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Home > Encyclopedia > 3-(Trifluoromethyl)aniline

3-(Trifluoromethyl)aniline

3-(Trifluoromethyl)aniline structure

3-(Trifluoromethyl)aniline 

structure
  • CAS No:

    98-16-8

  • Formula:

    C7H6F3N

  • Chemical Name:

    3-(Trifluoromethyl)aniline

  • Synonyms:

    Benzenamine,3-(trifluoromethyl)-;m-Toluidine,α,α,α-trifluoro-;3-(Trifluoromethyl)benzenamine;α,α,α-Trifluoro-m-toluidine;m-Aminobenzotrifluoride;3-(Trifluoromethyl)aniline;m-(Trifluoromethyl)aniline;m-Amino-α,α,α-trifluorotoluene;3-Aminobenzotrifluoride;1-Amino-3-(trifluoromethyl)benzene;m-Aminobenzal fluoride;3-Amino-α,α,α-trifluorotoluene;m-Trifluoromethylaniline;3-(Trifluoromethyl)phenylamine;NSC 4540

  • Categories:

    Organic Chemistry  >  Organic Fluorine Compound

Description

Clear light yellow liquid Benzenamine, 3-(trifluoromethyl)-is a combustible,colorless to yellow oily liquid. Unpleasant amine odor.


3-trifluoromethylaniline appears as a colorless liquid with a fishlike odor. Insoluble in water and denser than water. Toxic by ingestion and inhalation. Used to make dyes and pharmaceuticals.


3-trifluoromethylaniline appears as a colorless liquid with a fishlike odor. Insoluble in water and denser than water. Toxic by ingestion and inhalation. Used to make dyes and pharmaceuticals.

3-(Trifluoromethyl)aniline Basic Attributes

161.12

161.12

387672

206-884-6

Z1RWM538YN

4540

2948

DTXSID9024512

COLORLESS TO YELLOW OILY LIQ

29214300

Characteristics

26

2.39

Clear light yellow Liquid

1.2954 g/cm3 @ Temp: 204 °C

5.5 °C

187.5 °C @ Press: 764 Torr

185 °F

1.478

H2O: 5 g/L (20 ºC)

Store below +30°C.

0.3 mm Hg ( 20 °C)

5.56 (EPA, 1998) (Relative to Air)

Oral-rat LD50: 480 mg/kg; Oral-Mouse LD50: 220 mg/kg

Open flame flammable; liberates toxic aniline, nitrogen oxide and fluoride gas when exposed to heat

Fish-like

Insoluble in water.

Fluorinated Organic Compounds

3-TRIFLUOROMETHYLANILINE is a trifluoromethyl- and amine-substituted aromatic compound. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Safety Information

II

6.1

UN 2948 6.1/PG 2

2

36/37/38-33-23-21/22-26-24-22-20/21/22

26-36-45-36/37/39-28A

XU9180000

Xi,T,T+,Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Toxic/Irritant

Stable at room temperature in closed containers under normal storage and handling conditions.

P260-P280-P284-P310

H302 + H312-H330-H373

This material may burn but does not ignite readily. Cylinder may explode in heat of fire. When heated to decomposition, it emits very toxic fumes of fluorides and nitrogen oxides. (EPA, 1998)|Flammable - 2nd degree

|Danger|H302 (95.52%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P314, P320, P321, P322, P330, P332+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 67 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)|Wear positive pressure self contained breathing apparatus. ... Wear appropriate chemical protective clothing.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run off water out of sewers and water sources.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Do not use water.|Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personnal protective equipment.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for M-(TRIFLUOROMETHYL)ANILINE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Benzenamine, 3-(trifluoromethyl)- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Toxicity

highly

229.09 L/kg

Drug Information

Food and Environmental Agents: Effect on Breast-Feeding: Reported Sign or Symptom in Infant or Effect on Lactation: Fluorides: None. /from Table 7/

Contact may cause burns to skin and eyes. May be poisonous if inhaled, swallowed or absorbed through the skin. (EPA, 1998)

Note: No information on specific clinical effects of exposure was available. Signs and Symptoms of Benzeneamine, 3-(Trifluoromethyl)- Exposure: Signs and symptoms of acute exposure to benzeneamine, 3-(trifluoromethyl)- may include headache, dizziness, weakness, and nausea. May cause irritation of or burns to the eyes, skin, and respiratory tract. Esophageal or gastrointestinal tract irritation or burns may also be noted. Emergency Life-Support Procedures: Acute exposure to benzeneamine, 3-(trifluoromethyl)- may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to benzeneamine, 3-(trifluoromethyl)-. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to benzeneamine, 3-(trifluoromethyl)-. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. Speed in removing material from the skin is of extreme importance. 6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. DO NOT induce vomiting. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 6. Transport to a health care facility. (EPA, 1998)

3-aminobenzotrifluoride

3-(Trifluoromethyl)aniline Use and Manufacturing

Methods of Manufacturing

The preparation method is to add m-trifluoromethyl nitrobenzene, solvent ethanol and catalyst into the autoclave successively, replace the air in the autoclave with nitrogen, start stirring, and pass in hydrogen to keep the pressure in the autoclave at about 0.1 MPa. Control at (100±5)℃, react until no hydrogen is absorbed. The reaction time is about 1 h. Cool with cooling water to reduce the temperature in the kettle to below 40℃. Use the remaining pressure in the kettle to discharge the material, and filter the reaction liquid to remove The catalyst, the solvent and water are evaporated under normal pressure, and the finished product is obtained by distillation under reduced pressure.

Uses

3-Trifluoromethylaniline is an intermediate of the herbicides fluroxypyr, flurochloridone and pyrfluranil, as well as a pharmaceutical intermediate, such as used in the synthesis of flufenamate, moniflufen, fluphenazine , Triflupromazine, Fluxaran, etc. An important intermediate for dyes, medicines and pesticides. Used in the manufacture of antipsychotics, fluphenazine, triflurazine, trifloperidin, etc. Used in the synthesis of herbicides such as fluridone, flurochloridone, Norflurazon, etc., to control broad-leaved weeds and perennial weeds such as wheat fields and cotton fields. Mainly used as pharmaceutical, pesticide, dye intermediates

Production

(1978) PROBABLY GREATER THAN 2.27X10+6 G|(1979) PROBABLY GREATER THAN 2.27X10+6 G

ESSENTIALLY 100% AS A CHEM INT

GRADE: TECHNICAL (88% MIN); PURIFIED (98% MIN).

Benzenamine, 3-(trifluoromethyl)-: ACTIVE|SP - indicates a substance that is identified in a proposed Significant New Use Rule.

ANALYSIS OF M-AMINOBENZOTRIFLUORIDE BY NONAQUEOUS POTENTIOMETRIC TITRATION, IR SPECTROSCOPY, & QUANTITATIVE GLC.

Fire Hazards -> Flammable - 2nd degree

Computed Properties

Molecular Weight:161.12
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:161.04523368
Monoisotopic Mass:161.04523368
Topological Polar Surface Area:26
Heavy Atom Count:11
Complexity:132
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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