[ CAS No. 7467-35-8 ] {[proInfo.proName]}

Name: 7467-35-8|(1-Methyl-1H-benzo[d]imidazol-2-yl)methanol|95%
Brand: Ambeed
SKU: A822181
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COA NMR CNMR HPLC LC-MS

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CAS No. :	7467-35-8	MDL No. :	MFCD00464051
Formula :	C₉H₁₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SQRSIOZFPSFABI-UHFFFAOYSA-N
M.W :	162.19	Pubchem ID :	344177
Synonyms :

Safety of [ 7467-35-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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* 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 [ 7467-35-8 ]
Downstream synthetic route of [ 7467-35-8 ]

[ 7467-35-8 ] Synthesis Path-Upstream 1~1

1
[ 7467-35-8 ]
[ 3012-80-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4713 - 4726
[2] Monatshefte fur Chemie, 2016, vol. 147, # 12, p. 2209 - 2220
[3] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1272 - 1274
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1724 - 1730
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 933 - 936
[6] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 584 - 600
[7] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 608 - 621
[8] Molecules, 2016, vol. 21, # 11,

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Yield	Reaction Conditions	Operation in experiment
72%	With sodium hydroxide In ethanol; water at 0 - 5℃; for 0.5h;
72%	With potassium hydroxide In ethanol; water at 0 - 20℃; for 1.25h;	2.2.2. Synthesis of (1-methyl-1H-benzo[d]imidazol-2-yl)methanol (Hmbm) To 1.2 eq. (2.3 g, 0.041 mol) of KOH dissolved in a 50% (v/v) water-ethanol mixture (14 mL), 5.1 g (0.034 mol) of 1-(1H-benzimidazol-2-yl) methanol was added. The solution was cooled to 0 °C, and 5 mL of dimethyl sulfate was added dropwise over 30 min (the temperature of the mixture did not exceed 5 °C). The mixture was kept under stirring at 0 °C for 30 min and at room temperature for additional 15 min. The solid obtained was recovered by filtration and washed with water, giving the title compound as a white solid. It was purified by recrystallization from a mixture of CH3CN/EtOH. White solid; Yield: 4 g (72%); M.p. 122-124 °C; 1H NMR (250 MHz, CDCl3): δ 7.76-7.64 (m, 1H), 7.29-7.19 (m, 3H), 5.13 (OH, br s, 1H), 4.88 (CH2, s, 2H), 3.81 (N-CH3, s, 3H); FT-IR (4000-600 cm-1): 3450-2800, 1639, 1454, 1312, 1007, 860, 744, 567; UV-vis (MeOH) (λmax, nm (logε, M-1 cm-1): 280(5.35), 268(5.18), 244(5.14), 219(5.06).
48%	With sodium hydroxide In methanol; water at 100℃; for 10h;	General procedure for the preparation of N-methyl-2-hydroxymethylbenzimidazole derivatives (6a-c) General procedure: A mixture of 2-hydroxymethybenzimidazole derivatives (5ac,0.023 mol), dimethyl sulfate (2.37 ml, 0.025 mol), NaOH (1g,0.025 mol in 3 ml water) in methanol (15 ml) was refluxed for 10 h at 100 oC. The mixture was diluted with water (15 ml) and extracted with chloroform (3x30 ml). The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The precipitate formed was crystallized from water.

Yield	Reaction Conditions	Operation in experiment
100%	With dichlorosulfoxide In dichloromethane at 20℃;	13 Example 13; 2-Chloromethyl-1-methyl-1H-benzoimidazole; (1-Methyl-1H-benzoimidazol-2-yl)-methanol (330 mg, 2.03 mmol) was dissolved in dichloromethane (15 mL), thionyl chloride (1.5 mL) was added drop wise. The reaction mixture was stirred at room temperature for overnight. The solvent was then removed from the reaction mixture by concentration in vacuo. The residue was dried on vacuum pump. Yellow solid was obtained as product (520 mg, yield: quantity).1HNMR (300 MHz, CDCl3): (ppm) 7.98 (br, 1H), 7.86 (br, 1H), 7.72 (m, 2H), 5.32 (s, 2H), 4.15 (s, 3H)
94%	With dichlorosulfoxide In dichloromethane at 20℃; for 6h;
58.9%	With PS-triphenylphosphine resin In Carbon tetrachloride for 3h; Reflux;	49 2-chloromethyl-l -methyl- lH-benzoimidazole (Compound 49b)A suspension of Compound 49a (255 mg, 1.57 mmol) and PS-triphenylphosphine resin (loading 2.2 mmol/g) in CC14 (15 ml) was refluxed for 3 hours. The resin was filtered and washed and then the organic solvent was evaporated off in vacuo. The crude was used in the following step without any further purification. Yield: 58.9 %.MS: [M+H]+ = 181.3

50%	With dichlorosulfoxide In dichloromethane for 5h; Reflux;	General procedure for the preparation of N-methyl-2-chloromethylbenzimidazole derivatives (7a-c) General procedure: The mixture of appropriate N-methyl-2-hydroxymethylbenzimidazole derivatives (6a-c, 0.01 mol), thionyl chloride(0.1 mol) in 30 ml dichloromethane were heated to reflux and stirred for 5 hours. The solvent was evaporated, and the residue was subsequently used without further purification.
36%	In dichlorosulfoxide	42 Example 42 A solution of 2-hydroxymethyl-1-methylbenzimidazole (1.1 g, 6.7 mmol) in thionyl chloride (10 ml) was stirred at ambient temperature for 15 minutes and then heated at reflux for 15 minutes. The volatiles were removed by evaporation and the residue purified by column chromatography eluding with methylene chloride/methanol (95/5) to give 2-chloromethyl-1-methylbenzimidazole (506 mg, 36%). 1 H NMR Spectrum: (DMSOd6; CF3 COOD) 4.07(s, 3H); 5.38(s, 2H); 7.6-7.7(m, 2H); 7.9(d, 1H); 8.05(dd, 1H) MS-ESI: 181 [MH]+
36%	Stage #1: (1-methyl-1H-benzimidazol-2-yl)methanol With dichlorosulfoxide at 20℃; for 0.25h; Stage #2: for 0.25h; Heating / reflux;
	With dichlorosulfoxide
255 mg	With dichlorosulfoxide In dichloromethane for 3h;
	With dichlorosulfoxide

Yield	Reaction Conditions	Operation in experiment
45%	With sulfuric acid; silver nitrate In methanol; water for 3h; Heating;
45%	With paraformaldehyde In methanol; dichloromethane	42 Example 42 The starting material was prepared as follows: A solution of 1 -methylbenzimidazole (2.5 g, 19 mmol), (J. Chem. Soc. 1929, 2820-2828), and paraformaldehyde (2 g) was heated at 165° C. for 30 minutes. Further paraformaldehyde (1 g) was added and heating continued for 2 hours. The mixture was allowed to cool and was purified by column chromatography eluding with methylene chloride, followed by methylene chloride/methanol (95/5) to give 2-hydroxymethyl-1-methylbenzimidazole (1.34 g, 45%). 1 H NMR Spectrum: (DMSOd6) 3.84(s, 3H); 4.73(s, 2H); 5.57(br s, 1H); 7.19(t, 1H); 7.25(t, 1H); 7.54(d, 1H); 7.60(d, 1H) MS - ESI: 185 [MNa]+
	In formaldehyd; dichloromethane	81.a a a (1-Methyl-1H-benzimidazol-2-yl)methanol 1-Methylbenzimidazole (5.0 g, 0.038 mol) was stirred at reflux in 37 wt % aqueous formaldehyde (50 ml) for 24 h. The solution was allowed to cool to room temperature then basified with saturated sodium hydrogen carbonate solution and then extracted with. dichloromethane (3*50 ml). The combined organic layers were dried over magnesium sulfate and were concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluding with 2.5 to 10% methanol in dichloromethane. The resultant semi-solid was triturated with isohexane to yield a solid, which was then recrystallized from ethyl acetate/isohexane, yielding (1-methyl-1H-benzimidazol-2-yl)methanol as a white solid (0.71 g).

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[ 7467-35-8 ] Synthesis Path-Upstream 1~1

[ 7467-35-8 ] Synthesis Path-Downstream 1~51