1-(4-amino-3-fluorophenyl)ethan-1-one

1-(4-amino-3-fluorophenyl)ethan-1-one Property

Melting point:

86-88℃

Boiling point:

286℃

Density 

1.201

Flash point:

127℃

storage temp. 

2-8°C(protect from light)

pka

0.77±0.10(Predicted)

Appearance

Light yellow to brown Solid

Safety

HS Code 

2914790090

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..…

1-(4-amino-3-fluorophenyl)ethan-1-one Chemical Properties,Usage,Production

Uses

1-(4-Amino-3-fluorophenyl)ethanone can be used as a starting material in the preparation of 2-Amino-5-[(cyclopentylamino)acetyl]-3-fluoro-benzonitrile.

Synthesis

Example 7: Synthesis of (R)-N-(4-{1-[3-(4-tert-butyl-benzyl)-ureido]-ethyl}-2-fluoro-6-vinyl-phenyl)-methanesulfonamide; Step i: Preparation of 1-(4-amino-3-fluorophenyl)ethanone. In a 25 mL two-necked round-bottomed flask, filled with argon protection, a DMF solution of 2-fluoro-4-iodoaniline (1500 mg, 6.33 mmol) was added. Palladium(II) acetate (42.62 mg, 0.19 mmol), 1,3-bis(diphenylphosphino)propane (156.65 mg, 0.38 mmol, 0.06 equiv.), thallium(I) acetate (1834.19 mg, 6.96 mmol), and butyl vinyl ether (1.64 mL, 12.66 mmol, 2 equiv.) were then added sequentially. The reaction mixture was heated and stirred for 15 hours. After the reaction was completed, the mixture was poured into THF and 10% HCl solution was added slowly. The reaction mixture was extracted with ethyl acetate (300 mL x 3) and the organic phases were combined and washed sequentially with water and brine. The organic layer was dried with anhydrous Na2SO4, filtered and purified by column chromatography (n-hexane: ethyl acetate=3:1) to give a light yellow solid product (343.0 mg, yield 35.40%). Melting point: 77-79°C; IR (KBr pressed sheet, cm^-1): 3373, 3326, 1663, 1296; 1H NMR (400 MHz, CDCl3): δ 7.53 (m, 2H), 6.69 (m, 1H), 3.41 (s, 2H), 2.43 (s, 3H).

References

[1] Patent: WO2006/101318, 2006, A1. Location in patent: Page/Page column 44; 83-84
[2] Patent: EP1862454, 2007, A1. Location in patent: Page/Page column 6; 18