328-93-8

Basic information

• Product Name: 2,5-Bis(trifluoromethyl)aniline
• Synonyms: ALPHA,ALPHA,ALPHA,ALPHA',ALPHA',ALPHA'-HEXAFLUORO-2,5-XYLIDINE;2,5-DI(TRIFLUOROMETHYL)ANILINE;2,5-BIS(TRIFLUOROMETHYL)ANILINE;TIMTEC-BB SBB000691;2,5-BIS(TRIFLUOROMETHYL)AMILINE;2,5-Bis(trifluoromethyl)aniline 98%;2,5-Bis(trifluoromethyl)aniline98%;2,5-DIS(TRIFLUOROMETHYL)ANILINE
• CAS NO: 328-93-8
• Molecular Formula: C₈H₅F₆N
• Molecular Weight: 229.12
• EINECS: 206-490-4
• Product Categories: Fluorobenzene;Anilines, Aromatic Amines and Nitro Compounds;Nitrogen Compounds;Amines;C8;Aniline series
• Mol File: 328-93-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 70-71 °C15 mm Hg(lit.)
• Flash Point: 160 °F
• Appearance: Colorless or pale yellow liquid
• Density: 1.467 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 0.24±0.10(Predicted)
• BRN: 2653046
• CAS DataBase Reference: 2,5-Bis(trifluoromethyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Bis(trifluoromethyl)aniline(328-93-8)
• EPA Substance Registry System: 2,5-Bis(trifluoromethyl)aniline(328-93-8)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-45-36
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 328-93-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Different sources of media describe the Uses of 328-93-8 differently. You can refer to the following data:
1. 2,5-Bis(trifluoromethyl)aniline is a haloalkul substituted aniline used in the preparation of anti-benign prostatic hyperplasia drug, Dutasteride (D735000).
2. 2,5-Bis(trifluoromethyl)aniline may be used in chemical synthesis.

InChI:InChI=1/C6H5BClFO2/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,10-11H

Synthetic route

1,4-Bis(trifluoromethyl)-2-nitro-benzene (320-88-7) → 2,5-bis(trifluoromethyl)aniline (328-93-8)

Conditions	Yield
With hydrogen; nickel In isopropyl alcohol at 70 - 90℃; under 3677.86 Torr; for 8h;	73%
With hydrogenchloride; tin(ll) chloride
Stage #1: 1,4-Bis(trifluoromethyl)-2-nitro-benzene With hydrogenchloride; tin(II) chloride dihdyrate In methanol; water at 20 - 50℃; Stage #2: With sodium hydroxide In water pH=10;

1,4-bis(trifluoromethyl)benzene (433-19-2) → 2,5-bis(trifluoromethyl)aniline (328-93-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: disulfuric acid; sulfuric acid; nitric acid 2: SnCl2+2H2O; concentrated HCl View Scheme
Multi-step reaction with 2 steps 1.1: nitric acid; sulfuric acid / 0 - 110 °C 2.1: hydrogenchloride; tin(II) chloride dihdyrate / water; methanol / 20 - 50 °C 2.2: pH 10 View Scheme
durch Nitrierung und Reduktion;

2-chloro 1,4-bis(trifluoromethyl)benzene (328-91-6) → 2,5-bis(trifluoromethyl)aniline (328-93-8)

Conditions	Yield
With ammonia; water at 200℃;

2-chloro-1,4-bis-(trichloromethyl)-benzene (10388-10-0) → 2,5-bis(trifluoromethyl)aniline (328-93-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: SbCl5; HF / 70 - 80 °C 2: water; ammonia / 200 °C View Scheme

N-[3-(trifluoromethyl)phenyl]-2-pyridinecarboxamide (61350-01-4) → 2,5-bis(trifluoromethyl)aniline (328-93-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(I) bromide; dipotassium peroxodisulfate / acetonitrile / 12 h / 50 °C 2: hydrogenchloride / ethanol / 12 h / 100 °C View Scheme

C14H8F6N2O → 2,5-bis(trifluoromethyl)aniline (328-93-8)

Conditions	Yield
With hydrogenchloride In ethanol at 100℃; for 12h;

2,5-bis(trifluoromethyl)aniline (328-93-8) + salicylaldehyde (90-02-8) → (E)-2-(((2,5-bis(trifluoromethyl)phenyl)imino)methyl)phenol

Conditions	Yield
With formic acid In ethanol for 6h; Reflux;	96%

2,5-bis(trifluoromethyl)aniline (328-93-8) + (S)-3-keto-4-aza-5α-androstane-1-ene-17β-formyl chloride → (5α,17β)-N-(2,5-bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide

Conditions	Yield
With pyridine In toluene at 90℃; for 3h; Temperature;	95.2%

2,5-bis(trifluoromethyl)aniline (328-93-8) + 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester (73671-92-8) → (5α,17β)-N-[2,5-bis(trifluoromethyl)-phenyl]-3-oxo-4-aza-5-androstane-17-carboxamide (164656-22-8)

Conditions	Yield
Stage #1: 3-oxo-4-aza-5α-androstane-17β-carboxylic acid methyl ester With boron tribromide In dichloromethane at 25℃; for 0.333333h; Stage #2: 2,5-bis(trifluoromethyl)aniline In dichloromethane at 50℃;	93%

2,5-bis(trifluoromethyl)aniline (328-93-8) + androst-4-en-3-one-17β-carboxylic acid (302-97-6) → N-(2',5'-Bistrifluoromethylphenyl)-3-oxo-androst-4-ene-17β-carboxamide (164656-19-3)

Conditions	Yield
Stage #1: 2,5-bis(trifluoromethyl)aniline With methylmagnesium chloride In tetrahydrofuran; toluene at 20℃; Large scale; Stage #2: androst-4-en-3-one-17β-carboxylic acid With dmap; thionyl chloride; potassium carbonate In toluene at 20 - 30℃; for 3h; Large scale; Stage #3: In tetrahydrofuran; toluene at 50 - 55℃; for 8h; Large scale;	90.14%

3-allyl-2-methylthio-6-trifluoromethyl-4(3H)-pyrimidinone (216016-30-7) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → 3-allyl-2-{2,5-bis(trifluoromethyl)phenyl}amino-6-trifluoromethyl-4(3H)pyrimidinone (216240-50-5)

Conditions	Yield
With ammonium chloride In N,N-dimethyl-formamide	89%

2,5-bis(trifluoromethyl)aniline (328-93-8) + 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid (104239-97-6) → dutasteride

Conditions	Yield
Stage #1: 2,5-bis(trifluoromethyl)aniline With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 105 - 110℃; Stage #2: 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid In N,N-dimethyl-formamide	88.21%
Stage #1: 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid With pyridine; thionyl chloride In toluene at 0 - 18℃; for 4.66667h; Stage #2: 2,5-bis(trifluoromethyl)aniline In toluene at 110℃; for 20h;
Stage #1: 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid With pyridine; thionyl chloride In toluene at 0 - 18℃; for 5.6h; Stage #2: 2,5-bis(trifluoromethyl)aniline; dmap In toluene at 110℃; for 20h; Product distribution / selectivity;

2,5-bis(trifluoromethyl)aniline (328-93-8) + acetophenone (98-86-2) → (2,5-Bis-trifluoromethyl-phenyl)-[1-phenyl-eth-(E)-ylidene]-amine

Conditions	Yield
	85%

2-furyl(phenyl)methanol (60907-91-7, 113565-51-8, 132435-41-7, 4484-57-5) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → (4R,5S)-4-((2,5-bis(trifluoromethyl)phenyl)amino)-5-phenylcyclopent-2-enone

Conditions	Yield
Stage #1: 2,5-bis(trifluoromethyl)aniline With (S)-6,6’-bis(1-pyranyl)-1,1'-spirobiindane-7,7’-diyl hydrogenphosphate In 1,2-dichloro-ethane at 0℃; for 0.5h; Stage #2: 2-furyl(phenyl)methanol In 1,2-dichloro-ethane at 20℃; for 22h;	83%

2,5-bis(trifluoromethyl)aniline (328-93-8) + C23H33NO4 → dutasteride

Conditions	Yield
In tetrahydrofuran for 3h;	82.2%

2,5-bis(trifluoromethyl)aniline (328-93-8) + C23H33NO4 → dutasteride

Conditions	Yield
In dichloromethane at 20℃; for 3h;	81.9%

2,5-bis(trifluoromethyl)aniline (328-93-8) + C21H29NO4 → dutasteride

Conditions	Yield
In 1,4-dioxane at 20℃; for 6h;	81.2%

2,5-bis(trifluoromethyl)aniline (328-93-8) + C22H31NO4 → dutasteride

Conditions	Yield
With pyridine at 20℃; for 3h;	80.5%

(5α,17β)-3-oxo-4-aza-5-androstane-17-(ethoxycarbonyl)-carboxylate (1416955-19-5) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → (5α,17β)-N-[2,5-bis(trifluoromethyl)-phenyl]-3-oxo-4-aza-5-androstane-17-carboxamide (164656-22-8)

Conditions	Yield
With boron trifluoride diethyl etherate In acetonitrile at -10 - -8℃; for 4h;	80%

2,5-bis(trifluoromethyl)aniline (328-93-8) + methyl 3-oxo-4-aza-5α-androst-1-ene-17β-carboxylate (103335-41-7) → dutasteride

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 2-methyltetrahydrofuran at 80℃; for 12h;	78.23%

formaldehyd (50-00-0) + 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazole-2(3H)-thione + 2,5-bis(trifluoromethyl)aniline (328-93-8) → 3-(((2,5-bis(trifluoromethyl)phenyl)amino)methyl)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazole-2(3H)-thione

Conditions	Yield
In ethanol at 20℃; for 3h;	77%

2,5-bis(trifluoromethyl)aniline (328-93-8) + 1-(2-fluoro-4-methoxyphenyl)-1-ethanone (74457-86-6) → N-[2-(dimethylamino)ethyl]-7-trifluoromethyl-2-[(2-fluoro-4-methoxy)phenyl]quinolin-4-amine

Conditions	Yield
2,5-bis(trifluoromethyl)aniline; 1-(2-fluoro-4-methoxyphenyl)-1-ethanone With toluene-4-sulfonic acid In xylene Heating; Further stages.;	75%

2,5-bis(trifluoromethyl)aniline (328-93-8) + cyanoacetic acid (372-09-8) → N-[2,5-bis(trifluoromethyl)phenyl]cyanoacetamide (1140412-67-4)

Conditions	Yield
With diisopropyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 48h; Inert atmosphere;	75%
Stage #1: 2,5-bis(trifluoromethyl)aniline; cyanoacetic acid In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: With diisopropyl-carbodiimide In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;

2,5-bis(trifluoromethyl)aniline (328-93-8) + 1-(4-fluorophenyl)ethanone (403-42-9) → N-[2-(dimethylamino)ethyl]-7-trifluoromethyl-2-[(4-fluoro)phenyl]quinolin-4-amine

Conditions	Yield
2,5-bis(trifluoromethyl)aniline; 1-(4-fluorophenyl)ethanone With toluene-4-sulfonic acid In xylene Heating; Further stages.;	74%

2,5-bis(trifluoromethyl)aniline (328-93-8) → 1-azido-2,5-bis(trifluoromethyl)benzene

Conditions	Yield
Stage #1: 2,5-bis(trifluoromethyl)aniline With hydrogenchloride In water for 0.0833333h; Stage #2: With sodium nitrite In water at 0℃; for 2h; Stage #3: With sodium azide In water at 0 - 20℃; for 2h;	74%

(5α,17β)-3-oxo-4-azaandrost-1-ene-17-(ethoxycarbonyl)carboxylate (1416955-22-0) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → dutasteride

Conditions	Yield
With boron trifluoride diethyl etherate In acetonitrile at -15 - -8℃; for 4h;	73.8%

4-fluorobenzonitrile (1194-02-1) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → 4,4'-(2,5-bis(trifluoromethyl)phenylazanediyl)dibenzonitrile

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 165℃;	73%

2'-Fluoroacetophenone (445-27-2) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → N-<1-(2-fluorophenyl)ethylidene>-2,5-bis(trifluoromethyl)aniline (147218-04-0)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 15h; Heating;	70%

1-(4-trifluoromethylphenyl)ethanone (709-63-7) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → 2,5-bis(trifluoromethyl)-N-<1-<4-(trifluoromethyl)phenyl>ethylidene>aniline (147218-05-1)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 15h; Heating;	69%

2,5-bis(trifluoromethyl)aniline (328-93-8) + 1-(3-fluorophenyl)ethanone (455-36-7) → N-[2-(dimethylamino)ethyl]-7-trifluoromethyl-2-[(3-fluoro)phenyl]quinolin-4-amine

Conditions	Yield
2,5-bis(trifluoromethyl)aniline; 1-(3-fluorophenyl)ethanone With toluene-4-sulfonic acid In xylene Heating; Further stages.;	66%

1,1-Diphenylmethanol (91-01-0) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → N-benzhydryl-2,5-bis(trifluoromethyl)aniline

Conditions	Yield
With C15H25Cl2N3NiO3; potassium tert-butylate In octane at 140℃; for 12h; Schlenk technique;	57%

2,5-bis(trifluoromethyl)aniline (328-93-8) + 3-oxo-4-aza-5α-androstane-17β-carboxylic acid (103335-55-3) → (5α,17β)-N-[2,5-bis(trifluoromethyl)-phenyl]-3-oxo-4-aza-5-androstane-17-carboxamide (164656-22-8)

Conditions	Yield
Stage #1: 3-oxo-4-aza-5α-androstane-17β-carboxylic acid With pyridine; thionyl chloride In toluene at 2 - 20℃; for 2.5h; Stage #2: 2,5-bis(trifluoromethyl)aniline In toluene at 20℃; for 192h;	56%

2-methylthio-3-propyl-6-trifluoromethyl-4(3H)-pyrimidinone (216240-56-1) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-propyl-6-trifluoromethyl-4(3H)-pyrimidinone (216240-34-5)

Conditions	Yield
In N,N-dimethyl-formamide	54.5%

NH-pyrazole (288-13-1) + 2,5-bis(trifluoromethyl)aniline (328-93-8) → 2-(tri(1H-pyrazol-1-yl)methyl)-5-(trifluoromethyl)aniline

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 1h; Reflux;	53%

2,5-bis(trifluoromethyl)aniline (328-93-8) + 6-Hydroxy-2-naphthoic acid (16712-64-4) → N-[2,5-bis(trifluoromethyl)phenyl]-6-hydroxynaphthalene-2-carboxamide

Conditions	Yield
With phosphorus trichloride In chlorobenzene at 130℃; for 0.666667h; Microwave irradiation;	49%

Upstream product

• 328936-56-7 8-Azatricyclo[6.2.0.02,4]decane(9CI) 
• 32893-59-7 3-Cyclohexene-1-carbonyl chloride, 2-methyl- (8CI) 
• 3289-35-8 6-CHLOROCYTOSINE 
• 328933-67-1 Bazedoxifene Bis-β-D-Glucuronide 
• 328933-65-9 BenzeneMethanol, 4-[2-(hexahydro-1H-azepin-1-yl)ethoxy]- (hydrochloride) 
• 328933-64-8 Bazedoxifene 4’-β-D-Glucuronide 
• 328933-56-8 Bazedoxifene 5-β-D-Glucuronide 
• 328933-47-7 4-(2-Bromopropanoyl)phenyl 2,2-dimethylpropanoate 
• 328932-61-2 2-Fluoro-beta-oxo-4-pyridinepropanoicacidethylester 
• 328931-59-5 N-benzhydryl-3-methoxybenzamide 
• 328931-57-3 3-bromo-N-(2-phenylethyl)benzamide 
• 328931-56-2 BenzaMide, 4-broMo-N-(2-phenylethyl)- 
• 328929-91-5 N'-{2-hydroxy-3-nitrobenzylidene}-2-(5-phenyl-2H-tetraazol-2-yl)acetohydrazide 
• 328929-90-4 N'-{2-hydroxy-5-nitrobenzylidene}-2-(5-phenyl-2H-tetraazol-2-yl)acetohydrazide 

Downstream Products

• 3289-38-1 4-Amino-6-chloro-2-diethylaminopyrimidine 
• 328938-52-9 N'-[3-(1,3-benzodioxol-5-yl)-1-methyl-2-propenylidene]-2-(2-methylphenoxy)acetohydrazide 
• 328938-89-2 N'-(5-bromo-3-chloro-2-hydroxybenzylidene)-2-(3-methylphenoxy)acetohydrazide 
• 328939-06-6 2-(3-methylphenoxy)-N'-[4-(methylsulfanyl)benzylidene]acetohydrazide 
• 3289-39-2 6-CHLORO-2-(1-PYRROLIDINYL)-4-PYRIMIDINAMINE 
• 328939-30-6 N'-(5-chloro-2-hydroxy-3-methoxybenzylidene)-2-(4-methylphenoxy)acetohydrazide 
• 328940-33-6 2-chloro-N-{1-({2-[(2-chloro-3-quinolinyl)methylene]hydrazino}carbonyl)-2-[4-(dimethylamino)phenyl]vinyl}benzamide 
• 32894-07-8 BENZYL THIOACETIMIDATE HYDROCHLORIDE 
• 328942-25-2 2-bromo-6-methoxy-4-(4-oxo-1,2,3,4,5,6,7,8-octahydro[1]benzothieno[2,3-d]pyrimidin-2-yl)phenyl 4-methylbenzoate 
• 328943-01-7 N-[4-(5,6-dimethyl-1,3-benzoxazol-2-yl)-3-hydroxyphenyl]-4-iodobenzamide 
• 3289-43-8 Pyrimidine, 4-amino-6-ethoxy- (7CI,8CI) 
• 328943-97-1 N-[4-(5,7-dimethyl-1,3-benzoxazol-2-yl)-3-hydroxyphenyl]-2,5-diiodobenzamide 
• 328944-38-3 N-[4-hydroxy-3-(5-methyl-1,3-benzoxazol-2-yl)phenyl]-3,4,5-trimethoxybenzamide 
• 328944-70-3 N-[3-(5-ethyl-1,3-benzoxazol-2-yl)-4-hydroxyphenyl]acetamide 

Recommend Products

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• 216240-50-5  3-allyl-2-{2,5-bis(trifluoromethyl)phenyl}amino-6-trifluoromethyl-4(3H)pyrimidinone 
• 216016-30-7  3-allyl-2-methylthio-6-trifluoromethyl-4(3H)-pyrimidinone 
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• 216240-55-0  3-isobutyl-2-methylsulfonyl-6-trifluoromethyl-4(3H)-pyrimidinone 
• 216240-30-1  2-{2,5-bis(trifluoromethyl)phenyl}amino-3-methyl-6-trifluoromethyl-4(3H)-pyrimidinone 
• 216016-34-1  3-methyl-2-methylsulfonyl-6-trifluoromethyl-4(3H)-pyrimidinone 
• 216240-34-5  2-{2,5-bis(trifluoromethyl)phenyl}amino-3-propyl-6-trifluoromethyl-4(3H)-pyrimidinone 
• 216240-56-1  2-methylthio-3-propyl-6-trifluoromethyl-4(3H)-pyrimidinone 
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