[ CAS No. 20033-99-2 ] {[proInfo.proName]}

Name: 20033-99-2|2-(Hydroxymethyl)-5-methoxybenzimidazole|97%
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SKU: A806683
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Quality Control of [ 20033-99-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 20033-99-2 ]

CAS No. :	20033-99-2	MDL No. :	MFCD08059827
Formula :	C₉H₁₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VFKGGGIPGOQNRO-UHFFFAOYSA-N
M.W :	178.19	Pubchem ID :	819897
Synonyms :

Calculated chemistry of [ 20033-99-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.71
TPSA :	58.14 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) :	-6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.91
Log Po/w (XLOGP3) :	1.05
Log Po/w (WLOGP) :	0.91
Log Po/w (MLOGP) :	0.17
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	0.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.99
Solubility :	1.84 mg/ml ; 0.0103 mol/l
Class :	Very soluble
Log S (Ali) :	-1.86
Solubility :	2.45 mg/ml ; 0.0137 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.87
Solubility :	0.243 mg/ml ; 0.00136 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 20033-99-2 ]

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

Application In Synthesis of [ 20033-99-2 ]

* 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.

Downstream synthetic route of [ 20033-99-2 ]

[ 20033-99-2 ] Synthesis Path-Downstream 1~26

2
[ 20033-99-2 ]
[ 887572-60-3 ]

Yield	Reaction Conditions	Operation in experiment
		A suspension of (5-Methoxy-1H-benzimidazol-2-yl)methanol (preparation 1) (638 mg, 3.58 mmol) in 1N aqueous sodium hydroxide (0.95 ml) and water (40 ml) was heated to reflux and a solution of potassium permanganate (848 mg, 5.36 mmol) in water was added drop wise over a period of 30 minutes. The reaction mixture was refluxed for a further hour and then cooled to room temperature. The reaction mixture was acidified to pH4 by addition of acetic acid and the resulting solid filtered and dried in vacuo to give the title compound as a pale yellow solid (332 mg).

Reference： [1]Molecules,2015,vol. 20,p. 15206 - 15223
[2]Patent: US2006/111416,2006,A1 .Location in patent: Page/Page column 11

3
[ 79-14-1 ]
[ 102-51-2 ]
[ 20033-99-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; In water;Reflux;	(5-Methoxy-1H-benzimidazole-2-yl)-methanol 26 was prepared using the Phillips procedure [1], 4-Methoxy-1,2-phenylenediamine (0.7 g, 5 mmol) was heated under reflux temperature with glycolic acid (0.4 g, 5.25 mmol) in hydrochloric acid (15 mL, 5.5 M) for 6 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-methoxy-1H-benzimidazole-2-yl)-methanol as a bright brown solid Yield 100%.
		A solution of 4-methoxybenzene-1,2-diamine (1.13 g, 8.18 mmol) and hydroxyacetic acid (1.85 g, 24.5 mmol) in 6N hydrochloric acid (25 ml) was heated at reflux for 16 hours. The reaction mixture was cooled to room temperature and neutralised by addition of solid sodium hydroxide. The resulting precipitate was filtered off and dried in vacuo to give the title compound as a pale yellow solid (638 mg).

Reference： [1]Molecules,2015,vol. 20,p. 15206 - 15223
[2]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 1272 - 1274
[3]Patent: US2006/111416,2006,A1 .Location in patent: Page/Page column 11
[4]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 933 - 936
[5]MedChemComm,2018,vol. 9,p. 1194 - 1205

4
[ 20033-99-2 ]
[ 14625-40-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With thionyl chloride; In dichloromethane; at 10.0℃; for 3.0h;	Thionyl chloride (27.5 mmol, 2 mL) was added slowly to a solution of 5-methoxy-1H-benzimidazole-2-yl)-methanol) 26 (0.58 g, 3.31 mmol) in dichloromethane (10 mL) at 10 C, the mixture was stirred until no presence of the starting material. The solvent was then evaporated, and the residue was triturated with DCM, and suction filtered, then was washed with dichloromethane and ether. Yield 89% which 34 was recovered as a green powder.
	With thionyl chloride; In dichloromethane; at 20.0℃; for 2.0h;	Example 34: Synthesis of 2-chloromethyl-5-methoxy-lH-benzoimidazole 222[0265] 2-Chloromethyl-5-methoxy-l H-benzoimidazole 222 was synthesized in 1 step from (5- Methoxy-lH-benzoimidazol-2-yl)-methanol 221 as shown in Scheme 58.Scheme 58Step 1 - Preparation of2-chloromethyl-5-methoxy-lH-benzoimidazole (222): [0266] (5-Methoxy-lH-benzoimidazol-2-yl)-methanol (221, 0.5 g, 3 mmol) was combined with 30 mL dichloromethane. Thionyl chloride (0.51 mL, 7 mmol) was added and the reaction was stirred at room temperature for 2 hours. The reaction was concentrated. Ethyl acetate was added and washed with sodium bicarbonate saturated solution and brine. The organic portion was dried over anhydrous sodium sulfate, filtered through Celite and evaporated to dryness. The resulting desired compound was used without further purification. MS (ESI) : [M+lT] + == 197.2.

Reference： [1]Molecules,2015,vol. 20,p. 15206 - 15223
[2]Patent: WO2008/80001,2008,A2 .Location in patent: Page/Page column 110

5
[ 20033-99-2 ]
[ 1357162-24-3 ]

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

6
[ 20033-99-2 ]
[ 1357162-29-8 ]

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

7
[ 20033-99-2 ]
[ 1357162-32-3 ]

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

8
[ 20033-99-2 ]
[ 1357162-38-9 ]

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

9
[ 20033-99-2 ]
[ 1357162-41-4 ]

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

10
[ 20033-99-2 ]
[ 53004-19-6 ]

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

11
[ 20033-99-2 ]
[ 74-88-4 ]
[ 68426-83-5 ]

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

12
[ 20033-99-2 ]
C₂₂H₂₂N₂O₃ [ No CAS ]

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

13
[ 20033-99-2 ]
C₂₁H₂₀N₂O₃ [ No CAS ]

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

14
[ 20033-99-2 ]
C₂₂H₂₁NO₄ [ No CAS ]

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

15
[ 20033-99-2 ]
C₂₀H₁₈N₂O₄ [ No CAS ]

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

16
[ 1551-06-0 ]
[ 20033-99-2 ]
2-(bis(5-ethyl-1H-pyrrol-2-yl)methyl)-5-methoxy-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: (6-methoxy-1H-benzoimidazol-2-yl)methanol With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; Inert atmosphere; Stage #2: 2-ethyl-1H-pyrrole With trifluoroacetic acid In 1-methyl-pyrrolidin-2-one at 20℃; for 9h; Inert atmosphere;

Reference： [1]Patalag, Lukas J.; Jones, Peter G.; Werz, Daniel B. [Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13340 - 13344][Angew. Chem., 2016, vol. 128, # 42, p. 13534 - 13539,6]

17
[ 104-81-4 ]
[ 20033-99-2 ]
(5-methoxy-1-(4-methylbenzyl)-1H-benzo[d]imidazol-2-yl)methanol [ No CAS ]
(6-methoxy-1-(4-methylbenzyl)-1H-benzo[d]imidazol-2-yl)methanol [ No CAS ]