2-BROMO-5-NITROTOLUENE Chemical Properties

Melting point:

78-80 °C(lit.)

Boiling point:

143 °C / 17mmHg

Density 

1.6841 (rough estimate)

refractive index 

1.6120 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

Light yellow to Amber to Dark green

BRN 

1940342

InChI

1S/C7H6BrNO2/c1-5-4-6(9(10)11)2-3-7(5)8/h2-4H,1H3

InChIKey

HIMGPQVBNICCGL-UHFFFAOYSA-N

SMILES

Cc1cc(ccc1Br)[N+]([O-])=O

CAS DataBase Reference

7149-70-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

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

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

II

HS Code 

29049090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

MSDS

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

2-BROMO-5-NITROTOLUENE Usage And Synthesis

Chemical Properties

LIGHT BROWN-ORANGE TO BROWN CRYST. POWDER

Uses

2-Bromo-5-nitrotoluene has been used in the synthesis of :

• 4′-amino-4-hydroxy-2′-methylbiphenyl
• 3′:4-dinitro-2-methyldiphenyl ether via condensation with potassium m-nitrophenoxide

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 8448, 1998 DOI: 10.1021/jo981557o

Synthesis

1 mol of o-bromotoluene, 20 g of dried acid saponin and isobutanol were added to a reactor equipped with a water separator, 1,2-dibromoethane was used as solvent, and concentrated nitric acid was added dropwise at 83 for 4 h at this temperature. The reaction was carried out at 83 for 4 h. The synergistic catalytic nitrification with acid saponite and isobutanol showed an increase in the ratio of 5 isomers with the same amount of nitric acid on the one hand, and an increase in the ratio of 5 isomers on the other hand. On the one hand, the ratio of 5 isomer increased under the same dosage of nitric acid, which was probably caused by the reaction of isobutanol with concentrated nitric acid to form alkyl nitrate, which selectively catalyzed o-bromotoluene on the surface of acidic saponite; On the other hand, the addition of isobutanol resulted in a significant decrease in the nitrification conversion of o-bromotoluene, which was due to the somewhat poorer activity of the alkyl nitrate ester relative to concentrated nitric acid. Although the rate of nitrification is faster at high temperatures in high concentrations, nitric acid is volatile and decomposes to produce NO 2 gas, reduce the concentration of nitric acid and increase the reaction time can improve the nitrification conversion rate. When the concentration of nitric acid is 98%, the amount of nitric acid is 1.5 for o-bromotoluene. When the nitric acid concentration is 98% and the amount of nitric acid is 1.5 times that of o-bromotoluene, the nitrification conversion rate can reach 100%, and the proportion of the 5-position isomer 2-bromo-5-nitrotoluene is 70.1%.

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