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1897-52-5 Usage

Description

2,6-Difluorobenzonitrile is a halogenated benzonitrile compound characterized by its white to light yellow crystal powder appearance. It is known for its fungacidal activity and is the difluoro analogue of the herbicide Dichlobenil.

Uses

Used in Chemical Synthesis:
2,6-Difluorobenzonitrile is utilized as a key intermediate in the synthesis of various organic compounds and polymers, contributing to the development of new materials with enhanced properties.
Used in Agriculture:
In the agricultural industry, 2,6-Difluorobenzonitrile is used as a fungicide for its fungacidal activity, helping to protect crops from fungal infections and diseases.
Used in Polymer Synthesis:
2,6-Difluorobenzonitrile is used as a monomer in the synthesis of poly(cyanoaryl ethers) via the silyl-method, resulting in polymers with improved thermal stability and mechanical properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,6-Difluorobenzonitrile is used in the synthesis of 2-dimethylamino-6-fluorobenzamide, a compound with potential therapeutic applications.
Used in Material Science:
2,6-Difluorobenzonitrile is employed in the synthesis of phenolphthalein-modified polyarylene ether nitrile copolymers, which are used to create high-performance materials with unique properties for various applications.

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 1897-52-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,9 and 7 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1897-52:
(6*1)+(5*8)+(4*9)+(3*7)+(2*5)+(1*2)=115
115 % 10 = 5
So 1897-52-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H3F2N/c8-6-2-1-3-7(9)5(6)4-10/h1-3H

1897-52-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A10454)  2,6-Difluorobenzonitrile, 98%   

  • 1897-52-5

  • 10g

  • 240.0CNY

  • Detail
  • Alfa Aesar

  • (A10454)  2,6-Difluorobenzonitrile, 98%   

  • 1897-52-5

  • 50g

  • 963.0CNY

  • Detail
  • Alfa Aesar

  • (A10454)  2,6-Difluorobenzonitrile, 98%   

  • 1897-52-5

  • 250g

  • 3847.0CNY

  • Detail

1897-52-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6-Difluorobenzonitrile

1.2 Other means of identification

Product number -
Other names 6-Difluorobenzonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:1897-52-5 SDS

1897-52-5Synthetic route

2,6-difluorobenzamide
18063-03-1

2,6-difluorobenzamide

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With Triethoxysilane; o-Ph2P(C6H4)Si(Me)2Fe(H)(PMe3)3 In tetrahydrofuran at 60℃; for 24h; Schlenk technique;99%
With diphenylsilane; FeH(PMe3)2(SiPh(NCH2PPh2)2C6H4) In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Inert atmosphere;90%
With Triethoxysilane; [cis-Fe(H)(SPh)(PMe3)4] In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;87%
C26H18AuF2N2P

C26H18AuF2N2P

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
In 1,4-dioxane at 100℃; for 2h; Kinetics; Solvent; Temperature; Inert atmosphere; Schlenk technique; Sealed tube;99%
2,6-dichloro-benzonitrile
1194-65-6

2,6-dichloro-benzonitrile

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
Stage #1: 2,6-dichloro-benzonitrile With 1-Ethylpyridinium chloride In dimethyl sulfoxide; toluene at 110℃; for 2h;
Stage #2: With potassium fluoride In dimethyl sulfoxide; toluene at 90 - 150℃; for 15h; Reagent/catalyst; Temperature; Solvent;
98.34%
With potassium fluoride; tetrabutylammomium bromide at 170℃; for 12h;91%
With potassium fluoride; immobilized pyridinium salt In sulfolane at 180℃; for 4h;82%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

C34H43AuF3NP(1+)*F6Sb(1-)

C34H43AuF3NP(1+)*F6Sb(1-)

A

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

B

F6Sb(1-)*C32H49AuN2PSi(1+)

F6Sb(1-)*C32H49AuN2PSi(1+)

Conditions
ConditionsYield
In dichloromethane-d2 at 25℃; for 3h; Glovebox;A 96%
B n/a
2,6-dichloro-benzonitrile
1194-65-6

2,6-dichloro-benzonitrile

tetrakis(diethylamino)phosphonium bromide
81175-49-7

tetrakis(diethylamino)phosphonium bromide

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With potassium fluoride; dimethyl sulfoxide In sulfolane; chlorobenzene93%
2,6-dichloro-benzonitrile
1194-65-6

2,6-dichloro-benzonitrile

tetrakis(diethylamino)phosphonium bromide
81175-49-7

tetrakis(diethylamino)phosphonium bromide

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With potassium fluoride In sulfolane; chlorobenzene91%
Triethoxysilane
998-30-1

Triethoxysilane

2,6-difluorobenzamide
18063-03-1

2,6-difluorobenzamide

A

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

B

C12H30O7Si2

C12H30O7Si2

Conditions
ConditionsYield
With C22H48FeOP4 In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique;A 75%
B n/a
2-chloro-6-nitrobenzonitrile
6575-07-1

2-chloro-6-nitrobenzonitrile

A

2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

B

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With biphenyl; tetramethylammonium fluoride In N,N-dimethyl acetamide at 60℃; for 0.666667h;A 72%
B 5%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1.5h; Ambient temperature;A 75 % Chromat.
B 25 % Chromat.
2,6-difluoro-benzaldehyde oxime
19064-16-5

2,6-difluoro-benzaldehyde oxime

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With N-methyl-N,N,N-triethylammonium methylsulfate In acetonitrile at 22℃; Electrolysis;47%
1,3-Difluorobenzene
372-18-9

1,3-Difluorobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
Stage #1: 1,3-Difluorobenzene With lithium diisopropyl amide In tetrahydrofuran at 20℃; for 2h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2h;
Stage #3: With ammonia; iodine In tetrahydrofuran; water at 0 - 20℃; for 2h;
42%
C7H2F3N(1-)
96606-37-0

C7H2F3N(1-)

A

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

B

3,3',5,5'-tetrafluoro-[1,1'-biphenyl]-4,4'-dicarbonitrile
116720-37-7

3,3',5,5'-tetrafluoro-[1,1'-biphenyl]-4,4'-dicarbonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide Rate constant; kfr;
2,6-difluorobenzyl chloride
697-73-4

2,6-difluorobenzyl chloride

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With air; ammonia; water; V-8Ti-xO at 250℃; Product distribution; various temperatures, other catalyst;
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With tetramethylammonium hydrogen difluoride In N,N-dimethyl acetamide at 120℃; for 3h;77 % Chromat.
2-chloro-6-nitrobenzonitrile
6575-07-1

2-chloro-6-nitrobenzonitrile

A

2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

B

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

C

3-chloro-2-cyanophenol
89999-90-6

3-chloro-2-cyanophenol

D

2-Fluoro-6-hydroxybenzonitrile
140675-43-0

2-Fluoro-6-hydroxybenzonitrile

Conditions
ConditionsYield
With tetramethylammonium fluoride In dimethyl sulfoxide at 100℃; for 1h; Fluorination;
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

A

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

B

3-chloro-2-cyanophenol
89999-90-6

3-chloro-2-cyanophenol

C

2-Fluoro-6-hydroxybenzonitrile
140675-43-0

2-Fluoro-6-hydroxybenzonitrile

Conditions
ConditionsYield
With tetramethylammonium fluoride In dimethyl sulfoxide at 100℃; for 0.5h; Fluorination;
2-chloro-6-nitrobenzonitrile
6575-07-1

2-chloro-6-nitrobenzonitrile

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetramethylammonium fluoride / dimethylsulfoxide / 1 h / 100 °C
2: tetramethylammonium fluoride / dimethylsulfoxide / 0.5 h / 100 °C
View Scheme
1,3-Difluorobenzene
372-18-9

1,3-Difluorobenzene

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: (i) nBuLi, (ii) /BRN= 1900390/
2: SOCl2
3: NH3
4: SOCl2 / dimethylformamide
View Scheme
2,6-difluorobenzoylchloride
18063-02-0

2,6-difluorobenzoylchloride

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3
2: SOCl2 / dimethylformamide
View Scheme
2,6-difluorobenzoic acid
385-00-2

2,6-difluorobenzoic acid

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2
2: NH3
3: SOCl2 / dimethylformamide
View Scheme
2,6-dichloro-benzonitrile
1194-65-6

2,6-dichloro-benzonitrile

A

2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

B

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With potassium fluoride; 1-butyl-3-methylimidazolium tetrafluoroborate In sulfolane at 180℃; for 18h; Product distribution / selectivity;A 45 %Chromat.
B 52 %Chromat.
1-butyl-3-methylimidazolium hexafluorophosphate In sulfolane at 180℃; for 18h; Product distribution / selectivity;A 79 %Chromat.
B 19 %Chromat.
dimethyl-di(ethoxypolyoxypropyl)ammonium chloride

dimethyl-di(ethoxypolyoxypropyl)ammonium chloride

2,6-dichloro-benzonitrile
1194-65-6

2,6-dichloro-benzonitrile

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With potassium fluoride In 5,5-dimethyl-1,3-cyclohexadiene
trimethyl(ethoxypolyoxypropyl)ammonium chloride

trimethyl(ethoxypolyoxypropyl)ammonium chloride

2,6-dichloro-benzonitrile
1194-65-6

2,6-dichloro-benzonitrile

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With potassium fluoride In 5,5-dimethyl-1,3-cyclohexadiene
3-chloro-2,6-difluorobenzonitrile
86225-73-2

3-chloro-2,6-difluorobenzonitrile

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With sodium hydroxide; palladium-carbon catalyst In water
2,4,6-trifluorobenzonitrile
96606-37-0

2,4,6-trifluorobenzonitrile

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With Dimethylphenylsilane; o-phenylenebis(diphenylphosphine); potassium tert-butylate; copper(l) chloride In tetrahydrofuran for 12h; Inert atmosphere; Reflux; regioselective reaction;100 %Spectr.
2,6-difluorobenzylamine
69385-30-4

2,6-difluorobenzylamine

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With copper(l) iodide; oxygen In dichloromethane at 20℃; under 760.051 Torr; for 6h; Sealed tube;74 %Spectr.
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

C12H3F7O3S

C12H3F7O3S

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 40℃; for 3h; Sealed tube; Green chemistry;
C26H18AuF2N2P

C26H18AuF2N2P

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
In 1,4-dioxane at 65℃; Kinetics; Inert atmosphere; Schlenk technique; Sealed tube;
2,6-dichlorotoluene
118-69-4

2,6-dichlorotoluene

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphorus pentachloride; chlorine / 150 °C
2: acetic acid; zinc(II) chloride; hydroxylamine hydrochloride; sodium acetate / 8 h / Reflux
3: potassium fluoride; tetrabutylammomium bromide / 12 h / 170 °C
View Scheme
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

2,6-difluorobenzamide
18063-03-1

2,6-difluorobenzamide

Conditions
ConditionsYield
With water; nitrile hydratase from Rhodococcus rhodochrous J1 at 25℃; for 22h; KH2PO4-K2HPO4 puffer pH=8.0;100%
With dihydrogen peroxide; sodium hydroxide at 50℃; for 5h; Temperature;91.2%
With sulfuric acid at 70℃; for 4h;90%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

sodium methylate
124-41-4

sodium methylate

2-fluoro-6-methoxybenzonitrile
94088-46-7

2-fluoro-6-methoxybenzonitrile

Conditions
ConditionsYield
In methanol at 0 - 20℃;99%
In methanol at 0℃;86%
In methanol at 0 - 20℃;
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

2-amino-6-fluorobenzonitrile
77326-36-4

2-amino-6-fluorobenzonitrile

Conditions
ConditionsYield
With ammonia In dimethyl sulfoxide at 80℃; for 80h; closed bottle;99%
With ammonia In ethanol at 140℃; under 10343.2 Torr; for 6h;97%
With ammonia In dimethyl sulfoxide at 80 - 120℃;97.5%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

2,2-bis(4-hydroxyphenyl)propane bistrimethylsilyl ether
4387-16-0

2,2-bis(4-hydroxyphenyl)propane bistrimethylsilyl ether

polymer; monomer(s): 1,1-bis(4-trimethylsilyloxyphenyl)-1-methylethane; 2,6-difluorobenzonitrile

polymer; monomer(s): 1,1-bis(4-trimethylsilyloxyphenyl)-1-methylethane; 2,6-difluorobenzonitrile

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 140 - 145℃; for 48h;99%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

(+/-)-α-(o-(trifluoromethyl)phenyl)ethyl alcohol
79756-81-3

(+/-)-α-(o-(trifluoromethyl)phenyl)ethyl alcohol

2-fluoro-6-[1-(2-trifluoromethylphenyl)-ethoxy]-benzonitrile
872181-46-9

2-fluoro-6-[1-(2-trifluoromethylphenyl)-ethoxy]-benzonitrile

Conditions
ConditionsYield
Stage #1: (+/-)-α-(o-(trifluoromethyl)phenyl)ethyl alcohol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.75h;
Stage #2: 2,6 difluorobenzonitrile In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2.33333h;
99%
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h;
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

2-fluoro-6-[4-(2-fluorobenzyl)cyclohexylmethoxy]benzonitrile

2-fluoro-6-[4-(2-fluorobenzyl)cyclohexylmethoxy]benzonitrile

Conditions
ConditionsYield
Stage #1: [4-(2-fluorobenzyl)cyclohexyl]methanol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2.03333h;
Stage #2: 2,6 difluorobenzonitrile In N,N-dimethyl-formamide at 0℃; for 2.01667h;
98%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

ethylamine
75-04-7

ethylamine

2-ethylamino-6-fluorobenzonitrile
119584-72-4

2-ethylamino-6-fluorobenzonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide for 4h; Ambient temperature;97%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

thiophenol
108-98-5

thiophenol

2,6-bis(phenylthio)benzonitrile
1271825-04-7

2,6-bis(phenylthio)benzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 25℃;97%
4-Octyne
1942-45-6

4-Octyne

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

(Z)-3-(2,6-difluorophenyl)-2-propylhex-2-enenitrile
1453501-01-3

(Z)-3-(2,6-difluorophenyl)-2-propylhex-2-enenitrile

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylborane; bis[2-(diphenylphosphino)phenyl] ether at 100℃; for 8h; Inert atmosphere; chemoselective reaction;97%
nitromethane
75-52-5

nitromethane

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

(Z)-1-(2,6-difluorophenyl)-2-nitroethen-1-amine

(Z)-1-(2,6-difluorophenyl)-2-nitroethen-1-amine

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 85℃; for 0.5h; Aza-Henry Reaction; Molecular sieve;97%
phenoxazine
135-67-1

phenoxazine

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

2,6-di(10H-phenoxazin-10-yl)benzonitrile

2,6-di(10H-phenoxazin-10-yl)benzonitrile

Conditions
ConditionsYield
With sodium ethanolate In N,N-dimethyl-formamide at 70 - 150℃; for 48h;97%
With sodium hydride In hexane; N,N-dimethyl-formamide; mineral oil for 10h; Inert atmosphere;82%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

2-fluorobenzonitrile
394-47-8

2-fluorobenzonitrile

Conditions
ConditionsYield
With 9,10-phenanthrenequinone In N,N-dimethyl-formamide for 8.25h; Electrochemical reaction;95.7%
1,1,1-tris(4-trimethylsilyloxyphenyl)ethane

1,1,1-tris(4-trimethylsilyloxyphenyl)ethane

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

polymer, product of 1,1,1-tris(4-trimethylsilyloxyphenyl)ethane polycondensation with 2,6-difluorobenzonitrile at 140 - 145 deg C for 48 h, monomers feed ratio 1.0:1.1; monomer(s): 1,1,1-tris(4-trimethylsilyloxyphenyl)ethane; 2,6-difluorobenzonitrile

polymer, product of 1,1,1-tris(4-trimethylsilyloxyphenyl)ethane polycondensation with 2,6-difluorobenzonitrile at 140 - 145 deg C for 48 h, monomers feed ratio 1.0:1.1; monomer(s): 1,1,1-tris(4-trimethylsilyloxyphenyl)ethane; 2,6-difluorobenzonitrile

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 140 - 145℃; for 48h;95%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

benzyl alcohol
100-51-6

benzyl alcohol

2-(benzyloxy)-6-fluorobenzonitrile
94088-45-6

2-(benzyloxy)-6-fluorobenzonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 20℃;95%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

methylmagnesium chloride
676-58-4

methylmagnesium chloride

2,6-difluoroacetophenone
13670-99-0

2,6-difluoroacetophenone

Conditions
ConditionsYield
Stage #1: 2,6 difluorobenzonitrile; methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 20h; Inert atmosphere;
Stage #2: With sulfuric acid In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; water at 50℃;
95%
Stage #1: 2,6 difluorobenzonitrile; methylmagnesium chloride In tetrahydrofuran; toluene at 36 - 40℃; for 5h; Inert atmosphere;
Stage #2: With sulfuric acid; water In tetrahydrofuran; toluene at 27 - 30℃; for 2.5h; Inert atmosphere;
93 %Chromat.
1-methyl-1H-indole-2,3-dione
2058-74-4

1-methyl-1H-indole-2,3-dione

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

dimedone
126-81-8

dimedone

1-fluoro-1',10,10-trimethyl-10,11-dihydro-5H-spiro[indazolo[3,2-b]quinazoline-7,3'-indoline]-2',8(9H)-dione

1-fluoro-1',10,10-trimethyl-10,11-dihydro-5H-spiro[indazolo[3,2-b]quinazoline-7,3'-indoline]-2',8(9H)-dione

Conditions
ConditionsYield
Stage #1: 2,6 difluorobenzonitrile With hydrazine In ethanol at 80℃; for 0.5h; Green chemistry;
Stage #2: 1-methyl-1H-indole-2,3-dione; dimedone With toluene-4-sulfonic acid In ethanol at 80℃; for 4h; Green chemistry;
95%
10H-phenothiazine
92-84-2

10H-phenothiazine

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

C31H19N3S2

C31H19N3S2

Conditions
ConditionsYield
With sodium ethanolate In N,N-dimethyl-formamide at 70 - 150℃; for 48h;95%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

3-amino-4-fluoro-1H-indazole

3-amino-4-fluoro-1H-indazole

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 90℃; for 4h; Inert atmosphere;94%
With hydrazine hydrate In ethanol at 90℃; for 4h; Inert atmosphere;94%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

N-cyclopentyl-3-(hydroxymethyl)-2-oxopiperidine-3-carboxamide

N-cyclopentyl-3-(hydroxymethyl)-2-oxopiperidine-3-carboxamide

3-((2-cyano-3-fluorophenoxy)methyl)-N-cyclopentyl-2-oxopiperidine-3-carboxamide

3-((2-cyano-3-fluorophenoxy)methyl)-N-cyclopentyl-2-oxopiperidine-3-carboxamide

Conditions
ConditionsYield
Stage #1: N-cyclopentyl-3-(hydroxymethyl)-2-oxopiperidine-3-carboxamide With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: 2,6 difluorobenzonitrile In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
94%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

indole-2,3-dione
91-56-5

indole-2,3-dione

dimedone
126-81-8

dimedone

1-fluoro-10,10-dimethyl-10,11-dihydro-5H-spiro[indazolo[3,2-b]quinazoline-7,3'-indoline]-2',8(9H)-dione

1-fluoro-10,10-dimethyl-10,11-dihydro-5H-spiro[indazolo[3,2-b]quinazoline-7,3'-indoline]-2',8(9H)-dione

Conditions
ConditionsYield
Stage #1: 2,6 difluorobenzonitrile With hydrazine In ethanol at 80℃; for 0.5h; Green chemistry;
Stage #2: indole-2,3-dione; dimedone With toluene-4-sulfonic acid In ethanol at 80℃; for 4h; Green chemistry;
94%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

3-Trifluoromethylphenol
98-17-9

3-Trifluoromethylphenol

2-fluoro-6-(3-(trifluoromethyl)phenoxy)benzonitrile

2-fluoro-6-(3-(trifluoromethyl)phenoxy)benzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h;93%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

9,9-bis(4-hydroxyphenyl)fluorene
3236-71-3

9,9-bis(4-hydroxyphenyl)fluorene

C135H79F2N5O8

C135H79F2N5O8

Conditions
ConditionsYield
Stage #1: 2,6 difluorobenzonitrile; 9,9-bis(4-hydroxyphenyl)fluorene With potassium carbonate In N,N-dimethyl acetamide; toluene at 140 - 165℃; for 5h; Inert atmosphere; Dean-Stark;
Stage #2: 2,6 difluorobenzonitrile In N,N-dimethyl acetamide; toluene at 160℃; for 1h; Inert atmosphere; Dean-Stark;
92%
5-methoxyisatine
39755-95-8

5-methoxyisatine

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

dimedone
126-81-8

dimedone

1-fluoro-5'-methoxy-10,10-dimethyl-10,11-dihydro-5H-spiro[indazolo[3,2-b]quinazoline-7,3'-indoline]-2',8(9H)-dione

1-fluoro-5'-methoxy-10,10-dimethyl-10,11-dihydro-5H-spiro[indazolo[3,2-b]quinazoline-7,3'-indoline]-2',8(9H)-dione

Conditions
ConditionsYield
Stage #1: 2,6 difluorobenzonitrile With hydrazine In ethanol at 80℃; for 0.5h; Green chemistry;
Stage #2: 5-methoxyisatine; dimedone With toluene-4-sulfonic acid In ethanol at 80℃; for 4h; Green chemistry;
92%
2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

guanidine hydrogen carbonate
124-46-9, 20734-13-8, 100224-74-6, 593-85-1

guanidine hydrogen carbonate

2,4-diamino-5-fluoroquinazoline
119584-70-2

2,4-diamino-5-fluoroquinazoline

Conditions
ConditionsYield
In N,N-dimethyl acetamide at 140 - 142℃; for 5h;91%
In N,N-dimethyl acetamide at 140℃; for 8h;77%

1897-52-5Relevant articles and documents

Synthesis and Characterization of Bidentate (P^N)Gold(III) Fluoride Complexes: Reactivity Platforms for Reductive Elimination Studies

Genoux, Alexandre,Biedrzycki, Micha?,Merino, Estíbaliz,Rivera-Chao, Eva,Linden, Anthony,Nevado, Cristina

supporting information, p. 4164 - 4168 (2020/12/23)

A new family of cationic, bidentate (P^N)gold(III) fluoride complexes has been prepared and a detailed characterization of the gold-fluoride bond has been carried out. Our results correlate with the observed reactivity of the fluoro ligand, which undergoes facile exchange with both cyano and acetylene nucleophiles. The resulting (P^N)arylgold(III)C(sp) complexes have enabled the first study of reductive elimination on (P^N)gold(III) systems, which demonstrated that C(sp2)?C(sp) bond formation occurs at higher rates than those reported for analogous phosphine-based monodentate systems.

Method for dehydrating primary amide into nitriles under catalysis of cobalt

-

Paragraph 0114-0116, (2021/06/21)

The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.

Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides

Rajendra, Merla Arjuna,Sunil,Sajith, Ayyiliath Meleveetil,Joy, Muthipeedika Nibin,Bakulev, Vasiliy A.,Haridas, Karickal Raman

supporting information, p. 1629 - 1633 (2020/09/15)

A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.

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