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Chemical Structure| 22680-44-0

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Product Details of [ 22680-44-0 ]

CAS No. :22680-44-0
Formula : C7H9Cl2N
M.W : 178.06
SMILES Code : NCC1=CC=CC=C1Cl.[H]Cl
MDL No. :MFCD07375438
Boiling Point : No data available
InChI Key :LXFIZCSCVYTFBU-UHFFFAOYSA-N
Pubchem ID :18670922

Safety of [ 22680-44-0 ]

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

Computational Chemistry of [ 22680-44-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 46.09
TPSA ?

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

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

2.31
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.

2.46
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

2.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.86

Water Solubility

Log S (ESOL):?

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

-2.78
Solubility 0.297 mg/ml ; 0.00167 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.

-2.49
Solubility 0.57 mg/ml ; 0.0032 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

-3.03
Solubility 0.165 mg/ml ; 0.000927 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

No
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.

-5.75 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

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)

1.0

Application In Synthesis of [ 22680-44-0 ]

* 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 [ 22680-44-0 ]

[ 22680-44-0 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 15894-70-9 ]
  • [ 22680-44-0 ]
  • [ 115098-00-5 ]
  • 2
  • [ 638-37-9 ]
  • [ 22680-44-0 ]
  • [ 105-50-0 ]
  • [ 109690-05-3 ]
  • 3
  • [ 590-28-3 ]
  • [ 22680-44-0 ]
  • [ 4654-63-1 ]
  • 4
  • [ 22680-44-0 ]
  • [ 57-13-6 ]
  • [ 4654-63-1 ]
  • 5
  • [ 22680-44-0 ]
  • [ 156141-95-6 ]
  • C17H12ClN3O4 [ No CAS ]
  • 6
  • [ 22680-44-0 ]
  • [ 105686-01-9 ]
  • 7
  • [ 22680-44-0 ]
  • 3-Carboxymethyl-1-(2-chlorobenzyl)parabanic acid [ No CAS ]
  • 8
  • [ 22680-44-0 ]
  • [ 128043-66-3 ]
  • 9
  • [ 22680-44-0 ]
  • [ 110248-68-5 ]
  • 10
  • [ 22680-44-0 ]
  • [ 133103-08-9 ]
  • 11
  • [ 22680-44-0 ]
  • [ 102466-47-7 ]
  • 12
  • ammonium thiocyanate [ No CAS ]
  • [ 19380-80-4 ]
  • [ 22680-44-0 ]
  • [ 106-94-5 ]
  • [ 141771-20-2 ]
YieldReaction ConditionsOperation in experiment
In water; toluene; acetonitrile; (ii) 1-(2-chlorophenyl)methyl-2-propyl-2-thiopseudourea A solution of <strong>[22680-44-0]2-chlorobenzylamine hydrochloride</strong> (41 g, 0.23 mol) and ammonium thiocyanate (19.28 g, 0.253 mol) in water (170 mL) was heated on the steam bath for 18 hours. This mixture was concentrated in vacuo, and the residue was taken up in toluene (1 L) and azeotroped with a Dean-Stark head. The residue was triturated with wet diethyl ether to provide 27.6 g (60%) of 1-(2-chlorophenyl)methyl thiourea. The product was recrystallized from ethanol; mp 120-122 C. A mixture of 1-(2-chlorophenyl)methyl thiourea (3 g, 14.9 mmol) and propylbromide (13.5 g, 110 mmol) in acetonitrile (20 mL) was refluxed for 5 hours. The solvent was evaporated, the residue was dissolved in 200 mL of 50% water/ether and acidified with 48% hydrobromic acid solution. The two phases were separated, the aqueous layer was washed with ether and then the aqueous layer was basified with 10% sodium carbonate solution. The liberated product was extracted with diethyl ether, washed with water and brine, dried and concentrated to give 1-(2-chlorophenyl)methyl-2-propyl-2-thiopseudourea (2.82 g, 78%); mp 112-114 C.
  • 13
  • [ 96-26-4 ]
  • [ 22680-44-0 ]
  • [ 38993-84-9 ]
  • [ 226931-19-7 ]
YieldReaction ConditionsOperation in experiment
60% 45-1) 5-Hydroxymethyl-1-(2-chlorobenzyl)imidazole The title compound was obtained in a yield of 60percent according to the same procedure as Preparation 31-1) using dihydroxyacetone and <strong>[22680-44-0]2-chlorobenzylamine hydrochloride</strong> as sting materials. 1H NMR(CDCl3) delta3.24(s, 2H), 4.44(s, 2H), 5.26(s, 2H), 6.78(d, 1H), 6.90(s, 1H), 7.15(m, 1H), 7.21(m, 1H), 7.34(d, 1H), 7.38(s, 1H)
  • 14
  • [ 60852-95-1 ]
  • [ 22680-44-0 ]
  • N1-(2-chlorobenzyl)-N5-octylbiguanidine dihydrochloride [ No CAS ]
  • 15
  • [ 873-32-5 ]
  • [ 22680-44-0 ]
YieldReaction ConditionsOperation in experiment
98% General procedure: In a glove box, a flame-dried GLC vial equipped with a magnetic stir bar is charged with[3a]+[BArF4]- (1.0 mol%) and Me2PhSiH (2a) (2.1 or 5.0 equiv). The indicated nitrile is added eitherin the glove box (for solid starting materials) or by micro syringe outside the glove box, and theresulting reaction mixture is maintained at room temperature for the indicated time. The reaction isquenched by the addition of a mixture of cyclohexane and tert-butyl methyl ether (90:10) containing4% Et3N (0.5 mL), and the resulting solution is filtered through a pad of Celite coated by a smalllayer of silica gel with a solution of cyclohexane and tert-butyl methyl ether (90:10) containing 4%Et3N (3-4 mL) as eluent. Solvents are removed under reduced pressure, and the residue isdissolved in Et2O (1 mL) followed by addition of HCl (2M in Et2O, 1.0 mL, 2.0 mmol, 10 equiv). Theresulting suspension is stirred for 1 h and filtered, affording the amines as hydrochloride salts aswhite to yellow solids.
  • 16
  • C15H28ClNSi2 [ No CAS ]
  • [ 22680-44-0 ]
  • 17
  • [ 22680-44-0 ]
  • [ 79-07-2 ]
  • N-(o-chlorobenzyl)iminodiacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With sodium carbonate; potassium iodide; In water; at 80℃;pH Ca. 5 - 6;Heating; General procedure: Typically, 1.66 g (0.01 mol) potassium iodide and 0.05 molbenzylammonium chloride [Note 1] were added to a hot aqueous solution (ca. 80C) of 10.0 g chloroacetamide (0.11 mol in 100mL) in a 500-mL Erlenmeyer flask. Then, 1.25 g (0.012 mol) sodium carbonate was added in small portions while shaking the flask [CAUTION - foaming] in order to partially deprotonate the benzylammonium cation. After the effervescence has subsided, the reaction mixture was heated to boiling and set aside for 30 min [Note 2]. A second portion of 1.25 g sodium carbonate (0.012 mol) was then added; the reaction mixture was heated to boiling and set aside for 20 min. This addition of sodium carbonate-boiling-20 min waiting procedure was repeated three more times (five 1.25 g portions of sodium carbonate were added in total), after which the products started to crystallize upon spontaneous cooling of the hot solutions [Note 3]. After the reaction mixtures were left to stand overnight, the products were filtered off by suction, washed with ice-cold water (100 mL), dried by standing in air and protected from direct sunlight [Note 4]. Note 1. The corresponding benzylammonium chlorides were prepared from benzyl halides via the Reichert-Dornis modification of Delepine reaction. [17] N-Benzylhexamethylene tetraminium halides were prepared by mixing the solutions of hexamethylenetetramine and benzyl halide in chloroform, then filtered off by suction, washed with small volumes of chloroform,and air-dried as described. [18] These salts were dissolved or suspended in water, and the reaction mixtures were saturated with sulfur dioxide. The precipitated N-benzylaminomethylsulfites were filtered off by suction, washed with water, andair-dried. [17] Cleavage of N-benzylaminomethylsulfites into benzylammonium chlorides was performed by boiling with diluted hydrochloric acid (1 : 1 v/v). After the reaction mixtures were evaporated to a small volume, the desired benzylamine hydrochlorides crystallized in almost quantitative yields. All these reactions were performed in a fume cupboard. Note 2. The reaction mixture should be slightly acidic (pH ca. 5-6) before each addition of sodium carbonate. Some times, the products start to crystallize before the final step. In that case, the reaction mixture should be heated to dissolve the product before further addition of sodium carbonate. Note 3. The total amount of sodium carbonate is lower than required for complete neutralization of the acid released during the reaction. The final solution has to be acidic to keep the unreacted amine in its protonated (soluble) form, which is easily removed from the product by simple washing with water. The addition of the sixth 1.25 g portion of sodium carbonate did not improve the yield significantly, however, gave impure, yellow and vile smelling products contaminated with the starting amines. Note 4. The products are obtained in the form of white crystals and are sufficiently pure to be used as complexing agents. They should be stored in dark bottles because they usually become yellow upon exposure to sunlight.
  • 18
  • [ 22680-44-0 ]
  • [Cu(N-(o-chlorobenzyl)iminodiacetamide)2](NO3)2*H2O [ No CAS ]
  • 19
  • [ 22680-44-0 ]
  • [Ni(N-(o-chlorobenzyl)iminodiacetamide)2](NO3)2 [ No CAS ]
  • 20
  • 1-(2-chlorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione [ No CAS ]
  • [ 22680-44-0 ]
YieldReaction ConditionsOperation in experiment
86% (3) hydrolysis: the above-mentioned 1 - diphenyl - 3, 4 - (2 - chloro- phenmethyl) - 1H - pyrrole - 2, 5 - dione with NaOH (120.0 mg, 3 . 0mmol), water (2.0 ml) and ethanol (1.0 ml) is added to 10 ml microwave reaction tube, the power of the microwave reactor set to 90W, in 105 C microwave 8 minutes; after to be cooled, dropping 18% hydrochloric acid to pH value to 5.0, oscillation to the solid-liquid two-phase layer, filter to get solid, and in order to 2 ml of 5% hydrochloric acid two times washing the solid, the solid is drying constant weight after, to obtain raw material 3, 4 - diphenyl-furan - 2, 5 - dione (97.3 mg), the percent recovery is 97%; the filtrate is mixed with an aqueous acid wash, to the mixed liquid to carry out polyreaction 50% NaOH aqueous solution to pH value adjusted to 11.0, with 50 ml of methyl tert-butyl ether extraction three times, combined with the organic layer, adding anhydrous magnesium sulfate drying; filtering to remove the drying agent after the anhydrous magnesium sulfate, the filtrate of the drying in HCl gas, with a white flocculent solid precipitation, filtration the white solid obtained, after drying the solid constant weight, to obtain 2 - chloro- animal pen amine hydrochloride (61.1 mg), the product yield is 86% (to raw material 2 - chloro- chlorine animal pen idea).
  • 21
  • [ 89-97-4 ]
  • [ 22680-44-0 ]
 

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