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Chemical Structure| 877-88-3 Chemical Structure| 877-88-3
Chemical Structure| 877-88-3

*Storage: Inert atmosphere,2-8°C.

1-(Bromomethyl)-3,5-dimethoxybenzene

CAS No.: 877-88-3

4.5 *For Research Use Only !

Cat. No.: A586795 Purity: 97%

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Product Details of [ 877-88-3 ]

CAS No. :877-88-3
Formula : C9H11BrO2
Linear Structure Formula :BrC7H7(OCH2)2
M.W : 231.09
SMILES Code : COC1=CC(OC)=CC(CBr)=C1
MDL No. :MFCD01321368
InChI Key :BTHIGJGJAPYFSJ-UHFFFAOYSA-N
Pubchem ID :1274490

Safety of [ 877-88-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501
Class:8
UN#:3261
Packing Group:

Calculated chemistry of [ 877-88-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.33
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 52.26
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

18.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.63
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.42
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.45
Log Po/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.

2.25
Log Po/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

2.83
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.52

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.97
Solubility 0.248 mg/ml ; 0.00107 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.

-2.45
Solubility 0.82 mg/ml ; 0.00355 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

-3.92
Solubility 0.028 mg/ml ; 0.000121 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.

-5.99 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)

1.73

Application In Synthesis [ 877-88-3 ]

* 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 [ 877-88-3 ]

[ 877-88-3 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 877-88-3 ]
  • [ 137215-27-1 ]
  • [ 1362586-13-7 ]
YieldReaction ConditionsOperation in experiment
14% With potassium carbonate; In acetone; at 20℃; General procedure: A mixture of 44 (300 mg, 1.56 mmol), K2CO3 (372 mg, 2.34 mmol), and halogenated compound (1 equiv) in acetone (10 mL) was stirred for 0.5-3.5 h at rt. After filtering the mixture and removing the solvent in vacuo, the residue was purified by column chromatography (eluent: hexane/EtOAc 85:15) to obtain the target compounds (11-23) as white solids.
  • 2
  • [ 877-88-3 ]
  • [ 4983-28-2 ]
  • [ 1453211-57-8 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h; Potassium carbonate (1.05g, 7.6 mmol) was slowly added to a stirred solution of 2- chloropyrimidin-5-ol (0.5g, 3.8 mmol) in DMF (5mL) followed by the addition of 3- (bromomethyl)-l,5-dimethoxybenzene (0.97g, 4.2 mmol) at 0 °C. The reaction mass was stirred at room temperature for lh then the reaction mixture was quenched with ice cold water. The solid that separated was filtered and dried under reduced pressure to afford desired title compound (0.9 83percent). LCMS: m/z = 281.2 (M+H)+.
360 mg With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 7h;Cooling with ice; Preparation Example 13 A mixture of <strong>[4983-28-2]2-chloro-5-hydroxypyrimidine</strong> (278 mg), potassium carbonate (453 mg), and N,N-dimethylformamide (3 mL) was ice cooled, and 3,5-dimethoxybenzyl bromide (541 mg) was added thereto followed by stirring at room temperature for 7 hours. To the reaction mixture, water was added followed by extraction with ethyl acetate. An organic layer obtained was washed with saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 2-chloro-5-[(3,5-dimethoxybenzyl)oxy]pyrimidine (360 mg).
  • 3
  • [ 27037-34-9 ]
  • [ 877-88-3 ]
  • 4-(3,5-dimethoxybenzyloxy)-7-methoxyquinolin-2(1H)-one [ No CAS ]
  • 4
  • [ 42726-73-8 ]
  • [ 877-88-3 ]
  • 1-tert-butyl 3-methyl 2-(3,5-dimethoxybenzyl)malonate [ No CAS ]
  • 5
  • [ 42726-73-8 ]
  • [ 877-88-3 ]
  • 1-tert-butyl 3-methyl 2-benzoyloxy-2-(3,5-dimethoxybenzyl)malonate [ No CAS ]
  • 6
  • [ 877-88-3 ]
  • [ 102831-44-7 ]
  • diethyl 2-((tert-butoxycarbonyl)amino)-2-(3,5-dimethoxybenzyl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With caesium carbonate; In acetonitrile; at 20℃; for 25h; A solution of bromide12 (231 mg, 1 mmol),diethyl (Boc-amino)malonate (275 mg,1.1 mmol) and Cs2CO3(325 mg, 1.1 mmol) in acetonitrile (4.5 mL) was stirred for25 h at room temperature. The reaction was then diluted in30 mL of ethyl acetate and extracted with water and brine.The organic phase was dried with anhydrous Na2SO4 andconcentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel, using ethylacetate/hexane (4:1) as the eluent, affording a white solid(326.2 mg, 0.77 mmol, 77% yield). mp 69.7-72.5 C;1H NMR (500 MHz, CDCl3) δ 1.29 (t, 6H, J 7.1 Hz,CO2CH2CH3), 1.47 (s, 9H, t-Bu), 3.55 (s, 2H, Ar-CH2C),3.74 (s, 6H, Ar-OCH3), 4.17-4.26 (m, 2H, CO2CH2CH3),4.27-4.36 (m, 2H, CO2CH2CH3), 5.79 (s, 1H, N-H), 6.20 (d,2H, J 2.0 Hz, Ar-H), 6.34 (t, 1H, J 2.2 Hz, Ar-H); 13C NMR(126 MHz, CDCl3) δ 14.0 (2C), 28.2 (3C), 38.5, 55.1 (2C),62.5 (2C), 67.1, 80.1, 99.1, 108.1 (2C), 137.4, 153.8, 160.5(2C), 167.6 (2C); LRMS (ESI) m/z 426.2 [M + H]+.
  • 7
  • [ 877-88-3 ]
  • [ 56844-40-7 ]
  • 6-bromo-3-(3,5-dimethoxybenzyl)thieno[2,3-d]pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12.0h; General procedure: To a stirred solution of intermediate 6 (100 mg, 0.433 mmol) in DMF was added K2CO3 (179 mg, 1.299 mmol) and 3-fluorobenzyl bromide (54 muL, 0.433 mmol) at RT. After stirring for 12 h, the reaction mixture was concentrated to dryness under vacuum and the residue was extracted with CH2Cl2 and water. The organic layer was washed with brine and dried over MgSO4. Then the solution was concentrated to dryness under vacuum and puried via a ash chromatography silica gel plate (petroleum ether/ethyl acetate, 3/1) to afford title compound as a pale yellow solid in 43% yield.
 

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