[ CAS No. 20034-02-0 ] {[proInfo.proName]}

Name: 20034-02-0|(6-Methyl-1H-benzo[d]imidazol-2-yl)methanol|98%
Brand: Ambeed
SKU: A176136
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Quality Control of [ 20034-02-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 20034-02-0 ]

CAS No. :	20034-02-0	MDL No. :	MFCD01874328
Formula :	C₉H₁₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GUVUEQHXSSOYNR-UHFFFAOYSA-N
M.W :	162.19	Pubchem ID :	679482
Synonyms :

Calculated chemistry of [ 20034-02-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	47.19
TPSA :	48.91 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) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.45
Log Po/w (XLOGP3) :	1.0
Log Po/w (WLOGP) :	1.21
Log Po/w (MLOGP) :	0.75
Log Po/w (SILICOS-IT) :	2.3
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.96
Solubility :	1.76 mg/ml ; 0.0109 mol/l
Class :	Very soluble
Log S (Ali) :	-1.62
Solubility :	3.93 mg/ml ; 0.0242 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.12
Solubility :	0.124 mg/ml ; 0.000764 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.56

Safety of [ 20034-02-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 20034-02-0 ]

* 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 [ 20034-02-0 ]
Downstream synthetic route of [ 20034-02-0 ]

[ 20034-02-0 ] Synthesis Path-Upstream 1~1

1
[ 79-14-1 ]
[ 496-72-0 ]
[ 20034-02-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride In water for 3 h; Reflux	(5-Methyl-1H-benzimidazole-2-yl)-methanol 25 was prepared using the Phillips procedure [1], 4-Methyl-1,2-phenylenediamine (12.22 g; 0.1 mol) and glycolic acid (11.40 g; 0.15 mmol) in hydrochloric acid (50 ml, 5.5 M) were heated under reflux with for 3 h. The reaction mixture was cooled to room temperature and ammonia solution was added and the mixture cooled in ice until a bright brown precipitate formed. The resulting solid was recrystallised from aqueous ethanol to give (5-methyl-1H-benzimidazole-2-yl)-methanol as a pale creamy powdery solid Yield 100percent.
72%	at 130℃; for 3 h;	General procedure: To a mixture of 1a–1c (10 mmol) with glycolic acid (2.28 g, 30 mmol) was added concentrated H3PO4(20 mL). The reaction mixture was refluxed at 130°C for 3 h, then quenched with 20percent NaOH. The respective solid product was collected by filtration.
70%	at 150℃; for 3 h;	Step 1 The mixture of 4-methyl-benzene-1,2-diamine (500 mg, 4.10 mmol) and hydroxy-acetic acid (374 mg, 4.92 mmol) was heated to 150° C. with stirring for 3 hrs. After cooled to room temperature, the reactant was purified by silica gel column (DCM/MeOH=30/1) to afford (5-methyl-1H-benzoimidazol-2-yl)-methanol (400 mg, yield: 70percent) as a yellow solid.

Reference： [1] Molecules, 2015, vol. 20, # 8, p. 15206 - 15223
[2] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1272 - 1274
[3] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 3006 - 3016
[4] Patent: US2018/44324, 2018, A1, . Location in patent: Paragraph 0614
[5] Chemische Berichte, 1912, vol. 45, p. 3495
[6] Journal of the American Chemical Society, 1957, vol. 79, p. 4391,4393
[7] Journal of the Chemical Society, 1950, p. 1600,1602
[8] Biochemische Zeitschrift, 1955, vol. 327, p. 422,447
[9] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 933 - 936
[10] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 584 - 600

[ 20034-02-0 ] Synthesis Path-Downstream 1~30

1
[ 79-14-1 ]
[ 496-72-0 ]
[ 20034-02-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; In water; for 3h;Reflux;	(5-Methyl-1H-benzimidazole-2-yl)-methanol 25 was prepared using the Phillips procedure [1], 4-Methyl-1,2-phenylenediamine (12.22 g; 0.1 mol) and glycolic acid (11.40 g; 0.15 mmol) in hydrochloric acid (50 ml, 5.5 M) were heated under reflux with for 3 h. The reaction mixture was cooled to room temperature and ammonia solution was added and the mixture cooled in ice until a bright brown precipitate formed. The resulting solid was recrystallised from aqueous ethanol to give (5-methyl-1H-benzimidazole-2-yl)-methanol as a pale creamy powdery solid Yield 100%.
72%	With phosphoric acid; at 130℃; for 3h;	General procedure: To a mixture of 1a-1c (10 mmol) with glycolic acid (2.28 g, 30 mmol) was added concentrated H3PO4(20 mL). The reaction mixture was refluxed at 130C for 3 h, then quenched with 20% NaOH. The respective solid product was collected by filtration.
70%	at 150℃; for 3h;	Step 1 The mixture of 4-methyl-benzene-1,2-diamine (500 mg, 4.10 mmol) and hydroxy-acetic acid (374 mg, 4.92 mmol) was heated to 150 C. with stirring for 3 hrs. After cooled to room temperature, the reactant was purified by silica gel column (DCM/MeOH=30/1) to afford (5-methyl-1H-benzoimidazol-2-yl)-methanol (400 mg, yield: 70%) as a yellow solid.

Reference： [1]Molecules,2015,vol. 20,p. 15206 - 15223
[2]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1272 - 1274
[3]Russian Journal of General Chemistry,2017,vol. 87,p. 3006 - 3016
[4]Patent: US2018/44324,2018,A1 .Location in patent: Paragraph 0614
[5]Chemische Berichte,1912,vol. 45,p. 3495
[6]Journal of the American Chemical Society,1957,vol. 79,p. 4391,4393
[7]Journal of the Chemical Society,1950,p. 1600,1602
[8]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 933 - 936
[9]European Journal of Medicinal Chemistry,2016,vol. 122,p. 584 - 600

2
[ 20034-02-0 ]
[ 1357162-26-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 933 - 936

3
[ 20034-02-0 ]
[ 1357162-35-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 933 - 936

4
[ 20034-02-0 ]
[ 37735-10-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 933 - 936

5
[ 20034-02-0 ]
[ 74-88-4 ]
[ 68426-72-2 ]

Yield	Reaction Conditions	Operation in experiment
46%		N-Methyl-2-methanol-5-methylbenzimidazole 48 was prepared according to using the procedure by Harisha et al. [28]. A solution of 5-methyl-(1H-benzimidazole-2-yl)-methanol 25 (1.62 g, 0.01 mol), and sodium hydroxide (0.40 g, 0.01 mol) were stirred in dry acetone (30 mL) was stirred for 30 min. Then, iodomethane (1.41 g, 0.01 mol) was added to the mixture and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50% HCl to neutralize the excess potassium carbonate. Then, wash the solid with cold water (100 mL) and then aqueous ethanol. The product was purified by column chromatography (9:1 chloroform/ethanol) to give the desired product (FAS37) as a brown powder Yield 46%.

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1272 - 1274
[2]Molecules,2015,vol. 20,p. 15206 - 15223
[3]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 933 - 936

6
[ 20034-02-0 ]
C₂₂H₂₂N₂O₂ [ No CAS ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1272 - 1274

7
[ 20034-02-0 ]
C₂₁H₂₀N₂O₃ [ No CAS ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1272 - 1274

8
[ 20034-02-0 ]
[ 80567-68-6 ]

Reference： [1]Molecules,2015,vol. 20,p. 15206 - 15223

9
[ 20034-02-0 ]
[ 99459-47-9 ]