78430-91-8|1-(4-Vinylbenzyl)-1H-imidazole| Ambeed

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Quality Control of [ 78430-91-8 ] Purity: 95% SDS Specification

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Product Details of [ 78430-91-8 ]

CAS No. :	78430-91-8
Formula :	C₁₂H₁₂N₂
M.W :	184.24
SMILES Code :	C=CC1=CC=C(C=C1)CN2C=CN=C2
MDL No. :	MFCD28346936
InChI Key :	RURRSGMFTZVXKB-UHFFFAOYSA-N
Pubchem ID :	18000062

Safety of [ 78430-91-8 ]

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

Computational Chemistry of [ 78430-91-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	11
Fraction Csp3	0.08
Num. rotatable bonds	3
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	58.07
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.11
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	2.38
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.47
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.	1.85
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	2.65
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.29

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.87
Solubility	0.251 mg/ml ; 0.00136 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.	-2.4
Solubility	0.742 mg/ml ; 0.00403 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	-3.78
Solubility	0.0307 mg/ml ; 0.000167 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.	-5.73 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	1.0
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)	1.55

Application In Synthesis of [ 78430-91-8 ]

* 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 [ 78430-91-8 ]

[ 78430-91-8 ] Synthesis Path-Downstream 1~25

1
[ 288-32-4 ]
[ 1592-20-7 ]
[ 78430-91-8 ]

Yield	Reaction Conditions	Operation 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).

References: [1]Journal of Materials Chemistry A,2017,vol. 5,p. 25594 - 25600.
[2]Chemistry Letters,2016,vol. 45,p. 837 - 839.
[3]ChemSusChem,2019,vol. 12,p. 3996 - 4004.
[4]Chemistry - A European Journal,2018,vol. 24,p. 13322 - 13335.
[5]Polymer,2012,vol. 53,p. 3677 - 3686.
[6]Journal of the American Chemical Society,2013,vol. 135,p. 10602 - 10605.
[7]Chemical Communications,2013,vol. 50,p. 46 - 48.
[8]Synthetic Communications,2018,vol. 48,p. 387 - 394.
[9]Patent: CN114195651,2022,A .Location in patent: Paragraph 0031; 0051-0052.

2
[ 1120-71-4 ]
[ 78430-91-8 ]
3-(1-(4-vinylbenzyl)-1H-imidazol-3-ium-3-yl)propane-1-sulfonate [ No CAS ]

References: [1]Chemical Communications,2013,vol. 50,p. 46 - 48.

3
[ 78430-91-8 ]
[ 540-51-2 ]
1-(4-ethenylbenzyl)-3-(2-hydroxyethyl)-1H-imidazol-3-ium bromide [ No CAS ]

References: [1]Helvetica Chimica Acta,2016,vol. 99,p. 821 - 829.

4
[ 78430-91-8 ]
[ 6482-24-2 ]
1-(4-ethenylbenzyl)-3-(2-methoxyethyl)-1H-imidazol-3-ium bromide [ No CAS ]

References: [1]Helvetica Chimica Acta,2016,vol. 99,p. 821 - 829.

5
[ 2043-55-2 ]
[ 78430-91-8 ]
1-(4-ethenylbenzyl)-3-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-1H-imidazol-3-ium iodide [ No CAS ]

References: [1]Helvetica Chimica Acta,2016,vol. 99,p. 821 - 829.

6
[ 2043-57-4 ]
[ 78430-91-8 ]
1-(4-ethenylbenzyl)-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1H-imidazol-3-ium iodide [ No CAS ]

References: [1]Helvetica Chimica Acta,2016,vol. 99,p. 821 - 829.

7
[ 5392-81-4 ]
[ 78430-91-8 ]
3-[2-(diethylammonio)ethyl]-1-(4-ethenylbenzyl)-1H-imidazol-3-ium dibromide [ No CAS ]

References: [1]Helvetica Chimica Acta,2016,vol. 99,p. 821 - 829.

8
[ 78430-91-8 ]
[ 1765-40-8 ]
1-(4-ethenylbenzyl)-3-(pentafluorobenzyl)-1H-imidazol-3-ium bromide [ No CAS ]