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Home > Encyclopedia > 1H-Imidazole-2-methanol

1H-Imidazole-2-methanol

1H-Imidazole-2-methanol structure

1H-Imidazole-2-methanol 

structure
  • CAS No:

    3724-26-3

  • Formula:

    C4H6N2O

  • Chemical Name:

    1H-Imidazole-2-methanol

  • Synonyms:

    1H-Imidazole-2-methanol;Imidazole-2-methanol;2-(Hydroxymethyl)imidazole;1H-Imidazol-2-ylmethanol;2-Hydroxymethyl-1H-imidazole

  • Categories:

    Chemical Reagents  >  Organic Reagents

1H-Imidazole-2-methanol Basic Attributes

98.1

98.10

DTXSID30340729

2933290090

Characteristics

48.9

-0.8

1.3±0.1 g/cm3

>160 °C (decomp) @ Solvent: Methanol, Water

388.1°C at 760 mmHg

188.5±23.2 °C

1.590

Safety Information

37/38-41

26-39

Xi

|Warning|H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

1H-Imidazole-2-methanol Use and Manufacturing

To a solution of compound 1 H-imidazole-2-carbaldehyde (5g, 52.08 mmol) in MeOH (50 mL) was added sodium borohydride (3.93g, 104.16 mmol) portion-wise, at 5 00, and the reaction mixture was allowed to stir at RT for 3h. The reaction mixture was quenched with brine (25 mL) and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 10percent MeOH/CHCI3) to obtain (1H-imidazol-2-yl)-methanol as a pale yellow solid (4g, 78percent).R:0.1 (10percent MeOH/CHCI3).1H NMR (400MHz, CD3OD): O 6.97 (5, 2H), 4.61 (5, 2H).To a solution of 2-imidazolecarboxyaldehyde (18-1) (1.92 g, 20 mmol, 1.0 eq.) was suspended in methanol (30 ml), NaBHCompound 26-2 (0449) To a solution of 2-imidazolecarboxyaldehyde (26-1) (1.92 g, 20 mmol, 1.0 eq) was suspended in methanol (30 mL), NaBHPart A To a solution of compound 1 H-imidazole-2-carbaldehyde (5g, 52.08 mmol) in MeOH (50 mL) was added sodium borohydride (3.93g, 104.16 mmol) portion-wise, at 5 00, and the reaction mixture was allowed to stir at RT for 3h. The reaction mixture was quenched with brine (25 mL) and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 10percent MeOH/CHCI3) to obtain (1H-imidazol-2-yl)-methanol as a pale yellow solid (4g, 78percent).R:0.1 (10percent MeOH/CHCI3).1H NMR (400MHz, CD3OD): O 6.97 (5, 2H), 4.61 (5, 2H).To a solution of 2-imidazolecarboxyaldehyde (18-1) (1.92 g, 20 mmol, 1.0 eq.) was suspended in methanol (30 ml), NaBHCompound 26-2 (0449) To a solution of 2-imidazolecarboxyaldehyde (26-1) (1.92 g, 20 mmol, 1.0 eq) was suspended in methanol (30 mL), NaBHPart A To a solution of compound 1 H-imidazole-2-carbaldehyde (5g, 52.08 mmol) in MeOH (50 mL) was added sodium borohydride (3.93g, 104.16 mmol) portion-wise, at 5 00, and the reaction mixture was allowed to stir at RT for 3h. The reaction mixture was quenched with brine (25 mL) and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 10% MeOH/CHCI3) to obtain To a solution of Compound 26-2 (0449) To a solution of Part A Preparation To a solution of A mixture of 2-hydroxymethyl-imidazole from step 4 (150 mg, 0.4 mmol), OXONE(450 mg, excess), water (2 ml), methanol (5 ml) and tetrahydrofuran (3 ml) was stirred at 25 C. for 2 hours. The reaction mixture was diluted with water (20 ml) and extracted with methylene chloride. After removal of solvent, the crude material was recrystallized from toluene to give 80 mg (70%) of 4-(4-fluorophenyl)-2-hydroxymethyl-5-(4-methylsulfonylphenyl)-1H-imidazole: m.p. 115-117 C. Anal. Calc'd. for C17 H18 N2 O3 FS*H2 O: C, 56.03; 4.70; N, 7.69; S, 8.80. Found: C, 56.02; H, 4.64; N, 7.45; S, 8.90.A mixture of To a solution of

Computed Properties

Molecular Weight:98.10
XLogP3:-0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:98.048012819
Monoisotopic Mass:98.048012819
Topological Polar Surface Area:48.9
Heavy Atom Count:7
Complexity:57.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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