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3-(Trifluoromethyl)aniline

HCID 7375
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Basic information

CAS
98-16-8
Standard SMILES
Nc1cccc(C(F)(F)F)c1
InChIKey
VIUDTWATMPPKEL-UHFFFAOYSA-N
Molecular formula
C7H6F3N
Average molar mass
161.12 g/mol
Monoisotopic mass
161.04523368

Overview

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.

Names & identifiers

Preferred name
3-(Trifluoromethyl)aniline
IUPAC
3-(trifluoromethyl)aniline
English name
3-Aminobenzotrifluoride
Molecular formula
C7H6F3N
Molecular weight
161.12

Names & synonyms

3-(Trifluoromethyl)aniline98-16-83-Aminobenzotrifluoridem-Aminobenzotrifluoride3-Trifluoromethylaniline3-(Trifluoromethyl)benzenaminem-Aminobenzal fluorideBenzenamine, 3-(trifluoromethyl)-M-(TRIFLUOROMETHYL)ANILINEUSAF MA-41-Amino-3-(trifluoromethyl)benzenem-Amino-alpha,alpha,alpha-trifluorotoluene
Show more names
META-AMINOBENZOTRIFLUORIDE3-trifluoromethyl3-(trifluoromethyl)3-aminotrifluorotoluene3-Aminobenzotrifluoride 98%DK9593-ABTFusafma-4
DTXSID9024512m-Toluidine, alpha,alpha,alpha-trifluoro-Z1RWM538YNNSC-4540Toluene, 3-amino-alpha,alpha,alpha-trifluoro-DTXCID504512RefChem:92749202-643-4

Database identifiers

CAS
98-16-8
PubChem CID
7375
DTXSID
DTXSID9024512
ChEMBL
CHEMBL1162293
UNII
Z1RWM538YN
EC Number
202-643-4
Nikkaji
J54.405A

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
26 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
11
Formal charge
0
Complexity
132

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Amines, Aromatic

Flammable agents - 2nd degree

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PesticidesPesticide degradation product
LogP2.29
OdorFish-like
Density · 2 items

1.303 at 59.9 °F (EPA, 1998) - Denser than water; will sink

1.303 @25 °C

Color/FormCOLORLESS TO YELLOW OILY LIQ
Solubility · 2 items

Slightly soluble (NTP, 1992)

SLIGHTLY SOL IN WATER; SOL IN ALC, ETHER

Flash Point185 °F (NTP, 1992)
Boiling Point · 3 items

369.5 °F at 764 mmHg (EPA, 1998)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (95.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 70 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 6 items

Chemical: Benzenamine, 3-(trifluoromethyl)-

Commission Regulation (EC) No 33/2008

SP - indicates a substance that is identified in a proposed Significant New Use Rule.

REACH registered substance: α,α,α-trifluoro-m-toluidine (EC: 202-643-4)

3-Aminobenzotrifluoride: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire Hazards · 2 items

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)

· Combustible material: may burn but does not ignite readily.

Health Hazards · 2 items

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

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as intermediate for phenothiazine derivatives, herbicides, antihypertensives, and diuretics; [HSDB] Used to make dyes; [CAMEO]

INT IN MFR OF PHENOTHIAZINE DERIV.

CHEM INT FOR HERBICIDES (EG, FLUOMETRON & NORFLURAZON), ANTIHYPERTENSIVES & DIURETICS.

U.S. Imports · 2 items

(1977) 1.01X10+7 G (PRINCPL CUSTMS DISTS)

(1979) 2.94X10+8 G (PRINCPL CUSTMS DISTS)

U.S. Production · 2 items

(1978) PROBABLY GREATER THAN 2.27X10+6 G

(1979) PROBABLY GREATER THAN 2.27X10+6 G

Consumption PatternsESSENTIALLY 100% AS A CHEM INT
Methods of ManufacturingNITRATION OF BENZOTRIFLUORIDE TO 3-NITROBENZOTRIFLUORIDE FOLLOWED BY HYDROGENATION
Formulations/PreparationsGRADE: TECHNICAL (88% MIN); PURIFIED (98% MIN).
General Manufacturing InformationBenzenamine, 3-(trifluoromethyl)-: ACTIVE
Applications · 3 items

DescriptionBenzenamine, 3-(trifluoromethyl)- is a combustible, colorless to yellow oily liquid with an amine-likeodor. Molecular weight=161.14; Boiling point = 187.5℃;Freezing/Melting point= 3℃; Flash point =85℃.Hazard Identification (based on NFPA-704 M RatingSystem): Health 2, Flammability 1, Reactivity 0.

UsesUsed as pharmaceutical intermediate.

General DescriptionA colorless liquid with a fishlike odor. Insoluble in water and denser than water. Toxic by ingestion and inhalation. Used to make dyes and pharmaceuticals.

Related reactions

588 records
New reaction record
HRID 2155 reaction equation
HRID 2155As reactantuspto-grants-1998_03
HRID 2429 reaction equation
HRID 2429As reactantuspto-grants-1998_03
HRID 2934 reaction equation
HRID 2934As reactantuspto-grants-1998_03
HRID 3720 reaction equation
HRID 3720As reactantuspto-grants-1998_03
HRID 4180 reaction equation
HRID 4180As reactantuspto-grants-1988_02
HRID 5317 reaction equation
HRID 5317As reactantuspto-grants-1993_09
HRID 6425 reaction equation
HRID 6425As reactantuspto-grants-1993_09
HRID 9901 reaction equation
HRID 9901As reactantuspto-grants-2006_08
Page 1 of 74

Compound notes

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187.5 °C @ 764 MM HG

189 °C @760 [mm Hg]

Melting Point · 2 items

37 °F (EPA, 1998)

3 °C

Vapor Density5.56 (EPA, 1998) - Heavier than air; will sink (Relative to Air)

Physicochemical properties

Melting point
5 °C · 5 °C
Boiling point
187 °C · 187 °C(lit.)
Density
1.29 g/mL · 1.29 g/mL at 25 °C(lit.)
vapor pressure
0.3 mm · 0.3 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.480(lit.)
Flash point
185 °F · 185 °F
storage temp.
30 °C · Store below +30°C.
solubility
5 g/L · 5 g/L (20°C)
form
Liquid
pka
3.49 · 3.49(at 25℃)
Specific Gravity
1.29 · 1.290
color
Clear light yellow
Water Solubility
5 g/L · 5 g/L (20 ºC)
BRN
387672 · 387672
Henry's Law Constant
3.9 · 3.9×10-1 mol/(m3Pa) at 25℃, Ebert et al. (2023)
Exposure limits
2.5 mg/m3NIOSH: · ACGIH: TWA 2.5 mg/m3NIOSH: IDLH 250 mg/m3
InChI
1S/C7H6F3N/c8-7(9,10)5-2-1-3-6(11)4-5/h1-4H,11H2
InChIKey
VIUDTWATMPPKEL-UHFFFAOYSA-N
SMILES
Nc1cccc(c1)C(F)(F)F
LogP
2.09 · 2.09-2.16 at 25-30℃ and pH5.9
Surface tension
64.5 mN/m · 64.5mN/m at 1g/L and 22.2℃
CAS DataBase Reference
98 · 98-16-8(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
1 RWM538YN · Z1RWM538YN
NIST Chemistry Reference
3 · Benzenamine, 3-(trifluoromethyl)-(98-16-8)
EPA Substance Registry System
m-(Trifluoromethyl)aniline (98-16-8)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
5 · GHS05,GHS06,GHS09
Signal word
Danger
Hazard statements
330 · H330-H302-H315-H318-H411-H227
Precautionary statements
501 · P501-P273-P270-P260-P210-P271-P264-P280-P284-P302+P352-P370+P378-P391-P362+P364-P332+P313-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xi,T,T+,Xn
Risk Statements
36 · 36/37/38-33-23-21/22-26-24-22-20/21/22
Safety Statements
26 · 26-36-45-36/37/39-28A
RIDADR
2948 · UN 2948
WGK Germany
2 · 2
RTECS
9180000 · XU9180000
Hazard Note
Toxic/Irritant
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
II
HS Code
29214300 · 29214300
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2
Hazardous Substances Data
98 · 98-16-8(Hazardous Substances Data)
REACH Registrations
Active
Limited Quantities
100 ml · 100ml (liquid) or 0.5 Kg (solid)
Excepted Quantities
Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Hazards Summary · 1 item

A moderate eye irritant; In lethal-dose feeding studies, causes methemoglobinemia, somnolence, and fatty liver degeneration; [RTECS] A corrosive chemical that could cause chemical pneumonitis after inhalation; Methemoglobinemia reported in animal experiments; Monitor liver and kidney function after significant exposure; [HSDB] May burn skin and eyes; [CAMEO] An irritant; Can be absorbed through skin; [MSDSonline]

DOT ID and Guide2948 153
Reactive GroupFluorinated Organic Compounds
Reactivity Profile · 1 item

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.

DOT Emergency Guidelines · 5 items

/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.

DOT Hazard Classification · 4 items

3-Trifluoromethylaniline

UN2948

Div 6.1 Poisonous materials (49 eCFR § 173.132)

PG II: the degree of danger presented by the material is medium

Air and Water ReactionsInsoluble in water.
CERCLA Reportable Quantities · 1 item

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.

Safety & protection

Fire Fighting · 1 item

Wear positive pressure breathing apparatus and special protective clothing. Move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

Note: No information on specific clinical effects of exposure was available.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 1 item

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.

Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Preventive Measures · 2 items

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.

Isolation and Evacuation · 2 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Protective Action Criteria (PAC) · 3 items

0.40 [mg/m3]

4.4 [mg/m3]

19 [mg/m3]

Personal Protective Equipment (PPE) · 2 items

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.

Emergency Response Planning GuidelinesSmall Fire

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Non-Human Toxicity ExcerptsWHEN ADDED TO FOOD OF LARVAL & IMAGO DROSOPHILA, M-TRIFLUOROMETHYLANILINE INCR INCIDENCE OF DOMINANT LETHAL MUTATIONS AMONG OFFSPRING & INCR PERCENTAGE OF UNFERTILIZED EGGS.
Toxicity DataLC50 (rat) = 440 mg/m3/4h
USGS Health-Based Screening Levels for Evaluating Water-Quality · 4 items

3-Trifluoromethylaniline

Pesticide degradation product

Also see CASRN 2164172

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

Regulatory information

CERCLA Reportable Quantities · 1 item

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.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
XU9180000
ridadr
UN 2948
hs_code
29214300
risk_code
36/37/38-33-23-21/22-26-24-22-20/21/22
Signal word
Danger
Symbol(GHS)
GHS05,GHS06,GHS09
hazard_code
Xi,T,T+,Xn
hazard_note
Toxic/Irritant
safety_code
26-36-45-36/37/39-28A
hazard_class
6.1
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
Hazard statements
H330-H302-H315-H318-H411-H227
Limited Quantities
100ml (liquid) or 0.5 Kg (solid)
Excepted Quantities
Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2
Precautionary statements
P501-P273-P270-P260-P210-P271-P264-P280-P284-P302+P352-P370+P378-P391-P362+P364-P332+P313-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
Hazardous Substances Data
98-16-8(Hazardous Substances Data)

Upstream & downstream products

Upstream raw materials

3-NitrobenzotrifluorideBenzotrifluorideTolueneNitric acidInter-trifluoromethylnitrobenzeneIronSulfuric acid

Downstream products

N-(3-Trifluoromethylphenyl)piperazine7-(Trifluoromethyl)quinoline3-Bromobenzotrifluoride7-(Trifluoromethyl)-4-quinolinolFluometuronFlutamideFluorochloridoneBendroflumethiazide4-Hydroxy-7-trifluoromethyl-3-quinolinecarboxylic acid4-Chloro-7-(trifluoromethyl)quinoline3-(Trifluoromethyl)phenyl isocyanate3-Amino-4-nitrobenzitrifluorideFlufenamic acid4-AminobenzotrifluorideEthyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate7-Trifluoromethyl-4-quinolinethiol4-Amino-2-(trifluoromethyl)benzonitrile[1,1'-Biphenyl]-2-amine, 5-(trifluoromethyl)-2,4-Dibromo-5-(trifluoromethyl)aniline2-Bromo-5-(trifluoromethyl)aniline