[ CAS No. 89180-45-0 ] {[proInfo.proName]}

Name: 89180-45-0|5-Chloro-2-hydroxypyrazine|98%
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Quality Control of [ 89180-45-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89180-45-0 ]

SDS Specification

Alternatived Products of [ 89180-45-0 ]

Product Details of [ 89180-45-0 ]

CAS No. :	89180-45-0	MDL No. :	MFCD11109884
Formula :	C₄H₃ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MPQIKXKJHKXJQC-UHFFFAOYSA-N
M.W :	130.53	Pubchem ID :	14774300
Synonyms :

Calculated chemistry of [ 89180-45-0 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	29.06
TPSA :	46.01 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.56
Log Po/w (XLOGP3) :	0.6
Log Po/w (WLOGP) :	0.84
Log Po/w (MLOGP) :	-0.45
Log Po/w (SILICOS-IT) :	1.22
Consensus Log Po/w :	0.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.58
Solubility :	3.42 mg/ml ; 0.0262 mol/l
Class :	Very soluble
Log S (Ali) :	-1.14
Solubility :	9.46 mg/ml ; 0.0724 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.66
Solubility :	2.88 mg/ml ; 0.0221 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 89180-45-0 ]

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

Application In Synthesis of [ 89180-45-0 ]

* 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.

Upstream synthesis route of [ 89180-45-0 ]
Downstream synthetic route of [ 89180-45-0 ]

[ 89180-45-0 ] Synthesis Path-Upstream 1~3

1
[ 89180-45-0 ]
[ 19745-07-4 ]

Reference： [1] Patent: WO2008/46226, 2008, A1, . Location in patent: Page/Page column 60
[2] Patent: EP1698626, 2006, A1, . Location in patent: Page/Page column 28-29

2
[ 89180-45-0 ]
[ 19745-07-4 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 1131 - 1137

3
[ 5049-61-6 ]
[ 89180-45-0 ]

Reference： [1] Patent: EP1698626, 2006, A1, . Location in patent: Page/Page column 28-29

[ 89180-45-0 ] Synthesis Path-Downstream 1~8

1
[ 89180-45-0 ]
[ 19745-07-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1131 - 1137

3
[ 5049-61-6 ]
[ 89180-45-0 ]

Yield	Reaction Conditions	Operation in experiment
		[Referential Example 11] 1-(5-Methoxy-2-pyrazinyl)-5-(2-pyridyl)-1H-pyrazole-3-carboxylic acid; [Show Image] [Show Image] 1) 5-Chloro-2-hydrazinopyrazine; A solution of 5-chloro-2-hydroxpyrazine (1.84 g) synthesized from aminopyrazine by the method of Palamidessi et al. (J.Org.Chem., vol.29, pp 2491-2492, 1964) in phosphorus oxychloride (28ml) was placed in a sealed tube, and the solution was stirred at an outer temperature of 130C for 6 hours. After cooling with air, ice cold water and dichloromethane were added to the reaction liquid, then the phases were separated. The organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hydrazine monohydrate (1.39 ml) was added to a solution of the residue in ethanol (14 ml), and the mixture was stirred at room temperature for 150 minutes and for another 15 minutes at 80C. After cooling with air, the reaction liquid was evaporated under reduced pressure, and to the residue was added water and a mixed solvent of chloroform and methanol (1:10), then the phases were separated. The organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give 5-chloro-2-hydrazinopyrazine(0.325 g, 16%) as a solid. 1H-NMR (400 MHz, DMSO-d6)delta: 4.32 (2H, br s), 7.92 (1H, s), 7.99 (1H, s), 8.13 (1H, s). EI-MSm/z: 144 (M+).

Reference： [1]Patent: EP1698626,2006,A1 .Location in patent: Page/Page column 28-29

4
[ 89180-45-0 ]
[ 19745-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; at 120℃; for 2h;	A mixture of <strong>[89180-45-0]2-hydroxy-5-chloropyrazine</strong> in POCl3 (21 equiv.) was heated at 1200C for 2 h. The reaction mixture was cooled and poured on ice and extracted with dichloromethane. The organic solvent was collected, dried over Na2SO4 and filtered. The solvent was filtered over silica gel followed by ethyl acetate. The solvents were evaporated to provide the title compound
	With trichlorophosphate; at 130℃; for 6h;	[Referential Example 11] 1-(5-Methoxy-2-pyrazinyl)-5-(2-pyridyl)-1H-pyrazole-3-carboxylic acid; [Show Image] [Show Image] 1) 5-Chloro-2-hydrazinopyrazine; A solution of 5-chloro-2-hydroxpyrazine (1.84 g) synthesized from aminopyrazine by the method of Palamidessi et al. (J.Org.Chem., vol.29, pp 2491-2492, 1964) in phosphorus oxychloride (28ml) was placed in a sealed tube, and the solution was stirred at an outer temperature of 130°C for 6 hours. After cooling with air, ice cold water and dichloromethane were added to the reaction liquid, then the phases were separated. The organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hydrazine monohydrate (1.39 ml) was added to a solution of the residue in ethanol (14 ml), and the mixture was stirred at room temperature for 150 minutes and for another 15 minutes at 80°C. After cooling with air, the reaction liquid was evaporated under reduced pressure, and to the residue was added water and a mixed solvent of chloroform and methanol (1:10), then the phases were separated. The organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give 5-chloro-2-hydrazinopyrazine(0.325 g, 16percent) as a solid. 1H-NMR (400 MHz, DMSO-d6)delta: 4.32 (2H, br s), 7.92 (1H, s), 7.99 (1H, s), 8.13 (1H, s). EI-MSm/z: 144 (M+).

Reference： [1]Patent: WO2008/46226,2008,A1 .Location in patent: Page/Page column 60
[2]Patent: EP1698626,2006,A1 .Location in patent: Page/Page column 28-29

5
[ 7589-27-7 ]
[ 89180-45-0 ]
2-chloro-5-(4-fluorophenethoxy)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.2%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20.0℃; for 2.08333h;	To a 50 mL round bottom flask equipped with a stir bar was added 5- chloropyrazin-2-ol (250 mg, 1.9 15 mmol), 2-(4-fluorophenyl)ethanol (268 mg, 1.9 15 mmol), triphenylphosphine (603 mg, 2.298 mmol) and THF (10 mL). To the stirred solution was added DIAD (0.447 mL, 2.298 mmol). The solution had a mild exotherm, then cooled within 5 minutes. The solution was stirred at RT for 2 hrs. The reactionsolution was concentrated in vacuo and the resulting oil was purified via silica gel chromatography (40 g column, 5-40% EtOAc:Hex) to afford the product 2-chloro-5-(4-fluorophenethoxy)pyrazine (330 mg, 1.306 mmol, 68.2 % yield) as a white solid. ?H NMR (500 MHz, CDC13) 8.10 (d,J=1.3 Hz, 1H), 8.01 (d,J=1.3 Hz, 1H), 7.25 (dd, J=8.6, 5.4 Hz, 2H), 7.03 (t, J=8.7 Hz, 2H), 4.52 (t, J=6.9 Hz, 2H), 3.09 (t, J=6.9 Hz, 2H). LCMS (M+1) = 253.0.

Reference： [1]Patent: WO2018/127800,2018,A1 .Location in patent: Page/Page column 43; 44

6
[ 33332-29-5 ]
[ 89180-45-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With sulfuric acid; sodium nitrite; at 0 - 40℃;	General procedure: Sodium nitrite (3.4 g, 50 mmol, 1.3 eq.) was added in small portionsto 98% sulfuric acid (15 mL) ice bath, and the mixture was allowed towarm up and heated to 60. When getting clear, the solution wascooled in an ice bath again. A solution of 2-amino-pyrazine (9) (4 g,39.3 mmol, 1 eq.) in 98% sulfuric acid (15 mL) was added dropwise.The reaction mixture was stirred at 40 for 1 h. After cooling to roomtemperature, it was slowly poured onto crushed ice and stirred until nonitrogen run out. The solution was adjusted to pH 6 with a 40% solutionof sodium hydroxide, resulting in lots of sodium sulfate which wasfiltered off whereafter. The filtrate was extracted with EA (50 mL×3),and the combined organics were dried (Na2SO4), filtered and concentratedin vacuo to give the product as a white precipitate (6.38 g,53%).

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 748 - 759

7
[ 463-71-8 ]
[ 89180-45-0 ]
2-chloro-5-(trichloromethoxy)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		5-Chloropyrazin-2-ol 1 (40 g, 0.31 mol) was added in portions to the solution of NaOH (14.1 g,0.35 mol) in water (250 mL) at 5-10 C. The mixture was cooled to 0 C and the solution of thiophosgene(35.3 g, 0.31 mol) in chloroform (250 mL) was added dropwise over 1 h under vigorous stirring.After the addition was complete, the mixture was vigorously stirred for a further 3 h at 0 C beforebeing extracted with chloroform (5 100 mL). The combined organic layers were washed with waterand dried with MgSO4. After the dehydration agent had been filtered o, the mixture was saturatedwith chlorine and stirred for 3 days at 25 C. The excess of chlorine was removed with nitrogengas stream, the solvent was distilled o in a vacuum (300 mbar), and the residue was distilled in avacuum, yielding trichloromethoxypyrazine 2 as a colorless oil or solid. The yield was 47.9 g (63%);b.p. 100-101 C (1 mbar); m.p. 26-28 C. 1H-NMR (400 MHz, CDCl3) 8.32 (s, 1H, HPy), 8.37 (s, 1H,HPy). 13C-NMR (126 MHz, CDCl3) 108.9 (s, OCCl3), 136.0, 140.8, 145.6, 154.0. GC-MS, 70 eV, m/z (rel.int.): 248 (100) [M(335Cl + 37Cl)]+, 246 (80) [M(435Cl)]+, 250 (50) [M(235Cl + 237Cl)]+. Anal. Calcd. forC4H2ClFN2: Cl, 57.20; Found: Cl, 57.26.

Reference： [1]Molecules,2020,vol. 25

8
[ 75-61-6 ]
[ 89180-45-0 ]
2-(bromodifluoromethoxy)-5-chloropyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		To the solution of <strong>[89180-45-0]5-chloropyrazin-2-ol</strong> (40 g, 0.31 mol) and tetrabutylammonium bromide (4.9 g,15 mmol) in anhydrous DMF (300 mL), NaH (60% in mineral oil) (14.7 g, 0.37 mol) was added inportions at 0 C and the mixture was stirred for 2 h at r.t. The mixture was cooled to 30 C and dibromodifluoromethane (257 g, 1.23 mol) was added dropwise. The mixture was carefully warmedand stirred at 30-35 C for 6 h. Water (900 mL) was added dropwise to the mixture and the excess ofCBr2F2 was distilled in a dry ice trap. The residue was extracted with MTBE (tert-butyl-methyl ether)(7 100 mL), extract was washed with brine and dried with MgSO4. The solvent was distilled o atatmospheric pressure and the product was distilled in a vacuum. The yield was 29.4 g (37%); colorlessliquid or solid; b.p. 80-81 C (10 mbar); m.p. 14-17 C. 1H-NMR (400 MHz, CDCl3) 8.27 (s, 1H,HPy), 8.35 (s, 1H, HPy). 13C-NMR (126 MHz, CDCl3) 111.5 (t, 1JCF = 315.5 Hz, CBrF2), 135.2, 141.0,145.9, 152.6. 19F-NMR (376.5 MHz, CDCl3) 18.4 (s, CBrF2). GC-MS, 70 eV, m/z (rel. int.): 258 (75)[M(79Br + 35Cl)]+, 260 (100) [M(79Br + 37Cl) or (81Br + 35Cl)]+, 262 (25) [M(81Br + 37Cl)]+. Anal. Calcd.for C5H2BrClF2N2O: C, 23.15; H, 0.78; N, 10.80; Found: C, 23.12; H, 0.68; N, 10.72.

Reference： [1]Molecules,2020,vol. 25

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H222	Extremely flammable aerosol
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H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 89180-45-0 ] {[proInfo.proName]}

Quality Control of [ 89180-45-0 ]

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Calculated chemistry of [ 89180-45-0 ]

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[ 89180-45-0 ] Synthesis Path-Upstream 1~3

[ 89180-45-0 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 89180-45-0 ]

Chlorides

Alcohols

Related Parent Nucleus of [ 89180-45-0 ]

Pyrazines

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[ 89180-45-0 ]

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[ 89180-45-0 ]