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668-45-1 Usage

Synthesis

A further example of nitro rather than chloro acting as a leaving group is demonstrated in the reaction of Ph4PHF2 with 2-chloro-6-nitrobenzonitrile to give 2-fluoro-6- chlorobenzonitrile.

Chemical Properties

colourless to light beige crystals, crystalline

Uses

2-Chloro-6-fluorobenzonitrile was used in the synthesis of:rac-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrilehigh-molecular-weight, soluble polyarylether alternating copolymers containing pendent cyano groups

General Description

2-Chloro-6-fluorobenzonitrile is an inhibitor of cellulose synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 668-45-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,6 and 8 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 668-45:
(5*6)+(4*6)+(3*8)+(2*4)+(1*5)=91
91 % 10 = 1
So 668-45-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H7FO2/c10-6-1-2-9-7(5-6)8(11)3-4-12-9/h1-2,5H,3-4H2

668-45-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B21662)  2-Chloro-6-fluorobenzonitrile, 98%   

  • 668-45-1

  • 10g

  • 218.0CNY

  • Detail
  • Alfa Aesar

  • (B21662)  2-Chloro-6-fluorobenzonitrile, 98%   

  • 668-45-1

  • 50g

  • 710.0CNY

  • Detail

668-45-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Chloro-6-fluorobenzonitrile

1.2 Other means of identification

Product number -
Other names Benzonitrile, 2-chloro-6-fluoro-

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:668-45-1 SDS

668-45-1Synthetic route

N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine
443-33-4

N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine

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

2-chloro-6-fluorobenzonitrile

Conditions
ConditionsYield
With trifluoromethylsulfonic anhydride; triethylamine; triphenylphosphine In dichloromethane at 0℃; for 0.166667h;96%
With 1,1,3,3-tetraphenyl-2-oxa-1,3-phoshpinobenzene bis(trifluoromethanesulfonate); triethylamine In dichloromethane at 20℃; for 0.333333h;96%
Stage #1: N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine With bis(trichloromethyl) carbonate; N,N-dimethyl-formamide In acetonitrile at 20℃; for 0.166667h;
Stage #2: With water; sodium hydrogencarbonate In acetonitrile
94%
With [PdCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}] In acetonitrile at 100℃; for 24h; Inert atmosphere; Sealed tube;91%
With C24H33ClF3N3Os In acetonitrile at 80℃; for 1h; Sealed tube;82%
2-chloro-6-nitrobenzonitrile
6575-07-1

2-chloro-6-nitrobenzonitrile

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

2-chloro-6-fluorobenzonitrile

Conditions
ConditionsYield
With biphenyl; tetramethylammonium hydrogen difluoride In N,N-dimethyl acetamide at 60℃; for 3h;84%
With potassium fluoride; tetraphenylphosphonium bromide at 82℃; The ratio of the initial rates of flurine transfer reaction with KF alone and KF-Ph4PBr were measured in CH3CN and sulpholane.;
With potassium fluoride In dimethyl sulfoxide at 82℃; solvent effect of nucleophilie fluorine transfer, var. chloro-nitrobenzene;
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-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;
2,6-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.
2-chloro-6-nitrobenzonitrile
6575-07-1

2-chloro-6-nitrobenzonitrile

Ph4 P+ HF

Ph4 P+ HF

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

2-chloro-6-fluorobenzonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

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

3-chloro-2-cyanophenol

Conditions
ConditionsYield
With 2-(methylsulfonyl)ethyl alcohol; sodium hydride In tetrahydrofuran at 20℃; for 0.5h;100%
Stage #1: 2-chloro-6-fluorobenzonitrile With 18-crown-6 ether; potassium tert-butylate In acetonitrile Inert atmosphere; Reflux;
Stage #2: With sodium hydroxide In water; acetonitrile for 1h;
Stage #3: In water pH=4; Acidic conditions;
60%
With 18-crown-6 ether; potassium acetate In acetonitrile for 24h; Heating;2.20 g
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

phenol
108-95-2

phenol

2-chloro-6-phenyloxybenzonitrile
91692-70-5

2-chloro-6-phenyloxybenzonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 190℃; for 0.1h; Microwave irradiation; Sealed tube;97%
With potassium carbonate In dimethyl sulfoxide at 190℃; for 0.1h; Microwave irradiation; Sealed tube;97%
With potassium fluoride on basic alumina; 18-crown-6 ether In dimethyl sulfoxide at 140℃; for 20h;90%
3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

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

2-chloro-6-fluorobenzonitrile

C14H9ClFNO

C14H9ClFNO

Conditions
ConditionsYield
Stage #1: 2-chloro-6-fluorobenzonitrile With lithium chlorozincate; lithium dicyclohexylamide In tetrahydrofuran at 0℃; for 0.0111111h; Flow reactor;
Stage #2: 3-methoxy-1-iodobenzene With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 25℃; for 2h; Negishi Coupling; Flow reactor;
97%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

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

2-chloro-6-fluorobenzoic acid

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.5h; Green chemistry;95%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

methylhydrazine
60-34-4

methylhydrazine

4-chloro-1-methyl-1H-indazol-3-amine
959240-93-8

4-chloro-1-methyl-1H-indazol-3-amine

Conditions
ConditionsYield
In ethanol Reflux; regioselective reaction;94%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

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

guanidine hydrogen carbonate

5-chloro-2,4-diaminoquinazoline
17511-21-6

5-chloro-2,4-diaminoquinazoline

Conditions
ConditionsYield
In N,N-dimethyl acetamide at 140 - 142℃; for 7h;92%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2-chloro-6-hydrazinobenzonitrile

2-chloro-6-hydrazinobenzonitrile

Conditions
ConditionsYield
With hydrazine In tetrahydrofuran at 20 - 30℃; for 0.75h;90%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

S-tert-butylsulfinimide
146374-27-8

S-tert-butylsulfinimide

N-(2-cyano-3-fluorophenyl)-2-methylpropane-2-sulfinamide
1338209-85-0

N-(2-cyano-3-fluorophenyl)-2-methylpropane-2-sulfinamide

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 15h; Inert atmosphere;90%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

sodium methylate
124-41-4

sodium methylate

2-Chlor-6-methoxybenzoesaeurenitril
6575-10-6

2-Chlor-6-methoxybenzoesaeurenitril

Conditions
ConditionsYield
In methanol at 85℃;89.8%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2-chloro-6-fluorobenzyl amine
15205-15-9

2-chloro-6-fluorobenzyl amine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0℃; for 24h; Inert atmosphere;89%
With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 4h; Inert atmosphere;75%
With lithium borohydride In tetrahydrofuran at 25℃; for 3h;70%
With lithium borohydride; diisopropopylaminoborane In tetrahydrofuran for 2h; Reflux;70%
With diisobutylaluminum borohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;16%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2-chloro-6-ethoxybenzonitrile

2-chloro-6-ethoxybenzonitrile

Conditions
ConditionsYield
In tetrahydrofuran; ethanol87%
In tetrahydrofuran; ethanol87%
ethanol
64-17-5

ethanol

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

2-chloro-6-fluorobenzonitrile

2-chloro-6-ethoxybenzonitrile

2-chloro-6-ethoxybenzonitrile

Conditions
ConditionsYield
Stage #1: ethanol With sodium t-butanolate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 2-chloro-6-fluorobenzonitrile In tetrahydrofuran at 20℃; for 0.5h;
87%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2-chloro-6-mercapto-benzonitrile
72371-52-9

2-chloro-6-mercapto-benzonitrile

Conditions
ConditionsYield
Stage #1: 2-chloro-6-fluorobenzonitrile With sodium sulfide In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #2: With hydrogenchloride; zinc In water Cooling with ice; Inert atmosphere;
86%
Stage #1: 2-chloro-6-fluorobenzonitrile In dimethyl sulfoxide at 75℃; for 0.333333h;
Stage #2: With sodiumsulfide nonahydrate In dimethyl sulfoxide at 75℃; for 2h;
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

3-fluoro-4'-methylbiphenyl-2-carbonitrile
1239886-78-2

3-fluoro-4'-methylbiphenyl-2-carbonitrile

Conditions
ConditionsYield
With manganese(ll) chloride In tetrahydrofuran at 0℃; for 0.5h;83%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

2-chloro-6-(cyanomethyl)benzonitrile
1184843-24-0

2-chloro-6-(cyanomethyl)benzonitrile

Conditions
ConditionsYield
Stage #1: methyl 2-cyanoacetate With sodium hydride In dimethyl sulfoxide at 0 - 20℃; for 0.5h;
Stage #2: 2-chloro-6-fluorobenzonitrile In dimethyl sulfoxide at 90℃;
83%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2-chloro-6-fluoro-benzamide
66073-54-9

2-chloro-6-fluoro-benzamide

Conditions
ConditionsYield
With sulfuric acid at 75℃; for 3.5h;80%
With sulfuric acid at 70℃; for 4h;80%
With dihydrogen peroxide; potassium carbonate In dimethyl sulfoxide at 0 - 25℃;
With sulfuric acid at 60 - 70℃;5.5 g
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

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

N,N-dimethyl-formamide

6-chloro-2-fluoro-3-formylbenzonitrile

6-chloro-2-fluoro-3-formylbenzonitrile

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane at -40℃; Flow reactor;80%
Stage #1: 2-chloro-6-fluorobenzonitrile With lithium diisopropyl amide In tetrahydrofuran; n-heptane at -70℃; for 0.5h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; n-heptane at -70℃; for 0.5h;
17%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2-amino-phenol
95-55-6

2-amino-phenol

1-chlorodibenzo[b,f][1,4]oxazepin-11-amine

1-chlorodibenzo[b,f][1,4]oxazepin-11-amine

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 100℃; for 6h;80%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2-(2-fluorophenyl)-5,5-dimethyl-[1,3,2]dioxaborinane
346656-39-1

2-(2-fluorophenyl)-5,5-dimethyl-[1,3,2]dioxaborinane

2′-fluoro-3-fluorobiphenyl-2-carbonitrile
537036-82-1

2′-fluoro-3-fluorobiphenyl-2-carbonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; for 63h; Suzuki-Miyaura coupling;78%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

2-chloro-6-fluorobenzenecarbothioamide
769-05-1

2-chloro-6-fluorobenzenecarbothioamide

Conditions
ConditionsYield
With pyridine; diammonium sulfide; triethylamine at 50℃; for 4h;78%
With diammonium sulfide; triethylamine In pyridine at 50℃;75%
With pyridine; triethylamine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate72%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

5,8-dihydro-5-phenyl-5,8-diazaindeno[2,1-c]fluorene

5,8-dihydro-5-phenyl-5,8-diazaindeno[2,1-c]fluorene

C31H18ClN3

C31H18ClN3

Conditions
ConditionsYield
Stage #1: 2-chloro-6-fluorobenzonitrile; 5,8-dihydro-5-phenyl-5,8-diazaindeno[2,1-c]fluorene With sodium t-butanolate In toluene for 0.5h; Reflux;
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In toluene for 3h; Reflux;
78%
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

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

2-chloro-6-fluorobenzonitrile

3-chloro-6-2',2',2'-trifluoroethoxybenzonitrile
93624-59-0

3-chloro-6-2',2',2'-trifluoroethoxybenzonitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 150℃; for 15h;77%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

sodium 2,2,2-trifluoroethanolate
420-87-1

sodium 2,2,2-trifluoroethanolate

3-chloro-6-2',2',2'-trifluoroethoxybenzonitrile
93624-59-0

3-chloro-6-2',2',2'-trifluoroethoxybenzonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 90℃;77%
2-chloro-6-fluorobenzonitrile
668-45-1

2-chloro-6-fluorobenzonitrile

5,12-dihydro-5-phenyl indolo[3,2-a]carbazole
1247053-55-9

5,12-dihydro-5-phenyl indolo[3,2-a]carbazole

C31H18ClN3

C31H18ClN3

Conditions
ConditionsYield
Stage #1: 2-chloro-6-fluorobenzonitrile; 5,12-dihydro-5-phenyl indolo[3,2-a]carbazole With sodium t-butanolate In toluene for 0.5h; Reflux;
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In toluene for 3h; Reflux;
77%
Trimethyl borate
121-43-7

Trimethyl borate

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

2-chloro-6-fluorobenzonitrile

(4-chloro-3-cyano-2-fluorophenyl)boronic acid

(4-chloro-3-cyano-2-fluorophenyl)boronic acid

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane at -40℃; Flow reactor;76%
carbon dioxide
124-38-9

carbon dioxide

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

2-chloro-6-fluorobenzonitrile

4-chloro-3-cyano-2-fluorobenzoic acid

4-chloro-3-cyano-2-fluorobenzoic acid

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane at -50℃; Flow reactor;76%
Stage #1: 2-chloro-6-fluorobenzonitrile With lithium diisopropyl amide In tetrahydrofuran at -65℃; for 0.25h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran at -50 - 20℃; for 1.75h;
42%
9-phenyl-3,3'-bicarbazole
1060735-14-9

9-phenyl-3,3'-bicarbazole

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

2-chloro-6-fluorobenzonitrile

C37H22ClN3

C37H22ClN3

Conditions
ConditionsYield
Stage #1: 9-phenyl-3,3'-bicarbazole; 2-chloro-6-fluorobenzonitrile With sodium t-butanolate In toluene for 0.5h; Reflux;
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In toluene for 3h; Reflux;
75%
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

2-chloro-6-fluorobenzonitrile

6-chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

6-chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane; cyclohexane at -40℃; Flow reactor;73%

668-45-1Relevant articles and documents

Half-Sandwich Guanidinate-Osmium(II) Complexes: Synthesis and Application in the Selective Dehydration of Aldoximes

Francos, Javier,González-Liste, Pedro J.,Menéndez-Rodríguez, Lucía,Crochet, Pascale,Cadierno, Victorio,Borge, Javier,Anti?olo, Antonio,Fernández-Galán, Rafael,Carrillo-Hermosilla, Fernando

, p. 393 - 402 (2016/02/03)

The novel guanidinate-osmium(II) complexes [OsCl{κ2-(N,N′)-C(NR)(NiPr)NHiPr}(η6-p-cymene)] [R = Ph (3a), 4-C6H4F (3b), 4-C6H4Cl (3c), 4-C6H4CF3 (3d), 3-C6H4CF3 (3e), 3,5-C6H3(CF3)2 (3f), 4-C6H4CN (3g), 4-C6H4Me (3h), 3-C6H4Me (3i), 2-C6H4Me (3j), 4-C6H4tBu (3k), 2,6-C6H3iPr2 (3l), 2,4,6-C6H2Me3 (3m)] have been synthesized in high yields (70-88 %) by treatment of THF solutions of the dimeric precursor [{OsCl(μ-Cl)(η6-p-cymene)}2] (1) with 4 equivalents of the corresponding guanidine (iPrHN)2C=NR (2a-m) at room temperature. The easily separable guanidinium chloride salts [(iPrHN)2C(NHR)]Cl (4a-m) were also formed in these reactions. The structures of 3a, 3d, and 3h were unequivocally confirmed by X-ray diffraction methods. Complexes 3a-m proved to be active in the catalytic dehydration of aldoximes. The best results were obtained with [OsCl{κ2-(N,N′)-C(N-4-C6H4CF3)(NiPr)NHiPr}(η6-p-cymene)] (3d; 5 mol-%), which, in acetonitrile at 80C, was able to convert selectively a large variety of aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes into the corresponding nitriles in high yields and short reaction times. Novel osmium(II)-guanidinate complexes of general composition [OsCl{κ2-(N,N′)-C(NR)(NiPr)NHiPr}(η6-p-cymene)] (R = Ar) have been synthesized and successfully employed as catalysts for the selective conversion of aldoximes into nitriles.

Cyclic aromatic analogues of the hendrickson reagent; NMR studies and electrophilic properties

Moussa, Ziad

experimental part, p. 460 - 468 (2012/03/11)

Two novel cyclic aromatic analogues of the Hendrickson POP reagent, 1,1,3,3-tetraphenyl-1,3-dihydro-2,1,3-benzoxadiphosphole-1,3-diium bis(trifluoromethanesulfinate) and bis(trifluoromethanesulfonate), have been readily prepared by the treatment of 1,2-bis(diphenylphosphino)benzene or 1,2-bis(diphenylphosphoryl)benzene, respectively, with trifluoromethanesulfonic anhydride in dichloromethane. 31P and 19F NMR studies indicated that while the latter complex is formed as the sole product, the former species was shown to be the predominant component in equilibrium with 1-(diphenylphosphino)-2-[diphenyl(trifluoromethylsulfonyloxy)phosphonio]benzene trifluoromethanesulfinate and 1,2-bis[diphenyl(trifluoromethylsulfonyloxy) phosphonio]benzene bis(trifluoromethanesulfinate). The dehydrating POP systems were exploited in the conversion of aldoximes into nitriles. The dehydration occurred rapidly at room temperature and produced high yields with a variety of alkyl- and arylaldoximes, tolerating a wide range of substrates and functional groups. Georg Thieme Verlag Stuttgart New York.

NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles

Moussa, Ziad,Ahmed, Saleh A.,ElDouhaibi, Ahmad S.,Al-Raqa, Shaya Y.

experimental part, p. 1826 - 1831 (2010/09/07)

NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 °C is described. The reagent structure resulting from mixing 1.3 equiv of Ph3P with Tf2O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate dimer. The electrophilic properties of the system have been exploited in the development of a mild method for converting aldoximes into nitriles. The dehydration occurs at 0 °C under very mild conditions by initial activation of the oxime oxygen, followed by treatment with a base and subsequent elimination of triphenylphosphine oxide. The substrate scope and functional group tolerance of this useful method are explored.

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