1H-Benzotriazole-1-methanol

Uses

Catalyst for:

• Hydrolysis of phenyl esters of a-furoic acid

Used as:

• Corrosion inhibitor of iron in aerated acidic media
• Reactive oxygen scavenger

Reactant for:

• Synthesis of hydroxy-skipped bis-homo-inositols as potential glycosidase inhibitors via Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation
• Enantioselective synthesis of aplysin utilizing a palladium-catalyzed addition of an arylboronic acid to an allenic alcohol, followed by Eschenmoser/Claisen rearrangement
• Synthesis of substituted dihydroquinoline carboxylic acids as antitumor and HIV-1 integrase inhibitors
• Gosteli-Claisen rearrangement

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Example 30 Synthesis of 1H-benzotriazole-1-methanol: 10 g (83.94 mmol) of 1H-benzotriazole was dissolved in 6.81 mL (83.94 mmol) of 37% formaldehyde aqueous solution. The temperature of the mixture was adjusted to 25°C under stirring. After 5 minutes of reaction, the mixture was cured. Subsequently, the reaction mixture was cooled to room temperature, filtered and washed with ether. The resulting solid was ground in cold tetrahydrofuran and filtered again (Int.94). Product yield: 94%, melting point: 148-150°C (determined by recrystallization from tetrahydrofuran and ether).

References

[1] Patent: US2004/67998, 2004, A1. Location in patent: Page/Page column 24
[2] Journal of the American Chemical Society, 2017, vol. 139, # 27, p. 9281 - 9290
[3] Patent: CN102688233, 2016, B. Location in patent: Paragraph 0095; 0098
[4] Patent: CN106188103, 2016, A. Location in patent: Paragraph 0035; 0037
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 3868