2-Chloro-6-fluoroaniline supplier

Name
2-Chloro-6-fluoroaniline
EINECS 206-657-1
CAS No. 363-51-9
Density 1.349 g/cm³
Solubility Insoluble in water
Melting Point 32 °C
Formula C₆H₅ClFN
Boiling Point 182.9 °C at 760 mmHg
Molecular Weight 145.564
Flash Point 64.4 °C
Transport Information UN 2811
Appearance Clear pale yellow liquid
Safety 26-36/37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols R20/21/22:; R36/37/38:;
Synonyms Aniline,2-chloro-6-fluoro- (8CI);2-Chloro-6-fluorophenylamine;2-Fluoro-6-chloroaniline;2-chloro-6-fluoroaniline;2-Chloro-6-fluoro-phenylamine;
PSA 26.02000
LogP 2.64250

Synthetic route

: 90493-88-2
2'-Chloro-6'-fluorobenzanilide

: 363-51-9
2-chloro-6-fluoroaniline

Conditions

Conditions	Yield
With sulfuric acid for 3h; Heating;	71%

: 434-75-3
2-chloro-6-fluorobenzoic acid

: 363-51-9
2-chloro-6-fluoroaniline

Conditions

Conditions	Yield
With sodium azide; sulfuric acid
With hydrogenchloride; sodium hydroxide; sulfuric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform

: 2369-21-3
N-(2-fluorophenyl)hydroxylamine

: 363-51-9
2-chloro-6-fluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaHCO3 / diethyl ether; H2O / 1 h / T < 5 deg C; or in benzene 2: 75 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 3: 71 percent / 70percent H2SO4 / 3 h / Heating View Scheme

: 90493-82-6
N-(2-Fluorophenyl)benzohydroxamic acid

: 363-51-9
2-chloro-6-fluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 2: 71 percent / 70percent H2SO4 / 3 h / Heating View Scheme

: 1493-27-2
ortho-nitrofluorobenzene

: 363-51-9
2-chloro-6-fluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Zinc dust, NH4Cl (or NH4Br) 2: NaHCO3 / diethyl ether; H2O / 1 h / T < 5 deg C; or in benzene 3: 75 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 4: 71 percent / 70percent H2SO4 / 3 h / Heating View Scheme

: 363-51-9
2-chloro-6-fluoroaniline

: 213211-69-9
(2-ethoxyphenyl)boronic acid

: C14H14FNO

Conditions

Conditions	Yield
With palladium diacetate; 2-dicyclohexylphosphino-2',6'-dimethylbiphenyl In toluene at 100℃; for 3h;	99%

: 363-51-9
2-chloro-6-fluoroaniline

: 62-23-7
4-nitro-benzoic acid

: C13H8ClFN2O3

Conditions

Conditions	Yield
With covalent organic polymer from p-aminophenol and cyanuric chloride In 1,4-dioxane at 20℃; for 0.666667h;	94%

: 623-03-0
4-Cyanochlorobenzene

: 363-51-9
2-chloro-6-fluoroaniline

: 817621-48-0
4-(2-chloro-6-fluorophenylamino)benzonitrile

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluoroaniline With sodium hydride In N,N-dimethyl-formamide at 0 - 4℃; for 1h; Stage #2: 4-Cyanochlorobenzene In N,N-dimethyl-formamide at 50 - 55℃; for 20h;	91%

: 106-38-7
para-bromotoluene

: 363-51-9
2-chloro-6-fluoroaniline

: 332903-74-9
N-(2-chloro-6-fluoro-phenyl)-4-methylaniline

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In toluene at 110℃; for 14h; Buchwald-Hartwig coupling;	90%

: 446-48-0
o-fluorobenzyl bromide

: 363-51-9
2-chloro-6-fluoroaniline

: 140-89-6
potassium ethyl xanthogenate

: 4-fluoro-2-(2-fluoro-benzylsulfanyl)-benzothiazole

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluoroaniline; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 120℃; for 0.25h; microwave irradiation; Stage #2: o-fluorobenzyl bromide In N,N-dimethyl-formamide at 90℃; for 0.1h; microwave irradiation;	90%

...Expand

: 363-51-9
2-chloro-6-fluoroaniline

: 4-bromo-2-chloro-6-fluorobenzeneamine

Conditions

Conditions	Yield
With bromine In chloroform	88%
With bromine In chloroform at 20℃; for 2h;	83%

: 363-51-9
2-chloro-6-fluoroaniline

: 108-24-7
acetic anhydride

: 343-73-7
N-(2-chloro-6-fluorophenyl)acetamide

Conditions

Conditions	Yield
With acetic acid at 90℃; for 2h;	88%
With acetic acid at 90℃; for 1h;
Stage #1: 2-chloro-6-fluoroaniline; acetic anhydride With acetic acid at 90℃; for 1h; Stage #2: With sodium hydroxide In water
With acetic acid at 90℃; for 2h;
With acetic acid at 90℃; for 2h;

: 363-51-9
2-chloro-6-fluoroaniline

: 4-bromo-2-butoxy-5-fluorobenzoic acid

: 4-bromo-2-butoxy-N-(2-chloro-6-fluorophenyl)-5-fluorobenzamide

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-butoxy-5-fluorobenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide for 1h; Stage #2: 2-chloro-6-fluoroaniline With triethylamine In dichloromethane for 1h;	88%

: 363-51-9
2-chloro-6-fluoroaniline

: 85118-00-9
2,6-Difluorobenzyl bromide

: 140-89-6
potassium ethyl xanthogenate

: 2-(2,6-difluoro-benzylsulfanyl)-4-fluoro-benzothiazole

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluoroaniline; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 120℃; for 0.25h; microwave irradiation; Stage #2: 2,6-Difluorobenzyl bromide In N,N-dimethyl-formamide at 90℃; for 0.1h; microwave irradiation;	86%

...Expand

: 363-51-9
2-chloro-6-fluoroaniline

: 140-89-6
potassium ethyl xanthogenate

: 85118-01-0
alpha-bromo-3,4-difluorotoluene

: 2-(3,4-difluoro-benzylsulfanyl)-4-fluoro-benzothiazole

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluoroaniline; potassium ethyl xanthogenate In N,N-dimethyl-formamide at 120℃; for 0.25h; microwave irradiation; Stage #2: alpha-bromo-3,4-difluorotoluene In N,N-dimethyl-formamide at 90℃; for 0.1h; microwave irradiation;	86%

...Expand

: 363-51-9
2-chloro-6-fluoroaniline

: isopropyl 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-(2-ethoxyvinyl)-5-fluoronicotinate

: 2-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-(2-chloro-6-fluorophenyl)-3-fluoro-1,6-naphthyridin-5(6H)-one

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluoroaniline With trimethylaluminum In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: isopropyl 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-(2-ethoxyvinyl)-5-fluoronicotinate In dichloromethane; toluene at 20 - 50℃;	86%

: 363-51-9
2-chloro-6-fluoroaniline

: 4-bromo-5-fluoro-2-{[(2S)-1,1,1-trifluoropropan-2-yl]oxy}benzoyl chloride

: 4-bromo-N-(2-chloro-6-fluorophenyl)-5-fluoro-2-{[(2S)-1,1,1-trifluoropropan-2-yl]oxy}benzamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	84.5%
With triethylamine In dichloromethane at 20℃; for 0.5h;	84.5%
With triethylamine In dichloromethane at 20℃; for 0.5h;	39.3 g
With triethylamine In dichloromethane at 25℃; for 16.5h;

: 363-51-9
2-chloro-6-fluoroaniline

: 88419-56-1
2,4,5-trifluorobenzoyl chloride

: N-(2-chloro-6-fluorophenyl)-2,4,5-trifluorobenzamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; for 16h; Inert atmosphere;	83.43%

: 556-96-7
5-bromo-1,3-xylene

: 363-51-9
2-chloro-6-fluoroaniline

: 1041144-10-8
(2-chloro-6-fluorophenyl)(3,5-dimethylphenyl)amine

Conditions

Conditions	Yield
With sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate In toluene for 18h; Heating;	83%

: 363-51-9
2-chloro-6-fluoroaniline

: 76-05-1
trifluoroacetic acid

: (Z)-N-(2-chloro-6-fluorophenyl)-2,2,2-trifluoroacetimidoyl chloride

Conditions

Conditions	Yield
Stage #1: trifluoroacetic acid With tetrachloromethane; triethylamine; triphenylphosphine at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloro-6-fluoroaniline With tetrachloromethane at 80℃; for 3.16667h; Inert atmosphere;	82%

: 363-51-9
2-chloro-6-fluoroaniline

: 5-((benzyloxy)methyl)-4-ethyl-2-(7-fluoro-4-isopropyl-1-oxo-1H-isochromen-6-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one

: 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-(2-chloro-6-fluorophenyl)-7-fluoro-4-isopropylisoquinolin-1(2H)-one

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluoroaniline With trimethylaluminum In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 5-((benzyloxy)methyl)-4-ethyl-2-(7-fluoro-4-isopropyl-1-oxo-1H-isochromen-6-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one In dichloromethane at 20℃; Inert atmosphere;	82%

: 611-35-8
4-chloroquinoline

: 363-51-9
2-chloro-6-fluoroaniline

: 1111618-76-8
10-fluoro-11H-indolo[3,2-c]quinoline

Conditions

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In 1,4-dioxane; toluene at 125℃; for 24h; Inert atmosphere;	80%

: 363-51-9
2-chloro-6-fluoroaniline

: 355836-08-7
2-methoxy-4,6-dimethylbenzeneboronic acid

: C15H16FNO

Conditions

Conditions	Yield
With palladium diacetate; 2-dicyclohexylphosphino-2',6'-dimethylbiphenyl In toluene at 100℃; for 1.5h;	80%

: 363-51-9
2-chloro-6-fluoroaniline

: isopropyl 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-chloro-5-fluoronicotinate

: 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)-2-chloro-N-(2-chloro-6-fluorophenyl)-5-fluoronicotinamide

Conditions

Conditions	Yield
With trimethylaluminium In tetrahydrofuran; dichloromethane at 0 - 60℃; for 18.5h; Inert atmosphere;	79%

: 363-51-9
2-chloro-6-fluoroaniline

: 69887-12-3
(1-adamantyl)methyl isocyanate

: 1-(adamantan-1-ylmethyl)-3-(6-chloro-2-fluorophenyl)urea

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 12h;	79%

: 363-51-9
2-chloro-6-fluoroaniline

: 4-bromo-5-fluoro-2-[(2S)-pentan-2-yloxy]benzoic acid

: 4-bromo-N-(2-chloro-6-fluorophenyl)-5-fluoro-2-[(2S)-pentan-2-yloxy]benzamide

Conditions

Conditions	Yield
Stage #1: 4-bromo-5-fluoro-2-[(2S)-pentan-2-yloxy]benzoic acid With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-6-fluoroaniline With pyridine In dichloromethane at 20℃; for 1h;	78%

: 107-86-8
3,3-dimethyl acrylaldehyde

: 363-51-9
2-chloro-6-fluoroaniline

: N-(2-chloro-6-fluorophenyl)-3-methylbut-2-en-1-imine

Conditions

Conditions	Yield
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 25℃; for 5h; Inert atmosphere;	78%
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 25℃; for 5h;

: 363-51-9
2-chloro-6-fluoroaniline

: (S)-7-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluoro-1-(pentan-2-yl)-1H-benzo[d][1,3]oxazine-2,4-dione

: (S)-4-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol- 1-yl)-N-(2-chloro-6-fluorophenyl)-5-fluoro-2-(pentan-2-ylamino)benzamide

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-fluoroaniline With trimethylaluminium In toluene at 15℃; for 0.5h; Inert atmosphere; Stage #2: (S)-7-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-6-fluoro-1-(pentan-2-yl)-1H-benzo[d][1,3]oxazine-2,4-dione In toluene at 50℃; for 16h; Inert atmosphere;	77%

: 363-51-9
2-chloro-6-fluoroaniline

: 817621-74-2
(5-methyl-2-oxo-cyclohexylidene)acetic acid ethyl ester

: 817621-77-5
1-(2-chloro-6-fluoro-phenyl)-5-methyl-1,4,5,6-tetrahydro-indol-2-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Heating;	76%

: 363-51-9
2-chloro-6-fluoroaniline

: 2972-52-3
2,4-dichloropyrimidine-5-carbonyl chloride

: 2,4-dichloro-N-(2-chloro-6-fluorophenyl)pyrimidine-5-carboxamide

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 15h; Inert atmosphere;	75%
In tetrahydrofuran at 20℃; for 15h; Inert atmosphere;	75%

: 3592-19-6
3-methyl-2-pentenal

: 363-51-9
2-chloro-6-fluoroaniline

: 6-(3-((benzyloxy)methyl)-4-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-(2-chloro-6-fluorophenyl)-4-(3,3,3-trifluoroprop-1-en-2-yl)isoquinolin-1(2H)-one

Conditions

Conditions	Yield
With titanium tetrachloride; triethylamine In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	70%

: 3592-19-6
3-methyl-2-pentenal

: 363-51-9
2-chloro-6-fluoroaniline

: 2-chloro-6-fluoro-N-(3-methylpent-2-en-1-ylidene)aniline

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	69.87%

: 363-51-9
2-chloro-6-fluoroaniline

: 76-05-1
trifluoroacetic acid

: N-(2-chloro-6-hydroxyphenyl)-2,2,2-trifluoroacetamide

Conditions

Conditions	Yield
With Oxone In 1,4-dioxane at 90℃; Schlenk technique; Inert atmosphere; chemoselective reaction;	65%

: 363-51-9
2-chloro-6-fluoroaniline

: 103323-61-1
1-bromo-2,5-dimethoxy-3,4-dimethylbenzene

: 1432270-58-0
1-fluoro-5,8-dimethoxy-6,7-dimethyl-9H-carbazole

Conditions

Conditions	Yield
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 160℃; for 3h; Buchwald-Hartwig Coupling; Inert atmosphere; Microwave irradiation;	62%

2-Chloro-6-fluoroaniline Specification

The Benzenamine, 2-chloro-6-fluoro-, with the CAS registry number 363-51-9 and EINECS registry number 206-657-1, has the systematic name and IUPAC name of 2-chloro-6-fluoroaniline. It belongs to the product categories of Aniline and Miscellaneous. And the molecular formula of the chemical is C₆H₅ClFN.

The characteristics of Benzenamine, 2-chloro-6-fluoro- are as followings: (1)ACD/LogP: 1.81; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.8; (4)ACD/LogD (pH 7.4): 1.8; (5)ACD/BCF (pH 5.5): 13.86; (6)ACD/BCF (pH 7.4): 13.86; (7)ACD/KOC (pH 5.5): 228.48; (8)ACD/KOC (pH 7.4): 228.5; (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: 1.569; (14)Molar Refractivity: 35.37 cm³; (15)Molar Volume: 107.8 cm³; (16)Polarizability: 14.02×10^-24cm³; (17)Surface Tension: 42.9 dyne/cm; (18)Density: 1.349 g/cm³; (19)Flash Point: 64.4 °C; (20)Enthalpy of Vaporization: 41.92 kJ/mol; (21)Boiling Point: 182.9 °C at 760 mmHg; (22)Vapour Pressure: 0.79 mmHg at 25°C.

Preparation of Benzenamine, 2-chloro-6-fluoro-: This chemical can be prepared by N-(2-chloro-6-fluoro-phenyl)-benzamide. The reaction will need reagent 70% H₂SO₄. The reaction time is 3 hours with heating, and the yield is about 71%.

Uses of Benzenamine, 2-chloro-6-fluoro-: It can be used to produce 1-chloro-3-fluoro-2-nitrobenzene. This reaction will need reagent aq. fluoboric acid, sodium nitrite, aq. sodium nitrite and copper. And the yield is about 44%.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin, and it is also harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Fc1cccc(Cl)c1N
(2)InChI: InChI=1/C6H5ClFN/c7-4-2-1-3-5(8)6(4)9/h1-3H,9H2
(3)InChIKey: ZJLAWMDJTMMTQB-UHFFFAOYAF

Product Name

2-Chloro-6-fluoroaniline

Synthetic route

2-Chloro-6-fluoroaniline Specification

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