[ CAS No. 54916-65-3 ] {[proInfo.proName]}

Name: 54916-65-3|5-Chloro-2-methoxynicotinic acid|98%
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SKU: A158214
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Quality Control of [ 54916-65-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 54916-65-3 ]

SDS Specification

Alternatived Products of [ 54916-65-3 ]

Product Details of [ 54916-65-3 ]

CAS No. :	54916-65-3	MDL No. :	MFCD08236790
Formula :	C₇H₆ClNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DPIJNAABZCWXFD-UHFFFAOYSA-N
M.W :	187.58	Pubchem ID :	9836973
Synonyms :

Calculated chemistry of [ 54916-65-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.7
TPSA :	59.42 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) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	1.31
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	-0.36
Log Po/w (SILICOS-IT) :	1.37
Consensus Log Po/w :	1.04

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.07
Solubility :	1.61 mg/ml ; 0.00858 mol/l
Class :	Soluble
Log S (Ali) :	-2.16
Solubility :	1.3 mg/ml ; 0.00694 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.14
Solubility :	1.35 mg/ml ; 0.00718 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 54916-65-3 ]

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

Application In Synthesis of [ 54916-65-3 ]

* 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 [ 54916-65-3 ]
Downstream synthetic route of [ 54916-65-3 ]

[ 54916-65-3 ] Synthesis Path-Upstream 1~2

1
[ 16498-81-0 ]
[ 54916-65-3 ]

Yield	Reaction Conditions	Operation in experiment
52%	With hydrogenchloride In aqueous sodium hypochlorite	EXAMPLE 1 A 306 mg. (0.002 mole) sample of 2-methoxynicotinic acid (the product of Preparation A) was added in one portion to 20 ml. of well-stirred 5.25percent aqueous sodium hypochlorite solution (Clorox). The resulting mixture (now a solution) was then allowed to stir at room temperature (~20° C.) for a period of approximately 18 hours (i.e., overnight). Upon completion of this step, the reaction mixture was acidified with 10 ml. of 1N hydrochloric acid and the resulting precipitate was subsequently extracted with chloroform. The organic extracts were then combined, dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was subsequently concentrated in vacuo to afford 195 mg. (52percent) of pure 5-chloro-2-methoxynicotinic acid, m.p. 139°-141° C. (literature m.p. 149°-150° C., according to D. E. Kuhla et al. in U.S. Pat. No. 3,879,403). The pure product was further characterized by means of nuclear magnetic resonance data and mass spectroscopy.

Reference： [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 7, p. 1859 - 1865
[2] Synthetic Communications, 1989, vol. 19, # 9-10, p. 1505 - 1508
[3] Patent: US4980357, 1990, A,
[4] Patent: US4716231, 1987, A,
[5] Patent: EP306251, 1990, A3,
[6] Patent: EP306251, , A2, [6] Patent: , 1989, ,

2
[ 2942-59-8 ]
[ 54916-65-3 ]

Reference： [1] Synthetic Communications, 1989, vol. 19, # 9-10, p. 1505 - 1508

[ 54916-65-3 ] Synthesis Path-Downstream 1~15

1
[ 16498-81-0 ]
[ 54916-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; water;	PREPARATION B In a reaction flask equipped with a mechanical stirrer and dry ice condenser, there were placed 25.5 g. (0.166 mole) of <strong>[16498-81-0]2-methoxynicotinic acid</strong> (the product of Preparation A) and 1500 ml. of water. Stirring was then commenced and chlorine gas was bubbled into the resultant slurry until saturation of same was complete with respect to said gas. This step required a period of 30 minutes. At the end of this time, the reaction mixture was allowed to stir at room temperature (~20 C.) for a period of approximately 16 hours (i.e., overnight) and then was filtered to remove crude product. The latter material was then washed with water and air dried, prior to being taken up in chloroform. The chloroform solution was then washed once with saturated brine and dried over anhydrous magnesium sulfate. After removal of the drying agent by means of filtration and the solvent by means of evaporation under reduced pressure, there were ultimately obtained 26.2 g. (84%) of pure 5-chloro-<strong>[16498-81-0]2-methoxynicotinic acid</strong> in the form of a white solid material melting at 149-151 C. (literature m.p. 149-150 C., according to D. E.
195 mg. (52%)	With hydrogenchloride; In aqueous sodium hypochlorite;	EXAMPLE 1 A 306 mg. (0.002 mole) sample of <strong>[16498-81-0]2-methoxynicotinic acid</strong> (the product of Preparation A) was added in one portion to 20 ml. of well-stirred 5.25% aqueous sodium hypochlorite solution (Clorox). The resulting mixture (now a solution) was then allowed to stir at room temperature (~20 C.) for a period of approximately 18 hours (i.e., overnight). Upon completion of this step, the reaction mixture was acidified with 10 ml. of 1N hydrochloric acid and the resulting precipitate was subsequently extracted with chloroform. The organic extracts were then combined, dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was subsequently concentrated in vacuo to afford 195 mg. (52%) of pure 5-chloro-<strong>[16498-81-0]2-methoxynicotinic acid</strong>, m.p. 139-141 C. (literature m.p. 149-150 C., according to D. E. Kuhla et al. in U.S. Pat. No. 3,879,403). The pure product was further characterized by means of nuclear magnetic resonance data and mass spectroscopy.
	In chloroform; water;	PREPARATION B In a reaction flask equipped with a mechanical stirrer and dry ice condenser, there were placed 25.5 g. (0.166 mole) of <strong>[16498-81-0]2-methoxynicotinic acid</strong> (the product of Preparation A) and 1500 ml. of water. Stirring was then commenced and chlorine gas was bubbled into the resultant slurry until saturation of same was complete with respect to said gas. This step required a period of 30 minutes. At the end of this time, the reaction mixture was allowed to stir at room temperature (~20C.) for a period of approximately 16 hours (i.e., overnight) and then was filtered to remove crude product. The latter material was then washed with water and air dried, prior to being taken up in chloroform. The chloroform solution was then washed once with saturated brine and dried over anhydrous magnesium sulfate. After removal of the drying agent by means of filtration and the solvent by means of evaporation under reduced pressure, there were ultimately obtained 26.2 g. (84%) of pure 5-chloro-<strong>[16498-81-0]2-methoxynicotinic acid</strong> in the form of a white solid material melting at 149-151C. (literature m.p. 149-150C., according to D.E.

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1859 - 1865
[2]Synthetic Communications,1989,vol. 19,p. 1505 - 1508
[3]Patent: US4980357,1990,A
[4]Patent: US4716231,1987,A
[5]Patent: EP306251,A2
Patent: ,1989,

2
[ 67-56-1 ]
[ 54916-65-3 ]
[ 82060-51-3 ]