[ CAS No. 372118-00-8 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 372118-00-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 372118-00-8 ]

SDS Specification

Alternatived Products of [ 372118-00-8 ]

Product Details of [ 372118-00-8 ]

CAS No. :	372118-00-8	MDL No. :	MFCD09953611
Formula :	C₆H₆N₂O₄	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	SHJHUIKJFYHTDY-UHFFFAOYSA-N
M.W :	170.12	Pubchem ID :	56604115
Synonyms :

Calculated chemistry of [ 372118-00-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	37.36
TPSA :	92.54 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.01
Log Po/w (XLOGP3) :	0.21
Log Po/w (WLOGP) :	-0.33
Log Po/w (MLOGP) :	-0.77
Log Po/w (SILICOS-IT) :	-0.19
Consensus Log Po/w :	-0.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.27
Solubility :	9.24 mg/ml ; 0.0543 mol/l
Class :	Very soluble
Log S (Ali) :	-1.71
Solubility :	3.3 mg/ml ; 0.0194 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.57
Solubility :	45.5 mg/ml ; 0.267 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.19

Safety of [ 372118-00-8 ]

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

Application In Synthesis of [ 372118-00-8 ]

* 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 [ 372118-00-8 ]

[ 372118-00-8 ] Synthesis Path-Downstream 1~12

1
[ 83878-89-1 ]
[ 372118-00-8 ]

Yield	Reaction Conditions	Operation in experiment
30%		Step 2 4,6-Dihydroxy-pyridazine-3-carboxylic acid methyl ester A mixture of 2-diazo-3-oxo-pentanedioic acid dimethyl ester (50.0 g, 249.8 mmol) and triphenylphosphine (65.5 g, 249.8 mmol) in diethyl ether (500 mL) was stirred at room temperature for 24 h. The organic solvent was removed under vacuum and then acetic acid (500 mL) and water (50 mL) were added to the residue and the mixture was refluxed for 10 h. The reaction mixture was concentrated under reduced pressure to obtain a viscous residue. Trituration with ethyl acetate generated a yellow solid that was purified by chromatography (silica, 100-200 mesh, 1-5% methanol in dichloromethane) to give 4,6-dihydroxy-pyridazine-3-carboxylic acid methyl ester (12.8 g, 30%) as a yellow solid. LC-MS 169.2 [M+H]+.
		A mixture of 2-diazo-3-oxo-pentanedioic acid dimethyl or diethyl ester (0.1 mol) and PPh3 (26.3 g, 0.1 mol) in ether (200 mL) is stirred at room temperature for 24 hours. Ether is removed in vacuo and HOAc (200 mL) and water (20 mL) are added to the residue. The mixture is then refluxed for 10 hours under nitrogen. The solvent is removed in vacuo and CHCl3 (150 mL), MeOH (150 mL) and silica gel (65 g) are added to the residue. The mixture is evaporated to dryness. The resultant yellow powder is then packed on the top of a column (480 g silica) and eluted with CHCl3:MeOH, 50:1 to 5:1. The desired 4,6 dihydroxy-pyridazine-3-carboxylic acid methyl or ethyl ester is obtained as a light yellow solid.

Reference： [1]Patent: US2013/178478,2013,A1 .Location in patent: Paragraph 0299;0300
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691
[3]Patent: US2004/77653,2004,A1 .Location in patent: Page 18

2
[ 372118-00-8 ]
[ 372118-01-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With trichlorophosphate; at 95.0℃; for 5h;	Step 3 4,6-Dichloro-pyridazine-3-carboxylic acid methyl ester A mixture of <strong>[372118-00-8]4,6-dihydroxy-pyridazine-3-carboxylic acid methyl ester</strong> (10.5 g, 61.7 mmol) and POCl3 (70 mL) was heated to 95 C. for 5 h. The excess POCl3 was removed under reduced pressure, then the crude residue was added to ice-water (250 mL) and extracted with ethyl acetate (3*100 mL). The combined extracts were dried then concentrated to give a crude residue which was purified by chromatography (silica, 100-200 mesh, 30% ethyl acetate in hexane) to give 4,6-dichloro-pyridazine-3-carboxylic acid methyl ester (9.2 g, 72%) as an off white solid. LC-MS: 207.0 [M+H]+.
64.3%	With trichlorophosphate; for 3h;Reflux;	A slurry of <strong>[372118-00-8]methyl 4,6-dihydroxypyridazine-3-carboxylate</strong> (11.7 g, 68.8 mmol) in POCl3 (110 mL, 1180 mmol) was heated to reflux for 3h during which time the mixture became a nearly homogeneous dark brown solution. The reaction mixture was cooled to rt, allowed to stand overnight and concentrated in vacuo. The resulting dark brown residue was dissolved in DCM (?300 mL) and was slowly poured onto ?500 mL of crushed ice with swirling of the flask. After the addition was complete, water was slowly added (?200 mL) until the mixture became stirrable and the mixture was stirred while warming to rt over ?3 h. The resulting phases were separated and the aqueous portion was extracted with additional DCM (3*100 mL). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, decanted and concentrated under vacuum to afford a white solid as the pure product, methyl 4,6-dichloropyridazine-3-carboxylate (9.16 g, 44.2 mmol, 64.3% yield). Material was used as is without any further purification. MS (M+1) m/z: 206.9 (MH+). LC retention time 0.80 min [A].
	With trichlorophosphate; at 95.0℃; for 4h;	Step 3.Preparation of 4,6-dichloro-pyridazine-3-carboxylic acid methyl or ethyl ester 5 A mixture of 4,6-dihydroxy-pyridazine-3-carboxylic acid methyl or ethyl ester (50 mmol) and POCl3 (90 ML) is heated at 95 C. for 4 hours.The excess POCl3 is evaporated in vacuo and to the residue cooled to 0 C. was added ice (150 g) followed by EtOAc (200 ML).The layers are separated and the aqueous layer is extracted with EtOAc (2*100 ML).The combined extracts are washed with brine (200 ML), dried (Na2SO4) and evaporated in vacuo.This residue is purified by flash column chromatography (225 g silica gel, eluted with 4:1 hexane, EtOAc).The desired 4,6 dichloro-pyridazine-3-carboxylic acid methyl ester is obtained as a white solid, while the 4,6 dichloro-pyridazine-3-carboxylic acid ethyl ester is a colorless liquid.

Reference： [1]Patent: US2013/178478,2013,A1 .Location in patent: Paragraph 0301;0302
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691
[3]Patent: US2019/152948,2019,A1 .Location in patent: Paragraph 0416-0417; 0414
[4]Patent: US2004/77653,2004,A1 .Location in patent: Page 18

3
[ 1830-54-2 ]
[ 372118-00-8 ]

Reference： [1]Patent: US2013/178478,2013,A1
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 2683 - 2691
[3]Patent: US2004/77653,2004,A1
[4]Patent: US2019/152948,2019,A1

4
[ 372118-00-8 ]
[ 1446791-52-1 ]