[ CAS No. 22200-50-6 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 22200-50-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 22200-50-6 ]

SDS Specification

Alternatived Products of [ 22200-50-6 ]

Product Details of [ 22200-50-6 ]

CAS No. :	22200-50-6	MDL No. :	MFCD00511002
Formula :	C₉H₅ClIN	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	JKZGHMPCBJVWEL-UHFFFAOYSA-N
M.W :	289.50	Pubchem ID :	10589540
Synonyms :

Calculated chemistry of [ 22200-50-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.47
TPSA :	12.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.32
Log Po/w (XLOGP3) :	2.8
Log Po/w (WLOGP) :	3.49
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	4.05
Consensus Log Po/w :	3.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.02
Solubility :	0.0279 mg/ml ; 0.0000965 mol/l
Class :	Moderately soluble
Log S (Ali) :	-2.73
Solubility :	0.542 mg/ml ; 0.00187 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.26
Solubility :	0.00159 mg/ml ; 0.0000055 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.91

Safety of [ 22200-50-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22200-50-6 ]

* 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.

Upstream synthesis route of [ 22200-50-6 ]
Downstream synthetic route of [ 22200-50-6 ]

[ 22200-50-6 ] Synthesis Path-Upstream 1~1

1
[ 22200-50-6 ]
[ 81764-16-1 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 7, p. 754 - 757[2] Khimiya Geterotsiklicheskikh Soedinenii, 1980, # 7, p. 972 - 975

Yield	Reaction Conditions	Operation in experiment
95%	With thionyl chloride; N,N-dimethyl-formamide; at 90℃; for 18.0h;	Thionyl chloride [130 ml] was added to Intermediate 4 (7.9 g, 29.15 mmol) to give a suspension. A few drops of dimethylformamide were added and the mixture was heated in an oil bath at 90° C. under nitrogen for approximately 18 hours. The solution was cooled and concentrated in vacuo. The resulting residue was azeotroped with toluene and the solid obtained was triturated using diethyl ether. A pale yellow solid was collected by filtration and washed with more ether to provide the desired product (9.003 g, 95percent).
80%	With trichlorophosphate; for 2.0h;Heating / reflux;	Compound 6-F (4.5 g) was dissolved in 30 mL of POCI3. The solution was heated to reflux for 2 hours. The excess amount of POCI3 was removed by evaporation under vacuum. The residue was basified with NH40H and extracted with EtOAc. The organic layer was concentrated to give 3.95 g (80percent yield) of 4-chloro-7-iodoquinoline 6-G as a yellow solid.
	With trichlorophosphate; at 130℃; for 2.5h;	A mixtureof 3-iodoaniline (3, 5.75 g, 26 mmol)and diethyl ethoxymethylenemalonate (4,5.67 g, 26 mmol) was stirred at room temperature until homogeneous, then heatedat 100 °C for 3 hours under a continuous stream of argon to help removeethanol. After this time, diphenyl ether (25 g) was added to the moltenacrylate 5 and the mixture heated at250-260 °C for 3 hours (a precipitate formed). After cooling down to roomtemperature, petroleum ether (50 mL) was added and the precipitate collected byfiltration. The solid was washed with petroleum ether and allowed to dry toobtain 6. This intermediate ester 6 (3.40 g, 10 mmol) was refluxed in 10percent aqueous sodium hydroxide for 1.5 hours and, after cooling down to roomtemperature, the solution was acidified with concentrated hydrochloric acid.The precipitate was filtered, washed with water and dried. A suspension of theresulting solid in diphenyl ether (10 g) was then heated at 250-270 °C for 6hours until effervescence ceased. When cold, the mixture was diluted withpetroleum ether and the solid filtered, washed with pentane and dried. Finally,a portion of this solid (crude 7-iodo-quinolin-4-ol, 7, 0.50 g, 1.8 mmol) was reacted with phosphorus oxychloride (5 mL)at 130 °C for 2.5 hours. The excess POCl3 was removed under reducedpressure and the resulting oily residue treated with an ice-cold concentratedammonia solution. After extracting with dichloromethane (2 x 20 mL), theorganic layers were combined, dried over anhydrous magnesium sulphate andfiltered. The brownish solid obtained after removing solvents was purified bycolumn chromatography over silica gel eluting with petroleum ether/ethylacetate 20:1, then 10:1 to furnish pure 8as white crystals in 38 percent overall yield. 1H-NMR (500 MHz, CDCl3)delta in ppm: 7.47 (d, 3J=4.7Hz, 1H, H3), 7.87 (dd, 3J=8.9Hz, 4J=1.4 Hz, 1H, H6),7.91 (d, 3J=8.9 Hz, 1H,H5), 8.53 (d, 4J=1.4 Hz,1H, H8), 8.75 (d, 4J=4.7Hz, 1H, H2). 13C-NMR (125 MHz, CDCl3) delta in ppm: 97.0, 121.8 (CH), 125.4 (CH), 125.8, 136.5(CH),138.8 (CH), 143.0, 149.7, 150.7 (CH). HRMS-FAB [M+]: m/z288.9142 (calculated for C9H5NClI 288.9149).

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Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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Related Parent Nucleus of
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