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2,3,4-Trifluoroaniline

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Name

2,3,4-Trifluoroaniline

EINECS 253-703-1
CAS No. 3862-73-5 Density 1.409 g/cm3
PSA 26.02000 LogP 2.26730
Solubility N/A Melting Point 14-15°C
Formula C6H4F3N Boiling Point 173.8 °C at 760 mmHg
Molecular Weight 147.1 Flash Point 71.8 °C
Transport Information UN 3082 9/PG 3 Appearance Pale yellow liquid
Safety 23-26-36/37/39-61 Risk Codes 21/22-38-41-48/22-51/53
Molecular Structure Molecular Structure of 3862-73-5 (2,3,4-Trifluorobenzenamine) Hazard Symbols HarmfulXn; IrritantXi; DangerousN
Synonyms

4-12-00-01114 (Beilstein Handbook Reference);Aniline, 2,3,4-trifluoro-;Benzenamine, 2,3,4-trifluoro-;2,3,4-TFA;

Article Data 15

2,3,4-Trifluoroaniline Synthetic route

771-69-7

2,3,4-trifluoronitrobenzene

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
With sodium hypophosphite monohydrate; 1% platinum on charcoal; hydrogen at 65 - 80℃; under 6750.68 Torr; for 2.75h; Reagent/catalyst; Temperature; Autoclave;98.52%
With hydrogen; nickel Autoclave;91.8%
With iron; ammonium chloride
367-25-9

2,4-difluorophenylamine

A

367-34-0

2,4,5-trifluoroaniline

B

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; fluorine at 20℃; Title compound not separated from byproducts;
62-53-3

aniline

α-chloro-propionic acid amide

α-chloro-propionic acid amide

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: F2; TfOH / 20 °C
2: F2; TfOH / 20 °C
3: F2; TfOH / 20 °C
View Scheme
371-40-4

4-fluoroaniline

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: F2; TfOH / 20 °C
2: F2; TfOH / 20 °C
View Scheme
2268-05-5

1,3-dichloro-2-fluorobenzene

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid; aqueous nitric acid / 40 °C
2: dimethylformamide; potassium fluoride / 150 °C
3: iron; aqueous NH4Cl
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid; nitric acid / 2 h / Heating
2: sulfolane; potassium fluoride / 8 h / 200 - 210 °C
3: nickel; hydrogen / Autoclave
View Scheme
393-79-3

1,3-dichloro-2-fluoro-4-nitrobenzene

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide; potassium fluoride / 150 °C
2: iron; aqueous NH4Cl
View Scheme
Multi-step reaction with 2 steps
1: sulfolane; potassium fluoride / 8 h / 200 - 210 °C
2: nickel; hydrogen / Autoclave
View Scheme
771-69-7

2,3,4-trifluoronitrobenzene

A

369-34-6

3,4-difluoronitrobenzene

B

6921-22-8

1,2-difluoro-3-nitrobenzene

C

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
With Dimethylphenylsilane; o-phenylenebis(diphenylphosphine); potassium tert-butylate; copper(l) chloride In tetrahydrofuran for 12h; Inert atmosphere; Reflux; Overall yield = 95 %Spectr.; regioselective reaction;
20098-48-0

3,4,5-trichloronitrobenzen

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride / 11 h / 140 - 175 °C
2.1: hydrogen / methanol / Inert atmosphere
3.1: nitrosylsulfuric acid / 6 h / 10 - 15 °C
3.2: 1 h
4.1: sulfuric acid; nitric acid / 2 h / Heating
5.1: sulfolane; potassium fluoride / 8 h / 200 - 210 °C
6.1: nickel; hydrogen / Autoclave
View Scheme
3107-19-5

3,5-dichloro-4-fluoro-nitrobenzene

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogen / methanol / Inert atmosphere
2.1: nitrosylsulfuric acid / 6 h / 10 - 15 °C
2.2: 1 h
3.1: sulfuric acid; nitric acid / 2 h / Heating
4.1: sulfolane; potassium fluoride / 8 h / 200 - 210 °C
5.1: nickel; hydrogen / Autoclave
View Scheme
2729-34-2

3,5-dichloro-4-fluorophenylamine

3862-73-5

2,3,4-trifluoroaniline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: nitrosylsulfuric acid / 6 h / 10 - 15 °C
1.2: 1 h
2.1: sulfuric acid; nitric acid / 2 h / Heating
3.1: sulfolane; potassium fluoride / 8 h / 200 - 210 °C
4.1: nickel; hydrogen / Autoclave
View Scheme

2,3,4-Trifluoroaniline Specification

The IUPAC name of this chemical is 2,3,4-Trifluoroaniline. With the CAS registry number 3862-73-5, it is also named as Aniline, 2,3,4-trifluoro-. In addition, the molecular formula is C6H4F3N and the molecular weight is 147.10. It is a kind of clear purple to brown liquid and belongs to the classes of Anilines, Aromatic Amines and Nitro Compounds; Fluorobenzene; Amines; C2 to C6; Nitrogen Compounds. And it should be stored in a cool, ventilated and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 1.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.79; (4)ACD/LogD (pH 7.4): 1.79; (5)ACD/BCF (pH 5.5): 13.59; (6)ACD/BCF (pH 7.4): 13.6; (7)ACD/KOC (pH 5.5): 225.31; (8)ACD/KOC (pH 7.4): 225.43; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 3.24 Å2; (13)Index of Refraction: 1.495; (14)Molar Refractivity: 30.47 cm3; (15)Molar Volume: 104.3 cm3; (16)Polarizability: 12.07 ×10-24cm3; (17)Surface Tension: 35.3 dyne/cm; (18)Density: 1.409 g/cm3; (19)Flash Point: 71.8 °C; (20)Enthalpy of Vaporization: 41.01 kJ/mol; (21)Boiling Point: 173.8 °C at 760 mmHg; (22)Vapour Pressure: 1.25 mmHg at 25°C.

Preparation of 2,3,4-Trifluoroaniline: it can be prepared by 1,2,3-trifluorine-4-nitrobenzene through reduction.

2,3,4-Trifluoroaniline can be prepared by 1,2,3-trifluorine-4-nitrobenzene through reduction

Uses of 2,3,4-Trifluoroaniline: it can be used as intermediate of norfloxacin. And it can to used to synthetize ofloxacin which is a kind of antimicrobial. In addition, it can react with butyraldehyde to get dibutyl-(2,3,4-trifluoro-phenyl)-amine. This reaction will need reagents 3 M H2SO4 and NaBH4 and solvent tetrahydrofuran. The reaction time is 100 minutes at ambient temperature. The yield is about 90%.

2,3,4-Trifluoroaniline can react with butyraldehyde to get dibutyl-(2,3,4-trifluoro-phenyl)-amine.

When you are using this chemical, please be cautious about it as the following:
It is harmful in contact with skin and if swallowed, irritating to skin and toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. And it has risk of serious damage to the eyes and danger of serious damage to health by prolonged exposure if swallowed. During using it, do not breathe vapour and wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In addition,avoid release to the environment and refer to special instructions/safety data sheets.

You can still convert the following datas into molecular structure:
(1)SMILES: Fc1c(F)ccc(N)c1F
(2)InChI: InChI=1/C6H4F3N/c7-3-1-2-4(10)6(9)5(3)8/h1-2H,10H2
(3)InChIKey: WRDGNXCXTDDYBZ-UHFFFAOYAZ

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 699mg/kg (699mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 61, 1990.

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