2-BROMO-N,N-DIMETHYLANILINE Chemical Properties

Boiling point:

108°C 14mm

Density 

1.388

refractive index 

1.5745

Flash point:

108°C/14mm

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

pka

4.40±0.18(Predicted)

color 

Colorless to Light orange to Yellow

BRN 

2205741

InChI

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

InChIKey

ONMSBNJJCUCYED-UHFFFAOYSA-N

SMILES

C1(N(C)C)=CC=CC=C1Br

CAS DataBase Reference

698-00-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,T

Risk Statements 

36/37/38-42/43-50/53-40-36-33-23/24/25

Safety Statements 

26-36-61-60-36/37

RIDADR 

2810

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29214990

MSDS

• Language:English Provider:ALFA

2-BROMO-N,N-DIMETHYLANILINE Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

2-Bromo-N,N-dimethylaniline may be used in the synthesis of the following:

• bis[(2-dimethylamino)phenyl]amine via a multi-step reaction procedure
• 2-(N,N-dimethylaminophenyl)-bis(diethylamino)phosphine
• 6-[2-(dimethylamino)phenyl]-2,2-bipyridine obtained via lithiation followed by reaction with 2,2-bipyridine
• 1-(2′-(dimethylamino)phenyl)-2-diphenylphosphino-3-methylimidazolium trifluoromethanesulfonate via a multi-step reaction procedure

Uses

suzuki reaction

Synthesis

In a 250 mL round bottom flask, 4.0 g (23.3 mmol) of o-bromoaniline, 16.1 g (116.5 mmol) of anhydrous potassium carbonate, 7.3 mL (116.5 mmol) of iodomethane, and 50 mL of acetonitrile were added sequentially. The reaction mixture was heated to 70 °C and stirred at this temperature for 18 hours. Upon completion of the reaction, the mixture was cooled to room temperature. Subsequently, extraction was carried out with 100 mL of deionized water and 100 mL of diethyl ether. After separation of the organic phase, the aqueous phase was further washed with 3 x 50 mL of ether. All organic phases were combined and washed with 5 x 50 mL saturated saline. The organic phase was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the volatile solvent to obtain the crude product. The crude product was purified by silica gel column chromatography with the eluent of ether/hexane (5/95 v/v), resulting in 2.7 g of light yellow oily liquid product in 69% yield. The characterization data of the obtained product were consistent with those reported in the literature.

References

[1] Organic Letters, 2009, vol. 11, # 22, p. 5130 - 5133
[2] Organic Letters, 2014, vol. 16, # 14, p. 3832 - 3835
[3] Journal of Organic Chemistry, 2008, vol. 73, # 16, p. 6330 - 6340
[4] Patent: CN108586536, 2018, A. Location in patent: Paragraph 0011-0012; 0034-0036; 0038
[5] Chemische Berichte, 1907, vol. 40, p. 2528

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