2-AMINO-5-BROMO-4-TRIFLUOROMETHYLPYRIDINE

2-AMINO-5-BROMO-4-TRIFLUOROMETHYLPYRIDINE Property

Melting point:

71-74℃

Boiling point:

243.9±40.0 °C(Predicted)

Density 

1.790±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

soluble in Methanol

form 

Solid

pka

2.44±0.24(Predicted)

color 

Pale yellow to orange

InChI

InChI=1S/C6H4BrF3N2/c7-4-2-12-5(11)1-3(4)6(8,9)10/h1-2H,(H2,11,12)

InChIKey

AEWYLVDLWQPJGW-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C(C(F)(F)F)=C1

CAS DataBase Reference

944401-56-3

Safety

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-36-22

Safety Statements 

22-24/25-26-36/37/39

WGK Germany 

1

HazardClass 

IRRITANT

HS Code 

29333999

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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

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

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

P337+P313IF eye irritation persists: Get medical advice/attention.

2-AMINO-5-BROMO-4-TRIFLUOROMETHYLPYRIDINE Chemical Properties,Usage,Production

Uses

5-Bromo-4-(trifluoromethyl)pyridine-2-amine can be used as a pharmaceutical synthesis intermediate.

Synthesis

Step 1: Synthesis of 5-bromo-4-(trifluoromethyl)pyridin-2-amine To a stirred solution of 4-(trifluoromethyl)pyridin-2-amine (2.5 g, 15.42 mmol) in dichloromethane (250 mL) was added N-bromosuccinimide (2.74 g, 15.42 mmol) in batches. The reaction was carried out at room temperature and under light protection with continuous stirring for 6 hours. After completion of the reaction, the reaction mixture was diluted with 1N NaOH solution (20 mL) and extracted with dichloromethane (2 x 100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (3.2 g, 86% yield). 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 6.77 (s, 1H), 4.73 (brs, 2H). ESI-MS: Calculated: 239.95; Measured: 239.10 [M-H]?

References

[1] Patent: WO2017/219800, 2017, A1. Location in patent: Paragraph 00209; 00210
[2] Patent: CN105461714, 2016, A. Location in patent: Paragraph 0367; 0368; 0369
[3] Patent: CN103483345, 2016, B. Location in patent: Paragraph 0131-0134
[4] Patent: CN103694218, 2016, B. Location in patent: Paragraph 0093-0096
[5] Patent: WO2014/169167, 2014, A1. Location in patent: Page/Page column 56