[ CAS No. 136663-40-6 ] {[proInfo.proName]}

Name: 136663-40-6|(2-Methylbenzo[d]oxazol-6-yl)methanol|98%
Brand: Ambeed
SKU: A100665
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Quality Control of [ 136663-40-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 136663-40-6 ]

SDS Specification

Alternatived Products of [ 136663-40-6 ]

Product Details of [ 136663-40-6 ]

CAS No. :	136663-40-6	MDL No. :	MFCD22019828
Formula :	C₉H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SFCHIWNAOMJWLM-UHFFFAOYSA-N
M.W :	163.17	Pubchem ID :	15662270
Synonyms :

Calculated chemistry of [ 136663-40-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.1
TPSA :	46.26 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	1.28
Log Po/w (WLOGP) :	1.48
Log Po/w (MLOGP) :	0.75
Log Po/w (SILICOS-IT) :	2.17
Consensus Log Po/w :	1.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.15
Solubility :	1.16 mg/ml ; 0.00713 mol/l
Class :	Soluble
Log S (Ali) :	-1.85
Solubility :	2.3 mg/ml ; 0.0141 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.12
Solubility :	0.123 mg/ml ; 0.000757 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.27

Safety of [ 136663-40-6 ]

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 [ 136663-40-6 ]

* 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 [ 136663-40-6 ]
Downstream synthetic route of [ 136663-40-6 ]

[ 136663-40-6 ] Synthesis Path-Upstream 1~3

1
[ 136663-40-6 ]
[ 864274-04-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With pyridinium chlorochromate In dichloromethane at 20℃; for 1 h;	c) 2-Methvl-benzooxazole-6-carbaldehvde; To the solution (2-methyl-benzooxazol-6-yl)-methanol (12.5 g, 76 mmol) in dichloromethane (200 mL) was added pyridinium chlorochromate (20 g, 93 mmol, 1.2 eq) and the reaction mixture was stirred for 1 hour at the room temperature. Celite (10 g) was added followed by decolorizing carbon (2 g) and the reaction mixture was filtered after 15 min of stirring. After evaporation the crude product was purified column chromatography (1: 10 ethyl acetate : dichloromethane) of give 8.2 g (66 percent yield) of pure 2-methyl-benzooxazole-6-carbaldehyde. 1H-NMR (CDC13) : S 2. 73 (s, 3H), 7.79 (d, 1H, J=8. 1 Hz), 7. 88 (dd, 1H, J=8. 1 Hz, J'=1.2 Hz), 8. 03 (d, 1H, J=1. 2 Hz), 10.09 (s, 1H). LC MS (m/e) = 162.2 (MH+). Rt = 1.47 min.
66%	With pyridinium chlorochromate In dichloromethane at 20℃; for 1 h;	To the solution (2-methyl-benzooxazol-6-yl)-methanol (12.5 g, 76 mmol) in dichloromethane (200 mL) was added pyridinium chlorochromate (20 g, 93 mmol, 1.2 eq) and the reaction mixture was stirred for 1 hour at the room temperature. Celite (10 g) was added followed by decolorizing carbon (2 g) and the reaction mixture was filtered after 15 min of stirring. After evaporation the crude product was purified column chromatography (1 :10 ethyl acetate: dichloromethane) of give 8.2 g (66 percent yield) of pure 2-methyl-benzooxazole-6-carbaldehyde. ¹H-NMR (CDCI₃): D2.73 (s, 3H), 7.79 (d, 1 H, J=8.1 Hz), 7.88 (dd, 1 H, J=8.1 Hz, J'=1.2 Hz), 8.03 (d, 1 H, J=1.2 Hz), 10.09 (s, 1 H). LC MS (m/e) = 162.2 (MH+). Rt = 1.47 min.

Reference： [1] Patent: WO2005/82901, 2005, A1, . Location in patent: Page/Page column 33; 61-62
[2] Patent: WO2007/103755, 2007, A2, . Location in patent: Page/Page column 81; 83

2
[ 136663-23-5 ]
[ 136663-40-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With lithium aluminium tetrahydride In tetrahydrofuran at -20 - 20℃;	b) (2-Methyl-benzooxazol-6-vl)-methanol; To the solution of 2-methyl-benzooxazole-6-carboxylic acid methyl ester (25 g, 0.13 mol) in THF (500 mL) at-20 oC was added a solution of lithium aluminum hydride (4.81 g, 130 mL of 1 M solution in THF, 0.13 mmol, 1 eq) and the reaction mixture was allowed to warm up to the room temperature overnight. Water (5 mL) followed by 1 M NaOH solution (5 mL) followed by water (15 mL) was added and the reaction mixture was stirred for 15 min at the room temperature. The suspension was filtered, liquid evaporated and purified by column chromatography (1: 3 ethyl acetate: dichloromethane) to give 12.5 g (58 percent yield) of pure (2-methyl-benzooxazol-6-yl)-methanol. lH-NMR (CDCls) : otilde; 2.64 (s, 3H), 4.82 (s, 2H), 7.29 (d, 1H, J=8 Hz), 7. 53 (s, 1H), 7.62 (d, 1H, J=8 Hz). LC MS (m/e) = 164.2 (MH+).
58%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -20 - 20℃; Stage #2: With sodium hydroxide In water	To the solution of 2-methyl-benzooxazole-6-carboxylic acid methyl ester (25 g, 0.13 mol) in THF (500 mL) at -20 ⁰C was added a solution of lithium aluminum hydride (4.81 g, 130 mL of 1 M solution in THF, 0.13 mmol, 1 eq) and the reaction mixture was allowed to warm up to the room temperature overnight. Water (5 mL) followed by 1 M NaOH solution (5 mL) followed by water (15 mL) was added and the reaction mixture was stirred for 15 min at the room temperature. The suspension was filtered, liquid evaporated and purified by column chromatography (1 :3 ethyl acetate: dichloromethane) to give 12.5 g (58 percent yield) of pure (2-methyl- benzooxazol-6-yl)-methanol. ¹H-NMR (CDCI₃): P2.64 (s, 3H), 4.82 (s, 2H), 7.29 (d, 1 H, J=8 Hz), 7.53 (s, 1 H), 7.62 (d, 1 H, J=8 Hz). LC MS (m/e) = 164.2 (MH+). Rt = 1.03 min.

Reference： [1] Patent: WO2005/82901, 2005, A1, . Location in patent: Page/Page column 33; 61
[2] Patent: WO2007/103755, 2007, A2, . Location in patent: Page/Page column 51; 83

3
[ 63435-16-5 ]
[ 136663-40-6 ]

Reference： [1] Patent: WO2007/103755, 2007, A2,

[ 136663-40-6 ] Synthesis Path-Downstream 1~10

1
[ 136663-23-5 ]
[ 136663-40-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With lithium aluminium tetrahydride; In tetrahydrofuran; at -20 - 20℃;	b) (2-Methyl-benzooxazol-6-vl)-methanol; To the solution of <strong>[136663-23-5]2-methyl-benzooxazole-6-carboxylic acid methyl ester</strong> (25 g, 0.13 mol) in THF (500 mL) at-20 oC was added a solution of lithium aluminum hydride (4.81 g, 130 mL of 1 M solution in THF, 0.13 mmol, 1 eq) and the reaction mixture was allowed to warm up to the room temperature overnight. Water (5 mL) followed by 1 M NaOH solution (5 mL) followed by water (15 mL) was added and the reaction mixture was stirred for 15 min at the room temperature. The suspension was filtered, liquid evaporated and purified by column chromatography (1: 3 ethyl acetate: dichloromethane) to give 12.5 g (58 % yield) of pure (2-methyl-benzooxazol-6-yl)-methanol. lH-NMR (CDCls) : õ 2.64 (s, 3H), 4.82 (s, 2H), 7.29 (d, 1H, J=8 Hz), 7. 53 (s, 1H), 7.62 (d, 1H, J=8 Hz). LC MS (m/e) = 164.2 (MH+).
58%		To the solution of <strong>[136663-23-5]2-methyl-benzooxazole-6-carboxylic acid methyl ester</strong> (25 g, 0.13 mol) in THF (500 mL) at -20 0C was added a solution of lithium aluminum hydride (4.81 g, 130 mL of 1 M solution in THF, 0.13 mmol, 1 eq) and the reaction mixture was allowed to warm up to the room temperature overnight. Water (5 mL) followed by 1 M NaOH solution (5 mL) followed by water (15 mL) was added and the reaction mixture was stirred for 15 min at the room temperature. The suspension was filtered, liquid evaporated and purified by column chromatography (1 :3 ethyl acetate: dichloromethane) to give 12.5 g (58 % yield) of pure (2-methyl- benzooxazol-6-yl)-methanol. 1H-NMR (CDCI3): P2.64 (s, 3H), 4.82 (s, 2H), 7.29 (d, 1 H, J=8 Hz), 7.53 (s, 1 H), 7.62 (d, 1 H, J=8 Hz). LC MS (m/e) = 164.2 (MH+). Rt = 1.03 min.

Reference： [1]Patent: WO2005/82901,2005,A1 .Location in patent: Page/Page column 33; 61
[2]Patent: WO2007/103755,2007,A2 .Location in patent: Page/Page column 51; 83

2
[ 136663-40-6 ]
[ 864274-04-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With pyridinium chlorochromate; In dichloromethane; at 20.0℃; for 1h;	c) 2-Methvl-benzooxazole-6-carbaldehvde; To the solution (2-methyl-benzooxazol-6-yl)-methanol (12.5 g, 76 mmol) in dichloromethane (200 mL) was added pyridinium chlorochromate (20 g, 93 mmol, 1.2 eq) and the reaction mixture was stirred for 1 hour at the room temperature. Celite (10 g) was added followed by decolorizing carbon (2 g) and the reaction mixture was filtered after 15 min of stirring. After evaporation the crude product was purified column chromatography (1: 10 ethyl acetate : dichloromethane) of give 8.2 g (66 percent yield) of pure 2-methyl-benzooxazole-6-carbaldehyde. 1H-NMR (CDC13) : S 2. 73 (s, 3H), 7.79 (d, 1H, J=8. 1 Hz), 7. 88 (dd, 1H, J=8. 1 Hz, J'=1.2 Hz), 8. 03 (d, 1H, J=1. 2 Hz), 10.09 (s, 1H). LC MS (m/e) = 162.2 (MH+). Rt = 1.47 min.
66%	With pyridinium chlorochromate; In dichloromethane; at 20.0℃; for 1h;	To the solution (2-methyl-benzooxazol-6-yl)-methanol (12.5 g, 76 mmol) in dichloromethane (200 mL) was added pyridinium chlorochromate (20 g, 93 mmol, 1.2 eq) and the reaction mixture was stirred for 1 hour at the room temperature. Celite (10 g) was added followed by decolorizing carbon (2 g) and the reaction mixture was filtered after 15 min of stirring. After evaporation the crude product was purified column chromatography (1 :10 ethyl acetate: dichloromethane) of give 8.2 g (66 percent yield) of pure 2-methyl-benzooxazole-6-carbaldehyde. 1H-NMR (CDCI3): D2.73 (s, 3H), 7.79 (d, 1 H, J=8.1 Hz), 7.88 (dd, 1 H, J=8.1 Hz, J'=1.2 Hz), 8.03 (d, 1 H, J=1.2 Hz), 10.09 (s, 1 H). LC MS (m/e) = 162.2 (MH+). Rt = 1.47 min.

Reference： [1]Patent: WO2005/82901,2005,A1 .Location in patent: Page/Page column 33; 61-62
[2]Patent: WO2007/103755,2007,A2 .Location in patent: Page/Page column 81; 83

3
[ 136663-40-6 ]
[ 1224716-52-2 ]

Reference： [1]Patent: EP2351743,2011,A1

4
[ 136663-40-6 ]
[ 136663-55-3 ]