1-(2-amino-4-bromophenyl)ethanone

1-(2-amino-4-bromophenyl)ethanone Property

Melting point:

82-84℃

Boiling point:

322.9±27.0 °C(Predicted)

Density 

1.535

storage temp. 

2-8°C(protect from light)

pka

1.23±0.10(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C8H8BrNO/c1-5(11)7-3-2-6(9)4-8(7)10/h2-4H,10H2,1H3

InChIKey

RCGAXUAOILUCAA-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(Br)C=C1N)C

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-(2-amino-4-bromophenyl)ethanone Chemical Properties,Usage,Production

Synthesis

Step A Preparation of 1-(2-amino-4-bromophenyl)ethanone (162a): 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) were dissolved in anhydrous toluene (120 mL) under argon protection and cooled in an ice bath. The above solution was added dropwise to a hexane solution (200 mL) of boron trichloride (23.4 g, 200 mmol) over 2.5 hours. After dropwise addition, aluminum chloride (26.6 g, 200 mmol) was added in batches over 30 minutes. The reaction mixture was gradually warmed to room temperature and subsequently heated to reflux for 16 hours. Upon completion of the reaction, 3N HCl solution (100 mL) was slowly added dropwise to the reaction mixture with stirring at 10 °C. After the dropwise addition was completed, heating and refluxing was continued for 3.5 hours. The reaction mixture was cooled to room temperature and left to stratify. The aqueous layer was extracted with chloroform (3 x 250 mL). The organic layers were combined, dried with magnesium sulfate, filtered and the filtrate was concentrated to afford the target product 2'-amino-4'-bromoacetophenone 162a (9.58 g, 25% yield). The product was characterized by 1H NMR (CDCl3, 300 MHz): δ 7.54 (d, 1H, J = 8.8 Hz), 6.83 (d, 1H, J = 1.9 Hz), 6.75 (dd, 1H, J = 8.4, 1.8 Hz), 2.54 (s, 3H) ppm.

References

[1] Patent: US2003/166636, 2003, A1
[2] Patent: US2002/52360, 2002, A1
[3] Patent: US2002/137737, 2002, A1
[4] Patent: US6503902, 2003, B2
[5] Patent: US5061800, 1991, A