4-AMINO-2-METHOXY-BENZONITRILE

4-AMINO-2-METHOXY-BENZONITRILE Property

Melting point:

102℃

Boiling point:

351.2±27.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

1.30±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C8H8N2O/c1-11-8-4-7(10)3-2-6(8)5-9/h2-4H,10H2,1H3

InChIKey

KTDRJLRJAHBQDQ-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(N)C=C1OC

Safety

HS Code 

2926907090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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

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

P321Specific treatment (see … on this label).

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

P362Take off contaminated clothing and wash before reuse.

4-AMINO-2-METHOXY-BENZONITRILE Chemical Properties,Usage,Production

Synthesis

1. 2-Methoxy-4-nitrobenzonitrile (750 mg, 4.21 mmol) and palladium catalyst (50 mg, 0.47 mmol) were dissolved in methanol (15 mL) at room temperature. 2. The reaction system was subjected to a hydrogen atmosphere (1 atm) with continuous stirring for 48 h. 3. Upon completion of the reaction the palladium catalyst was removed by filtration. 4. The filtrate was concentrated under reduced pressure to give the brownish-red powdery product 4-amino-2-methoxybenzonitrile (679 mg, 4.58 mmol, quantitative yield). 5. The structure of the product was determined by 1H-anionic digestion. 6. The filtrate was concentrated under reduced pressure to give a brown-red powdery product, 4-amino-2-methoxybenzonitrile (679 mg, 4.58 mmol, quantitative yield). 5. The structure of the product was confirmed by 1H-NMR (300 MHz, DMSO-d6): δ 3.32 (3H, s), 6.05-6.29 (4H, m), 7.23 (1H, d, J = 8.3 Hz). ).

References

[1] Patent: EP2759533, 2014, A1. Location in patent: Paragraph 0484; 0485
[2] Synthesis, 2006, # 19, p. 3316 - 3340
[3] Chemistry - A European Journal, 2014, vol. 20, # 31, p. 9504 - 9509
[4] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[5] Patent: US2009/42967, 2009, A1. Location in patent: Page/Page column 22