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| | 3-Chloro-2-methylaniline Basic information | | Synthesis |
| | 3-Chloro-2-methylaniline Chemical Properties |
| Melting point | 2 °C (lit.) | | Boiling point | 115-117 °C/10 mmHg (lit.) | | density | 1.185 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.588(lit.) | | Fp | >230 °F | | storage temp. | Store below +30°C. | | solubility | 4.5g/l | | form | Liquid | | pka | pK1:2.49(+1) (25°C) | | Specific Gravity | 1.19 | | color | Clear yellow to red or red-brown | | Water Solubility | 1g/L at 20℃ | | BRN | 471697 | | InChIKey | ZUVPLKVDZNDZCM-UHFFFAOYSA-N | | LogP | 2.4 | | CAS DataBase Reference | 87-60-5(CAS DataBase Reference) | | NIST Chemistry Reference | Benzenamine, 3-chloro-2-methyl-(87-60-5) | | EPA Substance Registry System | 3-Chloro-2-methylaniline (87-60-5) |
| | 3-Chloro-2-methylaniline Usage And Synthesis |
| Synthesis | It is obtained by chlorination and reduction of o-nitrotoluene.
1. Chlorination reaction
In o-nitrotoluene, add 2% ferric chloride as a catalyst, pass chlorine gas at 50-60 ° C until the relative density of the reaction solution reaches 1.27-1.29 (50 ° C), wash with 5% hydrochloric acid, and then Wash with water, and finally adjust pH to 7 with liquid caustic soda. Divide the water layer, evaporate the water, carry out vacuum distillation, collect 120-150 ℃ (5.33-8.0kPa) fractions, crystallize by cooling and filter to obtain 2-chloro-6-nitrotoluene.
2. Reduction reaction
Add hydrochloric acid and iron powder to the reaction pot, stir and heat to 90°C, slowly add melted 2-chloro-6-nitrotoluene, complete the addition, and reflux for 3 hours. Cooling, adding liquid alkali to adjust pH to 8, steam distillation to obtain 3-chloro-o-toluidine. | | Chemical Properties | clear yellow to red or red-brown liquid | | Chemical Properties | The chloromethylanilines are colorless or
white crystalline solids or liquids, some have a mild
fishy odor. | | Uses | Intermediate. | | Uses | 3-Chloro-2-Methylaniline can be used for dyeing cotton, viscose, silk, nylon and acetate, as well as printing on cotton. It is mainly used for dyeing red, such as coupling with chromophenol AS, AS-BO, AS-ITR, etc. | | Preparation | By 1-Methyl-2-nitrobenzene chlorination byproducts 3-Chloro-2-methylbenzenamine?reduction. | | Hazard | Toxic by ingestion or inhalation. | | Safety Profile | Poison by ingestion.
Mutation data reported. When heated to
decomposition it emits toxic fumes of Cl
and NOx. See also other chloro toluidine
entries. | | 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. | | Incompatibilities | Incompatible with oxidizers, strong
acids; chloroformates, and acid anhydrides, isocyanates,
aldehydes forming fire and explosive hazards. |
| | 3-Chloro-2-methylaniline Preparation Products And Raw materials |
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