3,4-Difluoroaniline supplier

Name
3,4-Difluoroaniline
EINECS 223-381-7
CAS No. 3863-11-4
Article Data22
CAS DataBase
Density 1.289 g/cm³
Solubility slightly soluble in water
Melting Point 22 °C
Formula C₆H₅F₂N
Boiling Point 205 °C at 760 mmHg
Molecular Weight 129.109
Flash Point 85 °C
Transport Information UN 2941 6.1/PG 3
Appearance clear yellow to straw liquid after melting
Safety 26-36-36/37/39
Risk Codes 22-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 4-12-00-01113 (Beilstein Handbook Reference);Aniline, 3,4-difluoro- (6CI);3,4-Difluorobenzenamine;Benzenamine, 3,4-difluoro-;3,4-Difluoro-phenylamine;
PSA 26.02000
LogP 2.12820

Synthetic route

: 1321455-41-7
1-tert-butyl-N-(3,4-difluorophenyl)-1,1-dimethylsilanamine

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
With silica gel In ethanol; water at 20℃; for 2h;	100%

: 369-34-6
3,4-difluoronitrobenzene

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
With sodium tetrahydroborate; water at 0 - 20℃; for 4h;	95%
With palladium on activated charcoal; hydrogen In toluene at 25 - 35℃; under 1500.15 - 4500.45 Torr; Autoclave;	93.8%
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation;	82%

: 369-34-6
3,4-difluoronitrobenzene

: 7439-89-6
iron

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
With hydrogenchloride In methanol	86%

: 250372-11-3
(3,4-difluoro-phenyl)-carbamic acid benzyl ester

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction;	83%

: 85118-04-3
(3,4-difluoro-phenyl)-amide

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
With potassium hydroxide; bromine In water at 0 - 88℃; for 1h;	65%

: 371-40-4
4-fluoroaniline

A: 367-25-9
2,4-difluorophenylamine

B: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
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

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: F2; TfOH / 20 °C 2: F2; TfOH / 20 °C View Scheme

: 367-11-3
ortho-difluorobenzene

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3, H2SO4 2: Fe, HCl View Scheme

: 5216-25-1
4-chlorotrichloromethylbenzene

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: chlorosulfuric acid / 1) 120 deg C, 1 h 2) 150 deg C, 2 h 2: 94 percent / SOCl2 / benzene / 8 h / Heating 3: 71 percent / KF, Ph4PBr / acetonitrile / 16 h / Heating 4: 45 percent / KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 270 Torr 5: 82 percent / 25 aq. NH3 / H2O / 2 h 6: 65 percent / Br2, aq. KOH / H2O / 1 h / 0 - 88 °C View Scheme

: 2494-79-3
4-chloro-3-(chlorosulfonyl)benzoic acid

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 94 percent / SOCl2 / benzene / 8 h / Heating 2: 71 percent / KF, Ph4PBr / acetonitrile / 16 h / Heating 3: 45 percent / KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 270 Torr 4: 82 percent / 25 aq. NH3 / H2O / 2 h 5: 65 percent / Br2, aq. KOH / H2O / 1 h / 0 - 88 °C View Scheme

: 62574-66-7
3-chlorosulfonyl-4-chlorobenzoyl chloride

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 71 percent / KF, Ph4PBr / acetonitrile / 16 h / Heating 2: 45 percent / KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 270 Torr 3: 82 percent / 25 aq. NH3 / H2O / 2 h 4: 65 percent / Br2, aq. KOH / H2O / 1 h / 0 - 88 °C View Scheme

: 127269-25-4
3,4-difluorobenzoyl fluoride

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / 25 aq. NH3 / H2O / 2 h 2: 65 percent / Br2, aq. KOH / H2O / 1 h / 0 - 88 °C View Scheme

: 127986-80-5
4-fluoro-3-(fluorosulfonyl)benzoyl fluoride

: 3863-11-4
3,4-difluoroaniline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 45 percent / KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 270 Torr 2: 82 percent / 25 aq. NH3 / H2O / 2 h 3: 65 percent / Br2, aq. KOH / H2O / 1 h / 0 - 88 °C View Scheme

: 107-31-3
Methyl formate

: 3863-11-4
3,4-difluoroaniline

: 138563-55-0
3,4-di-fluorophenyl formamide

Conditions

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃;	100%

: 10310-21-1
2-Amino-6-chloropurin

: 3863-11-4
3,4-difluoroaniline

: N6-(3,4-difluorophenyl)-9H-purine-2,6-diamine

Conditions

Conditions	Yield
at 130℃; for 0.0833333h; Irradiation;	100%

: ethyl 3-fluoro-4-((2-(hydroxymethyl)azetidin-1-yl)sulfonyl)-1-methyl-1H-pyrrole-2-carboxylate

: 3863-11-4
3,4-difluoroaniline

: N-(3,4-difluorophenyl)-3-fluoro-4-((2-(hydroxymethyl)azetidin-1-yl)sulfonyl)-1-methyl-1H-pyrrole-2-carboxamide

Conditions

Conditions	Yield
With ammonium chloride; lithium hexamethyldisilazane In tetrahydrofuran; dichloromethane at 20℃;	100%

: 108-24-7
acetic anhydride

: 3863-11-4
3,4-difluoroaniline

: 458-11-7
3,4-difluoroacetanilide

Conditions

Conditions	Yield
In 1,4-dioxane at 0℃; for 1h; Inert atmosphere; Schlenk technique;	99%
at 20℃; for 0.5h;	95%
With triethylamine In dichloromethane at 20℃; for 1h;	91%

: 762-42-5
dimethyl acetylenedicarboxylate

: 3863-11-4
3,4-difluoroaniline

: 251986-50-2
methyl 3-carbomethoxy-3-(3',4'-difluorophenyl)amino-2-propenoate

Conditions

Conditions	Yield
In methanol at 20℃; Addition;	99%

: 3282-30-2
pivaloyl chloride

: 3863-11-4
3,4-difluoroaniline

: 205756-46-3
N-pivaloyl-3,4-difluoroaniline

Conditions

Conditions	Yield
With triethylamine at 0 - 20℃; for 1h;	99%
With triethylamine In benzene at 0℃;	98%
With TEA In dichloromethane at 0 - 25℃; for 3h; Acylation;
With triethylamine In dichloromethane at 0 - 20℃; for 1h;
With triethylamine In toluene at 20℃;

: 7623-09-8
2-chloropropionyl chloride

: 3863-11-4
3,4-difluoroaniline

: 868771-20-4
2-chloro-N-(3,4-difluoro-phenyl)-propionamide

Conditions

Conditions	Yield
In toluene at 120℃; for 1h;	99%
In toluene Heating;

: 1117-37-9
ethyl (E)-3-(dimethylamino)acrylate

: 3863-11-4
3,4-difluoroaniline

: ethyl 2-[2-(3,4-difluorophenyl)hydrazinylidene]-3-oxopropanoate

Conditions

Conditions	Yield
Stage #1: 3,4-difluoroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.0833333h; Stage #2: ethyl (E)-3-(dimethylamino)acrylate With potassium acetate In ethanol; water at 0 - 20℃; for 14h;	99%

: 160893-07-2
2-chloro-5-methoxyquinoline

: 3863-11-4
3,4-difluoroaniline

: N-(3,4-difluorophenyl)-5-methoxyquinolin-2-amine

Conditions

Conditions	Yield
In neat (no solvent) at 160℃;	98%
In neat (no solvent) at 160℃;

: 91-21-4
1,2,3,4-tetrahydroisoquinoline

: 3863-11-4
3,4-difluoroaniline

: C15H15FN2

Conditions

Conditions	Yield
With silver(I) hexafluorophosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; C17H21O3P In tetrahydrofuran at 120℃; for 20h; Inert atmosphere; Molecular sieve;	98%

: 111-49-9
hexamethylene imine

: 3863-11-4
3,4-difluoroaniline

: C12H17FN2

Conditions

Conditions	Yield
With silver(I) hexafluorophosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; C17H21O3P In tetrahydrofuran at 120℃; for 20h; Inert atmosphere; Molecular sieve;	98%
With C17H21O3P; [Ru(cymene)]PF6 In tetrahydrofuran at 120℃; Molecular sieve;	98%

: 5-(2-bromo-ethyl)-phenanthridinium bromide

: 3863-11-4
3,4-difluoroaniline

: 1192571-37-1
1-(3,4-difluorophenyl)-1,2,3,12b-tetrahydroimidazo[1,2-f]phenanthridine

Conditions

Conditions	Yield
With triethylamine In chloroform Inert atmosphere;	97.9%

: 24424-99-5
di-tert-butyl dicarbonate

: 3863-11-4
3,4-difluoroaniline

: 144298-04-4
(3,4-difluorophenyl)-carbamic acid-tert-butyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at 60℃; for 15h;	97%
In tetrahydrofuran at 20℃; for 12h;	93%
In tetrahydrofuran at 70℃; for 96h;	91%
In tetrahydrofuran at 20℃; for 12h;	65%
In tetrahydrofuran at 60℃; for 16h;

: 3863-11-4
3,4-difluoroaniline

: 847685-01-2
2-iodo-4,5-difluoroaniline

Conditions

Conditions	Yield
With iodine; sodium hydrogencarbonate In water at 20℃; for 0.5h;	97%
With Iodine monochloride In acetic acid at 20℃; for 0.5h;	96%
With iodine; sodium hydrogencarbonate In water at 20℃; for 0.5h;	92%

: 50329-91-4
4-chloro-3-formylcoumarin

: 3863-11-4
3,4-difluoroaniline

: 1394232-16-6
6,7-difluoro-4-(2-hydroxyphenyl)quinoline-3-carboxylic acid

Conditions

Conditions	Yield
With sulfuric acid In methanol at 20℃; for 0.25h;	97%

: 75-52-5
nitromethane

: 1266617-35-9
methyl 2-butoxy-6-methyl-3,4-dihydro-2H-pyran-5-carboxylate

: 3863-11-4
3,4-difluoroaniline

: methyl 1-(3,4-difluorophenyl)-2-methyl-6-(nitromethyl)-1,4,5,6-tetrahydropyridine-3-carboxylate

Conditions

Conditions	Yield
With lithium bromide monohydrate at 100℃; for 11h;	97%

...Expand

: 86-57-7
1-Nitronaphthalene

: 3863-11-4
3,4-difluoroaniline

: C16H11F2N

Conditions

Conditions	Yield
With bis(acetylacetonato)palladium(II); potassium phosphate tribasic trihydrate; 2-(2,6-diethyl-4-methylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;	97%

: 4-(2,6-dichloropyrido[3,4-d]pyrimidin-4-yl)morpholine

: 3863-11-4
3,4-difluoroaniline

: 6-chloro-N-(3,4-difluorophenyl)-4-morpholinopyrido[3,4-d]pyrimidin-2-amine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In iso-butanol Reflux; Inert atmosphere;	96.4%

: 3863-11-4
3,4-difluoroaniline

: 123330-51-8
4-azido-1,2-difluorobenzene

Conditions

Conditions	Yield
Stage #1: 3,4-difluoroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0℃; for 1h;	96.1%
Stage #1: 3,4-difluoroaniline With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With sodium azide In water at 0℃;	96.1%
With sodium azide; sulfuric acid; trifluoroacetic acid; sodium nitrite 1.) H2O, RT, 30 min, 2.) 1 h; Yield given. Multistep reaction;

: 50329-91-4
4-chloro-3-formylcoumarin

: 3863-11-4
3,4-difluoroaniline

: 1357063-67-2
9,10-difluoro-6H-chromeno[4,3-b]quinolin-6-one

Conditions

Conditions	Yield
In ethanol at 20℃; for 0.25h; ultrasound irradiation;	96%
In methanol at 20℃; for 0.133333h; ultrasound irradiation;	90%
With Amberlyst-15 In ethanol for 2h; Reflux; Inert atmosphere;	81%

: 3863-11-4
3,4-difluoroaniline

: 195137-30-5
1-(2-methylphenyl)-1,4-pentanedione

: 1445874-27-0
1-(3,4-difluorophenyl)-2-methyl-5-(2-methylphenyl)pyrrole

Conditions

Conditions	Yield
With gadolinium(III) trifluoromethanesulfonate In acetonitrile at 30℃; for 0.5h; Paal-Knorr Pyrrole Synthesis;	96%

: 140-88-5
ethyl acrylate

: 3863-11-4
3,4-difluoroaniline

: ethyl 3-((3,4-difluorophenyl)amino)propanoate

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In neat (no solvent) at 100℃; for 24h;	96%
With trifluorormethanesulfonic acid at 100℃;
With trifluorormethanesulfonic acid at 100℃; for 16h; Inert atmosphere;

: 471-25-0
Propiolic acid

: 3863-11-4
3,4-difluoroaniline

: N-(3,4-difluorophenyl)prop-2-ynamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 5℃; for 1h;	96%

: 1934-75-4
sodium dicyanamide

: 3863-11-4
3,4-difluoroaniline

: 1-(3,4-difluoro)phenyl-3-cyanoguanidine

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 1h;	95.2%
With hydrogenchloride In water at 80℃; for 1h;	95.2%

: 541-41-3
chloroformic acid ethyl ester

: 3863-11-4
3,4-difluoroaniline

: 2145-85-9
(3,4-difluorophenyl)carbamic acid ethyl ester

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 0.5h;	95%
With sodium carbonate

: 75-15-0
carbon disulfide

: 121-44-8
triethylamine

: 3863-11-4
3,4-difluoroaniline

: 144514-15-8
3,4-difluorophenyl dithiocarbamic acid triethylammonium

Conditions

Conditions	Yield
at 0℃;	95%
at 0℃;
In toluene at 25 - 30℃; for 12h; Product distribution / selectivity; Cooling with ice;

...Expand

: 3863-11-4
3,4-difluoroaniline

: 3,3',4,4'-tetrafluoroazobenzene

Conditions

Conditions	Yield
With copper-manganese spinel oxide In ethyl acetate at 80℃; for 8h;	95%
With potassium hydroxide; potassium hexacyanoferrate(III) In ethanol; water for 8h; Heating;	65%
With potassium hydroxide; potassium hexacyanoferrate(III) In ethanol; water for 6h; Heating;	60%

: 625-36-5
2-chloropropionyl chloride

: 3863-11-4
3,4-difluoroaniline

: 132669-28-4
3-chloro-N-(3,4-difluoro-phenyl)-propionamide

Conditions

Conditions	Yield
With pyridine In acetone at 55℃; for 3h;	95%
With triethylamine In ethyl acetate at 20 - 30℃;	73%
With triethylamine In ethyl acetate at 20 - 30℃;

3,4-Difluoroaniline Specification

The IUPAC name of this chemical is 3,4-difluoroaniline. With the CAS registry number 3863-11-4 and EINECS 223-381-7, it is also named as Benzenamine, 3,4-difluoro-. The product's categories are Fluorobenzene Series; Anilines, Aromatic Amines and Nitro Compounds; Anilines, Amides & Amines; Fluorine Compounds; Amines; C2 to C6; Nitrogen Compounds. It is clear yellow to straw liquid after melting, which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container, avoided direct sunshine and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.5; (4)ACD/LogD (pH 7.4): 1.51; (5)ACD/BCF (pH 5.5): 8.16; (6)ACD/BCF (pH 7.4): 8.27; (7)ACD/KOC (pH 5.5): 155.76; (8)ACD/KOC (pH 7.4): 157.89; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.52; (13)Molar Refractivity: 30.47 cm³; (14)Molar Volume: 100.1 cm³; (15)Polarizability: 12.08×10^-24 cm³; (16)Surface Tension: 37.2 dyne/cm; (17)Enthalpy of Vaporization: 44.12 kJ/mol; (18)Vapour Pressure: 0.256 mmHg at 25°C; (19)Exact Mass: 129.039006; (20)MonoIsotopic Mass: 129.039006; (21)Topological Polar Surface Area: 26; (22)Heavy Atom Count: 9; (23)Complexity: 97.1.

Preparation of 3,4-Difluoroaniline: It can be obtained by 1,2-difluoro-4-nitro-benzene. This reaction needs reagents In, aq. HCl and solvent tetrahydrofuran at temperature of 20 °C. The reaction time is 0.5 hours. The yield is 75%.

Uses of 3,4-Difluoroaniline: It is used as pharmaceutical intermediate. It also can react with acetic acid anhydride to get acetic acid-(3,4-difluoro-anilide). The reaction reacts at 20 °C for 30 min.. The yield is 95%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:Fc1ccc(N)cc1F
2. InChI:InChI=1/C6H5F2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2
3. InChIKey:AXNUZKSSQHTNPZ-UHFFFAOYAH

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	260mg/kg (260mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Toksikologicheskii Vestnik. Vol. (3), Pg. 31, 1993.
rat	LC50	inhalation	10720mg/m³ (10720mg/m³)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION	Toksikologicheskii Vestnik. Vol. (3), Pg. 31, 1993.
rat	LD50	oral	340mg/kg (340mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Toksikologicheskii Vestnik. Vol. (3), Pg. 31, 1993.

Product Name

3,4-Difluoroaniline

Synthetic route

3,4-Difluoroaniline Specification

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