[ CAS No. 401568-70-5 ] {[proInfo.proName]}

Name: 401568-70-5|Methyl 2-amino-4-hydroxybenzoate|98%
Brand: Ambeed
SKU: A148171
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Quality Control of [ 401568-70-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 401568-70-5 ]

SDS Specification

Alternatived Products of [ 401568-70-5 ]

Product Details of [ 401568-70-5 ]

CAS No. :	401568-70-5	MDL No. :	MFCD08274816
Formula :	C₈H₉NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JQBBOJKNCVSVOF-UHFFFAOYSA-N
M.W :	167.16	Pubchem ID :	20327956
Synonyms :

Calculated chemistry of [ 401568-70-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	44.15
TPSA :	72.55 Å²

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) :	-5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.31
Log Po/w (XLOGP3) :	2.32
Log Po/w (WLOGP) :	0.77
Log Po/w (MLOGP) :	0.74
Log Po/w (SILICOS-IT) :	0.5
Consensus Log Po/w :	1.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.58
Solubility :	0.444 mg/ml ; 0.00265 mol/l
Class :	Soluble
Log S (Ali) :	-3.48
Solubility :	0.0551 mg/ml ; 0.000329 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.53
Solubility :	4.91 mg/ml ; 0.0294 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 401568-70-5 ]

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 [ 401568-70-5 ]

* 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 [ 401568-70-5 ]
Downstream synthetic route of [ 401568-70-5 ]

[ 401568-70-5 ] Synthesis Path-Upstream 1~4

1
[ 178758-50-4 ]
[ 401568-70-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With ammonium formate In methanol at 20℃; for 5 h;	Step 3: To a stirred solution of 4-hydroxy-2-nitrobenzoic acid methyl ester (4.410 g, 22.369 mmol) in methanol (80 ml) under nitrogen at room temperature was added ammonium formate (5.642 g, 89.475 mmol) and 5percent Pd/C (450 mg). After 5 hours the reaction mixture was filtered through celite and rinsed. The filtrate was concentrated and the residue partitioned between EtOAc (150 ml) and water (40 ml). The layers were shaken, separated and the organic layer washed with water (3.x.30 ml), brine (2.x.30 ml), dried over Na₂SO₄, filtered, concentrated and dried to give 2-amino-4-hydroxy-benzoic acid methyl ester (3.593 g, 21.494 mmol, 96percent) as an off-white solid, dec. 113-118° C. ¹H NMR (DMSO-d₆) δ 3.70 (s, 3H), 5.98 (dd, 1H), 6.10 (s, 1H), 6.59 (s, 1H), 7.54 (d, 1H), 9.81 (s, 1H); mass spectrum [ES(-)], m/z 166 (M-H)-.

Reference： [1] Patent: US2005/70584, 2005, A1, . Location in patent: Page/Page column 24
[2] Journal of the Chemical Society, 1949, p. 1498,1502

2
[ 67-56-1 ]
[ 33844-21-2 ]
[ 401568-70-5 ]

Yield	Reaction Conditions	Operation in experiment
10.6 g	Stage #1: at 150℃; for 23 h; Stage #2: Cooling; Reflux	4-Methoxy-2-nitrobenzoic acid (24.0 g) was dissolved in 25percent hydrogen bromide acetic acid solution (480 mL), and the reaction mixture was stirred at 150°C for 23 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (500 mL). Concentrated sulfuric acid (12.0 g) was added under water-cooling, and the reaction mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) and dissolved in THF (250 mL). Imidazole (4.9 g) and N,N-dimethyl-4-aminopyridine (1 piece) were added, tert-butyl(chloro)dimethylsilane (10.9 g) was added and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) and dissolved in ethanol (170 mL) and water (170 mL). Ammonium chloride (2.9 g) and reduced iron (15.2 g) were added, and the reaction mixture was stirred at 85°C for 3 days. The insoluble material was filtered off with celite, the filtrate was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (10.6 g). MS (ESI+) : [M+H]⁺168.2.

Reference： [1] Patent: EP2889291, 2015, A1, . Location in patent: Paragraph 0709

3
[ 610-36-6 ]
[ 401568-70-5 ]

Reference： [1] Journal of the Chemical Society, 1949, p. 1498,1502

4
[ 74230-08-3 ]
[ 401568-70-5 ]

Reference： [1] Journal of the Chemical Society, 1949, p. 1498,1502

[ 401568-70-5 ] Synthesis Path-Downstream 1~13

2
[ 7647-01-0 ]
[ 401568-70-5 ]
[ 7782-50-5 ]
[ 64-19-7 ]
[ 98556-58-2 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1956,vol. 75,p. 504,508

3
[ 610-36-6 ]
[ 401568-70-5 ]

Reference： [1]Journal of the Chemical Society,1949,p. 1498,1502

4
[ 74230-08-3 ]
[ 401568-70-5 ]

Reference： [1]Journal of the Chemical Society,1949,p. 1498,1502

5
[ 401568-70-5 ]
[ 2243-83-6 ]
[ 848826-18-6 ]