4-Bromo-2,6-dimethylaniline

4-Bromo-2,6-dimethylaniline Property

Melting point:

48-51 °C (lit.)

Boiling point:

120°C 0,2mm

Density 

1.4423 (rough estimate)

refractive index 

1.5748 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Methanol

pka

3.60±0.10(Predicted)

form 

Liquid

color 

Clear yellow to orange to amber

BRN 

1936300

InChI

InChI=1S/C8H10BrN/c1-5-3-7(9)4-6(2)8(5)10/h3-4H,10H2,1-2H3

InChIKey

QGLAYJCJLHNIGJ-UHFFFAOYSA-N

SMILES

C1(N)=C(C)C=C(Br)C=C1C

CAS DataBase Reference

24596-19-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 4-bromo-2,6-dimethyl-(24596-19-8)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

38-43-36/37/38-20/21/22

Safety Statements 

36/37-36/37/39-26

RIDADR 

UN2811/6.1/III

WGK Germany 

3

F 

8-10-23

Hazard Note 

Harmful

HazardClass 

6.1

HS Code 

29214990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H335May cause respiratory irritation

H351Suspected of causing cancer

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

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

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

P308+P313IF exposed or concerned: Get medical advice/attention.

4-Bromo-2,6-dimethylaniline Chemical Properties,Usage,Production

Chemical Properties

brown crystals

Uses

4-Bromo-2,6-dimethylaniline has been used in the preparation of:

• 4-bromo-N-(1-(6-(1-isopropyl-1H-benzo[d]imidazol-2-yl)pyridin-2-yl)ethylidene)-2,6-dimethylbenzenamine
• N-(4-Bromo-2,6-dimethylphenyl)-5-trimethylammoniumsalicylaldimine chloride
• ethynyl-functionalized persistent perylene diimide-multichromophore

Reactions

4-Bromo-2,6-dimethylaniline has been shown to react with acid solutions to form hydrogen bromide gas and ammonium chloride crystals.

Synthesis

The general procedure for the synthesis of 4-bromo-2,6-dimethylaniline from 2,6-dimethylaniline was as follows: 1-methoxy-3,5-dimethylbenzene (100 mg, 0.73 mmol), N-bromosuccinimide (NBS, 260 mg, 1.46 mmol), and a stainless steel ball (5 mm in diameter) were placed in a 10 mL stainless steel grinding jar. The ball milling reaction was carried out and the reaction process was monitored by thin layer chromatography (TLC) and proton nuclear magnetic resonance (1H NMR). Upon completion of the reaction, the reaction mixture was transferred to 30 mL of ethyl acetate and cooled at 0°C. The filtrate (containing product) and precipitate (spent succinimide) were obtained by filtration through filter paper and separated. The filtrate was concentrated under vacuum to give 250 mg (85% yield) of 4-bromo-2,6-dimethylaniline (2b) as a colorless powder. To test the efficiency of the large-scale reaction, monobromination was carried out under the same conditions using 1.3 g of 1-methoxy-3,5-dimethylbenzene for 1 h. The product was isolated in 87% yield. During the reaction, the grinding equipment was suspended and a small amount of sample was removed from the reaction tank for TLC and 1H NMR analysis, after which the reaction was continued, and the time of this operation was not included in the total reaction time.

References

[1] Tetrahedron Letters, 2005, vol. 46, # 51, p. 8959 - 8963
[2] Tetrahedron Letters, 2009, vol. 50, # 9, p. 1007 - 1009
[3] Synthetic Communications, 2010, vol. 40, # 5, p. 647 - 653
[4] Synthetic Communications, 2009, vol. 39, # 23, p. 4212 - 4220
[5] Journal fuer Praktische Chemie (Leipzig), 1988, vol. 330, # 2, p. 161 - 174