3-hydroxy-2,2-dimethylpropanenitrile

3-hydroxy-2,2-dimethylpropanenitrile Property

Boiling point:

86-87 °C(Press: 18 Torr)

Density 

0.971±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

13.75±0.10(Predicted)

Appearance

Colorless to off-white Solid-liquid mixture

Safety

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

3-hydroxy-2,2-dimethylpropanenitrile Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 3-hydroxy-2,2-dimethylpropionitrile from ethyl 2-cyano-2-methylpropionate was as follows: 1) Dissolve ethyl 2-cyano-2-methylpropionate (5.0 g, 35.4 mmol) in a solvent mixture of tetrahydrofuran (40 mL) and water (100 mL). 2) Sodium borohydride (4.47 g, 106 mmol) was added slowly and the reaction mixture was stirred at room temperature for 3 hours. 3) Upon completion of the reaction, 6N hydrochloric acid was slowly added to the mixture to quench the reaction. 4) The reaction mixture was extracted with ethyl acetate and the organic phases were combined. 5) The organic phase was washed with water, dried over anhydrous magnesium sulfate, filtered and passed through a small amount of silica gel column. 6) The filtrate was concentrated under pressure to give the title compound 3-hydroxy-2,2-dimethylpropionitrile (3.4 g, 97% yield) as an oil. The product was characterized by 1H-NMR (CDCl3): δ 1.36 (6H, s), 3.58 (2H, s).

References

[1] Patent: US2009/156582, 2009, A1. Location in patent: Page/Page column 35
[2] Patent: EP1847531, 2007, A1. Location in patent: Page/Page column 51
[3] Patent: EP1717238, 2006, A1. Location in patent: Page/Page column 61
[4] Patent: WO2017/48675, 2017, A1. Location in patent: Paragraph 0434
[5] Patent: CN106478651, 2017, A. Location in patent: Paragraph 0900; 0901; 0902