2-Chloro-m-toluidine. Chemical Properties

Melting point:

6.6 °C

Boiling point:

219.8±20.0 °C(Predicted)

Density 

1.180±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chlorooform (Sparingly), Methanol (Slightly)

pka

2.78±0.10(Predicted)

form 

liquid

color 

Light yellow to yellow green

InChI

InChI=1S/C7H8ClN/c1-5-3-2-4-6(9)7(5)8/h2-4H,9H2,1H3

InChIKey

RQRKMXABSUYQBV-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(C)=C1Cl

Safety Information

HS Code 

2921420090

2-Chloro-m-toluidine. Usage And Synthesis

Chemical Properties

The chloromethylanilines are colorless or white crystalline solids or liquids, some have a mild fishy odor.

Synthesis

General procedure for the synthesis of 2-chloro-3-methylaniline (CAS: 29027-17-6) from 2-chloro-3-nitrotoluene: 2-chloro-1-methyl-3-nitrobenzene (1 eq.) was dissolved in acetic acid (0.5 M) followed by addition of iron powder (4 eq.). The reaction mixture was heated to reflux at 100 °C for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure and methanol was added to the residue. The mixture was stirred at room temperature for 12 hours and then filtered. The filtrate was concentrated and purified by silica gel column chromatography to afford 2-chloro-3-methylaniline in 60% yield, the product was a red oil.1H NMR (400 MHz, DMSO-d6) δ ppm: 6.90 (t, J = 7.7 Hz, 1H), 6.66 (d, J = 7.9 Hz, 1H), 6.50 (d, J = 7.4 Hz, 1H). 5.23 (brs, 2H), 2.24 (s, 3H).

Potential Exposure

Most of the isomers are used in dyestuff manufacture. The 3-chloro-para isomer is used to kill birds. It is marketed as pelleted bait for control of bird populations.

Shipping

UN2239 Chlorotoluidines, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3429 Chlorotoluidines, liquid, Hazard Class: 6.1; Labels: 6.1- Poisonous materials

Incompatibilities

Incompatible with oxidizers, strong acids; chloroformates, and acid anhydrides, isocyanates, aldehydes forming fire and explosive hazards.

References

[1] Organic Letters, 2014, vol. 16, # 17, p. 4420 - 4423
[2] Patent: US2016/96841, 2016, A1. Location in patent: Paragraph 0349
[3] Journal of the Chemical Society, 1901, vol. 79, p. 1128
[4] Journal of the Chemical Society, 1902, vol. 81, p. 1327,1347
[5] Recueil des Travaux Chimiques des Pays-Bas, 1913, vol. 32, p. 247

2-Chloro-m-toluidine.(29027-17-6)Related Product Information

• Meclofenamic acid
• 2,4-DICHLORO-3,5-DINITROBENZOIC ACID
• 2,5-Dichloro-3-nitrobenzoic acid
• 2,6-Dichloro-3-nitrobenzaldehyde
• 2,6-DICHLORO-3-NITROTOLUENE
• Chloramben
• 2,6-DICHLORO-3-NITROBENZOIC ACID
• MECLOFENAMATE SODIUM
• 2,6-DICHLORO-3-NITROBENZONITRILE
• 2-Chloro-3-nitrobenzoic acid
• 2,6-Dichloro-3-methylaniline
• 2-Chloro-3,5-dinitrobenzotrifluoride
• 2-Chloro-3,5-dinitrobenzoic acid
• 2,4-Dichloro-3,5-dinitrobenzotrifluoride
• 2,4-DICHLORO-3,5-DINITROBENZAMIDE
• METHYL 2-CHLORO-3,5-DINITROBENZOATE
• sodium 3-amino-2,5-dichloro-benzoate
• 2-CHLORO-6-FLUORO-3-NITROBENZONITRILE