4-Bromo-3-methylaniline Chemical Properties

Melting point:

80-82 °C (lit.)

Boiling point:

240 °C (lit.)

Density 

1.4700 (rough estimate)

refractive index 

1.6190 (estimate)

Flash point:

239-241°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Powder

pka

4.02±0.10(Predicted)

color 

Off-white to beige to light brown

BRN 

2689600

InChI

InChI=1S/C7H8BrN/c1-5-4-6(9)2-3-7(5)8/h2-4H,9H2,1H3

InChIKey

MMEGELSFOYDPQW-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(Br)C(C)=C1

CAS DataBase Reference

6933-10-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 4-bromo-3-methyl-(6933-10-4)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38-33

Safety Statements 

26-37/39-24/25

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Harmful/Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

2921420090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromo-3-methylaniline Usage And Synthesis

Chemical Properties

grey to brownish crystalline powder

Uses

4-Bromo-3-methylaniline was used in the preparation of 1-(4-bromo-3-methylphenyl)pyrrolidin-2-one.

Synthesis

General procedure for the synthesis of 4-bromo-3-methylaniline from 2-bromo-5-nitrotoluene: First, N-(4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-methylphenyl)methanesulfonamide (4-bromo-3-methylphenyl)amine was prepared. Subsequently, activated Raney nickel (0.4 g) was added to a suspension of 1-bromo-2-methyl-4-nitrobenzene (4 g, 18.51 mmol) in 200 mL of methanol. The mixture was stirred under hydrogen atmosphere (30 psi) for 3 hours. Upon completion of the reaction, the reaction mixture was filtered through Celite, the solvent was removed under reduced pressure and the residue was dried under vacuum to afford 4-bromo-3-methylaniline (3.4 g, 99% yield) as a white solid.1H-NMR data (CDCl3): δ 2.28 (s, 3H), 3.39 (brs, 2H), 6.38 (d, J = 8Hz, 1H), and 6.55 (s, 1H), 7.27 (d, J = 8Hz, 1H).

References

[1] Patent: WO2008/17461, 2008, A1. Location in patent: Page/Page column 60
[2] Synthesis, 2001, # 1, p. 81 - 84
[3] Tetrahedron Letters, 2011, vol. 52, # 49, p. 6652 - 6654
[4] Tetrahedron Letters, 2000, vol. 41, # 2, p. 175 - 177
[5] Chemische Berichte, 1880, vol. 13, p. 963

4-Bromo-3-methylaniline(6933-10-4)Related Product Information

• o-Toluidine
• 2-Bromoaniline
• N-Methylaniline
• 3,3',5,5'-Tetramethylbenzidine dihydrochloride
• 3-Bromoanisole
• m-Toluidine
• Toluidine Blue O
• 4-Bromoaniline
• p-Toluidine
• N,N-Dimethyl-1,4-phenylenediamine
• N,N-Dimethylaniline
• 2-BROMO-5-NITROTOLUENE
• 4-Bromo-3-(trifluoromethyl)aniline
• 1-AMINO-4-BROMO-2-METHYLANTHRAQUINONE
• 1-Methylamino-4-bromo anthraquinone
• 1-Amino-2,4-dibromoanthraquinone
• 6-bromo-3-methyl-3H-dibenz[f,ij]isoquinoline-2,7-dione
• Bromine