[ CAS No. 67973-80-2 ]

Name: 67973-80-2|Methyl 3-amino-5-hydroxybenzoate|95%
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Quality Control of [ 67973-80-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 67973-80-2 ]

Product Details of [ 67973-80-2 ]

CAS No. :	67973-80-2	MDL No. :	MFCD09263220
Formula :	C₈H₉NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DMNGQQIFOZYIRA-UHFFFAOYSA-N
M.W :	167.16	Pubchem ID :	12438277
Synonyms :

Calculated chemistry of [ 67973-80-2 ]

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) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.28
Log Po/w (XLOGP3) :	1.15
Log Po/w (WLOGP) :	0.77
Log Po/w (MLOGP) :	0.74
Log Po/w (SILICOS-IT) :	0.5
Consensus Log Po/w :	0.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.42 mg/ml ; 0.0145 mol/l
Class :	Very soluble
Log S (Ali) :	-2.27
Solubility :	0.902 mg/ml ; 0.00539 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 :	1.45

Safety of [ 67973-80-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 67973-80-2 ]

* 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 [ 67973-80-2 ]
Downstream synthetic route of [ 67973-80-2 ]

[ 67973-80-2 ] Synthesis Path-Upstream 1~5

1
[ 67-56-1 ]
[ 99-10-5 ]
[ 2150-44-9 ]
[ 67973-80-2 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 11, p. 5587 - 5603

2
[ 67-56-1 ]
[ 99-10-5 ]
[ 2150-44-9 ]
[ 1949-55-9 ]
[ 67973-80-2 ]
[ 90618-98-7 ]

Reference： [1] Tetrahedron, 1983, vol. 39, # 24, p. 4189 - 4192
[2] Tetrahedron, 1983, vol. 39, # 24, p. 4189 - 4192

3
[ 67-56-1 ]
[ 99-10-5 ]
[ 2150-44-9 ]
[ 67973-80-2 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 11, p. 5587 - 5603

4
[ 67-56-1 ]
[ 76045-71-1 ]
[ 67973-80-2 ]

Reference： [1] Patent: WO2004/60376, 2004, A1, . Location in patent: Page/Page column 245-246

5
[ 67-56-1 ]
[ 99-10-5 ]
[ 2150-44-9 ]
[ 1949-55-9 ]
[ 67973-80-2 ]
[ 90618-98-7 ]

Reference： [1] Tetrahedron, 1983, vol. 39, # 24, p. 4189 - 4192
[2] Tetrahedron, 1983, vol. 39, # 24, p. 4189 - 4192

[ 67973-80-2 ] Synthesis Path-Downstream 1~31

1
[ 67-56-1 ]
[ 99-10-5 ]
[ 2150-44-9 ]
[ 1949-55-9 ]
[ 67973-80-2 ]
[ 90618-98-7 ]

Reference： [1]Tetrahedron,1983,vol. 39,p. 4189 - 4192
[2]Tetrahedron,1983,vol. 39,p. 4189 - 4192

2
[ 67973-80-2 ]
[ 93561-92-3 ]
[ 93561-91-2 ]
[ 93561-90-1 ]

Reference： [1]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109
[2]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109

3
[ 67973-80-2 ]
[ 93561-95-6 ]
[ 93561-96-7 ]

Reference： [1]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109

4
[ 67973-80-2 ]
3-amino-5-hydroxybenzyl alkohol hydrochloride [ No CAS ]

Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1011 - 1015

5
[ 67973-80-2 ]
(methylene-⁽²⁾H₂)-3-amino-5-hydroxybenzyl alkohol hydrochloride [ No CAS ]

Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1011 - 1015

6
[ 24424-99-5 ]
[ 67973-80-2 ]
[ 141311-38-8 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 135 - 138

7
[ 67973-80-2 ]
[ 875439-70-6 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 135 - 138

8
[ 67973-80-2 ]
[ 875439-61-5 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 135 - 138

9
[ 67973-80-2 ]
[ 875439-69-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 135 - 138

10
[ 67973-80-2 ]
[ 93561-99-0 ]

Reference： [1]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109
[2]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109

11
[ 67973-80-2 ]
3-amino-2-chloro-5-hydroxybenzoic acid hydrochloride [ No CAS ]

Reference： [1]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109

12
[ 67973-80-2 ]
5-amino-2-chloro-3-hydroxybenzoic acid hydrochloride [ No CAS ]

Reference： [1]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109

13
[ 67973-80-2 ]
[ 93561-97-8 ]

Reference： [1]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109
[2]Australian Journal of Chemistry,1984,vol. 37,p. 2103 - 2109

14
[ 632627-48-6 ]
[ 67973-80-2 ]
3-{2-[5-chloro-2-(4-bromo-2-fluorobenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-5-hydroxybenzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With toluene-4-sulfonic acid; In acetonitrile; at 160℃; for 0.166667h;Microwave irradiation;	[1- [5-CHLORO-2- (4-BROMO-2-FLUORO-BENZYLOXY)-PHENYL]-PENTANE-1,] 4-dione (150mg, 0. [363MMOL),] <strong>[67973-80-2]3-amino-5-hydroxybenzoic acid methyl ester</strong> (61 mg, 0. [363MMOL)] and [PTSA] (5mg) were heated in acetonitrile [(2ML)] at [160C] for 10 minutes in the microwave. Upon cooling, the mixture was diluted with DCM and washed with 2M [HCI,] dried [(NA2SO4),] filtered and concentrated. The residue was purified by chromatography, on silica, with cyclohexane containing a gradient of EtOAc (10-20%) to give the title compound [(112MG,] 57%). 'H NMR [(400MHZ,] CDCI3) 2.17 (3H, s), 3.85 (3H, s), 4.77 (2H, s), 6.12 (1H, d, J=3.3Hz), 6.29 (1H, d, J=3.5Hz), 6.61-6. 63 (2H, m), 6.93 (1H, t, J=7.8Hz), 7.09 (1 H, dd, J=2.8Hz, J=8.8Hz), 7.21-7. 23 (3H, m), 7.31 (1H, s), 7.39 (1H, s)

Reference： [1]Patent: WO2003/101959,2003,A1 .Location in patent: Page 192

15
[ 632627-55-5 ]
[ 67973-80-2 ]
3-{2-[5-chloro-2-(2,6-difluorobenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-5-hydroxybenzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With toluene-4-sulfonic acid; In acetonitrile; at 160℃; for 0.166667h;Microwave irradiation;	1-[5-Chloro-2-(2,6-difluoro-benzyloxy)-phenyl]-pentane-1, 4-dione (150mg, 0. [43MMOL),] 3- amino-5-hydroxybenzoic acid methyl ester (71 mg, 0. 43mmol) and [PTSA] (5mg) were heated in acetonitrile (2ml) at [160C] for 10 minutes in the microwave. Upon cooling, the mixture was diluted with DCM and washed with 2M HCI, dried [(NA2SO4),] filtered and concentrated. The residue was purified by chromatography, on silica, with cyclohexane containing a gradient of EtOAc (10-20%) to give the title compound (68mg, 33%). ['H] NMR [(400MHZ,] [CDCI3)] 2.13 (3H, s), 3.88 (3H, s), 4.87 (2H, s), 6.05 [(1H,] d, J=3.5Hz), 6.28 (1H, d, J=3.5Hz), 6.62-6. 64 (1H, m), 6. [83-6.] 91 (3H, m), 7.06-7. 12 (2H, m), 7.28-7. 34 (2H, m), 7.40-7. 41 (1 H, m).

Reference： [1]Patent: WO2003/101959,2003,A1 .Location in patent: Page 200

16
[ 632627-62-4 ]
[ 67973-80-2 ]
3-{2-[5-chloro-2-(2,3-difluorobenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-5-hydroxybenzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With toluene-4-sulfonic acid; In acetonitrile; at 160℃; for 0.166667h;Microwave irradiation;	[1- [5-CHLORO-2- (2, 3-DIFLUORO-BENZYLOXY)-PHENYL]-PENTANE-1,] 4-dione (150mg, 0. [42MOL),] 3- amino-5-hydroxybenzoic acid methyl ester (71 mg, 0. [42MMOL)] and [PTSA] (5mg) were heated in acetonitrile [(2ML)] at [160C] for 10 minutes in the microwave. Upon cooling, the mixture was diluted with DCM and washed with 2M HCI, dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography, on silica, with cyclohexane containing a gradient of EtOAc (10-20%) to give the title compound (91 mg, 45%). 'H NMR [(400MHZ,] [CDCI3)] 2.16 (3H, s), 3.84 (3H, s), 4.84 (2H, s), 5.19 (1H, s), 6.12 (1H, d, J=2.8Hz), 6.29 (1H, d, J=3.5Hz), 6.61-6. 67 (2H, m), 6.80-6. 87 (1H, m), 6.97-7. 04 [(1H,] m), 7.05-7. 13 (1H, m), 7.20-7. 24 (1H, m), 7.30 (1H, t, J=1.5Hz), 7.41 (1H, m).

Reference： [1]Patent: WO2003/101959,2003,A1 .Location in patent: Page 208

17
[ 2525-16-8 ]
[ 67973-80-2 ]
[ 726191-28-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	at 140℃; for 1h;	A mixture of <strong>[67973-80-2]methyl 3-hydroxy-5-aminobenzoate</strong>, prepared from the corresponding acid and ethanol and hydrochloric acid (2 g, 11.96 MMOL) and 1- aza-2-methoxy-1-cycloheptene (2 g, 15.7 MMOL) was heated neat in an oil bath at 140 C for a period of 1 hour. The resulting solid mass was cooled to room temperature and triturated with ethyl acetate. The solid was filtered and dried and used in the next step without further purification. The yield was 2.7 g (86 %) of the title compound. ESI MS (MH+) FOR C14H18N203 CALCULATED 263 found 263

Reference： [1]Patent: WO2004/60376,2004,A1 .Location in patent: Page/Page column 244-245

18
[ 67-56-1 ]
[ 76045-71-1 ]
[ 67973-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;	A mixture of methyl 3-hydroxy-5-aminobenzoate, prepared from the corresponding acid and ethanol and hydrochloric acid (2 g, 11.96 MMOL) and 1- aza-2-methoxy-1-cycloheptene (2 g, 15.7 MMOL) was heated neat in an oil bath at 140 C for a period of 1 hour. The resulting solid mass was cooled to room temperature and triturated with ethyl acetate. The solid was filtered and dried and used in the next step without further purification. The yield was 2.7 g (86 %) of the title compound. ESI MS (MH+) FOR C14H18N203 CALCULATED 263 found 263

Reference： [1]Patent: WO2004/60376,2004,A1 .Location in patent: Page/Page column 245-246

19
[ 67973-80-2 ]
[ 50765-22-5 ]