Product Name

  • Name

    2,3-Difluoropyridine

  • EINECS
  • CAS No. 1513-66-2
  • Article Data10
  • CAS DataBase
  • Density 1.264 g/cm3
  • Solubility
  • Melting Point
  • Formula C5H3F2N
  • Boiling Point 116.476 °C at 760 mmHg
  • Molecular Weight 115.082
  • Flash Point 24.244 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 10-36/37/38
  • Molecular Structure Molecular Structure of 1513-66-2 (2,3-Difluoropyridine)
  • Hazard Symbols ToxicT,FlammableF,IrritantXi
  • Synonyms 2,3-Difluorpyridin;
  • PSA 12.89000
  • LogP 1.35980

Synthetic route

5-chloro-2,3-difluoropyridine
89402-43-7

5-chloro-2,3-difluoropyridine

2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

Conditions
ConditionsYield
With ammonium formate; acetic acid; palladium on activated charcoal at 25℃; for 6h;75%
palladium-carbon
palladium-carbon
pyridine
110-86-1

pyridine

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

C

Pentafluoropyridine
700-16-3

Pentafluoropyridine

D

N,N-Bis(trifluoromethyl)amine
371-77-7

N,N-Bis(trifluoromethyl)amine

Conditions
ConditionsYield
With caesium tetrafluorocobaltate(III) In gaseous matrix at 310℃; for 3.5h; Further byproducts given;A 35.3%
B 2.2%
C 13.6%
D 8.2%
...Expand
pyridine
110-86-1

pyridine

A

2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

B

4H,5H-heptafluoro-2-azahex-2(Z),4(E)-diene
54471-09-9

4H,5H-heptafluoro-2-azahex-2(Z),4(E)-diene

C

5H-decafluoro-2-azahex-2(Z)-ene
54471-08-8

5H-decafluoro-2-azahex-2(Z)-ene

D

undecafluoro-2-azahex-2(Z)-ene
54471-05-5

undecafluoro-2-azahex-2(Z)-ene

Conditions
ConditionsYield
With potassium tetrafluorocobaltate In gaseous matrix at 215 - 225℃; 1.) 3.5-4 h; 2.) 2 h; Further byproducts given;
...Expand
2-chloro-3-aminopyridine
6298-19-7

2-chloro-3-aminopyridine

2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

Conditions
ConditionsYield
Stage #1: 2-chloro-3-aminopyridine With hexafluorophosphoric acid; sodium nitrite In water at 0℃;
Stage #2: In xylene at 85℃; for 3h;
Stage #3: With sodium hydrogencarbonate; triethylamine In water; xylene
3-Fluoropyridine
372-47-4

3-Fluoropyridine

2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

Conditions
ConditionsYield
With silver(II) fluoride In acetonitrile at 20℃; for 1h; Mechanism;55 %Spectr.
2-chloro-3-fluoropyridine
17282-04-1

2-chloro-3-fluoropyridine

2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

Conditions
ConditionsYield
With tetramethylammonium fluoride In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; Sealed tube;65 %Spectr.
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3-fluoro-2-hydrazinylpyridine
887266-57-1

3-fluoro-2-hydrazinylpyridine

Conditions
ConditionsYield
With hydrazine hydrate at 120℃; for 1h;93%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

ethyl (ethoxymethylene)cyanoacetate
94-05-3

ethyl (ethoxymethylene)cyanoacetate

ethyl 5-amino-1-(3-fluoropyridin-2-yl)-1H-pyrazole-4-carboxylate

ethyl 5-amino-1-(3-fluoropyridin-2-yl)-1H-pyrazole-4-carboxylate

Conditions
ConditionsYield
Stage #1: 2,3-difluoropyridine With hydrazine hydrate In ethanol for 3h; Reflux;
Stage #2: ethyl (ethoxymethylene)cyanoacetate In ethanol Reflux;		91%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

9H-carbazole
86-74-8

9H-carbazole

2,3-di(9H-carbazol-9-yl)pyridine

2,3-di(9H-carbazol-9-yl)pyridine

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 150℃; for 12h; Inert atmosphere;90%
With potassium carbonate In dimethyl sulfoxide at 150℃; for 12h; Inert atmosphere;85%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3,3'-difluoro-2H-[1,2'-bipyridin]-2-one

3,3'-difluoro-2H-[1,2'-bipyridin]-2-one

Conditions
ConditionsYield
With water; caesium carbonate In dimethyl sulfoxide at 110℃; for 12h;90%
With water; caesium carbonate In dimethyl sulfoxide at 110℃; for 12h;90%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

acetamidine hydrochloride
124-42-5

acetamidine hydrochloride

C7H7FN2O

C7H7FN2O

Conditions
ConditionsYield
With water; caesium carbonate In dimethyl sulfoxide at 90℃; for 18h; Schlenk technique; chemoselective reaction;89%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate
115186-37-3

tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate

C15H18F2N2O3

C15H18F2N2O3

Conditions
ConditionsYield
Stage #1: 2,3-difluoropyridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;		85%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

4-chloro-2,3-difluoropyridine
851178-99-9

4-chloro-2,3-difluoropyridine

Conditions
ConditionsYield
Stage #1: 2,3-difluoropyridine With n-butyllithium In tetrahydrofuran; hexane
Stage #2: With 1,1,2-Trichloro-1,2,2-trifluoroethane In tetrahydrofuran; hexane		81%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

(E)-3-(pyridin-2-ylethynyl)cyclohex-2-enone oxime
1224432-92-1

(E)-3-(pyridin-2-ylethynyl)cyclohex-2-enone oxime

(E)-3-(pyridin-2-ylethynyl)cyclohex-2-enone O-3-fluoropyridin-2-yl oxime
1224433-00-4

(E)-3-(pyridin-2-ylethynyl)cyclohex-2-enone O-3-fluoropyridin-2-yl oxime

Conditions
ConditionsYield
Stage #1: (E)-3-(pyridin-2-ylethynyl)cyclohex-2-enone oxime With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2,3-difluoropyridine In N,N-dimethyl-formamide; mineral oil at 20℃; for 1.5h; Inert atmosphere;		81%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3-fluoropyridin-2-amine
21717-95-3

3-fluoropyridin-2-amine

Conditions
ConditionsYield
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; chemoselective reaction;81%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

4-benzyl-3-ethoxy-5-methyl-1H-pyrazole
1116655-96-9

4-benzyl-3-ethoxy-5-methyl-1H-pyrazole

2-(4-benzyl-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-3-fluoropyridine

2-(4-benzyl-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-3-fluoropyridine

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 180℃; for 2h; Microwave irradiation;74%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

1-(3-fluoropyridin-2-yl)cyclopropane-1-carbonitrile

1-(3-fluoropyridin-2-yl)cyclopropane-1-carbonitrile

Conditions
ConditionsYield
Stage #1: cyclopropropanecarbonitrile With lithium hexamethyldisilazane In 2-methyltetrahydrofuran; hexane at 0℃; for 0.166667h;
Stage #2: 2,3-difluoropyridine In 2-methyltetrahydrofuran; hexane at 0 - 20℃; for 3h;		72%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

1,2-dicarba-closo-dodecaborane(12)
16872-09-6

1,2-dicarba-closo-dodecaborane(12)

C7H14B10FN

C7H14B10FN

Conditions
ConditionsYield
Stage #1: 1,2-dicarba-closo-dodecaborane(12) With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: 2,3-difluoropyridine In tetrahydrofuran; hexane at 70℃; for 3h; Inert atmosphere; Schlenk technique;		69%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

2,3-difluoro-4-iodopyridine
851386-34-0

2,3-difluoro-4-iodopyridine

Conditions
ConditionsYield
Stage #1: 2,3-difluoropyridine With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; for 1h;		63%
With iodine; lithium diisopropyl amide In tetrahydrofuran at -78℃; regioselective reaction;
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

1-(4-methyl-4-piperidyl)pyrazole-4-carbaldehyde

1-(4-methyl-4-piperidyl)pyrazole-4-carbaldehyde

1-[1-(3-fluoro-2-pyridyl)-4-methyl-4-piperidyl]pyrazole-4-carbaldehyde

1-[1-(3-fluoro-2-pyridyl)-4-methyl-4-piperidyl]pyrazole-4-carbaldehyde

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 135℃; for 12h; Sealed tube;61.25%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

diethyl malonate
105-53-3

diethyl malonate

diethyl 2-(3-fluoropyridin-2-yl)malonate
940933-39-1

diethyl 2-(3-fluoropyridin-2-yl)malonate

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 100℃; for 4.5h;60%
With caesium carbonate In dimethyl sulfoxide at 100℃; for 4.5h;60%
With caesium carbonate In dimethyl sulfoxide at 100℃; for 3h;
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

C14H21N3O2

C14H21N3O2

C19H23FN4O2

C19H23FN4O2

Conditions
ConditionsYield
at 130℃; for 48h;52%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3-amino-2-pyridone
33630-99-8

3-amino-2-pyridone

3-amino-3‘-fluoro-2H-[1,2’-bipyridin]-2-one

3-amino-3‘-fluoro-2H-[1,2’-bipyridin]-2-one

Conditions
ConditionsYield
With potassium phosphate In 1-methyl-pyrrolidin-2-one at 90 - 100℃; for 22h;49.37%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3-methyl-1H-pyrazole-4-carbaldehyde
112758-40-4

3-methyl-1H-pyrazole-4-carbaldehyde

1-(3-fluoro-2-pyridyl)-3-methylpyrazole-4-carbaldehyde
1307248-77-6

1-(3-fluoro-2-pyridyl)-3-methylpyrazole-4-carbaldehyde

Conditions
ConditionsYield
Stage #1: 3-methyl-1H-pyrazole-4-carbaldehyde With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 2,3-difluoropyridine In N,N-dimethyl-formamide at 20℃; for 20h;		43%
Stage #1: 3-methyl-1H-pyrazole-4-carbaldehyde With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 2,3-difluoropyridine In N,N-dimethyl-formamide at 20℃; for 20h;
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

4,6-dimethoxypyrimidin-2-ylacetonitrile
128276-52-8

4,6-dimethoxypyrimidin-2-ylacetonitrile

4,6-dimethoxy-2-(3-fluoro-2-pyridyl)formylpyrimidine

4,6-dimethoxy-2-(3-fluoro-2-pyridyl)formylpyrimidine

Conditions
ConditionsYield
Stage #1: 4,6-dimethoxypyrimidin-2-ylacetonitrile With sodium hydride In N,N-dimethyl acetamide at 0℃; for 0.5h;
Stage #2: 2,3-difluoropyridine In N,N-dimethyl acetamide at 20℃; for 8h;
Stage #3: With dihydrogen peroxide In N,N-dimethyl acetamide at 0 - 20℃;		42.7%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

ethyl 1-methyl-5-(4-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrazole-3-carboxylate

ethyl 1-methyl-5-(4-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-pyrazole-3-carboxylate

C18H21FN4O2

C18H21FN4O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 24h;40%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

methyl 3-[(6-hydroxy-1-methyl-1H-benzimidazol-2-yl)methoxy]benzoate
1242328-95-5

methyl 3-[(6-hydroxy-1-methyl-1H-benzimidazol-2-yl)methoxy]benzoate

methyl 3-({6-[(3-fluoropyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate

methyl 3-({6-[(3-fluoropyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;28%
3-bromo-pyridin-2-ol
13466-43-8

3-bromo-pyridin-2-ol

2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3-bromo-3‘-fluoro-2H-[1,2’-bipyridin]-2-one

3-bromo-3‘-fluoro-2H-[1,2’-bipyridin]-2-one

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 15h;21.47%
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 15h;21%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3-hydroxy-2,2-dimethyl-N-(1-methylpiperidin-4-yl)propanamide

3-hydroxy-2,2-dimethyl-N-(1-methylpiperidin-4-yl)propanamide

3-((3-fluoropyridin-2-yl)oxy)-2,2-dimethyl-N-(1-methylpiperidin-4-yl)propanamide

3-((3-fluoropyridin-2-yl)oxy)-2,2-dimethyl-N-(1-methylpiperidin-4-yl)propanamide

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2,2-dimethyl-N-(1-methylpiperidin-4-yl)propanamide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 2,3-difluoropyridine In N,N-dimethyl-formamide at 20℃;		19%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3-bromopyridin-2(1H)-one
13466-43-8

3-bromopyridin-2(1H)-one

3-bromo-3‘-fluoro-2H-[1,2’-bipyridin]-2-one

3-bromo-3‘-fluoro-2H-[1,2’-bipyridin]-2-one

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 15h;16.81%
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 15h; Time;16.81%
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3,4-difluoropyridine

3,4-difluoropyridine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: BuLi / tetrahydrofuran; hexane
1.2: 81 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane
2.1: 75 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 2 h / 150 °C
3.1: i-Pr2NH; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C
3.2: 82 percent / tetrahydrofuran; hexane / 1 h / -75 °C
4.1: 96 percent / hydrazine monohydrate / tetrahydrofuran / 20 h / 50 °C
5.1: 72 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 25 °C
6.1: 60 percent / MnO2 / octan-1-ol / 15 - 25 °C
View Scheme
2,3-difluoropyridine
1513-66-2

2,3-difluoropyridine

3,4-difluoro-2-hydrazinopyridine
874907-81-0

3,4-difluoro-2-hydrazinopyridine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: BuLi / tetrahydrofuran; hexane
1.2: 81 percent / 1,1,2-trichloro-1,2,2-trifluoroethane / tetrahydrofuran; hexane
2.1: 75 percent / KF; tetramethylammonium chloride / dimethylsulfoxide / 2 h / 150 °C
3.1: i-Pr2NH; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C
3.2: 82 percent / tetrahydrofuran; hexane / 1 h / -75 °C
4.1: 96 percent / hydrazine monohydrate / tetrahydrofuran / 20 h / 50 °C
5.1: 72 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 25 °C
View Scheme

2,3-Difluoropyridine Specification

The 2,3-Difluoropyridine, with the CAS registry number 1513-66-2, is also known as Pyridine, 2,3-difluoro-. And the molecular formula of this chemical is C5H3F2N. It belongs to the following product categories: Fluorin-contained pyridine series; Pyridine; Pyridines.
 
The physical properties of 2,3-Difluoropyridine are as following: (1)ACD/LogP: 1.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.299; (4)ACD/LogD (pH 7.4): 1.299; (5)ACD/BCF (pH 5.5): 5.717; (6)ACD/BCF (pH 7.4): 5.717; (7)ACD/KOC (pH 5.5): 121.23; (8)ACD/KOC (pH 7.4): 121.23; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 12.89 Å2; (13)Index of Refraction: 1.447; (14)Molar Refractivity: 24.332 cm3; (15)Molar Volume: 91.077 cm3; (16)Polarizability: 9.646×10-24cm3; (17)Surface Tension: 31.445 dyne/cm; (18)Density: 1.264 g/cm3; (19)Flash Point: 24.244 °C; (20)Enthalpy of Vaporization: 34.012 kJ/mol; (21)Boiling Point: 116.476 °C at 760 mmHg; (22)Vapour Pressure: 21.635 mmHg at 25°C.

You should be cautious while dealing with this chemical. It is a kind of flammable chemical which irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(c(nc1)F)F
(2)InChI: InChI=1/C5H3F2N/c6-4-2-1-3-8-5(4)7/h1-3H
(3)InChIKey: OGVLEPMNNPZAPS-UHFFFAOYAJ

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