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700-16-3

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700-16-3 Usage

Synthesis

Historically, potassium fluoride has been? used with solvents to perform the Halex reaction and Finger and Kruse established the? use of polar aprotic solvents in the Halex reaction, with DMSO and DMF being used for the conversion of pentachloropyridine to pentafluoropyridine.

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Pentafluoropyridine was used in the preparation of η2-C,C coordinated pentafluoropyridine complex. It was also used in the preparation of polyfluorinated coupling products via Pd(0)-catalyzed cross-coupling reaction with diarylzinc compounds. It was also used as derivatizing reagent in the sensitive GC-MS method for determination of the four endocrine disrupting chemicals.

General Description

The reactions of pentafluoropyridine with cobalt(0) complex, Co(PMe3)4 was investigated.

Purification Methods

Distil it through a concentric tube column; it has in cyclohexane at 256.8nm. [Chambers et al. J Chem Soc 3573 1964, NMR: Bell et al. J Fluorine Chem 1 51 1971.] The hexafluoroantimonate has m 98-102o(dec) after crystallisation from liquid SO2. [Beilstein 20/5 V 401.]

Check Digit Verification of cas no

The CAS Registry Mumber 700-16-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 0 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 700-16:
(5*7)+(4*0)+(3*0)+(2*1)+(1*6)=43
43 % 10 = 3
So 700-16-3 is a valid CAS Registry Number.
InChI:InChI=1/C5HF3O3/c6-5(7,8)2-1-3(9)11-4(2)10/h1H

700-16-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (P0926)  Pentafluoropyridine  >98.0%(GC)

  • 700-16-3

  • 5g

  • 380.00CNY

  • Detail
  • TCI America

  • (P0926)  Pentafluoropyridine  >98.0%(GC)

  • 700-16-3

  • 25g

  • 990.00CNY

  • Detail
  • Alfa Aesar

  • (A19656)  Pentafluoropyridine, 99%   

  • 700-16-3

  • 5g

  • 471.0CNY

  • Detail
  • Alfa Aesar

  • (A19656)  Pentafluoropyridine, 99%   

  • 700-16-3

  • 25g

  • 1605.0CNY

  • Detail
  • Aldrich

  • (158798)  Pentafluoropyridine  ≥99%

  • 700-16-3

  • 158798-25G

  • 712.53CNY

  • Detail

700-16-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Pentafluoropyridine

1.2 Other means of identification

Product number -
Other names Pyridine, pentafluoro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:700-16-3 SDS

700-16-3Synthetic route

2,3,4,5,6-pentachloropyridine
2176-62-7

2,3,4,5,6-pentachloropyridine

Pentafluoropyridine
700-16-3

Pentafluoropyridine

Conditions
ConditionsYield
With potassium fluoride; B(2,2-bis(hydroxymethyl)propionate(3-)) In 1-methyl-pyrrolidin-2-one at 180℃; for 3h; Inert atmosphere;84%
With potassium fluoride at 480℃; for 2h; Product distribution; various temperature, reactant volume, F(1-) ion concentration and contact time;
potassium fluoride

potassium fluoride

2,3,4,5,6-pentachloropyridine
2176-62-7

2,3,4,5,6-pentachloropyridine

Pentafluoropyridine
700-16-3

Pentafluoropyridine

Conditions
ConditionsYield
In neat (no solvent) molar ratio C5Cl5N/KF = 1/20.0, 500 °C, 18 h;;83%
In neat (no solvent) molar ratio C5Cl5N/KF = 1/20.0, 500 °C, 18 h;;83%
In neat (no solvent) weight-ratio KF/C5Cl5N = 8/3, 450 °C, 24 h;;68.5%
4-N,N-dichloroamino-2,3,5,6-tetrafluoropyridine
57310-43-7

4-N,N-dichloroamino-2,3,5,6-tetrafluoropyridine

A

trifluoro-[1,3,5]triazine
675-14-9

trifluoro-[1,3,5]triazine

B

4-chloro-2,3,5,6-tetrafluoropyridine
52026-98-9

4-chloro-2,3,5,6-tetrafluoropyridine

C

Pentafluoropyridine
700-16-3

Pentafluoropyridine

D

trichlorofluoromethane
75-69-4

trichlorofluoromethane

E

2-chloro-3,3-difluoro-acrylonitrile
667-42-5

2-chloro-3,3-difluoro-acrylonitrile

F

tetrafluoropyrazine
13177-77-0

tetrafluoropyrazine

Conditions
ConditionsYield
at 550℃; under 2 Torr; Mechanism; vacuum pyrolysis, other fluoropyridine compounds;A n/a
B 75%
C n/a
D n/a
E n/a
F n/a
potassium fluoride

potassium fluoride

2,3,4,5,6-pentachloropyridine
2176-62-7

2,3,4,5,6-pentachloropyridine

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

3-chloro-2,4,5,6-tetrafluoropyridine
1735-84-8

3-chloro-2,4,5,6-tetrafluoropyridine

C

3,5-dichloro-2,4,6-trifluoropyridine
1737-93-5

3,5-dichloro-2,4,6-trifluoropyridine

Conditions
ConditionsYield
In neat (no solvent) autoclave, 470 °C (12 h), 2-fold molar excess of KF;;A 65%
B 18%
C 5%
In neat (no solvent) autoclave, 470 °C (12 h), 2-fold molar excess of KF;;A 65%
B 18%
C 5%
In neat (no solvent) 450 °C, excess of KF;;A 40%
B n/a
C n/a
3,5-dichloro-2,4,6-trifluoropyridine
1737-93-5

3,5-dichloro-2,4,6-trifluoropyridine

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

3-chloro-2,4,5,6-tetrafluoropyridine
1735-84-8

3-chloro-2,4,5,6-tetrafluoropyridine

Conditions
ConditionsYield
With potassium fluoride; tetraphenylphosphonium bromide In sulfolane at 200℃; for 7h; Fluorination;A 21%
B 61%
With potassium fluoride In sulfolane; chlorobenzene at 215℃; for 22h;
With potassium fluoride; tetraphenylphosphonium bromide In sulfolane; chlorobenzene at 215℃; for 22h;
potassium fluoride

potassium fluoride

C5Cl2F3N

C5Cl2F3N

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

C5ClF4N

C5ClF4N

Conditions
ConditionsYield
In sulfolane 223-227 °C (10 h);;A 21%
B 50%
In sulfolane 223-227 °C (10 h);;A 21%
B 50%
pyridine
110-86-1

pyridine

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

2,3,4,5-tetrafluoropyridine
3512-16-1

2,3,4,5-tetrafluoropyridine

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 395 - 405℃; for 0.5h; Further byproducts given;A 32.9%
B 3.9%
C 39.9%
D 8.5%
With caesium tetrafluorocobaltate(III) In gaseous matrix at 310℃; for 3.5h; Further byproducts given;A 35.3%
B 5.3%
C 13.6%
D 8.2%
piperidine
110-89-4

piperidine

2,3,4,5,6-pentachloropyridine
2176-62-7

2,3,4,5,6-pentachloropyridine

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

3-chloro-2,4,5,6-tetrafluoropyridine
1735-84-8

3-chloro-2,4,5,6-tetrafluoropyridine

C

3,5-dichloro-2,4,6-trifluoropyridine
1737-93-5

3,5-dichloro-2,4,6-trifluoropyridine

D

2,3,5,6-tetrachloro-4-fluoropyridine
34415-32-2

2,3,5,6-tetrachloro-4-fluoropyridine

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide at 80℃; for 9h; Product distribution; other reagents;A 2%
B 4%
C 9%
D 39%
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%
pyridine
110-86-1

pyridine

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

2,3,6-trifluoropyridine
3512-18-3

2,3,6-trifluoropyridine

C

2,3,4,5-tetrafluoropyridine
3512-16-1

2,3,4,5-tetrafluoropyridine

D

Pentafluoropyridine
700-16-3

Pentafluoropyridine

E

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

N,N-Bis(trifluoromethyl)amine

F

tetrafluoro-3-(fluoromethyl)pyridine

tetrafluoro-3-(fluoromethyl)pyridine

Conditions
ConditionsYield
With caesium tetrafluorocobaltate(III) In gaseous matrix at 310℃; for 3.5h; Product distribution; other reactor geometry, temperature, time;A 35.3%
B 3.2%
C 5.3%
D 13.6%
E 8.2%
F 2.7%
pyridine
110-86-1

pyridine

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

2,3,6-trifluoropyridine
3512-18-3

2,3,6-trifluoropyridine

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 3.2%
C 13.6%
D 8.2%
pyridine
110-86-1

pyridine

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

2,6-difluoro pyridine
1513-65-1

2,6-difluoro pyridine

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 1.6%
C 13.6%
D 8.2%
pyridine
110-86-1

pyridine

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

Pentafluoropyridine
700-16-3

Pentafluoropyridine

C

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

N,N-Bis(trifluoromethyl)amine

D

2,3,4-trifluoropyridine
84477-04-3

2,3,4-trifluoropyridine

Conditions
ConditionsYield
With caesium tetrafluorocobaltate(III) In gaseous matrix at 310℃; for 3.5h; Further byproducts given;A 35.3%
B 13.6%
C 8.2%
D 2.3%
pyridine
110-86-1

pyridine

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

Pentafluoropyridine
700-16-3

Pentafluoropyridine

C

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

N,N-Bis(trifluoromethyl)amine

D

2,5-difluoropyridine
84476-99-3

2,5-difluoropyridine

Conditions
ConditionsYield
With caesium tetrafluorocobaltate(III) In gaseous matrix at 310℃; for 3.5h; Further byproducts given;A 35.3%
B 13.6%
C 8.2%
D 2.1%
pyridine
110-86-1

pyridine

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

Pentafluoropyridine
700-16-3

Pentafluoropyridine

C

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

N,N-Bis(trifluoromethyl)amine

D

tetrafluoro-3-(fluoromethyl)pyridine

tetrafluoro-3-(fluoromethyl)pyridine

Conditions
ConditionsYield
With caesium tetrafluorocobaltate(III) In gaseous matrix at 310℃; for 3.5h; Further byproducts given;A 35.3%
B 13.6%
C 8.2%
D 2.7%
perfluoro-N-fluoropiperidine
836-77-1

perfluoro-N-fluoropiperidine

Pentafluoropyridine
700-16-3

Pentafluoropyridine

Conditions
ConditionsYield
In neat (no solvent) Defluorination with oxide-free Fe at 580-610 °C/ > 1 Torr (dwell time 17 s);;26%
In neat (no solvent) Defluorination with oxide-free Fe at 580-610 °C/ > 1 Torr (dwell time 17 s);;26%
In neat (no solvent) Defluorination with oxide-free Fe at 580-610 °C/ > 1 Torr (dwell time 1 s).;> 20
In neat (no solvent) Defluorination with oxide-free Fe at 580-610 °C/ > 1 Torr (dwell time 1 s).;> 20
perfluoro-N-fluoropiperidine
836-77-1

perfluoro-N-fluoropiperidine

Pentafluoropyridine
700-16-3

Pentafluoropyridine

Conditions
ConditionsYield
With steel wool In neat (no solvent) 550 °C (40 min), steel tube filled with steel wool;;19%
With steel wool In neat (no solvent) 550 °C (40 min), steel tube filled with steel wool;;19%
With steel wool In neat (no solvent) 600 °C (95 min), steel tube filled with steel wool;;18%
perfluoro-N-fluoropiperidine
836-77-1

perfluoro-N-fluoropiperidine

nickel
7440-02-0

nickel

Pentafluoropyridine
700-16-3

Pentafluoropyridine

Conditions
ConditionsYield
In gaseous matrix Defluorination in N2 atmosphere (flow rate 4l/h) at 560 °C/760 Torr.;12%
2,3,4,5,6-pentachloropyridine
2176-62-7

2,3,4,5,6-pentachloropyridine

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

C5Cl3F2N

C5Cl3F2N

C

C5Cl4FN

C5Cl4FN

D

C5ClF4N

C5ClF4N

Conditions
ConditionsYield
With KF-KCl melt In neat (no solvent) Inlet of the formed C5F3Cl2N (3g/10 min) at 645 °C into the KF-KCl melt (carrier gas = Ar, flow rate 70 ml/min), yields of C5FnCl5-nN (n= 1 to 5) are indicated for the fluorination of the temperature range 630 - 740 °C;;A 7%
B n/a
C n/a
D n/a
With KF-KCl melt In neat (no solvent) Inlet of the formed C5F3Cl2N (3g/10 min) at 645 °C into the KF-KCl melt (carrier gas = Ar, flow rate 70 ml/min), yields of C5FnCl5-nN (n= 1 to 5) are indicated for the fluorination of the temperature range 630 - 740 °C;;A 7%
B n/a
C n/a
D n/a
α-picoline
109-06-8

α-picoline

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

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

N,N-Bis(trifluoromethyl)amine

C

1-pentafluoroethyl-octafluoropyrrolidine
78159-15-6

1-pentafluoroethyl-octafluoropyrrolidine

D

tetrafluoro-2-difluoromethylpyridine

tetrafluoro-2-difluoromethylpyridine

Conditions
ConditionsYield
With caesium tetrafluorocobaltate(III) at 270℃; Further byproducts given;A 1.9 g
B 8.8 g
C 1.7 g
D 2%
2,3,4,5,6-pentachloropyridine
2176-62-7

2,3,4,5,6-pentachloropyridine

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

C5Cl2F3N

C5Cl2F3N

C

C5Cl3F2N

C5Cl3F2N

D

C5Cl4FN

C5Cl4FN

E

C5ClF4N

C5ClF4N

Conditions
ConditionsYield
With KF-KCl melt In neat (no solvent) Fluorination at 740 .degree C., yields of C5FnCl5-nN (n= 1 to 5) are indicated for the fluorination of the temperature range 630 - 740 °C;;A 0.5%
B n/a
C n/a
D n/a
E n/a
With KF-KCl melt In neat (no solvent) Fluorination at 720 .degree C., yields of C5FnCl5-nN (n= 1 to 5) are indicated for the fluorination of the temperature range 630 - 740 °C;;A 0.1%
B n/a
C n/a
D n/a
E n/a
With KF-KCl melt In neat (no solvent) Fluorination at 720 .degree C., yields of C5FnCl5-nN (n= 1 to 5) are indicated for the fluorination of the temperature range 630 - 740 °C;;A 0.1%
B n/a
C n/a
D n/a
E n/a
With KF-KCl melt In neat (no solvent) Fluorination at 740 .degree C., yields of C5FnCl5-nN (n= 1 to 5) are indicated for the fluorination of the temperature range 630 - 740 °C;;A 0.5%
B n/a
C n/a
D n/a
E n/a
pyridine
110-86-1

pyridine

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

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;
α-picoline
109-06-8

α-picoline

A

perfluoro-N-ethylpyrrolidine
2344-10-7

perfluoro-N-ethylpyrrolidine

B

2,3,4,5-tetrafluoro-6-(trifluoromethylpyridine)
3146-94-9

2,3,4,5-tetrafluoro-6-(trifluoromethylpyridine)

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) at 270℃; Further byproducts given. Title compound not separated from byproducts;A n/a
B 1.4 g
C 1.9 g
D 8.8 g
α-picoline
109-06-8

α-picoline

A

2,3,4,5-tetrafluoro-6-(trifluoromethylpyridine)
3146-94-9

2,3,4,5-tetrafluoro-6-(trifluoromethylpyridine)

B

Pentafluoropyridine
700-16-3

Pentafluoropyridine

Conditions
ConditionsYield
iron 1.) fluorination 2.) defluorination, 525 deg C; Yield given. Yields of byproduct given;
iron 1.) fluorination, 2.) defluorination, 525 deg C; Yield given. Yields of byproduct given;
α-picoline
109-06-8

α-picoline

A

2,3,4,5-tetrafluoro-6-(trifluoromethylpyridine)
3146-94-9

2,3,4,5-tetrafluoro-6-(trifluoromethylpyridine)

B

Pentafluoropyridine
700-16-3

Pentafluoropyridine

C

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

N,N-Bis(trifluoromethyl)amine

D

1-pentafluoroethyl-octafluoropyrrolidine
78159-15-6

1-pentafluoroethyl-octafluoropyrrolidine

Conditions
ConditionsYield
With caesium tetrafluorocobaltate(III) at 270℃; Further byproducts given;A 1.4 g
B 1.9 g
C 8.8 g
D 1.7 g
α-picoline
109-06-8

α-picoline

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

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

N,N-Bis(trifluoromethyl)amine

C

1-pentafluoroethyl-octafluoropyrrolidine
78159-15-6

1-pentafluoroethyl-octafluoropyrrolidine

D

tetrafluoro-2-fluoromethylpyridine

tetrafluoro-2-fluoromethylpyridine

Conditions
ConditionsYield
With caesium tetrafluorocobaltate(III) at 270℃; Further byproducts given;A 1.9 g
B 8.8 g
C 1.7 g
D 0.72 g
C5F5N(1+)*AsF6(1-)

C5F5N(1+)*AsF6(1-)

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

1-azaheptafluoro-1,3-cyclohexadiene
51957-26-7

1-azaheptafluoro-1,3-cyclohexadiene

Conditions
ConditionsYield
1) 0 deg C, 2) CH3CN; Multistep reaction;
1-fluoromethyl-octafluoropyrrolidine
56154-85-9

1-fluoromethyl-octafluoropyrrolidine

A

2,3,4,5-tetrafluoropyridine
3512-16-1

2,3,4,5-tetrafluoropyridine

B

Pentafluoropyridine
700-16-3

Pentafluoropyridine

Conditions
ConditionsYield
iron at 520℃; Yield given. Yields of byproduct given;
1-difluormethyl-octafluoropyrrolidine
56154-80-4

1-difluormethyl-octafluoropyrrolidine

Pentafluoropyridine
700-16-3

Pentafluoropyridine

Conditions
ConditionsYield
iron at 520℃; Yield given;
iodotrifluoromethane
2314-97-8

iodotrifluoromethane

2,3,4,5,6-Pentafluoro-pyridine

2,3,4,5,6-Pentafluoro-pyridine

A

Pentafluoropyridine
700-16-3

Pentafluoropyridine

B

C5F5N*CF3

C5F5N*CF3

C

trifluoro-iodo-methane radical anion
2314-97-8

trifluoro-iodo-methane radical anion

Conditions
ConditionsYield
In gas at 36.9℃; Rate constant;
Pentafluoropyridine
700-16-3

Pentafluoropyridine

2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

4-pentafluorophenoxy-2,3,5,6-tetrafluoropyridine
69585-26-8

4-pentafluorophenoxy-2,3,5,6-tetrafluoropyridine

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether In acetonitrile at 80℃; for 1h; ratio of pentafluoropyridine and pentafluorophenol 1:0.1;100%
With cesium fluoride In N,N-dimethyl-formamide at 80℃; for 1h; Product distribution; other reagents, time;95%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

2,3,5,6-tetrafluoropyridine
2875-18-5

2,3,5,6-tetrafluoropyridine

Conditions
ConditionsYield
With [(bis(diisopropylphosphino)ethane)Ni(H)]2; triethylphosphine In 1,4-dioxane at 120℃; for 72h;100%
With (1,3-dimethylimidazolin-2-ylidene)*AlH3 In benzene-d6 at 20℃; for 0.0833333h; Reagent/catalyst;99%
With bis(cyclopentadienyl)dihydrozirconium; [{((2,6-dimethylphenyl)NC(methyl))2CH}AlH2] at 25℃; for 24h; Reagent/catalyst; Temperature; Inert atmosphere;93%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

ethyl vanillate
617-05-0

ethyl vanillate

4-(2,3,5,6-tetrafluoropyridin-4-yl)oxy-3-methoxybenzoic acid, ethyl ester
199784-56-0

4-(2,3,5,6-tetrafluoropyridin-4-yl)oxy-3-methoxybenzoic acid, ethyl ester

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 12h;100%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

C10H13F4N3
1193367-04-2

C10H13F4N3

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; regioselective reaction;100%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

[Rh{Si(OEt)3}(PEt3)3]
1446417-30-6

[Rh{Si(OEt)3}(PEt3)3]

[Rh(C6F5)(PEt3)3]
1231760-58-9

[Rh(C6F5)(PEt3)3]

Conditions
ConditionsYield
In (2)H8-toluene at -30.16℃; for 3h; Reagent/catalyst; Schlenk technique; Inert atmosphere;100%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

C30H70B2O4P3Rh

C30H70B2O4P3Rh

C23H45F4NP3Rh

C23H45F4NP3Rh

Conditions
ConditionsYield
In benzene-d6 for 0.0833333h; Inert atmosphere;100%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

meso-N,N’-bis(2,3,5,6-tetrafluoropyridin-4-yl)-1,2-diphenylethane-1,2-diamine

meso-N,N’-bis(2,3,5,6-tetrafluoropyridin-4-yl)-1,2-diphenylethane-1,2-diamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; regioselective reaction;100%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

4-methyl-1H-imidazole
822-36-6

4-methyl-1H-imidazole

1-(2,3,5,6-tetrafluoropyridyl)-4-methylimidazole

1-(2,3,5,6-tetrafluoropyridyl)-4-methylimidazole

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 20h;100%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

piperidine
110-89-4

piperidine

Conditions
ConditionsYield
With water In aq. phosphate buffer at 25℃; for 7.5h; pH=2.7 - 3.2; Electrochemical reaction;100%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

phenol
108-95-2

phenol

2,3,5,6-tetrafluoro-4-phenoxypyridine
113521-62-3

2,3,5,6-tetrafluoro-4-phenoxypyridine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; regioselective reaction;99.5%
Stage #1: phenol With cholin hydroxide In water at 20℃; for 0.25h;
Stage #2: Pentafluoropyridine In water at 20℃; for 24h;
86%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Pentafluoropyridine
700-16-3

Pentafluoropyridine

2,3,5,6-tetrachloropyridine
2402-79-1

2,3,5,6-tetrachloropyridine

Conditions
ConditionsYield
With hydrogen; potassium carbonate at 200℃; under 15001.5 Torr; for 2h; Autoclave;99.2%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

tris(trimethylsilyl) phosphite
1795-31-9

tris(trimethylsilyl) phosphite

C11H18F4NO3PSi2

C11H18F4NO3PSi2

Conditions
ConditionsYield
With nickel dichloride at 150℃; for 0.5h;99%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

N,N-bistrifluoromethylhydroxylamine sodium salt

N,N-bistrifluoromethylhydroxylamine sodium salt

4-tetrafluoropyridine
78708-00-6

4-tetrafluoropyridine

Conditions
ConditionsYield
In diethyl ether at 20℃; for 72h;99%
morpholine
110-91-8

morpholine

Pentafluoropyridine
700-16-3

Pentafluoropyridine

4-(2,3,5,6-tetrafluoropyridin-4-yl)morpholine
185742-33-0

4-(2,3,5,6-tetrafluoropyridin-4-yl)morpholine

Conditions
ConditionsYield
With triethylamine In dichloromethane at -7 - 20℃; Inert atmosphere; regioselective reaction;99%
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; regioselective reaction;99%
In ethanol at 0℃; for 168h;87%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

α-naphthol
90-15-3

α-naphthol

2,3,5,6-Tetrafluoro-4-(naphthalen-1-yloxy)pyridine
901594-51-2

2,3,5,6-Tetrafluoro-4-(naphthalen-1-yloxy)pyridine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
4-morpholinopyridine
2767-91-1

4-morpholinopyridine

Pentafluoropyridine
700-16-3

Pentafluoropyridine

2',3',5',6'-tetrafluoro-4-(morpholin-4-yl)-[1,4]bipyridinyl-1-ylium fluoride
943868-09-5

2',3',5',6'-tetrafluoro-4-(morpholin-4-yl)-[1,4]bipyridinyl-1-ylium fluoride

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 6h;99%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

(2,4,6-triisopropylphenyl)ethynyl piperidine-1-carbodithioate
1309151-10-7

(2,4,6-triisopropylphenyl)ethynyl piperidine-1-carbodithioate

2-fluoro-2-(piperidin-1-yl)-4-(2,3,5,6-tetrafluoropyridin-4-yl)-5-(2,4,6-triisopropylphenyl)-1,3-dithiole

2-fluoro-2-(piperidin-1-yl)-4-(2,3,5,6-tetrafluoropyridin-4-yl)-5-(2,4,6-triisopropylphenyl)-1,3-dithiole

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 18h; Solvent; Inert atmosphere;99%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

N,N`-dimethylethylenediamine
110-70-3

N,N`-dimethylethylenediamine

N,N’-dimethyl-N,N’-bis(2,3,5,6-tetrafluoropyridin-4-yl)-ethane-1,2-diamine
1256619-41-6

N,N’-dimethyl-N,N’-bis(2,3,5,6-tetrafluoropyridin-4-yl)-ethane-1,2-diamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -7 - 20℃; Inert atmosphere; regioselective reaction;99%
With triethylamine In tetrahydrofuran Inert atmosphere; Reflux; regioselective reaction;99%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(R,R)-N,N’’-bis(2,3,5,6-tetrafluoropyridin-4-yl)cyclohexane-1,2-diamine

(R,R)-N,N’’-bis(2,3,5,6-tetrafluoropyridin-4-yl)cyclohexane-1,2-diamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; regioselective reaction;99%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

4-Iodophenol
540-38-5

4-Iodophenol

2,3,5,6-tetrafluoro-4-(4-iodophenoxy)pyridine

2,3,5,6-tetrafluoro-4-(4-iodophenoxy)pyridine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 16h;99%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

3-Iodophenol
626-02-8

3-Iodophenol

2,3,5,6-tetrafluoro-4-(3-iodophenoxy)pyridine

2,3,5,6-tetrafluoro-4-(3-iodophenoxy)pyridine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 16h;99%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

Pentafluoropyridine
700-16-3

Pentafluoropyridine

1-(tetrafluoro-4'-pyridyl)-benzotriazol-1,2,3=1-(Tetrafluor-4'-pyridyl)-benzotriazol-1,2,3
39066-47-2

1-(tetrafluoro-4'-pyridyl)-benzotriazol-1,2,3=1-(Tetrafluor-4'-pyridyl)-benzotriazol-1,2,3

Conditions
ConditionsYield
With copper 2-phenylcyclopropanecarboxylate; cetyltrimethylammonim bromide; potassium carbonate In toluene for 6h; Arylation; Heating;98%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

Trimethylenediamine
109-76-2

Trimethylenediamine

N1,N3-bis(perfluoropyridine-4-yl)propane-1,3-diamine

N1,N3-bis(perfluoropyridine-4-yl)propane-1,3-diamine

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h; Arylation;98%
With triethylamine In tetrahydrofuran at 20℃; for 1h; Amination;98%
In ethanol at 0℃; for 0.0833333h;84%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

4-methoxy-phenol
150-76-5

4-methoxy-phenol

2,3,5,6-tetrafluoro-4-(4-methoxyphenoxy)pyridine
901594-61-4

2,3,5,6-tetrafluoro-4-(4-methoxyphenoxy)pyridine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 16h;98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Pentafluoropyridine
700-16-3

Pentafluoropyridine

β-naphthol
135-19-3

β-naphthol

2,3,5,6-tetrafluoro-4-[(naphthalen-2-yl)oxy]pyridine
901594-53-4

2,3,5,6-tetrafluoro-4-[(naphthalen-2-yl)oxy]pyridine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Pentafluoropyridine
700-16-3

Pentafluoropyridine

4-isocyano-1,1’-biphenyl
208242-43-7

4-isocyano-1,1’-biphenyl

(Z)-N-([1,1'-biphenyl]-4-yl)-2,4,5,6-tetrafluoronicotinimidoyl fluoride

(Z)-N-([1,1'-biphenyl]-4-yl)-2,4,5,6-tetrafluoronicotinimidoyl fluoride

Conditions
ConditionsYield
In benzene at 35℃; Inert atmosphere; UV-irradiation; regioselective reaction;98%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

(S,S)-1,2-diphenyl-1,2-diaminoethane
29841-69-8

(S,S)-1,2-diphenyl-1,2-diaminoethane

(S,S)-N,N’-bis(2,3,5,6-tetrafluoropyridin-4-yl)-1,2-diphenylethane-1,2-diamine

(S,S)-N,N’-bis(2,3,5,6-tetrafluoropyridin-4-yl)-1,2-diphenylethane-1,2-diamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; regioselective reaction;98%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

Pentafluoropyridine
700-16-3

Pentafluoropyridine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

C11H7F4NO4*C8H19N

C11H7F4NO4*C8H19N

Conditions
ConditionsYield
In acetonitrile at 45℃; for 0.5h;98%
4-nitro-phenol
100-02-7

4-nitro-phenol

Pentafluoropyridine
700-16-3

Pentafluoropyridine

4-(4'-Nitrophenoxy)-2,3,5,6-tetrafluoropyridine
83235-15-8

4-(4'-Nitrophenoxy)-2,3,5,6-tetrafluoropyridine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 16h;97%
With potassium fluoride; 18-crown-6 ether In sulfolane at 80℃; for 1h;84%
pyrographite; cesium fluoride In N,N-dimethyl-formamide at 80℃; for 5h;97 % Chromat.
Pentafluoropyridine
700-16-3

Pentafluoropyridine

benzyl alcohol
100-51-6

benzyl alcohol

3,5,6-Trifluoropyridin-2,4-diol dibenzyl ether

3,5,6-Trifluoropyridin-2,4-diol dibenzyl ether

Conditions
ConditionsYield
Stage #1: benzyl alcohol With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Metallation;
Stage #2: Pentafluoropyridine In tetrahydrofuran Etherification;
97%

700-16-3Relevant articles and documents

Burdon, J.,Gilman, D. J.,Patrick, C. R.,Stacey, M.,Tatlow, J. C.

, p. 231 - 232 (1960)

Method for preparing 2, 3, 5-trichloropyridine on basis of layered manganese oxide catalysts with nanometer zinc

-

Paragraph 0025; 0029; 0033; 0037; 0039; 0041; 0045; 0048, (2018/05/16)

The invention provides a method for preparing 2, 3, 5-trichloropyridine on the basis of layered manganese oxide catalysts with nanometer zinc. The method includes steps of dissolving manganese nitrateand zinc acetate in water, uniformly mixing the manganese nitrate and the zinc acetate with each other to obtain first liquid, dropwise adding alkali liquor into the first liquid to obtain second liquid, stirring and precipitating the second liquid to obtain manganese/iron mixed precipitates, adding the manganese/iron mixed precipitates into potassium permanganate solution to obtain third liquid,oxidizing the third liquid, filtering and washing the third liquid, adding carbon powder into the third liquid to obtain mixtures and calcining the mixtures at the high temperatures to obtain the layered manganese oxide catalysts with the nanometer zinc; carrying out reaction on pentafluoropyridine, DMF (dimethyl formamide) and active potassium fluoride powder under the effects of the layered manganese oxide catalysts with the nanometer zinc under strong-alkali conditions, filtering reaction products, and adding filter cake into calcium fluoride solution to obtain the 2, 3, 5-trichloropyridine on the basis of the layered manganese oxide catalysts with the nanometer zinc. The pentafluoropyridine is used as a raw material, the DMF is used as a solvent, and the active potassium fluoride powder is used as fluorinating agent. The method for preparing the 2, 3, 5-trichloropyridine on the basis of the layered manganese oxide catalysts with the nanometer zinc has the advantages that the reaction is mild and is high in efficiency, and the 2, 3, 5-trichloropyridine which is a product prepared by the aid of the method is high in purity.

From hypervalent xenon difluoride and aryliodine(III) difluorides to onium salts: Scope and limitation of acidic fluoroorganic reagents in the synthesis of fluoroorgano xenon(II) and iodine(III) onium salts

Abo-Amer, Anwar,Frohn, Hermann-Josef,Steinberg, Christoph,Westphal, Ulrich

, p. 1311 - 1323 (2008/12/21)

Fluorinated organodifluoroboranes RfBF2 are in general suitable reagents to transform XeF2 and RIF2 into the corresponding onium tetrafluoroborate salts [RfXe][BF4] and [R(Rf)I][BF4], respectively. (4-C5F4N)BF2 and trans-CF3CF{double bond, long}CFBF2 which represent boranes of high acidity form no Xe-C onium salts in reactions with XeF2 but give the desired iodonium salts with RIF2 (R = C6F5, o-, m-, p-C6FH4). The reaction of (4-C5F4N)BF2 with XeF2 ends with a XeF2-borane adduct. C6F5Xe(4-C5F4N), the first Xe-(4-C5F4N) compound, was obtained when C6F5XeF was reacted with Cd(4-C5F4N)2. We describe the synthesis of (4-C5F4N)IF2 and reactions of (4-C5F4N)IF2 and C6F5IF2 with (4-C5F4N)BF2. Analogous to [(4-C5F4N)2I][BF4] and [C6F5(4-C5F4N)I][BF4] aryl(perfluoroalkenyl)iodonium salts [R(R′)I][BF4] were obtained from RIF2 (R = C6F5, o-, m-, p-C6FH4) and R′BF2 (R′ = trans-CF3CF{double bond, long}CF, CF2{double bond, long}CF). The gas phase fluoride affinities pF- of selected fluoroorganodifluoroboranes RfBF2 and their hydrocarbon analogs are calculated (B3LYP/6-31+G*) and discussed with respect to their potential to introduce Rf-groups into hypervalent EF2 bonds. Four aspects which influence the transformation of hypervalent EF2 bonds (E = Xe, R′I) under the action of Lewis acidic reagents RAFn-1 (A = B, P; n = 3, 5) into the corresponding [RE][AFn+1] salts are presented and the important role of the acidity is emphasized. Fluoride affinities may help to plan the introduction of organo groups into EF2 moieties and to expand the types of acidic reagents. Thus C6H5PF4 with a pF- value comparable to that of RfBF2 compounds is able to introduce the C6H5 group into RIF2 (R = C6F5, p-C6FH4).

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