13321-74-9|4-Bromo-2,5-dimethoxytoluene| Ambeed

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Quality Control of [ 13321-74-9 ] Purity: 97% SDS Specification

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Product Details of [ 13321-74-9 ]

CAS No. :	13321-74-9
Formula :	C₉H₁₁BrO₂
M.W :	231.09
SMILES Code :	CC1=CC(OC)=C(Br)C=C1OC
MDL No. :	MFCD00666999
InChI Key :	YDRBZEYUYXQONG-UHFFFAOYSA-N
Pubchem ID :	643375

Safety of [ 13321-74-9 ]

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

Computational Chemistry of [ 13321-74-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
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	52.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	18.46 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.75
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	3.19
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.77
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.	2.51
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	2.96
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.84

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.52
Solubility	0.0697 mg/ml ; 0.000302 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.	-3.25
Solubility	0.13 mg/ml ; 0.000563 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	-3.9
Solubility	0.0292 mg/ml ; 0.000126 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.	-5.44 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	0.0 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)	1.54

Application In Synthesis of [ 13321-74-9 ]

* 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 [ 13321-74-9 ]

[ 13321-74-9 ] Synthesis Path-Downstream 1~35

1
[ 150-19-6 ]
[ 13321-74-9 ]
(2,5-dimethoxy-4-methyl-phenyl)-(3-methoxy-phenyl)-ether [ No CAS ]

References: [1]Biochemical Journal,1936,vol. 30,p. 1303,1313.

2
[ 13321-74-9 ]
[ 35458-39-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1942,vol. 550,p. 67,83.

3
[ 67289-05-8 ]
[ 77-78-1 ]
[ 13321-74-9 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 8243 - 8246.
[2]Biochemical Journal,1936,vol. 30,p. 1303,1313.
[3]Justus Liebigs Annalen der Chemie,1942,vol. 550,p. 67,83.

4
[ 67289-05-8 ]
[ 74-88-4 ]
[ 13321-74-9 ]

References: [1]Journal of the Chemical Society,1958,p. 1600,1603.

5
[ 186581-53-3 ]
[ 14963-96-3 ]
[ 13321-74-9 ]
[ 68409-21-2 ]
[ 68409-20-1 ]

References: [1]Liebigs Annalen der Chemie,1981,vol. No. 12,p. 2247 - 2257.

6
[ 14963-96-3 ]
[ 13321-74-9 ]
[ 68409-19-8 ]

References: [1]Liebigs Annalen der Chemie,1981,vol. No. 12,p. 2247 - 2257.

7
[ 4670-17-1 ]
[ 13321-74-9 ]
[ 35894-57-6 ]

References: [1]Liebigs Annalen der Chemie,1981,vol. No. 12,p. 2247 - 2257.

8
[ 4670-17-1 ]
[ 13321-74-9 ]
[ 53498-27-4 ]

References: [1]Liebigs Annalen der Chemie,1981,vol. No. 12,p. 2247 - 2257.

9
[ 110-93-0 ]
[ 13321-74-9 ]
[ 78919-97-8 ]

References: [1]Journal of Organic Chemistry,1981,vol. 46,p. 4666 - 4667.
[2]Molecules,2011,vol. 16,p. 8053 - 8061.

10
[ 13321-74-9 ]
[ 81060-27-7 ]
[ 50457-06-2 ]
[ 51837-73-1 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 5685-5690.

11
[ 13321-74-9 ]
[ 27613-27-0 ]
[ 52541-72-7 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 5685-5690.

12
[ 13321-74-9 ]
[ 71887-28-0 ]
[ 71887-29-1 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 12 - 15.

13
[ 13321-74-9 ]
[ 111210-22-1 ]
[ 72003-92-0 ]
[ 111210-31-2 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 5685-5690.

14
[ 13321-74-9 ]
[ 33857-76-0 ]
[ 122502-64-1 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1989,vol. 108,p. 64 - 72.

15
[ 13321-74-9 ]
[ 120966-83-8 ]
[ 122502-82-3 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1989,vol. 108,p. 64 - 72.

16
[ 24599-58-4 ]
[ 13321-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; sodium acetate; acetic acid; for 1.41667h;Inert atmosphere;	2-Bromo-5-methylcyclohexa-2,5-diene-1,4-dione (23). To a solution of toluquinol (1) (2.5 g, 20.14mmol,1.0 equiv.) in acetone (15 mL) was added K2CO3 (14 g, 100.70 mmol, 5.0 equiv.) and Me2SO4 (5.7 mL,60.41 mmol, 3.0 equiv.) and the reaction mixture was stirred for 3 h. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O. The organic phasewas washed with brine, dried over MgSO4, filtered, and the solvent removed under reduced pressureto obtain the corresponding dimethoxy derivative (~20 mmol), which was used in the next stepswithout purification. To a solution of the dimethoxy derivative obtained above (~20 mmol) and NaOAc(3.3 g, 40.28 mmol, 2.0 equiv.) in AcOH (20 mL) was added bromine (1.2 mL, 2.15 mmol, 1.1 equiv.)over 25 min and, after the addition, the reaction mixture was stirred for 1 h. Then, the reaction mixturewas quenched by a slow addition of a saturated aqueous NaHCO3 solution at 0 C. The aqueousphase was then extracted with EtOAc and the organic phase washed with brine, dried over MgSO4,ltered, and the solvent removed under reduced pressure to obtain the corresponding bromo derivative(~20 mmol), which was used in the next step without purication. The bromo derivative obtainedabove (~20 mmol) was dissolved in CH3CN (35 mL). Then, CAN (28 g, 50.34mmol, 2.5 equiv.) and H2O(20 mL) were added and the reaction mixture was stirred for 1 h at 25 C. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O twice. The combinedorganic phases were washed with brine, dried over MgSO4, filtered, and the solvent removed underreduced pressure. The residue was purified by flash column chromatography (silica gel, 1% EtOAc inhexanes) to obtain compound 23 (1.5 g, 37% over 3 steps) as an orange solid [13]: Rf = 0.45 (silica gel,20% EtOAc in hexanes); 1H NMR (400 MHz, CDCl3) delta 7.29 (s, 1 H), 7.26 (s, 2 H), 2.08 (d, J = 1.6 Hz,3 H); 13C NMR (100 MHz, CDCl3) delta 185.1, 179.5, 146.5, 138.1, 137.5, 132.6, 15.7.

References: [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6375 - 6387.
[2]Organic Letters,2009,vol. 11,p. 1441 - 1443.
[3]Journal of Organic Chemistry,1995,vol. 60,p. 5328 - 5331.
[4]Journal of Chemical Research,2009,p. 468 - 472.
[5]Tetrahedron Letters,2006,vol. 47,p. 2535 - 2538.
[6]Synlett,1999,p. 1474 - 1476.
[7]Tetrahedron Asymmetry,2003,vol. 14,p. 2119 - 2125.
[8]Tetrahedron Letters,2006,vol. 47,p. 8243 - 8246.
[9]Molecules,2011,vol. 16,p. 8053 - 8061.
[10]Organic Letters,2016,vol. 18,p. 1752 - 1755.
[11]Marine Drugs,2019,vol. 17.

17
[ 75-21-8 ]
[ 13321-74-9 ]
[ 38439-76-8 ]

References: [1]Science China Chemistry,2011,vol. 54,p. 43 - 55.
[2]Acta Chemica Scandinavica (1947),1968,vol. 22,p. 3160 - 3170.

18
[ 13321-74-9 ]
[ 75-56-9 ]
[ 38844-23-4 ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 2119 - 2125.
[2]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 1968 - 1979.

19
[ 13321-74-9 ]
[ 112439-97-1 ]
2,3-Bis-(2,5-dimethoxy-4-methyl-phenyl)-bicyclo[2.2.2]oct-2-ene [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 5246 - 5256.

20
[ 13321-74-9 ]
[ 82-86-0 ]
2-(2,5-Dimethoxy-4-methyl-phenyl)-2-hydroxy-2H-acenaphthylen-1-one [ No CAS ]
(1R,2R)-1,2-Bis-(2,5-dimethoxy-4-methyl-phenyl)-acenaphthene-1,2-diol [ No CAS ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 5246 - 5256.

21
[ 13321-74-9 ]
[ 1517-82-4 ]
(S)S-1,4-dimethoxy-2-methyl-5-p-tolylsulfinylbenzene [ No CAS ]

References: [1]Tetrahedron Asymmetry,1997,vol. 8,p. 913 - 921.

22
[ 865-50-9 ]
[ 13321-74-9 ]
[ 203579-44-6 ]

References: [1]European Journal of Organic Chemistry,1998,p. 335 - 348.

23
[ 13321-74-9 ]
[ 180578-98-7 ]

References: [1]European Journal of Organic Chemistry,1999,p. 917 - 922.

24
[ 13321-74-9 ]
[ 13070-25-2 ]

Yield	Reaction Conditions	Operation in experiment
1.5 g	With ammonium cerium (IV) nitrate; In water; acetonitrile; at 25℃; for 1h;Inert atmosphere;	2-Bromo-5-methylcyclohexa-2,5-diene-1,4-dione (23). To a solution of toluquinol (1) (2.5 g, 20.14mmol,1.0 equiv.) in acetone (15 mL) was added K2CO3 (14 g, 100.70 mmol, 5.0 equiv.) and Me2SO4 (5.7 mL,60.41 mmol, 3.0 equiv.) and the reaction mixture was stirred for 3 h. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O. The organic phasewas washed with brine, dried over MgSO4, filtered, and the solvent removed under reduced pressureto obtain the corresponding dimethoxy derivative (~20 mmol), which was used in the next stepswithout purification. To a solution of the dimethoxy derivative obtained above (~20 mmol) and NaOAc(3.3 g, 40.28 mmol, 2.0 equiv.) in AcOH (20 mL) was added bromine (1.2 mL, 2.15 mmol, 1.1 equiv.)over 25 min and, after the addition, the reaction mixture was stirred for 1 h. Then, the reaction mixturewas quenched by a slow addition of a saturated aqueous NaHCO3 solution at 0 C. The aqueousphase was then extracted with EtOAc and the organic phase washed with brine, dried over MgSO4,ltered, and the solvent removed under reduced pressure to obtain the corresponding bromo derivative(~20 mmol), which was used in the next step without purication. The bromo derivative obtainedabove (~20 mmol) was dissolved in CH3CN (35 mL). Then, CAN (28 g, 50.34mmol, 2.5 equiv.) and H2O(20 mL) were added and the reaction mixture was stirred for 1 h at 25 C. After this time, the reactionmixture was diluted with water and the aqueous phase was extracted with Et2O twice. The combinedorganic phases were washed with brine, dried over MgSO4, filtered, and the solvent removed underreduced pressure. The residue was purified by flash column chromatography (silica gel, 1% EtOAc inhexanes) to obtain compound 23 (1.5 g, 37% over 3 steps) as an orange solid [13]: Rf = 0.45 (silica gel,20% EtOAc in hexanes); 1H NMR (400 MHz, CDCl3) delta 7.29 (s, 1 H), 7.26 (s, 2 H), 2.08 (d, J = 1.6 Hz,3 H); 13C NMR (100 MHz, CDCl3) delta 185.1, 179.5, 146.5, 138.1, 137.5, 132.6, 15.7.

References: [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6375 - 6387.
[2]European Journal of Organic Chemistry,2016,vol. 2016,p. 1982 - 1993.
[3]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2731 - 2742.
[4]Synlett,1999,p. 1474 - 1476.
[5]Marine Drugs,2019,vol. 17.

26
diazotized 2,5-dimethoxy-<i>p</i>-toluidine [ No CAS ]
[ 13321-74-9 ]

References: [1]Journal of the Chemical Society,1959,p. 3350,3356.

27
[ 615-59-8 ]
[ 13321-74-9 ]
4,2',4''-trimethyl-2,5,2'',5''-tetramethoxy-1,1':4',1''-terphenyl [ No CAS ]