N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide Chemical Properties

Melting point:

137-139 °C

Boiling point:

395.5±42.0 °C(Predicted)

Density 

1.28

storage temp. 

2-8°C

solubility 

Acetonitrile (Slightly), Chloroform (Slightly)

pka

12.19±0.70(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Light Sensitive

InChI

InChI=1S/C12H9F3N2O/c1-7(2)11(18)17-9-4-3-8(6-16)10(5-9)12(13,14)15/h3-5H,1H2,2H3,(H,17,18)

InChIKey

HHWDZLSGDDXUSM-UHFFFAOYSA-N

SMILES

C(NC1=CC=C(C#N)C(C(F)(F)F)=C1)(=O)C(C)=C

Safety Information

RIDADR 

3077

HS Code 

2926.90.5050

HazardClass 

9

PackingGroup 

III

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide Usage And Synthesis

Uses

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide was used to prepare and observe selective androgen receptor modulator activity.

Synthesis

Methacryloyl chloride (2.63 mL, 27.16 mmol) was slowly added dropwise to a stirred N,N-dimethylacetamide (14 mL) solution of 4-amino-2-trifluoromethylbenzonitrile (3.4 mmol) under nitrogen protection for a controlled time period of 10 min and the reaction was carried out at room temperature. The progress of the reaction was monitored by TLC for 3 h or overnight (o.n.). Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (100 mL) and washed sequentially with saturated aqueous sodium bicarbonate solution (3 x 25 mL) and cold brine (4 x 50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography to afford N-(4-cyano-3-trifluoromethylphenyl)methacrylamide in white solid form in 95% yield. The structure of the product was confirmed by 1H-NMR (CDCl3): δ 8.06 (d, J = 2.0 Hz, 1H), 7.99 (dd, J = 8.5 Hz, 2.0 Hz, 1H), 7.87 (bs, 1H), 7.82 (d, J = 8.5 Hz, 1H), 5.90-5.88 (m, 1H), 5.63-5.61 (m, 1H). 2.11-2.10 (m, 3H).

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 118, p. 230 - 243
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 1028 - 1040
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 13, p. 4020 - 4031
[4] Journal of Medicinal Chemistry, 1988, vol. 31, # 5, p. 954 - 959
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 16, p. 3857 - 3869

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide(90357-53-2)Related Product Information

• Methacrylamide
• Basic Violet 1
• Acrylamide
• Phenylhydrazine
• 2,2-Dibromo-2-cyanoacetamide
• N-Isopropylacrylamide
• POLY(N-ISOPROPYL ACRYLAMIDE)
• Acetonitrile
• Methyl acrylate
• N-Methylolacrylamide
• N,N'-Methylenebisacrylamide
• PHENYL VALERATE
• Methylparaben
• Kresoxim-methyl
• Methanol
• 4-Amino-2-(trifluoromethyl)benzonitrile
• Methyl
• Desfluoro Bicalutamide