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Chemical Structure| 1592-20-7 Chemical Structure| 1592-20-7
Chemical Structure| 1592-20-7

1-(Chloromethyl)-4-vinylbenzene

CAS No.: 1592-20-7

4.5 *For Research Use Only !

Cat. No.: A672315 Purity: 90% (stabilized with TBC)

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Product Details of [ 1592-20-7 ]

CAS No. :1592-20-7
Formula : C9H9Cl
M.W : 152.62
SMILES Code : C=CC1=CC=C(CCl)C=C1
MDL No. :MFCD00051362

Safety of [ 1592-20-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H311-H314-H317
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Calculated chemistry of [ 1592-20-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.11
Num. rotatable bonds 2
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 46.3
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.27
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

3.09
Log Po/w (WLOGP)?

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

2.81
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.

3.47
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

3.59
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.05

Water Solubility

Log S (ESOL):?

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

-3.04
Solubility 0.138 mg/ml ; 0.000902 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.

-2.76
Solubility 0.267 mg/ml ; 0.00175 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

-3.85
Solubility 0.0217 mg/ml ; 0.000142 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

Low
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

Yes
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.

-5.04 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

2.0
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)

1.55

Application In Synthesis [ 1592-20-7 ]

* 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 [ 1592-20-7 ]

[ 1592-20-7 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 1592-20-7 ]
  • [ 86688-96-2 ]
  • [ 134226-20-3 ]
  • 2
  • [ 35237-37-7 ]
  • [ 1592-20-7 ]
  • 2-(4-Vinyl-benzylamino)-dodecanoic acid [ No CAS ]
  • 3
  • [ 1592-20-7 ]
  • [ 83345-46-4 ]
  • N-t-butoxycarbonyl-O-(p-vinylbenzyl)-L-tyrosinol [ No CAS ]
  • 4
  • [ 1592-20-7 ]
  • [ 69655-76-1 ]
  • octa(4-(benzylchloride)ethenyl)silsesquioxane [ No CAS ]
  • 5
  • [ 68631-52-7 ]
  • [ 1592-20-7 ]
  • [ 1245503-96-1 ]
  • 6
  • [ 1592-20-7 ]
  • [ 14173-30-9 ]
  • [ 1331826-40-4 ]
  • 7
  • [ 288-32-4 ]
  • [ 1592-20-7 ]
  • [ 78430-91-8 ]
YieldReaction ConditionsOperation in experiment
71% With Sodium hydrogenocarbonate; In water monomer; acetone; at 20 - 50℃; for 20h; NaHCO3 (5.25 g, 62.40 mmol, 1.25 eq) was added to aceton/water (1:1 v:v, 160 mL) and this solution wasstirred 1 hour. To this mixture, imidazole (13.61 g, 199.00 mmol, 4 eq) was added and stirred until it wascompletely dissolved, then 1-(chloromethyl)-4-vinylbenzene (7.1 ml, 49.80 mmol, 1 eq) was added dropwiseat room temperature. After the addition, reaction mixture was heated to 50 oC and stirred for 20 h (monitoredby TLC). Acetone was removed in vacuo, and remaining solution was extracted with diethyl ether. 2 M HClwas added to the organic phase until pH = 4-5, and it was washed with 2 M HCl (save the aqueous phase). 4 M NaOH wasadded to this aqueous phase until pH = 7-8 (cloudy solution), and this solution was extracted with diethyl ether. Finalorganic phase was dried over Na2SO4, and diethyl ether was removed in vacuo to afford the desired 1-(4-vinylbenzyl)-1Himidazole(S5) (6.55 g, 71% yield)
With Sodium hydrogenocarbonate; In water monomer; acetone; at 50℃; for 20h; The 1-(4-vinylbenzyl)imidazole was prepared by the reported procedure[27]by heating 4-vinylbenzylchloride (1.0 equivalent) and imidazole (4.0 equivalent) in acetone:water (1:1, 10 volume) with sodium bicarbonate (1.25 equivalent) at 50 C for 20 h. It was characterised by FT-IR and1H-NMR.The mixture of 1-(4-vinylbenzyl)imidazole (32.7 mmol), DVB and azobisisobutyronitrile (AIBN, 5 mol %) in acetonitrile (50 mL) was taken in a round bottom flask. The flask was heated to 80 C in an oil bath and the temperature was maintained for 8 h. The solid product obtained by filtration, was washed with acetonitrile (3 X 20 mL) and dried in an oven at 100 C. Thus, using 3, 5, and 7 mol% of DVB the catalysts CPVBIm-3, CPVBIm-5 and CPVBIm-7, respectively were prepared.
In a 500mL three-necked round bottom flask equipped with condensation reflux, thermometer and magnetic stirring, first dissolve 10.5g (0.12mol) sodium bicarbonate in 200mL water/acetone (v/v=1:1), then add 27.22g (0.3 mol) imidazole, stirred well at room temperature for about 30 min.Then, 15.22 g (0.1 mol) of p-chloromethylstyrene was slowly added dropwise with a constant pressure dropping funnel, and nitrogen was passed through for 30 minutes. The reaction system was stirred at 50 C. for 24 hours.After the reaction is complete, cool to room temperature, filter out the solid salt to obtain a wine-red liquid, remove the acetone through rotary evaporation of the filtrate, dilute the remaining solution with 500 mL of ether, and wash with 50 mL of deionized water for 6 times to remove unreacted imidazole, and the obtained organic phase uses 300 mL of 2M HCl solution was back-extracted, and the lower aqueous phase solution was neutralized with 200 mL of 4M NaOH solution. Then it was extracted three times with 50 mL of ether, and dried with anhydrous MgSO4.After distillation under reduced pressure, 11 mL of pale yellow oily liquid, namely monomer II, was obtained (FIG. 1B).
  • 8
  • [ 13093-04-4 ]
  • [ 1592-20-7 ]
  • C17H28N2 [ No CAS ]
  • 9
  • [ 1592-20-7 ]
  • [ 30757-50-7 ]
  • 4-((4-vinylbenzyl)oxy)phthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 6.5h;Inert atmosphere; <strong>[30757-50-7]4-hydroxyphthalonitrile</strong> (11.20 g, 78.057 mmol) and K2CO3 (1.47 g, 106.441 mmol) are placed in a 200 mL round-bottomed flask and 100 mL of distilled DMF is added to dissolve the reaction product. 4-vinylbenzyl chloride (10 mL, 70.961 mmol) is put under a nitrogen atmosphere for 30 minutes and then injected into a reaction flask. The temperature is 80 [deg.] C. After 6 h, the reaction is recrystallized in hexane. 15.052 g of brown solid product was obtained (yield ~ 71%).
 

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