0 cm in diameter [eluent: methylene chloride/petroleum ether (40/60 by volume)], collecting 125 cm3 fractions. Fractions 5 to 12 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40 C. 5.6 g of 2-methoxy-5-nitrobenzyl bromide melting at 78 C. are thus obtained.

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 6254 - 6276.
[2]Anales de la Real Sociedad Espanola de Fisica y Quimica,1932,vol. 30,p. 767,775.
[3]Patent: US5382590,1995,A .

2
[ 693-95-8 ]
[ 3913-23-3 ]
[ 77-78-1 ]
N-(2-methoxy-5-nitrobenzyl)-N-(1-methylthio-2-propenyl)formamide [ No CAS ]

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,1983,vol. 39,p. 805 - 808.

3
[ 1779-81-3 ]
[ 3913-23-3 ]
[ 143543-78-6 ]

References: [1]Bioscience, Biotechnology and Biochemistry,1992,vol. 56,p. 1062 - 1065.

4
[ 50-00-0 ]
[ 100-17-4 ]
[ 3913-23-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sulfuric acid; acetic acid; sodium bromide; at 28 - 85℃; for 20h;	Example 8: Synthesis of Compound XIII-6; Step 1: Synthesis of 2-(bromomethyI)-l-methoxy-4-nitrobenzene (2); A mixture of p-nitro anisole (1, 1 g, 6.529 mmol), paraformaldehyde (0.218 g), sodium bromide (0.8 g) in glacial acetic acid (1.3 mL) was heated to 85 C. H2SO4 (0.8 mL) and glacial acetic acid (0.8 mL) were gradually added to the mixture over 5 h. The resulting reaction mixture was then stirred for 3 h at 85 C and then for 12 h at 28 C. After completion of the reaction, the reaction mixture was extracted with diethyl ether and the ethereal extract was washed successively with 5% NaHC03 solution and water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to afford 2-(bromomethyl)- l-methoxy-4-nitrobenzene (2, 0.965 g, 60 %). NMR (400 MHz, CDC13): delta 8.30-8.22 (m, 2H), 7.00- 6.95 (d, 1 H), 4.55 (s, 2H), 4.05 (s, 3H).

References: [1]Patent: WO2011/140338,2011,A1 .Location in patent: Page/Page column 56-57.
[2]Journal of Medicinal Chemistry,1981,vol. 24,p. 1471 - 1475.
[3]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 527 - 532.

5
[ 85006-25-3 ]
[ 3913-23-3 ]
C₁₈H₂₆N₂O₈ [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 6021 - 6024.

6
[ 3913-23-3 ]
[ 50741-92-9 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 6908 - 6910.

7
[ 3913-23-3 ]
[ 146-92-9 ]
(2R,3S,4R,5R)-2-Hydroxymethyl-5-[6-imino-1-(2-methoxy-5-nitro-benzyloxy)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3,4-diol; compound with perchloric acid [ No CAS ]

References: [1]Nucleosides and Nucleotides,1998,vol. 17,p. 1409 - 1443.

8
[ 3913-23-3 ]
[ 60013-09-4 ]
C₄₈H₆₂N₆O₈⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]Archiv der Pharmazie,1999,vol. 332,p. 179 - 181.

Yield	Reaction Conditions	Operation in experiment
70%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃; for 12h;	General procedure: IF3a (0403) A mixture of IF2a (1.60 g, 9.58 mmol), CBr4 (3.81 g, 11.50 mmol) and Ph3P (3.02 g, 11.50 mmol) in CH2Cl2 (100 mL) was allowed to stir at rt for 12 h. After removal of the solvent, the residue was purified by flash column chromatography (EtOAc/hexanes) to afford IF3a as a white solid (1.22 g, 55%). 1H NMR (CDCl3, 600 MHz) delta 8.20 (d, J=1.2 Hz, 1H), 8.08 (dd, J=8.4, 2.4 Hz, 1H), 7.36 (d, J=9.0 Hz, 1H), 4.53 (s, 2H), 1.58 (s, 3H).
		Example 12 Preparation of 3-aryl-1-(2-methoxy-5-nitrophenylmethyl)indole-2-carboxylic acid ten member sublibrary Following the procedure of Examples 10(a)-10(f), with the exception of substitution of 2-methoxy-5-nitrobenzyl bromide for 6-chloropiperonyl chloride in step (e), the title sublibrary was prepared (40 mg). MS m/e (M-H)-: 401.0, 431.0, 435.0, 451.0, 453.0, 461.0, 469.0, 477.0, 493.0.

11
[ 5804-49-9 ]
[ 10035-10-6 ]
[ 3913-23-3 ]

References: [1]Anales de la Real Sociedad Espanola de Fisica y Quimica,1932,vol. 30,p. 767,775.

12
[ 455-19-6 ]
[ 3913-23-3 ]
[ 16730-20-4 ]
5-[(2-methoxy-5-nitro-benzyl)-(4-trifluoromethyl-benzyl)-amino]-1H-indole-2-carboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,2000,vol. 41,p. 2443 - 2446.

13
[ 3913-23-3 ]
[ 340255-41-6 ]
2-Methoxy-5-nitrobenzyl (4,5-dimethoxy-2-[(phenylacetyl)amino]methyl}phenyl)acetate [ No CAS ]

References: [1]Chemistry - A European Journal,2001,vol. 7,p. 959 - 971.

14
[ 3913-23-3 ]
(4-(2-Hydroxyethoxy)-5-methoxy-2-[(phenylacetyl)amino]methyl}phenyl)acetic acid [ No CAS ]
[ 340255-37-0 ]

References: [1]Chemistry - A European Journal,2001,vol. 7,p. 959 - 971.

15
[ 3913-23-3 ]
[ 81477-94-3 ]
2-(benzhydrylidene-amino)-3-(2-methoxy-5-nitro-phenyl)-propionic acid tert-butyl ester [ No CAS ]

References: [1]Organic letters,2002,vol. 4,p. 4245 - 4248.

16
[ 3913-23-3 ]
adipic acid, monoamide with amino-functionalized polystyrene [ No CAS ]
2-methoxy-5-nitrobenzyl adipate, amide with amino-functionalized polystyrene [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2002,vol. 41,p. 4757 - 4761.

17
[ 3913-23-3 ]
2-methoxy-5-nitrobenzyl sulfonamide [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 8479 - 8483.

18
[ 3913-23-3 ]
[ 736933-15-6 ]
(2S)-2-benzhydryloxy-1-(2,5-dimethoxy-phenyl)-3-(2-methoxy-5-nitro-phenyl)-propan-1-one [ No CAS ]
(2R)-2-benzhydryloxy-1-(2,5-dimethoxy-phenyl)-3-(2-methoxy-5-nitro-phenyl)-propan-1-one [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 2289 - 2292.
[2]Journal of Organic Chemistry,2005,vol. 70,p. 9470 - 9479.

19
cyclopropanecarboxylic acid (1-isopropyl-2-thioxo-2,3-dihydro-1H-benzoimidazol-5-yl)-amide [ No CAS ]
[ 3913-23-3 ]
cyclopropanecarboxylic acid [1-isopropyl-2-(2-methoxy-5-nitro-benzylsulfanyl)-1H-benzoimidazol-5-yl]-amide [ No CAS ]