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| Product Name: | 3-Chloro-2-methylaniline |
| Synonyms: | 2-Chloro-2-Methyl Aniline;3-Chloro-2-methylaniline, 98+%;3-CHLORO-ORTHO-TOLUIDINE;3-Chlor-o-toluidin;3-chloro-2-toluidin;3-CHLORO-2-METHYLANILINE / 2-AMINO-6-CHLOROTOLUENE;3-chloro-o-toluidin;6-Chloro-2-amino-1-methylbenzene |
| CAS: | 87-60-5 |
| MF: | C7H8ClN |
| MW: | 141.6 |
| EINECS: | 201-756-6 |
| Product Categories: | API intermediates;Aromatic Hydrocarbons (substituted) & Derivatives |
| Mol File: | 87-60-5.mol |
| Melting point | 2 °C (lit.) |
| Boiling point | 115-117 °C/10 mmHg (lit.) |
| density | 1.185 g/mL at 25 °C (lit.) |
| refractive index | n |
| 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) |
| Hazard Codes | C,N,Xn |
| Risk Statements | 22-34-43-51/53-36/37/38 |
| Safety Statements | 26-36/37/39-45-61-37/39 |
| RIDADR | UN 3429 6.1/PG 3 |
| WGK Germany | 2 |
| RTECS | XU4760000 |
| TSCA | Yes |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 29214300 |
| Hazardous Substances Data | 87-60-5(Hazardous Substances Data) |
| Provider | Language |
|---|---|
| Fast Scarlet TR Base | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| 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. |
| The chloromethylanilines are colorless orwhite crystalline solids or liquids, some have a mild fishyodor. Molecular weight (all isomers) =141.61. HazardIdentification (based on NFPA 704 M Rating System): (87-60-5) Health 2, Flammability 1, Reactivity 0. All are soluble in water and include: | |
| Chemical Properties | clear yellow to red or red-brown liquid |
| The chloromethylanilines are colorless orwhite crystalline solids or liquids, some have a mildfishy odor. | |
| Uses | Intermediate. |
| 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. |
| Toxic by ingestion or inhalation. | |
| Safety Profile | Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland NOx. See also other chloro toluidine entries. |
| Most of the isomers are used in dyestuff manufacture. The 3-chloro-para isomer is used to killbirds. It is marketed as pelleted bait for control of birdpopulations. | |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. Note to physician: Treat for methemoglobinemia.Spectrophotometry may be required for precise determination of levels of methemoglobinemia in urine. |
| Color Code—Blue: Health Hazard/Poison: Store ina secure poison location. Prior to working with chloromethylanilines you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, well-ventilated area. Sources of ignition, such as smoking and openflames, are prohibited where Choromethyl anilines are handled, or stored in a manner that could create a potential fireor explosion hazard. A regulated, marked area should beestablished where this chemical is handled, used, or stored incompliance with OSHA Standard 1910.1045. | |
| Shipping | Chlorotoluidines require a label of“POISONOUS/TOXIC MATERIALS.” They fall in DOTHazard Class 6.1 and Packing Group III. |
| Incompatible with oxidizers, strongacids; chloroformates, and acid anhydrides, isocyanates,aldehydes forming fire and explosive hazards. | |
| References | [1] Materials Research Bulletin, 2013, vol. 48, # 5, p. 1885 - 1890 [2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 9, p. 2851 - 2852 [3] Patent: CN104725242, 2017, B. Location in patent: Paragraph 0026-0027 [4] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 9, p. 955 - 977 [5] Synthetic Communications, 1981, vol. 11, # 11, p. 925 - 930 |
| Raw materials | Iron-->Ferric chloride-->2-Nitrotoluene-->2-Chloro-6-nitrotoluene-->Sodium propanolate-->Carbamic acid, [3-chloro-2-(2-oxopropyl)phenyl]-, 1,1-dimethylethyl ester (9CI)-->Ethanol-->4-CHLORO-2-METHYL-1H-INDOLE-->2-Nitrotoluene-->3-Chloro-2-methylaniline |
| Preparation Products | 2,6-Dichlorotoluene-->Quinclorac-->3-CHLORO-2-METHYLBENZONITRILE-->7-Dimethylamino-4-methylcoumarin-->pigment yellow 155-->2-Chloro-6-fluorotoluene-->7-CHLORO-8-METHYLQUINOLINE-->3-CHLORO-2-METHYLPHENYL ISOTHIOCYANATE-->3-Amino-2-methylphenylboronic acid, pinacol ester-->Clonixin-->4-CHLORO (1H)INDAZOLE-->3-Chloro-2-methylbenzoic acid-->3-Chloro-2-methylaniline-->Mordant Violet 10-->N-(3-CHLORO-2-METHYL-PHENYL)-2,2-DIMETHYL-PROPIONAMIDE-->7-CHLORO-8-METHYL-2-PHENYLQUINOLINE-4-CARBOXYLICACID |
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