3-TERT-BUTYL-4-HYDROXYBENZONITRILE

3-TERT-BUTYL-4-HYDROXYBENZONITRILE Property

Boiling point:

293.5±28.0 °C(Predicted)

Density 

1.07±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

9.21±0.18(Predicted)

Appearance

Light brown to brown Solid

Safety

HS Code 

2926907090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-TERT-BUTYL-4-HYDROXYBENZONITRILE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 3-(tert-butyl)-4-hydroxybenzonitrile from 3-(tert-butyl)-4-hydroxybenzaldehyde is as follows: with reference to the synthesis of intermediate R10 3-(1,1-dimethylethyl)-4-hydroxybenzenecarbonitrile [1399], 3-(1,1-dimethylethyl)-4-hydroxybenzaldehyde (550 mg with reference to intermediate R9) was mixed with hydroxylamine hydrochloride (322 mg , 4.63 mmol) in 8.0 mL of acetic acid under reflux conditions for 1 hour. Upon completion of the reaction, the mixture was cooled to 0 °C and subsequently poured into ether (Et2O). The mixture was washed sequentially with water and 5% aqueous sodium hydroxide solution each. The aqueous phase was extracted twice with ether (Et2O), all organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and the solvent evaporated. The residue was ground with pentane to give 540 mg of 3-tert-butyl-4-hydroxybenzonitrile. The product was characterized by 1H-NMR (400 MHz, DMSO-d6): δ 10.92 (1H, broad single peak), 7.53-7.45 (2H, multiple peaks), 6.92 (1H, double peaks), 1.34 (9H, single peak); UPLC_ipqc analysis: retention time 1.03 min, mass spectrometry detected [M-H]-peak m/z 174.

References

[1] Patent: WO2011/69951, 2011, A1. Location in patent: Page/Page column 82-83
[2] Patent: WO2012/76877, 2012, A1. Location in patent: Page/Page column 226-227
[3] Patent: US2013/267510, 2013, A1. Location in patent: Paragraph 1399-1401