4-Aminobenzotrifluoride
- Iupac Name：4-(trifluoromethyl)aniline
- CAS No.: 455-14-1
- Molecular Weight：161.12
- Modify Date.: 2022-12-12 06:16
- Introduction: 4-Substituted aniline derivatives exert special hematotoxicity on the red blood cells and induce leukocytosis.
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1. Names and Identifiers
- 1.1 Name
- 4-Aminobenzotrifluoride
- 1.2 Synonyms
1-AMINO-4-(TRIFLUOROMETHYL)BENZENE 4-(TRIFLUOROMETHYL)ANILINE 4-AMINO-A,A,A-TRIFLUOROTOLUENE 4-AMINOBENZOTRIFLOURIDE 4-Aminobenzotrifluororide 4-aminotrifluorotoluene 4-trifluoromethylphenylamine A,A,A-TRIFLUORO-P-TOLUIDINE aminobenzotrifluoride EINECS 207-236-5 Leflunomide Impurity 1 MFCD00064396 P-(TRIFLUOROMETHYL)ANILINE P-AMINOBENZOTRIFLUORIDE para-trifluoromethylaniline p-trifluoromethylphenylamine TIMTEC-BB SBB003956 TRIFLUOROMETHYLANILINE α,α,α-Trifluoro-p-toluidine
- 1.3 CAS No.
- 455-14-1
- 1.4 CID
- 11248
- 1.5 EINECS(EC#)
- 207-236-5
- 1.6 Molecular Formula
- C7H6F3N (isomer)
- 1.7 Inchi
- InChI=1S/C7H6F3N/c8-7(9,10)5-1-3-6(11)4-2-5/h1-4H,11H2
- 1.8 InChkey
- ODGIMMLDVSWADK-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- NC1=CC=C(C=C1)C(F)(F)F
- 1.10 Isomers Smiles
- C(=O)([O-])[O-].[Fe+2]
2. Properties
- 2.1 Density
- 1.283?g/mL?at 25?°C(lit.)
- 2.1 Melting point
- 3-8?°C
- 2.1 Boiling point
- 83?°C12?mm Hg(lit.)
- 2.1 Refractive index
- 1.483-1.485
- 2.1 Flash Point
- 188?°F
- 2.1 Precise Quality
- 161.04500
- 2.1 PSA
- 26.02000
- 2.1 logP
- 2.86880
- 2.1 Solubility
- <0.1 g/100 mL
- 2.2 Appearance
- Clear colorless to yellow Liquid
- 2.3 Chemical Properties
- clear colorless to yellow liquid
- 2.4 Color/Form
- Clear colorless to yellow
- 2.5 pKa
- 2.45(at 25℃)
- 2.6 Water Solubility
- H2O: <0.1 g/100 mL
- 2.7 Stability
- Stable at room temperature in closed containers under normal storage and handling conditions.
- 2.8 StorageTemp
- Keep in dark place,Inert atmosphere,2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A substituted aniline that is a benzene ring substituted with an amino group at position 1 and a trifluoromethyl group at position 4.
- 3.2 Methods of Manufacturing
- The preparation methods are as follows.?The method of p-nitrotoluene as the raw material uses p-nitrotoluene as the raw material to perform bromination with bromine to form p-dibromomethylnitrobenzene, and then bromine with sodium hypobromite to generate p-tribromomethylnitrobenzene, It is then fluorinated with antimony trifluoride and then reduced with tin dichloride to obtain p-trifluoromethylaniline.?This method is a classic method, the raw materials used are easily available, but bromine requires more bromine, and it is only an intermediate transition, but also needs to be fluorinated with SbF3, SnCl2 reduction, the process is complicated, and the three wastes are more difficult to industrialize.?If chlorination can be used instead of bromination, HF can be used for fluorination, and conventional reduction methods are used for reduction, it will have certain industrial significance.?P-chlorotrifluorotoluene is used as a raw material to react p-chlorotrifluorotoluene with ammonia under high pressure and high temperature (150-240°C) to produce p-trifluoromethylaniline.?Although p-chlorotrifluorotoluene is already an industrialized commodity, the conditions of ammonolysis are more severe, and industrialization is difficult.?P-trichloromethylbenzene isocyanate is used as a raw material method to produce p-trifluoromethylaniline hydrofluoride by reacting p-trichloromethylbenzene isocyanate with hydrogen fluoride, and then reacting with alkali.?This method is a method developed in recent years abroad, and p-trichloromethylbenzene isocyanate can use p-methylaniline as a raw material, and can generate p-trichloromethylchloroformanilide through phosgene, and further generate p-trichloromethylbenzene Isocyanate.
- 3.3 Usage
- 4-Substituted aniline derivatives exert special hematotoxicity on the red blood cells and induce leukocytosis.
4. Safety and Handling
- 4.1 Symbol
- GHS06, GHS09
- 4.1 Hazard Codes
- T,N,Xi,Xn
- 4.1 Signal Word
- Danger
- 4.1 Risk Statements
- 25-36-50/53-36/37/38-33-20/21/22
- 4.1 Safety Statements
- 26-45-60-61-36/37/39-36
- 4.1 Packing Group
- III
- 4.1 Hazard Class
- 6.1
- 4.1 Hazard Declaration
- H301-H319-H410
- 4.1 RIDADR
- UN 2810 6.1/PG 3
- 4.1 Caution Statement
- P273-P301 + P310-P305 + P351 + P338-P501
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- XU9260000
- 4.1 Safety
- Hazard Codes:T,N,Xi,Xn
Risk Statements:25-36-50/53-36/37/38-33-20/21/22
25:Toxic if swallowed
36:Irritating to the eyes
50/53:Very Toxic to aquatic organisms, may cause long-term adverse
effects in the aquatic environment
36/37/38:Irritating to eyes, respiratory system and skin
33:Danger of cumulative effects
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:26-45-60-61-36/37/39-36
26:In case of contact with eyes, rinse immediately with plenty
of water and seek medical advice
45:In case of accident or if you feel unwell, seek medical
advice immediately (show label where possible)
60:This material and/or its container must be disposed of
as hazardous waste
61:Avoid release to the environment. Refer to special instructions
safety data sheet
36/37/39:Wear suitable protective clothing, gloves and eye/face
protection
36:Wear suitable protective clothing
RIDADR:UN 2810 6.1/PG 3
WGK Germany:3
HazardClass:6.1
PackingGroup:III
Hazard Note:Toxic/Irritant
HS Code:29214300
- 4.2 Specification
-
clear colorless to yellow liquid
usageEng:4-Substituted aniline derivatives exert special hematotoxicity on the red blood cells and induce leukocytosis.
Safety Statements:26-45-60-61-36/37/39-36
26:In case of contact with eyes, rinse immediately with plenty
of water and seek medical advice
45:In case of accident or if you feel unwell, seek medical
advice immediately (show label where possible)
60:This material and/or its container must be disposed of
as hazardous waste
61:Avoid release to the environment. Refer to special instructions
safety data sheet
36/37/39:Wear suitable protective clothing, gloves and eye/face
protection
36:Wear suitable protective clothing
- 4.3 Toxicity
-
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- XU9260000
- CHEMICAL NAME :
- p-Toluidine, alpha,alpha,alpha-trifluoro-
- CAS REGISTRY NUMBER :
- 455-14-1
- BEILSTEIN REFERENCE NO. :
- 1564853
- LAST UPDATED :
- 199709
- DATA ITEMS CITED :
- 5
- MOLECULAR FORMULA :
- C7-H6-F3-N
- MOLECULAR WEIGHT :
- 161.14
- WISWESSER LINE NOTATION :
- ZR CXFFF
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 101 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 58 mg/kg/3D-I
- TOXIC EFFECTS :
- Endocrine - changes in spleen weight
Blood - changes in bone marrow (not otherwise specified)
Blood - changes in erythrocyte (RBC) count
MUTATION DATA
- TYPE OF TEST :
- Mutation in microorganisms
- TEST SYSTEM :
- Bacteria - Escherichia coli
- DOSE/DURATION :
- 10 mg/L
- REFERENCE :
- ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For
publisher information, see EMMUEG. Volume(issue)/page/year: 5,803,1983
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 3
Serious eye damage, Category 1
Acute toxicity - Inhalation, Category 3
Specific target organ toxicity \u2013 repeated exposure, Category 1
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |     |
| Signal word | Danger |
| Hazard statement(s) | H301 Toxic if swallowed H318 Causes serious eye damage H331 Toxic if inhaled H372 Causes damage to organs through prolonged or repeated exposure H400 Very toxic to aquatic life H410 Very toxic to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P273 Avoid release to the environment. |
| Response | P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P311 Call a POISON CENTER/doctor/\u2026 P314 Get medical advice/attention if you feel unwell. P391 Collect spillage. |
| Storage | P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
455-14-1Total: 37 Synthesis Route
9. Other Information
- 9.0 Definition
- ChEBI: A substituted aniline that is a benzene ring substituted with an amino group at position 1 and a trifluoromethyl group at position 4.
- 9.1 Synthesis Reference(s)
- The Journal of Organic Chemistry, 54, p. 2873, 1989 DOI: 10.1021/jo00273a020
- 9.2 General Description
- Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
- 9.3 Storage Conditions
- The preparation methods are as follows.?The method of p-nitrotoluene as the raw material uses p-nitrotoluene as the raw material to perform bromination with bromine to form p-dibromomethylnitrobenzene, and then bromine with sodium hypobromite to generate p-tribromomethylnitrobenzene, It is then fluorinated with antimony trifluoride and then reduced with tin dichloride to obtain p-trifluoromethylaniline.?This method is a classic method, the raw materials used are easily available, but bromine requires more bromine, and it is only an intermediate transition, but also needs to be fluorinated with SbF3, SnCl2 reduction, the process is complicated, and the three wastes are more difficult to industrialize.?If chlorination can be used instead of bromination, HF can be used for fluorination, and conventional reduction methods are used for reduction, it will have certain industrial significance.?P-chlorotrifluorotoluene is used as a raw material to react p-chlorotrifluorotoluene with ammonia under high pressure and high temperature (150-240°C) to produce p-trifluoromethylaniline.?Although p-chlorotrifluorotoluene is already an industrialized commodity, the conditions of ammonolysis are more severe, and industrialization is difficult.?P-trichloromethylbenzene isocyanate is used as a raw material method to produce p-trifluoromethylaniline hydrofluoride by reacting p-trichloromethylbenzene isocyanate with hydrogen fluoride, and then reacting with alkali.?This method is a method developed in recent years abroad, and p-trichloromethylbenzene isocyanate can use p-methylaniline as a raw material, and can generate p-trichloromethylchloroformanilide through phosgene, and further generate p-trichloromethylbenzene Isocyanate.
- 9.4 Mesh Entry Terms
- 4-trifluoromethylaniline
- 9.5 Manufacturing Info
- Benzenamine, 4-(trifluoromethyl)-: ACTIVE
- 9.6 BRN
- 1564853
- 9.7 Chemical Properties
- clear colorless to yellow liquid
- 9.8 Uses
- 4-Substituted aniline derivatives exert special hematotoxicity on the red blood cells and induce leukocytosis.
- 9.9 Uses
-
4-(Trifluoromethyl)aniline was used in the synthesis of 4-(trialkylmethyl)anilines. It was also used as a synthetic building block.
10. Computational chemical data
- Molecular Weight: 161.12g/mol
- Molecular Formula: C7H6F3N
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 115.919679
- Monoisotopic Mass: 115.919679
- Complexity: 18.8
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 63.2
- Heavy Atom Count: 5
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 2
- CACTVS Substructure Key Fingerprint: AAADcQAAMAAAAAAgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAACAAAAAAIAAAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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