[ CAS No. 4774-14-5 ] {[proInfo.proName]}

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Quality Control of [ 4774-14-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4774-14-5 ]

SDS Specification

Alternatived Products of [ 4774-14-5 ]

Product Details of [ 4774-14-5 ]

CAS No. :	4774-14-5	MDL No. :	MFCD00006125
Formula :	C₄H₂Cl₂N₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	LSEAAPGIZCDEEH-UHFFFAOYSA-N
M.W :	148.98	Pubchem ID :	78504
Synonyms :

Calculated chemistry of [ 4774-14-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.05
TPSA :	25.78 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	1.53
Log Po/w (WLOGP) :	1.78
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	2.34
Consensus Log Po/w :	1.51

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.28
Solubility :	0.777 mg/ml ; 0.00522 mol/l
Class :	Soluble
Log S (Ali) :	-1.68
Solubility :	3.11 mg/ml ; 0.0209 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.203 mg/ml ; 0.00136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.05

Safety of [ 4774-14-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4774-14-5 ]

* 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 [ 4774-14-5 ]
Downstream synthetic route of [ 4774-14-5 ]

[ 4774-14-5 ] Synthesis Path-Upstream 1~1

1
[ 4774-14-5 ]
[ 77287-34-4 ]
[ 312736-50-8 ]

Yield	Reaction Conditions	Operation in experiment
36%	at 20 - 90℃; for 14 h;	To a mixture of 2,6-dichloropyrazine (11.0 g, 73.8 mmol) and formamide (58.6 mL, 1,476 mmol) was added dropwise sodium persulfate (17.1 g, 71.7 mmol). The reaction mixture was stirred at 90 for 2 h and was further stirred at rt for 12 h. After dilution with water, the mixture was extracted with isopropanol/chloroform (1/3) and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (70percent n-hexane/EtOAc) to afford 3,5-dichloropyrazin-2-carboxamide (5.06 g, 36percent) as an oil.
36%	at 90℃;	107241 2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heatedto 90 °C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90 °C in portions (1 g)20-3 0 second intervals. An exotherm was observed and the color of the mixture turned from yellowto dark red/brown. The mixture was stirred at 90 °C for 2 h and then cooled to room temperature.The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. Theaqueous layer was extracted with IPAchloroform (1/3, 3 x 750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent EtOAc in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield). ‘HNMR (400 IVIHz, DMSO-d6): ppm 8.87 (s, 1H), 8.18 (br. s.,1H), 8.01 (br. s., 1H).
36%	at 90℃; for 2 h;	2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heated to 90° C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90° C. in Ig portions at 20-30 seconds intervals. An exotherm was observed and the color of the mixture turned from yellow to dark red/brown. The mixture was stirred at 90° C. for 2 h and then cooled to room temperature. The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. The aqueous layer was extracted with IPA:chloroform (1:3, 3*750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent ethyl acetate in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield).

Reference： [1] Organic Letters, 2013, vol. 15, # 9, p. 2156 - 2159
[2] Patent: WO2016/6975, 2016, A2, . Location in patent: Paragraph 457-459
[3] Patent: KR2016/7347, 2016, A, . Location in patent: Paragraph 0359; 0360; 0361; 0362
[4] Patent: WO2018/22992, 2018, A1, . Location in patent: Paragraph 0723; 0724
[5] Patent: US2018/72743, 2018, A1, . Location in patent: Paragraph 1328-1329

[ 4774-14-5 ] Synthesis Path-Downstream 1~5

1
[ 6863-76-9 ]
[ 19745-07-4 ]
[ 4858-85-9 ]
[ 4774-14-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 1177 - 1180
[2]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 1177 - 1180

2
[ 6863-76-9 ]
[ 14508-49-7 ]
[ 19745-07-4 ]
[ 4858-85-9 ]
[ 4774-14-5 ]

Reference： [1]Journal of Chemical Research, Miniprint,1984,p. 2860 - 2875

3
[ 290-37-9 ]
[ 7732-18-5 ]
[ 7782-50-5 ]
[ 14508-49-7 ]
[ 19745-07-4 ]
[ 4858-85-9 ]
[ 4774-14-5 ]

Reference： [1]Patent: US2540476,1948,

4
[ 1123-93-9 ]
[ 4774-14-5 ]
[ 1175018-53-7 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium t-butanolate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃; for 16h;Product distribution / selectivity;	A mixture of 2,6-dichloropyrazine (0.150 g, 1.006 mmol), 5-amino-benzothiazole (0.151 g , 1.006 mmol), BINAP (0.0137 g, 0.02215 mmol), sodium tertiary butoxide (0.136 g, 1.409 mmol) and palladium acetate (0.005 g, 0.02215 mmol) in toluene (8 mL) was heated at 85 0C for 16 h under nitrogen. CH2CI2 was added, the reaction mixture was filtered through Celite, and the solvent was evaporated. The residue was purified by column chromatography (5percent methanol in CH2CI2 as eluent) to give 0.140 g (53percent) of intermediate benzothiazol-5-yl-(6-chloro-pyrazin-2-yl)-amine. 1H NMR (CDCl3) delta 10.12 (s, IH), 9.38 (s, IH), 8.59 (s, IH), 8.22 (s, IH), 8.11-8.08 (d, J= 8.67 Hz, 1 H), 8.02 (s, IH), 7.6-7.57 (d, J= 8.67 Hz, 1 H); MS (API-E S/Positive); m/z: 263 (M+H)+.

Reference： [1]Patent: WO2009/95399,2009,A2 .Location in patent: Page/Page column 36

5
[ 13726-16-4 ]
[ 4774-14-5 ]
(4-chloro-3-methoxyphenyl)(3,5-dichloropyrazin-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%		(4-Chloro-3-methoxyphenyl)(3,5-dichloropyrazin-2-yl)methanol To a -78° C. solution of LDA (2.0M in hexane, 22.0 mmol) in dry THF (40 mL), under argon was added a solution of 2,6-dichloropyrazine (1.648 g, 11.0 mmol) in THF (10 mL). After addition was completed, the resulting mixture was stirred at -78° C. for an additional 1 h, then <strong>[13726-16-4]4-chloro-3-methoxybenzaldehyde</strong> (2.81 g, 16.5 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred for another hour, then quenched with hydrochloric acid (1.8 mL)/EtOH (7.5 mL)/THF (9.0 mL) mixture, and warmed to RT. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:EtOAc=4:1) to give the title compound (600 mg, 17percent). MS (ES+) C12H9Cl3N2O2 requires: 318, found: 319 [M+H]+.

Reference： [1]Patent: US2017/342078,2017,A1 .Location in patent: Paragraph 0515; 0516

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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 ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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