Chemical Properties
The chloromethylanilines are colorless or
white crystalline solids or liquids, some have a mild
fishy odor.
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.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
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.
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).
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
