2-Bromo-5-fluoroaniline Property

Melting point:

43-47 °C (lit.)

Boiling point:

154 °C / 23mmHg

Density 

1.694±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

1.52±0.10(Predicted)

color 

White to Light yellow to Dark green

InChI

InChI=1S/C6H5BrFN/c7-5-2-1-4(8)3-6(5)9/h1-3H,9H2

InChIKey

FWTXFEKVHSFTDQ-UHFFFAOYSA-N

SMILES

C1(N)=CC(F)=CC=C1Br

CAS DataBase Reference

1003-99-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,T

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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.

2-Bromo-5-fluoroaniline Chemical Properties,Usage,Production

Description

2-bromo-5-fluoroaniline: a intermediate of antitumor drug.
2-bromo-5-fluoroaniline is the intermediate of antitumor drug Phortress, phortress is the benzothiazoles CYP1A1 antitumor drugs targeting by Univ Nottingham UK invention, solution becomes lipophilic compound 5F2O3(10 in the sensitive cells but Phortress enters), the latter is as potential aromatic hydrocarbon receptor (AhR) agonist, induce CYP1A1 to express, CYP1A1 metabolism through expressing produces and has high electrophilic active substance again, finally causes DNA damage and apoptosis. The method that, at present, synthetic 2-bromo-5-fluoronitrobenzene prepares 2-bromo-5-fluoroaniline is divided into two large classes:
The one: adopt a chemical reduction method, utilizing the chemical reducing agent reductase 2-bromo-5-fluoronitrobenzenes such as protochloride glass putty, iron powder, vat powder, hydrazine, and sodium borohydride (potassium), which is 2-bromo-5-fluoroaniline.
The 2nd: adopt hydro-reduction. What we do more often both at home and abroad at present is chloride or the catalytic hydrogenation of fluorine-containing arylamine, and the brominated less report of arylamine hydrogenation mainly is easily by hydrogenolysis because of bromine.

Chemical Properties

Yellow to brown crystalline powder

Uses

2-Bromo-5-fluoroaniline may be used to synthesize:

• orthobromothiobenzanilide of 5-fluoronitrobenzothiazole
• 2-bromo-5-fluorobenzo[¹⁴C]nitrile
• [3-¹⁴C]-5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole
• 2-bromo-5-fluoro-phenyl)-(2-methoxy-6-pentadecyl-benzyl)amine

Synthesis

A preparation method of 2-Bromo-5-fluoroaniline is as follows: methanol, 2-bromo-5-fluoronitrobenzene, W-4 type Raney nickel and bromine inhibitor are put into a hydrogenation kettle to carry out hydrogenation reaction. After the reaction is completed, the reaction solution is filtered under nitrogen protection. The filtered filtrate is then distilled under reduced pressure to remove methanol, and n-hexane is added. Then, the product is washed with process water, and after washing, the product is allowed to stand and separate. Then, the organic phase is cooled and crystallized, an off-white to brownish-yellow solid is precipitated, and a wet product is obtained by suction filtration. The wet product is dried to obtain the finished product 2-Bromo-5-fluoroaniline.