General Description
Brown solid with a mild odor.
Reactivity Profile
3-CHLORO-P-TOLUIDINE(95-74-9) may be sensitive to prolonged exposure to air and light. This chemical may react with oxidizing agents. 3-CHLORO-P-TOLUIDINE(95-74-9) is incompatible with acids, acid chlorides, acid anhydrides and chloroformates. 3-CHLORO-P-TOLUIDINE(95-74-9) is also incompatible with reducing agents.
Air & Water Reactions
May be sensitive to prolonged exposure to air and light. Insoluble in water.
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.
Fire Hazard
This chemical is combustible.
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.
Chemical Properties
brown solid
Chemical Properties
The chloromethylanilines are colorless or
white crystalline solids or liquids, some have a mild
fishy odor.
Uses
2-Chloro-4-aminotoluene has been used in the preparation of 2-chloro-4-cyanotoluene by Sandmeyer reaction with cuprous cyanide.
Definition
ChEBI: A monochloroaniline that is p-toluidine in which one of the hydrogens that is meta to the amino group is replaced by a chlorine.
Synthesis
General procedure for the synthesis of 3-chloro-p-toluidine from 2-chloro-4-nitrotoluene: General method: Nitro compounds (1 eq.), hexafluoroisopropanol (HFIP, 10 eq.) and iron powder (5 eq.) were added to the reaction tube and mixed. Subsequently, a 2N aqueous hydrochloric acid solution was slowly added to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes and then neutralized with saturated aqueous sodium bicarbonate (NaHCO3) solution. Next, it was extracted three times with saturated aqueous sodium bicarbonate solution. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. Finally, the crude product was purified by silica gel column chromatography to obtain the target product 3-chloro-p-toluidine.
References
[1] Journal of the American Chemical Society, 2017, vol. 139, # 47, p. 17089 - 17097
[2] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3646 - 3649
[3] Chemische Berichte, 1884, vol. 17, p. 534
[4] Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 98,109
[5] Chem. Zentralbl., 1910, vol. 81, # I, p. 260
