2-Amino-5-thiazolemethanol
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2-Amino-5-thiazolemethanol
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CAS No:
131184-73-1
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Formula:
C4H6N2OS
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Chemical Name:
2-Amino-5-thiazolemethanol
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Synonyms:
5-Thiazolemethanol,2-amino-(9CI);5-Thiazolemethanol, 2-amino;(2-Amino-1,3-thiazol-5-yl)methanol;2-Amino-5-thiazolemethanol;5-(Hydroxymethyl)thiazol-2-ylamine;2-Amino-5-(hydroxymethyl)thiazole;(2-AMinothiazol-5-yl)Methanol;2-Amino-5-(hydroxymethyl)-1,3-thiazole
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CAS No:
Safety Information
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
H302
|Warning|H302 (100%): 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, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
2-Amino-5-thiazolemethanol Use and Manufacturing
2-Amino-5-formylthiazole (11.5 g, 90 mmol) was dissolved in methanol (120 mL), and sodium borohydride (5.11 g, 135 mmol) was added thereto while cooling with ice, followed by stirring at the same temperature for 1 hour. [00363] A suspension of ethyl 2-amino-1, 3-thiazole-5-carboxylate (1.72 g, 10 mmol) in anhydrous THF (100 mL) was cooled in an ice bath and treated with LiAIH4 (0.76 g, 20 mmol) portionwise, under nitrogen. The reaction mixture was warmed to room temperature and stirred for 90 minutes. After this time, additional LiAIH4 (0.76 g, 20 mmol) was added and thesuspension was heated to reflux for 45 minutes. After this time, the suspension was cooled in an ice bath and cautiously treated with ice chips, followed by concentrated aqueous ammonium hydroxide solution (10 mL) and stirred for 60 hours. The orange suspension was filtered through CeliteTM, washing with MeOH. The filtrate was evaporated under reduced pressure, adsorbed onto silica and purified by flash column chromatography, eluting with MeOH/DCM (5-10percent), with the desired fractions combined and concentrated under reduced pressure to afford the title compound (225 mg). LCMS method: Method 5, RT: 0.55 mm, Ml: 131 [M+1]2-Amino-5-formylthiazole (11.5 g, 90 mmol) was dissolved in methanol (120 mL), and sodium borohydride (5.11 g, 135 mmol) was added thereto while cooling with ice, followed by stirring at the same temperature for 1 hour. [00363] A suspension of ethyl 2-amino-1, 3-thiazole-5-carboxylate (1.72 g, 10 mmol) in anhydrous THF (100 mL) was cooled in an ice bath and treated with LiAIH4 (0.76 g, 20 mmol) portionwise, under nitrogen. The reaction mixture was warmed to room temperature and stirred for 90 minutes. After this time, additional LiAIH4 (0.76 g, 20 mmol) was added and thesuspension was heated to reflux for 45 minutes. After this time, the suspension was cooled in an ice bath and cautiously treated with ice chips, followed by concentrated aqueous ammonium hydroxide solution (10 mL) and stirred for 60 hours. The orange suspension was filtered through CeliteTM, washing with MeOH. The filtrate was evaporated under reduced pressure, adsorbed onto silica and purified by flash column chromatography, eluting with MeOH/DCM (5-10percent), with the desired fractions combined and concentrated under reduced pressure to afford the title compound (225 mg). LCMS method: Method 5, RT: 0.55 mm, Ml: 131 [M+1]
2-Amino-5-(hydroxymethyl)thiazole is a reactant used in the preparation of imino-quinone methide type intermediates.
Computed Properties
Molecular Weight:130.17
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:130.02008399
Monoisotopic Mass:130.02008399
Topological Polar Surface Area:87.4
Heavy Atom Count:8
Complexity:80.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
