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100-47-0 Usage

Chemical Description

Different sources of media describe the Chemical Description of 100-47-0 differently. You can refer to the following data:
1. Benzonitrile is an aromatic compound with the chemical formula C6H5CN, while isopropyl chloride is a colorless liquid with the chemical formula (CH3)2CHCl.
2. Benzonitrile is a colorless liquid with a sweet almond-like odor.
3. Benzonitrile is an organic compound that is used as a solvent and in the production of other chemicals.

Chemical Properties

Bezonitrile is a colorless, oily liquid. It has a almond odor and a bitter taste. Slightly soluble in cold water, the solubility in water at 100°C is 1%; miscible with common organic solvents. When heated to decomposition, benzonitrile emits toxic hydrogen cyanide and oxides of nitrogen (HSDB 1988).

Occurrence

Benzonitrile is reported to be found in natural cocoa aroma), in milk products, roasted filberts and peanuts and cooked trassi . Benzonitrile also has been detected in the thermal decomposition products of flexible polyurethane foam.

Uses

The most important commercial use for benzonitrile is the synthesis of benzoguanamine, which is a derivative of melamine and is used in protective coatings and molding resins. It is used intermediate for rubber chemicals; solvent for nitrile rubber, specialty lacquers, and many resins and polymers, and for many anhydrous metallic salts.

Application

Benzonitrile is a widely utilized as a solvent and an intermediate in industries making drugs, perfumes, dyes, rubber, textiles, resins and specialty lacquers. It finds application as a versatile precursor for many derivatives. It coordinates with transition metal to form complexes which act as synthetic intermediates.

Preparation

Benzonitrile can be prepared by following methods:1) on a small scale by the dehydration in an inert solvent with phosphorus oxychloride or benzenesulfonyl chloride and an organic amine.2) from benzoic acid by heating with lead thiocyanate.3) by heating sodium benzenesulfonate with sodium cyanide.4) by adding benzenediazonium chloride solution to a hot aq sodium cyanide solution containing cupric sulfate and distilling by ammoxidation of toluene.Benzonitrile can also be produced in high yield by the vapor-phase catalytic ammoxidation of toluene.

Definition

ChEBI: Benzonitrile is a nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group. It is a member of benzenes and a nitrile.

Synthesis Reference(s)

Chemistry Letters, 13, p. 1913, 1984Journal of the American Chemical Society, 111, p. 4903, 1989 DOI: 10.1021/ja00195a050Tetrahedron Letters, 11, p. 2085, 1970

General Description

Benzonitrile appears as a clear colorless liquid with an almond-like odor. Flash point 161°F. Denser (at 8.4 lb / gal) than water and slightly soluble in water. Used as a specialty solvent and to make other chemicals.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

The cyano group can be readily hydrolyzed in the presence of mineral acids to produce stable, moderately toxic benzoic acid . When heated to decomposition, Benzonitrile emits highly toxic fumes of nitrogen oxides and hydrogen cyanide [Sax, 9th ed., 1996, p. 353].

Hazard

High toxicity; absorbed by skin.

Health Hazard

Benzonitrile may enter the human body by ingestion, absorption through the skin, or inhalation. The earliest symptoms of cyano compound intoxication may be weakness, headaches, confusion, and occasionally nausea and vomiting. The respiratory rate and depth will usually be increased at the beginning and at later stages become slow and gasping. Blood pressure is usually normal, especially in the mild or moderately severe cases, although the pulse rate is usually more rapid than normal.

Fire Hazard

Special Hazards of Combustion Products: Toxic hydrogen cyanide and oxides of nitrogen may form in fire.

Industrial uses

Benzonitrile is used as an intermediate for rubber chemicals and as a solvent for nitrile rubber, specialty lacquers, many resins, polymers and for many anhydrous metallic salts (HSDB 1988; Hawley 1981). It is principally used as an intermediate for benzoguanamine (HSDB 1988). It is also used as an additive in nickel-plating baths, separating naphthalene and alkylnaphthalenes from non-aromatics by azetropic distillation; as jet-fuel additive; in cotton bleaching baths; as a drying additive for acrylic fibers; and in the removal of titanium tetrachloride and vanadium oxychloride from silicon tetrachloride (HSDB 1988; Smiley 1981). Benzonitrile is also used in perfumes at a maximum level of 0.2% in the final product (Opdyke 1979).

Safety Profile

Poison by intraperitoneal andsubcutaneous routes. Moderately toxic by ingestion,inhalation, and skin contact. A skinirritant. Combustible liquid. When heated todecomposition it emits toxic fumes of CN- and NOx.

Metabolism

Benzonitrile is mainly hydroxylated in vivo to cyanophenols, a small amount being hydrolysed to benzoic acid (Williams 1959). Benzonitrile also forms 6>-hydroxybenzonitrile, m-hydroxybenzonitrile, and /p-hydroxybenzonitrile in rabbits (HSDB 1988). In rabbit, 50% of a dose of 150 mg/kg was converted to conjugated cyanophenols and 10% of the benzonitrile fed was excreted as benzoic acid. Hydrogen cyanide is not a metabolite of benzonitrile (Williams 1959) and cyanide was not found to be formed by benzonitrile either in vivo or in vitro (Tanii and Hashimoto 1984). The in vivo microsomal hydroxylation of specifically deuterated benzonitrile in the rat yielded mainly 4-hydroxybenzonitrile with 41% retention of deuterium (Daly et al 1968).

Shipping

UN2224 Benzonitrile, Hazard Class: 6.1; Labels: 6.1—Poisonous materials.

Purification Methods

Dry benzonitrile with CaSO4, CaCl2, MgSO4 or K2CO3, and distil it from P2O5 in an all-glass apparatus, under reduced pressure (b 69o/10mm), collecting the middle fraction. Distillation from CaH2 causes some decomposition of benzonitrile. Isonitriles can be removed by preliminary treatment with conc HCl until the odour of isonitrile (carbylamine) has gone, followed by preliminary drying with K2CO3. (This treatment also removes amines.) Steam distil (to remove small quantities of carbylamine). The distillate is extracted into ether, washed with dilute Na2CO3, dried overnight with CaCl2, and the ether is removed by evaporation. The residue is distilled at 40mm (b 96o) [Kice et al. J Am Chem Soc 82 834 1960]. Conductivity grade benzonitrile (specific conductance 2 x 10-8 mho) is obtained by treatment with anhydrous AlCl3, followed by rapid distillation at 40-50o under vacuum. After washing with alkali and drying with CaCl2, the distillate is redistilled in a vacuum several times at 35o before fractionally crystallising several times by partial freezing. It is dried over finely divided activated alumina from which it is withdrawn when required [Van Dyke & Harrison J Am Chem Soc 73 402 1951]. [Beilstein 9 IV 892.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. They are incompatible Benzonitrile with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions.

Waste Disposal

(1) Mix with calcium hypochlorite and flush to sewer with water or (2) incinerate.

Check Digit Verification of cas no

The CAS Registry Mumber 100-47-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 100-47:
(5*1)+(4*0)+(3*0)+(2*4)+(1*7)=20
20 % 10 = 0
So 100-47-0 is a valid CAS Registry Number.
InChI:InChI:1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H

100-47-0 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (A11173)  Benzonitrile, 99%   

  • 100-47-0

  • 100g

  • 273.0CNY

  • Detail
  • Alfa Aesar

  • (A11173)  Benzonitrile, 99%   

  • 100-47-0

  • 500g

  • 416.0CNY

  • Detail
  • Alfa Aesar

  • (A11173)  Benzonitrile, 99%   

  • 100-47-0

  • 2500g

  • 1324.0CNY

  • Detail
  • Sigma-Aldrich

  • (294098)  Benzonitrile  anhydrous, ≥99%

  • 100-47-0

  • 294098-100ML

  • 1,370.07CNY

  • Detail
  • Sigma-Aldrich

  • (294098)  Benzonitrile  anhydrous, ≥99%

  • 100-47-0

  • 294098-1L

  • 2,858.31CNY

  • Detail
  • Sigma-Aldrich

  • (B8959)  Benzonitrile  ReagentPlus®, 99%

  • 100-47-0

  • B8959-100ML

  • 273.78CNY

  • Detail
  • Sigma-Aldrich

  • (B8959)  Benzonitrile  ReagentPlus®, 99%

  • 100-47-0

  • B8959-1L

  • 409.50CNY

  • Detail
  • Sigma-Aldrich

  • (B8959)  Benzonitrile  ReagentPlus®, 99%

  • 100-47-0

  • B8959-20L

  • 6,343.74CNY

  • Detail
  • Sigma-Aldrich

  • (270318)  Benzonitrile  for HPLC, 99.9%

  • 100-47-0

  • 270318-100ML

  • 1,333.80CNY

  • Detail
  • Sigma-Aldrich

  • (270318)  Benzonitrile  for HPLC, 99.9%

  • 100-47-0

  • 270318-1L

  • 2,610.27CNY

  • Detail

100-47-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name benzonitrile

1.2 Other means of identification

Product number -
Other names Benzonitrile

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:100-47-0 SDS

100-47-0Synthetic route

benzamide
55-21-0

benzamide

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With phosphorus pentoxide In methanol at 20℃; for 1h;100%
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide In acetonitrile at 20℃; for 0.166667h; Solvent;98%
With trimethylsilylphosphate for 0.666667h; Heating;97%
benzaldehyde
100-52-7

benzaldehyde

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With iron(III) chloride; hydroxylamine hydrochloride In dimethyl sulfoxide Molecular sieve;100%
With [bis(acetoxy)iodo]benzene; ammonium bicarbonate In methanol; water at 36℃; for 12h; Sealed tube;100%
With N-(4-sulphonic acid)butylpyridinium hydrogen sulphate; 1-sulfobutylpyridine hydrogensulfate hydroxylamine In toluene at 100℃; under 760.051 Torr; for 2h; Temperature; Solvent; Reagent/catalyst;100%
Benzaldoxime
932-90-1

Benzaldoxime

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With nickel(II) chloride dihydrate In acetonitrile at 80℃; Molecular sieve; Inert atmosphere;100%
With oxalyl dichloride; triethylamine In dimethyl sulfoxide; acetonitrile at 20℃; for 0.333333h; Reagent/catalyst; Swern Oxidation;100%
With zinc trifluoromethanesulfonate In toluene at 100℃; for 24h;99%
benzoyl cyanide
613-90-1

benzoyl cyanide

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In benzene at 120℃; for 12h; Product distribution; other acyl cyanides, var. solvents, temp. and time;100%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 180℃; for 24h; Temperature; Glovebox; Inert atmosphere; Sealed tube;95 %Chromat.
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With potassium tert-butylate; N,N-dimethyl-formamide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;100%
With C60H48BP3Pd; potassium formate; [2.2.2]cryptande In tetrahydrofuran at 60℃; for 72h; Schlenk technique; Inert atmosphere;99%
With formic acid; Cyclohexanethiol; 10-phenyl-10H-phenothiazine; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; under 2625.26 Torr; for 0.05h; Catalytic behavior; Reagent/catalyst; Time; Wavelength; Irradiation; Flow reactor;96%
Conditions
ConditionsYield
With triethylamine; 2,4-Dichloro-5-nitropyrimidine In acetonitrile for 5h; Ambient temperature;100%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 20℃; Beckmann rearrangement;100%
With oxalyl dichloride; Triphenylphosphine oxide In chloroform at 20℃; for 1h;99%
benzamide
55-21-0

benzamide

chloro(tert-butyl)diethylamino(methylene)phosphorane
78303-22-7

chloro(tert-butyl)diethylamino(methylene)phosphorane

A

benzonitrile
100-47-0

benzonitrile

B

C9H22Cl2NP

C9H22Cl2NP

C

P-tert-butyl-N,N-diethyl-P-methylphosphinic amide

P-tert-butyl-N,N-diethyl-P-methylphosphinic amide

Conditions
ConditionsYield
In diethyl ether -10 dec C, then +20 deg C.;A 70%
B 100%
C 85%
(E)-benzaldehyde O-pivaloyloxime
149540-88-5

(E)-benzaldehyde O-pivaloyloxime

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With triethylamine In acetonitrile at 25℃; Rate constant; Mechanism; variation of base/solvent system;100%
With diisobutylamine In acetonitrile at 20℃; for 10h;94 %Chromat.
With diisopropylamine In acetonitrile at 25℃; Kinetics;
C12H14(2)HNO2
149540-89-6

C12H14(2)HNO2

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With triethylamine In acetonitrile at 25℃; Rate constant; variation of base/solvent system;100%
chlorobenzene
108-90-7

chlorobenzene

potassium ferrocyanide

potassium ferrocyanide

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one; Hexadecane at 140℃; for 16h; Product distribution / selectivity;100%
With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.166667h; Microwave irradiation;94%
With sodium carbonate; palladium diacetate; tri-tert-butyl phosphine In 1-methyl-pyrrolidin-2-one; Hexadecane at 140℃; for 16h; Product distribution / selectivity;88%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

A

biphenyl-2,2'-dicarbonitrile
4341-02-0

biphenyl-2,2'-dicarbonitrile

B

benzonitrile
100-47-0

benzonitrile

C

2-cyanophenylzinc bromide
131379-17-4

2-cyanophenylzinc bromide

Conditions
ConditionsYield
With trifluoroacetic acid; cobalt(II) bromide; zinc dibromide In acetonitrile the mixt. in CH3CN was stirred at room temp., then arylbromide was added, stirred at room temp.; GC analysis;A 0%
B 0%
C 100%
(η5-indenyl)(η1-phenylacetylide)bis(triphenylphosphine)ruthenium

(η5-indenyl)(η1-phenylacetylide)bis(triphenylphosphine)ruthenium

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

A

((η5-indenyl)(carbonyl)bis(triphenylphosphine)ruthenium) perchlorate * 0.5CH2Cl2

((η5-indenyl)(carbonyl)bis(triphenylphosphine)ruthenium) perchlorate * 0.5CH2Cl2

B

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With NaClO4; CH2Cl2 In dichloromethane room temp., 15 min;A 80%
B 100%
With CH2Cl2 In dichloromethane room temp., 15 min;A n/a
B 73%
bromobenzene
108-86-1

bromobenzene

potassium ferrocyanide

potassium ferrocyanide

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one; Hexadecane at 140℃; for 16h; Product distribution / selectivity;100%
With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.116667h; Microwave irradiation;95%
With 1-methyl-pyrrolidin-2-one; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate at 120℃; for 12h; Schlenk technique; Inert atmosphere;95%
benzenecarbothioamide
2227-79-4

benzenecarbothioamide

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With oxygen; sodium hydroxide In tetrahydrofuran; water at 20℃; for 3h;99%
With p-methoxybenzenetellurinic acid anhydride In dichloromethane for 0.5h; Ambient temperature;95%
With bis(4-methoxyphenyl)telluride; tetrabutylammonium acetate In water; acetonitrile electrolysis;95%
benzylamine
100-46-9

benzylamine

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With oxygen In acetone at 20℃; for 5.3h; Electrochemical reaction;99%
With aluminum oxide In N,N-dimethyl-formamide at 120℃; for 6h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;99%
With water; potassium hydroxide at 25℃; pH=13.6; Electrochemical reaction;98%
benzyl alcohol
100-51-6

benzyl alcohol

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 130℃; under 3750.38 Torr; for 24h; Reagent/catalyst; Solvent;99%
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 5h; Autoclave; High pressure;99%
With ammonia at 320℃; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Flow reactor;98%
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With ammonium formate In water at 20℃; for 6h;99%
With Triethoxysilane; C20H24N4Ni; sodium t-butanolate In toluene at 80℃; for 8h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;83%
With cyclohexa-1,4-diene; 9-ethyl-N3,N3,N6,N6,-tetramethyl-9H-carbazole-3,6-diamine; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 23℃; for 0.8h; Inert atmosphere; UV-irradiation; Schlenk technique;83%
bromobenzene
108-86-1

bromobenzene

potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;99%
With tetrabutylammomium bromide; copper(II) acetate monohydrate; potassium iodide; N,N`-dimethylethylenediamine In water at 20 - 140℃; Microwave irradiation;89%
With sodium carbonate In N,N-dimethyl-formamide at 110℃; for 20h; Catalytic behavior; Sealed tube;99 %Chromat.
iodobenzene
591-50-4

iodobenzene

potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Time; Temperature; Inert atmosphere;99%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h;95%
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.0833333h; Microwave irradiation;92%
2-iodobenzonitrile
4387-36-4

2-iodobenzonitrile

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With triethylamine In water at 25℃; for 1h; UV-irradiation;99%
With triethylamine In tetrahydrofuran at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube;80.7%
With triethylamine; Lumogen F Orange 240 In N,N-dimethyl-formamide at 40℃; for 4h; Irradiation;98 %Chromat.
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

isopropyl alcohol
67-63-0

isopropyl alcohol

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With sodium hydroxide at 24.84℃; under 760.051 Torr; for 96h; Inert atmosphere; UV-irradiation; Sealed tube;99%
(E)-2-hydroxy-2-methyl-1-phenylpropan-1-one O-acetyl oxime

(E)-2-hydroxy-2-methyl-1-phenylpropan-1-one O-acetyl oxime

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With copper(l) iodide In dimethyl sulfoxide at 90℃; for 12h;99%
benzaldehyde oxime benzoyl ester
3848-27-9

benzaldehyde oxime benzoyl ester

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In dichloromethane; toluene at 20℃; for 0.0333333h; Reagent/catalyst;99%
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 0.0333333h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique;64%
syn-O-(4-Chlorbenzoyl)-benzaldoxim
18322-87-7, 63561-63-7

syn-O-(4-Chlorbenzoyl)-benzaldoxim

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In dichloromethane; toluene at 20℃; for 0.05h;99%
C15H13NO3

C15H13NO3

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In dichloromethane; toluene at 20℃; for 0.05h;99%
iodobenzene
591-50-4

iodobenzene

potassium cyanide
151-50-8

potassium cyanide

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In various solvent(s) at 60℃; for 1h;98%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In various solvent(s) at 60℃; for 1h; other catalyst, other solvent, other temperature;98%
Stage #1: potassium cyanide; (E)-N1,N1-dimethyl-N2-(pyridin-2-ylmethylene)ethane-1,2-diamine; copper(I) oxide at 100℃;
Stage #2: iodobenzene In N,N-dimethyl-formamide at 110℃; for 24h; Product distribution / selectivity;
83%
Stage #1: potassium cyanide; copper(I) oxide; trans-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine at 100℃;
Stage #2: iodobenzene In N,N-dimethyl-formamide at 110℃; for 24 - 48h; Product distribution / selectivity;
73.7%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 1h; Substitution; Heating;
2-nitropropane
79-46-9

2-nitropropane

3-diazo-5-phenyl-3H-1,2,4-triazole
80670-36-6

3-diazo-5-phenyl-3H-1,2,4-triazole

A

benzonitrile
100-47-0

benzonitrile

B

acetone oxime
127-06-0

acetone oxime

Conditions
ConditionsYield
at 80℃; Yields of byproduct given;A n/a
B 98%
α-nitrobenzyl phenyl sulfone
21272-78-6

α-nitrobenzyl phenyl sulfone

A

Benzenethiosulfonic acid; compound with ammonia
77853-07-7

Benzenethiosulfonic acid; compound with ammonia

B

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 4h;A 98%
B 70%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

benzenecarbothioamide
2227-79-4

benzenecarbothioamide

A

dibenzyl selenide
1842-38-2

dibenzyl selenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
In methanol for 0.5h; Mechanism; Ambient temperature;A 98%
B 98%
C 81%
4-hydroxy-4-octyl-3-phenylisoxazoline-5-one
80503-58-8

4-hydroxy-4-octyl-3-phenylisoxazoline-5-one

A

2-oxodecanoic acid
333-60-8

2-oxodecanoic acid

B

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With 2,6-dichloro-benzonitrile In benzene for 3h; Heating;A 98%
B n/a
benzonitrile
100-47-0

benzonitrile

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide In dimethyl sulfoxide at 140℃; for 1h; Solvent; Time; Temperature;100%
With sodium azide In dimethyl sulfoxide at 120℃; for 0.166667h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Green chemistry;100%
With sodium azide In N,N-dimethyl-formamide at 120℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Green chemistry;100%
benzonitrile
100-47-0

benzonitrile

2,4,6-triphenyl-1,3,5-triazine
493-77-6

2,4,6-triphenyl-1,3,5-triazine

Conditions
ConditionsYield
With ammonia; lanthanum(lll) triflate at 200℃; for 24h; in a stainless steel pressure vessel;100%
With samarium diiodide; hexan-1-amine at 80℃; for 3h; cyclotrimerization;96%
With samarium diiodide; hexan-1-amine at 80℃; for 3h; Product distribution; Further Variations:; Reagents; Temperatures; nitrile:amine mole ratio; cyclotrimerization;96%
benzonitrile
100-47-0

benzonitrile

benzamide
55-21-0

benzamide

Conditions
ConditionsYield
With water; nitrile hydratase from Rhodococcus rhodochrous J1 at 25℃; for 24h; K2HPO4-KH2PO4 puffer pH=8.0;100%
With manganese(IV) oxide; silica gel In 2,2,4-trimethylpentane for 2h; Heating;100%
With sodium hydroxide; trisodium tris(3-sulfophenyl)phosphine; water; chloro(1,5-cyclooctadiene)rhodium(I) dimer In ethyl acetate at 90℃; for 24h; pH=11.7; hydration;100%
benzonitrile
100-47-0

benzonitrile

benzenecarbothioamide
2227-79-4

benzenecarbothioamide

Conditions
ConditionsYield
With pyridine; diammonium sulfide; triethylamine In water at 50℃;100%
With sodium hydrogensulfide; diethyl amine hydrochloride In 1,4-dioxane; water at 55℃; for 6h;98%
With diisopropyldithiophosphoric acid In methanol at 60℃; for 4h;97%
benzonitrile
100-47-0

benzonitrile

N-hydroxybenzenecarboximidamide
613-92-3

N-hydroxybenzenecarboximidamide

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride In methanol Heating;100%
With hydroxylamine In ethanol; water for 48h; Heating / reflux;100%
With hydroxylamine In ethanol; water Reflux;100%
benzonitrile
100-47-0

benzonitrile

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With water at 45℃; pH=7.2; Microbiological reaction; aq. buffer;100%
With potassium tert-butylate; water In isopropyl alcohol at 25℃; Inert atmosphere;100%
With benzene-1,2-dicarboxylic acid at 250℃; under 7600 Torr; for 0.25h; microwave irradiation;99%
benzonitrile
100-47-0

benzonitrile

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With lithium borohydride; 9-methoxy-9-BBN In diethyl ether at 25℃; for 5h; Product distribution; rate of reduction;100%
With borane N-ethyl-N-isopropylaniline complex In tetrahydrofuran for 0.1h; Heating;100%
With hydrogen; palladium In methanol at 20℃; for 432h;100%
benzonitrile
100-47-0

benzonitrile

selenobenzamide
5977-82-2

selenobenzamide

Conditions
ConditionsYield
Stage #1: benzonitrile With woollins’ reagent In toluene for 4h; Heating;
Stage #2: With water In toluene for 1h;
100%
With selenium; sodium tetrahydroborate In pyridine; ethanol Heating;98%
Stage #1: benzonitrile With woollins’ reagent In toluene under 760.051 Torr; for 8h; Inert atmosphere; Schlenk technique; Reflux;
Stage #2: With water In toluene at 90℃; under 760.051 Torr; for 1h; Inert atmosphere; Schlenk technique; Reflux;
98%
benzonitrile
100-47-0

benzonitrile

dimethyl amine
124-40-3

dimethyl amine

N,N-Dimethyl-benzamidine
20548-18-9, 39116-58-0

N,N-Dimethyl-benzamidine

Conditions
ConditionsYield
Stage #1: dimethyl amine With n-butyllithium In diethyl ether; hexane at -20℃; for 0.166667h;
Stage #2: benzonitrile at -20℃; for 1h;
100%
α-picoline
109-06-8

α-picoline

benzonitrile
100-47-0

benzonitrile

N-((E)-1-Phenyl-2-pyridin-2-yl-vinyl)-benzamide

N-((E)-1-Phenyl-2-pyridin-2-yl-vinyl)-benzamide

Conditions
ConditionsYield
With phenyllithium In diethyl ether for 2.5h; Heating;100%
1-indoline
496-15-1

1-indoline

benzonitrile
100-47-0

benzonitrile

7-benzoyl-1H-indoline
33244-57-4

7-benzoyl-1H-indoline

Conditions
ConditionsYield
Stage #1: 1-indoline; benzonitrile With aluminum (III) chloride; water; boron trichloride In dichloromethane; toluene at 110℃;
Stage #2: With hydrogenchloride; water In dichloromethane; toluene at 80℃; for 1h;
100%
Stage #1: 1-indoline; benzonitrile With aluminum (III) chloride; boron trichloride In dichloromethane; toluene at 0 - 110℃;
Stage #2: With hydrogenchloride; water at 80℃; for 1h;
100%
With aluminum (III) chloride; boron trichloride In toluene Friedel-Crafts Acylation; Inert atmosphere; Reflux;84%
dimethylacetylene
503-17-3

dimethylacetylene

benzonitrile
100-47-0

benzonitrile

2,3,4,5-tetramethyl-6-phenylpyridine
80206-51-5

2,3,4,5-tetramethyl-6-phenylpyridine

Conditions
ConditionsYield
(η3-allyl)(η5-pentamethylcyclopentadienyl)cobalt In hexane at 20℃; for 72h;100%
With aluminium trichloride 1.) CH2Cl2, -85 deg C, 2.) -50 deg C; Yield given. Multistep reaction;
benzonitrile
100-47-0

benzonitrile

3β-acetoxy-16β,17β-epoxymethyleneandrost-5-ene
20046-60-0, 38774-32-2

3β-acetoxy-16β,17β-epoxymethyleneandrost-5-ene

C29H37NO3*BF4(1-)*H(1+)

C29H37NO3*BF4(1-)*H(1+)

Conditions
ConditionsYield
With tetrafluoroboric acid diethyl ether In diethyl ether; dichloromethane for 30h; Ambient temperature;100%
benzonitrile
100-47-0

benzonitrile

benzylamine hydrochloride
3287-99-8, 39110-74-2

benzylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen In propan-1-ol; water at 60℃; under 375.038 Torr; for 18h; Flow reactor;100%
Stage #1: benzonitrile With [2,6-η6:η1-bis(2,4,6-trimethylphenyl)phenylthiolato]triethylphosphineruthenium(II)tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; diethylphenylsilane at 20℃; for 18h; Glovebox; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1h; Glovebox; Inert atmosphere;
99%
Stage #1: benzonitrile With hydrogen at 130℃; under 750.075 Torr; for 6h;
Stage #2: Acidic conditions; chemoselective reaction;
99%
benzonitrile
100-47-0

benzonitrile

2-iodobenzonitrile
4387-36-4

2-iodobenzonitrile

Conditions
ConditionsYield
Stage #1: benzonitrile With Li(2,2,6,6-tetramethylpiperidide)*Al(iBu)3 In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: With iodine In tetrahydrofuran; hexane at 0℃; for 1h;
100%
Stage #1: benzonitrile With Li(2,2,6,6-tetramethylpiperidide)*Al(iBu)3 In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 0℃; for 1h;
100%
Stage #1: benzonitrile With 2,2,6,6-tetramethylpiperidin-4-yl heptanoate; n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere;
100%
benzonitrile
100-47-0

benzonitrile

N-hydroxyl-benzamidine
613-92-3

N-hydroxyl-benzamidine

Conditions
ConditionsYield
With hydroxylamine In ethanol for 1h; Heating / reflux;100%
With hydroxylamine In ethanol for 1h; Reflux;100%
With hydroxylamine hydrochloride; sodium carbonate In ethanol for 17h; Reflux;100%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

benzonitrile
100-47-0

benzonitrile

phenyl(1,2,3,4-tetrahydroquinolin-8-yl)methanone
28748-92-7

phenyl(1,2,3,4-tetrahydroquinolin-8-yl)methanone

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; benzonitrile With aluminum (III) chloride; water; boron trichloride In dichloromethane; toluene at 110℃;
Stage #2: With hydrogenchloride; water In dichloromethane; toluene at 80℃; for 1h;
100%
Stage #1: 1,2,3,4-tetrahydroisoquinoline; benzonitrile With aluminum (III) chloride; boron trichloride In dichloromethane; toluene at 0 - 110℃;
Stage #2: With hydrogenchloride; water at 80℃; for 1h;
100%
With aluminium trichloride; boron trichloride In 1,2-dichloro-ethane Acylation;
(2-picolyl)trimethylsilane
17881-80-0

(2-picolyl)trimethylsilane

benzonitrile
100-47-0

benzonitrile

C16H21N2Si(1-)

C16H21N2Si(1-)

Conditions
ConditionsYield
Stage #1: (2-picolyl)trimethylsilane With lithium diisopropyl amide In tetrahydrofuran at -80℃; for 1h;
Stage #2: benzonitrile In tetrahydrofuran at -80 - 20℃; for 3h;
100%
N,N-dimethyl(trimethylsilyl)acetamide
23184-28-3

N,N-dimethyl(trimethylsilyl)acetamide

benzonitrile
100-47-0

benzonitrile

C14H23N2OSi(1-)

C14H23N2OSi(1-)

Conditions
ConditionsYield
Stage #1: N,N-dimethyl(trimethylsilyl)acetamide With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 1h;
Stage #2: benzonitrile In tetrahydrofuran at -80 - 20℃; for 3h;
100%
benzonitrile
100-47-0

benzonitrile

allyl bromide
106-95-6

allyl bromide

ethyl(diphenyl)phosphine borane

ethyl(diphenyl)phosphine borane

1-allyl-4-(1-diphenylphosphanyl-ethyl)-cyclohexa-2,5-dienecarbonitrile; compound with borane

1-allyl-4-(1-diphenylphosphanyl-ethyl)-cyclohexa-2,5-dienecarbonitrile; compound with borane

Conditions
ConditionsYield
Stage #1: benzonitrile; ethyl(diphenyl)phosphine borane With N,N,N,N,N,N-hexamethylphosphoric triamide; sec.-butyllithium In tetrahydrofuran at -90℃; for 0.5h;
Stage #2: allyl bromide In tetrahydrofuran at -90℃; for 2h;
100%
benzonitrile
100-47-0

benzonitrile

ethyl(diphenyl)phosphine borane

ethyl(diphenyl)phosphine borane

methyl iodide
74-88-4

methyl iodide

4-(1-diphenylphosphanyl-ethyl)-1-methyl-cyclohexa-2,5-dienecarbonitrile; compound with borane

4-(1-diphenylphosphanyl-ethyl)-1-methyl-cyclohexa-2,5-dienecarbonitrile; compound with borane

Conditions
ConditionsYield
Stage #1: benzonitrile; ethyl(diphenyl)phosphine borane With N,N,N,N,N,N-hexamethylphosphoric triamide; sec.-butyllithium In tetrahydrofuran at -90℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at -90℃; for 2h;
100%

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100-47-0Relevant articles and documents

Improving Robustness: In Situ Generation of a Pd(0) Catalyst for the Cyanation of Aryl Bromides

Coombs, John R.,Fraunhoffer, Kenneth J.,Simmons, Eric M.,Stevens, Jason M.,Wisniewski, Steven R.,Yu, Miao

, p. 7040 - 7044 (2017)

Conditions have been developed for the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl2 precatalyst. By employing a trialkylamine as a reducing agent, the active Pd(0) species is generated in situ, alleviating the need to employ the air-sensitive Pd2(dba)3. Twenty-two substituted benzonitriles have been synthesized using this method.

KINETICS OF REACTIONS OF O-(2,4-DINITROPHENYL) BENZALDOXIMES WITH METHYLAMINE, CYCLOHEXYLAMINE AND PIPERIDINE. REACTIVITY AT DIFFERENT ELECTROPHILIC SITES

Bhattacharjee, Gurudas,Singh, Ashok K.,Saikia, Ranjumoni

, p. 4537 - 4540 (1988)

Kinetics of reaction of E-O-(2,4-dinitrophenyl) benzaldoximes have been studied with MeNH2, cyclohexylamine (CHA) and piperdine (PiP) in 1:1 (v/v) ethanol-water at 35+/-0.1 deg C under pseudo first order conditions.The reactions are overall second order, first order with respect to each reactant.Hammett plots are linear with a ρ value of +0.75 for MeNH2, +0.61 for CHA and +1.25 for PiP.MeNH2 and CHA predominantly give the corresponding N-(2,4-dinitrophenyl)amine with attack at the aromatic carbon in sharp contrast to earlier observation with OH-.With piperidine both elimination and substitution products are obtained, the former product predominanting when strong electron-withdrawing substituents are present in the phenyl ring of the oxime.

Efficient synthesis of aromatic nitriles via cyanation of aryl bromides and K4[Fe(CN)6] catalyzed by a palladium(II) complex

Guo, Mengping,Ge, Junying,Zhu, Zhiyong,Wu, Xiaochun

, p. 213 - 215 (2013)

Cyanation of aryl bromides and K4[Fe(CN)6] were carried out in the presence of catalytic amounts of {[(PhCH2O) 2P(CH3)2CHNCH(CH3)2] 2PdCl2} (PdCl2L2) in DMF and a variety of Aromatic nitriles were obtained in good yields under aerobic conditions.

Reaction of Thioamides with Silver Carboxylates in Aprotic Media. A Nucleophilic Approach to the Synthesis of Imides, Amides, and Nitriles.

Avalos, Martin,Babiano, Reyes,Duran, Carlos J.,Jimenez, Jose L.,Palacios, Juan C.

, p. 477 - 480 (1994)

Synthesis of nitriles, imides, and amides by reaction of silver carboxylates with unsubstituted, N-substituted, and N,N-disubstituted thiomaides in aprotic media are described.

Douglas et al.

, p. 1127 (1953)

A base-induced ring-opening process of 2-substituted-1,3,4-oxadiazoles for the generation of nitriles at room temperature

Lu, Guo-Ping,Lin, Ya-Mei

, p. 371 - 374 (2014)

A novel base-catalysed 1,3,4-oxadiazole fragmentation for the synthesis of nitriles at room temperature has been developed. This reaction is performed under transition-metal-free conditions, and provides a new ring cleavage reaction of 1,3,4-oxadiazoles in organic synthesis.

Effect of Zn Substitutions in YBa2Cu3O6+x Phases on Reactivity during the Ammoxidation of Toluene

Otamiri, Jonathan C.,Andersson, Arne,Andersson, S. Lars T.,Crow, Jack E.,Gao, Ye

, p. 1265 - 1271 (1991)

Zn substitution in Y-Ba-Cu-O-phases influences the catalytic ammoxidation of toluene.The activity for formation of both benzonitrile and CO2 at low and high O2 pressures, respectively, decreases strongly with increasing Zn content up to 4percent.Above this substitution level, the activity, however, increases slightly.Characterisations of the surface by XPS and of the bulk by XRD analysis, indicate the presence of overlayers on the catalysts.In these overlayers, irrespective of the Zn content of catalysts, CuI states predominate at low O2 pressure and CuII at high pressure.These states are associated with selective and non-selective properties, respectively.The activity of the catalysts shows a general tendency to increase with surface copper concentrations as found from XPS studies.However, strong deviations from linearity indicate that the activity of the overlayer is greatly influenced by the bulk acting as a support.

Substituent effect on exo stereoselectivity in the 1,3-dipolar cycloaddition reaction of tulipalin A with nitrile ylides

Melsa, Petr,Cajan, Michal,Havlas, Zdenek,Mazal, Ctibor

, p. 3032 - 3039 (2008)

(Chemical Equation Presented) 1,3-Dipolar cycloaddition reactions of dihydro-3-methylene-2(3H)-furanone (tulipalin A) with various benzonitrile(p-X-benzylide) ylides prefer formation of exo-cycloadducts in the extent corresponding to an increasing electron donor character of the substituent X in the para-position of the benzylide phenyl ring of the 1,3-dipolar reagent. The substituent effect on diastereoselectivity of the 1,3-DC reaction is rationalized in terms of CH/π interaction between the dipole and the dipolarophile in an exo-transition state. The determining role of such an interaction is demonstrated by the correlation of the observed diastereoselectivities with substituent Hammett σ constants, which shows a small negative ρ value. A certain contribution of CO/π interaction between the lactone carbonyl and the substituted phenyl ring to mediation of the substituent effect is also discussed. The energy profiles of both reaction pathways were analyzed using DFT and RI-MP2 theoretical approaches. Calculated energy and structural differences between located transition states are consistent with reaction diastereoselectivities.

The Dual Reactivity of 5-S/5-O-Phenyl-1,4,2-oxathiazoles: A Fragmentation Pathway That Affords Nitriles in the Presence of Water

Lim, Yi Wee,Hewitt, Russell J.,Burkett, Brendan A.

, p. 4840 - 4842 (2015)

The rearrangement of substituted 1,4,2-oxathiazoles to nitriles in the presence of water is described. Preliminary investigations suggest that the reaction pathway proceeds via a 1,4,2-oxathiazolium intermediate, followed by trapping with water and subsequent decomposition to products. An unprecedented rearrangement of 5-phenyl-1,4,2-oxathiazoles bearing a C5 leaving group to nitriles in the presence of water is described.

-

Binkley

, p. 1893 (1969)

-

-

Mukaiyama,T.,Hata,T.

, p. 1712 - 1715 (1960)

-

A new method for the generation of nitriles from aldoximes

Jose, Binoy,Sulatha,Madhavan Pillai,Prathapan, Sreedharan

, p. 1509 - 1514 (2000)

A mild and efficient method for the stereoselective dehydration of α-aldoximes to the corresponding nitriles is described which utilises methyl (carboxysulfamoyl)triethylammonium hydroxide inner salt (Burgess reagent) as the dehydrating agent.

The facile fragmentation of trifluoroacetyl groups to nitriles

Kende, Andrew S.

, p. 4035 - 4038 (1995)

Trifluoroacetyl groups attached to a carbon atom devoid of hydrogen undergo facile, high-yield conversion to nitriles by reaction with MeAlClNH2, followed by KOtBu, in a 'one-pot' reaction sequence.

Ultrasound enhanced PTC conversion of benzamide to benzonitrile

Sivakumar,Senthilkumar,Pandit

, p. 2583 - 2587 (2001)

Enhancement of the reaction rate by combining the beneficial effects of PTC and ultrasound has been explored in the present study by taking the transformation of benzamide by dehydration to give benzonitrile as a model system. It was found that there is a

-

Cantacuzene et al.

, p. 1365 (1967)

-

Microwave assisted, solvent free one pot synthesis of nitriles from aryl aldehydes on melamin formaldehyde as solid support

Rezaei, Ramin,Mohammadi, Mohammad Kazem,Rastin, Nedaa

, p. 993 - 996 (2010)

Various aryl aldehydes underwent prompt one pot conversion into the corresponding nitriles in high yields by reacting with hydroxylamine hydrochloride supported on melamine formaldehyde under microwave irradiation in the presence of ammonium acetate as catalyst.

Electrochemical Behaviour of Diazirines

Elson, Clive M.,Liu, Michael T. H.

, p. 415 - 416 (1982)

The electrochemical reductions of 3-aryl-3-chlorodiazirines and 3-n-butyl-3-phenyldiazirine have been studied by cyclic voltammetry and controlled potential electrolysis in acetonitrile.

A thiophosphoryl chloride assisted transformation of arylaldoximes to thioamides

Pandey, Lokesh Kumar,Pathak, Uma,Mathur, Sweta,Suryanarayana

, p. 377 - 379 (2012)

Primary benzothioamides were accessed from benzaldoximes (benzaldehyde oximes) via benzonitriles in a sequential tandem approach utilizing thiophosphoryl chloride as a dehydrating and thionating agent. Georg Thieme Verlag Stuttgart New York.

Quantum Dots in Visible-Light Photoredox Catalysis: Reductive Dehalogenations and C-H Arylation Reactions Using Aryl Bromides

Pal, Anuushka,Ghosh, Indrajit,Sapra, Sameer,K?nig, Burkhard

, p. 5225 - 5231 (2017)

In the recent past, visible-light-mediated photoredox catalysis has made a huge impact on the development of new synthetic methods under very mild and ecologically benign conditions. Although semiconductor nanocrystals or quantum dots (QDs) possess suitable optoelectronic and redox properties for photoredox catalytic applications, surprisingly, their use for the activation of challenging chemical bonds in the synthesis of organic molecules is little explored. We report here the application of ZnSe/CdS core/shell QDs for the synthetically important photoredox catalytic activation of carbon-halogen bonds in dehalogenation and C-H arylation reactions using (hetero)aryl halides as bench-stable inexpensive bulk starting materials, under very mild reaction conditions. The outstanding catalytic activity of ZnSe/CdS core/shell QDs is a direct consequence of the high specific surface area and homogeneity of QDs in solution and their high photostability toward oxidation.

Catalytic oxidative conversion of alcohols, aldehydes and amines into nitriles using KI/I2-TBHP system

Rajender Reddy,Uma Maheswari,Venkateshwar,Prashanthi,Lakshmi Kantam

, p. 2050 - 2053 (2009)

The oxidative conversion of alcohols, aldehydes and amines to give corresponding nitriles in excellent yields was easily achieved by the catalytic amount of KI or I2 in combination with TBHP as an external oxidant. This non-transition metal catalyst is cost effective and provides easy work-up and separation of the product.

OsO4-mediated conversion of primary amines to nitriles

Gao,Herzig,Wang

, p. 544 - 546 (2001)

Nitriles are very important intermediates in synthetic organic chemistry. Herein, we report our observation that certain primary amines can be converted to nitriles by trimethylamine N-oxide (TMO) under mild conditions in the presence of a catalytic amount of OsO4. Such a reaction could be used for synthetic purposes as well as for the analysis of functional group compatibility in designing reactions involving OsO4.

CN-Dimeric ortho-palladated complex catalyzed cyanation of aryl halides under microwave irradiation

Hajipour, Abdol Reza,Rafiee, Fatemeh

, p. 1391 - 1395 (2014)

The catalytic activity of dimeric [Pd{C6H2(CH 2CH2NH2)-(OMe)2,2,3}(m-Br)] 2 complex was investigated in the synthesis of benzonitriles under microwave irradiation conditions. The substituted benzonitriles were produced from various aryl halides in excellent yields and short reaction times using a catalytic amount of this complex as efficient, stable and air- and moisture-tolerant catalyst, and K4[Fe(CN)6] as a green cyanide source in DMF at 130 °C.

Activity enhancement in cyanation of aryl halides through confinement of ionic liquid in the nanospaces of SBA-15 -supported Pd complex

Karimi, Babak,Zamani, Asghar,Mansouri, Fariborz

, p. 57639 - 57645 (2014)

A novel and practical ionic-liquid mediated route for the synthesis of various aromatic nitriles has been developed via the cyanation of aryl halides with K4[Fe(CN)6] as a low cost, non-toxic and easily handled cyanating reagent in the presence of SBA-15 functionalized palladium complex partially confined with ionic liquids (IL@SBA-15-Pd) as the catalyst. Among the various ionic liquids tested in the cyanation reaction, 1-butyl-3-methylimidazolium hexafluorophosphate was found to provide the best medium for Pd-catalyzed cyanation of aryl halides. A variety of electron-rich and electron-poor aryl iodides and bromides gave the corresponding benzonitrile derivatives in good yield. Moreover, the catalyst was reused in four consecutive cycles with consistent catalytic activity. It was found that the presence of ionic liquid in the mesochannels of the mesoporous support not only provides a means of stabilizing Pd nanoparticles during the reaction but also the salient phase transfer feature of the imidazolium moieties may also serve as handles for faster penetration of Fe(CN)63- into the system pores to achieve highly concentrated reaction sites in close proximity to the catalytic (Pd NPs) centers, which resulted in an enhancement of the catalyst activity performance. This journal is

-

Wislicenus,Goldschmidt

, p. 1471 (1900)

-

Highly selective aerobic oxidation of primary amines to nitriles by ruthenium hydroxide

Zhang, Yuan,Xu, Kunling,Chen, Xiaorong,Hu, Tongjie,Yu, Yanpeng,Zhang, Junli,Huang, Jun

, p. 951 - 954 (2010)

A highly selective ruthenium catalyzed aerobic oxidation of primary amines to corresponding nitriles was developed in water and organic solvents. The catalyst system was highly efficient and widely applicable, and several functional groups were tolerated under the reaction conditions employed.

Highly dispersed Co species in N-doped carbon enhanced the aldehydes ammoxidation reaction activity

Fu, Wenqian,Pan, Liuming,Tang, Tiandi,Wang, Siming,Zhang, Lei

, (2022/01/04)

Developing environmentally friendly catalysts with high activity for the ammoxidation of aromatic aldehydes to aromatic nitriles is greatly important for this industrial transformation. Herein, natural vitamin B12 was used as a carbon source for the preparation of a cobalt- and nitrogen-doped catalyst precursor, which was pyrolyzed at different temperatures to obtain cobalt- and nitrogen-doped carbon (Co@NC-T) (T denotes pyrolysis temperature) catalysts. The Co@NC-800 exhibited excellent activity and selectivity in the ammoxidation of aromatic aldehydes with ammonium carbonate to aromatic nitriles compared to the Co@NC-700, Co@NC-600 and Co@NC-500 catalysts. The high catalytic performance of Co@NC-800 could be due to the presence of the low-density electron cloud of the highly dispersed Co species, which could interact with the benzene ring of benzaldehyde bearing p-π conjugate, thereby promoting the adsorption and activation of benzaldehyde. Consequently, the activated benzaldehyde reacted with amino groups that were decomposed from ammonium carbonate and subsequently underwent a dehydration process to form nitriles.

Tandem Fe/Zn or Fe/In Catalysis for the Selective Synthesis of Primary and Secondary Amines?via Selective Reduction of Primary Amides

Darcel, Christophe,Wu, Jiajun

, (2022/03/18)

Tandem iron/zinc or iron/indium-catalysed reductions of various primary amides to amines under hydrosilylation conditions are reported under visible light activation. By a simple modification of the nature of the co-catalyst (Zn(OTf)2 vs In(OTf)3), Fe(CO)4(IMes) can promote the highly chemoselective reduction of primary amides into primary amines (21 examples, up to 93 % isolated yields) and secondary amines (8 examples, up to 51 % isolated yields), respectively. Notably, both benzamide and alkanamide derivatives can be reduced.

Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors

Sharma, Brijesh M.,Nikam, Arun V.,Lahore, Santosh,Ahn, Gwang-Noh,Kim, Dong-Pyo

supporting information, (2022/02/25)

This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask

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