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[ CAS No. 22916-47-8 ] {[proInfo.proName]}

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Chemical Structure| 22916-47-8
Chemical Structure| 22916-47-8
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Product Details of [ 22916-47-8 ]

CAS No. :22916-47-8 MDL No. :MFCD00216019
Formula : C18H14Cl4N2O Boiling Point : -
Linear Structure Formula :- InChI Key :BYBLEWFAAKGYCD-UHFFFAOYSA-N
M.W : 416.13 Pubchem ID :4189
Synonyms :
R18134
Chemical Name :1-(2-((2,4-Dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole

Calculated chemistry of [ 22916-47-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.17
Num. rotatable bonds : 6
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 103.2
TPSA : 27.05 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.69
Log Po/w (XLOGP3) : 5.93
Log Po/w (WLOGP) : 5.98
Log Po/w (MLOGP) : 4.31
Log Po/w (SILICOS-IT) : 5.88
Consensus Log Po/w : 5.16

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.26
Solubility : 0.000227 mg/ml ; 0.000000546 mol/l
Class : Poorly soluble
Log S (Ali) : -6.27
Solubility : 0.000222 mg/ml ; 0.000000534 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.41
Solubility : 0.0000016 mg/ml ; 0.0000000038 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.13

Safety of [ 22916-47-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22916-47-8 ]

* 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 [ 22916-47-8 ]

[ 22916-47-8 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 2550-36-9 ]
  • [ 22916-47-8 ]
  • 1-cyclohexylmethyl-3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-3<i>H</i>-imidazol-1-ium; bromide [ No CAS ]
  • 2
  • [ 141776-91-2 ]
  • [ 22916-47-8 ]
  • 3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1-(3,5-difluoro-benzyl)-3<i>H</i>-imidazol-1-ium; bromide [ No CAS ]
  • 5
  • [ 104-81-4 ]
  • [ 22916-47-8 ]
  • [ 57265-38-0 ]
YieldReaction ConditionsOperation in experiment
1-[2,4-Dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-methylbenzyl)imidazolium bromide; mp. 152.2° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazole and p-methylbenzyl bromide.
  • 6
  • 2-chloroaceto-2',5'-dimethoxyanilide [ No CAS ]
  • [ 108-20-3 ]
  • [ 22916-47-8 ]
  • 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,5-dimethoxyphenyl)carbamoylmethyl]imidazolium chloride monohydrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; EXAMPLE XXXIII In a similar operation and employing recovery techniques similar to Example XXXII, but employing different amounts of reactants or different purification techniques as indicated, the following compounds are prepared: 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,5-dimethoxyphenyl)carbamoylmethyl]imidazolium chloride monohydrate, m.p. 121.1° C., by (a) refluxing for 2 days, 4.2 parts of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole, 2.5 parts of 2-chloroaceto-2',5'-dimethoxyanilide and 40 parts of acetonitrile, (b) recovering as in Example XXXII, and (c) washing the crude product with ether.
  • 7
  • [ 94-99-5 ]
  • [ 22916-47-8 ]
  • [ 57265-33-5 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; acetone; EXAMPLE XVI 15 parts of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)-phenethyl]imidazole and 60 parts of 2,4-dichlorobenzyl chloride are mixed together in 120 parts of acetone as solvent and the resulting mixture is stirred at reflux temperature for 40 hours. At the end of this period, the mixture is warmed to evaporate off most of the solvent and the residue is poured onto diisopropyl ether, whereupon the 1-(2,4-dichlorobenzyl)-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazolium chloride product separates as an oil. The ether is decanted off and the oily residue is washed with warm xylene and thereafter triturated in 2-propanol whereupon the oily product solidified. The solid product is filtered off, washed with 2-propanol and dried to obtain a purified product, 1-(2,4-dichlorobenzyl)-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazolium chloride, mp. 178.9° C.
  • 8
  • [ 620-13-3 ]
  • [ 22916-47-8 ]
  • [ 57265-37-9 ]
YieldReaction ConditionsOperation in experiment
1-[2,4-Dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-(m-methylbenzyl)imidazolium bromide; mp. 99°-101° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazole and m-methylbenzyl bromide.
  • 9
  • [ 111-83-1 ]
  • [ 22916-47-8 ]
  • [ 57264-59-2 ]
YieldReaction ConditionsOperation in experiment
1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]3-n-octylimidazolium bromide; mp. 141.5°-143° C., from 1-[2,4dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and n-octyl bromide after an overnight reflux.
  • 10
  • [ 112-29-8 ]
  • [ 22916-47-8 ]
  • [ 57264-60-5 ]
YieldReaction ConditionsOperation in experiment
1-decyl-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazolium bromide; mp. 90°-94° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and n-decyl bromide after an overnight reflux.
  • 11
  • [ 1131-01-7 ]
  • [ 22916-47-8 ]
  • 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,6-xylyl)carbamoylmethyl]-imidazolium chloride hydrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-3-[N-(2,6-xylyl)carbamoylmethyl]-imidazolium chloride hydrate, m.p. 143°-150° C., by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and 2-chloroaceto-2',6'-xylidide.
  • 12
  • [ 77975-44-1 ]
  • [ 22916-47-8 ]
  • 1-(2,4-dichlorocinnamyl)-3-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-imidazolium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In di-isopropyl ether; acetonitrile; A. A mixture of 4.2 parts of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole, 2.7 parts of 2,4-dichlorocinnamylchloride and 40 parts of acetonitrile is stirred and refluxed overnight. Upon the addition of diisopropyl ether, the product crystallizes. It is filtered off and dried, yielding 5.8 parts of 1-(2,4-dichlorocinnamyl)-3-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazolium chloride; mp. 142.2° C.
  • 13
  • [ 4209-02-3 ]
  • [ 108-10-1 ]
  • [ 22916-47-8 ]
  • [ 57265-17-5 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE XV In a manner similar to that described in Examples XIII and XIV, 1-(p-bromobenzoylmethyl)-3-[2,4-dichloro-beta-(2,4 -dichlorobenzyloxy)phenethyl]imidazolium chloride is prepared by the reaction of 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole and 4'-bromo-2-chloroacetophenone. The product after successive treatment steps of stirring with 4-methyl-2-pentanone, stirring a chloroform solution thereof with silica gel and triturating with 4-methyl-2-pentanone has a melting point of 198.2° C.
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[ 22916-47-8 ]

Chemical Structure| 22832-87-7

A625321[ 22832-87-7 ]

1-(2-((2,4-Dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole nitrate

Reason: Free-salt

; ;