619-24-9

Basic information

• Product Name: 3-Nitrobenzonitrile
• Synonyms: M-NITROBENZONITRILE;1-Cyano-3-nitrobenzene;3-Cyano-1-nitrobenzene;3-Nitrobenzoesαurenitril;3-nitro-benzonitril;Benzonitrile, m-nitro-;Benzonitrile,3-nitro-;Benzonitrile,m-nitro-
• CAS NO: 619-24-9
• Molecular Formula: C₇H₄N₂O₂
• Molecular Weight: 148.12
• EINECS: 210-587-7
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Nitriles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Miscellaneous Reagents;Building Blocks;C6 to C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 619-24-9.mol
• Article Data: 210

Chemical Properties

• Melting Point: 114-117 °C(lit.)
• Boiling Point: 165 °C (21 mmHg)
• Flash Point: 165°C/21mm
• Appearance: Yellow/Crystalline Powder or Needles
• Density: 0.33 g/cm3 (20℃)
• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: very soluble in Ether
• BRN: 637674
• CAS DataBase Reference: 3-Nitrobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitrobenzonitrile(619-24-9)
• EPA Substance Registry System: 3-Nitrobenzonitrile(619-24-9)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/22-20/21/22-23/24/25
• Safety Statements: 22-24/25-36/37-45-36/37/39-26
• RIDADR: UN 3439 6.1/PG 2
• WGK Germany: 3
• RTECS: DI4900000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 619-24-9(Hazardous Substances Data)

Usage

Chemical Properties

YELLOWISH CRYSTALLINE POWDER OR NEEDLES

Uses

Different sources of media describe the Uses of 619-24-9 differently. You can refer to the following data:
1. 3-Nitrobenzonitrile is a compound useful in organic synthesis.
2. 3-Nitrobenzonitrile (cas# 619-24-9) is a compound useful in organic synthesis.

Application

3-Nitrobenzonitrile was employed as matrix for matrix assisted ionization vacuum method for mass spectrometery.

InChI:InChI=1/C7H4N2O2/c8-5-6-2-1-3-7(4-6)9(10)11/h1-4H

Synthetic route

3-nitrobenzaldoxime (3431-62-7) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With dmap; thionyl chloride In dichloromethane for 0.5h; Ambient temperature;	100%
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In dichloromethane at 20℃; for 24h; Dehydration;	99%
With chlorosulfonic acid In toluene at 90℃; for 0.5h;	99%

3-nitro-benzaldehyde (99-61-6) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With ammonia; iodine In water; acetonitrile at 20℃; for 0.666667h;	99%
With hydroxylamine hydrochloride In 1-methyl-pyrrolidin-2-one for 0.25h; Heating;	98%
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride at 100℃; for 0.5h; Condensation; microwave irradiation;	97%

3-Nitrobenzyl alcohol (619-25-0) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
Stage #1: 3-Nitrobenzyl alcohol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;	99%
With ammonium hydroxide; iodine at 60℃; for 3h;	92%
With ammonium hydroxide; iodine at 60℃; for 3h;	92%

m-nitrobenzene boronic acid (13331-27-6) + acetonitrile (75-05-8) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With N-iodo-succinimide; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 1,1,1,2,2,2-hexamethyldisilane; oxygen; copper diacetate; diisopropylamine at 20 - 150℃; Schlenk technique;	99%

1,1-dimethyl-2-[(3-nitrophenyl)methylidene]hydrazine (32787-76-1) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone at 0℃; for 0.05h;	97%

E-3-nitrobenzaldoxime (3717-29-1) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With aluminum oxide; methanesulfonyl chloride at 100℃; for 0.0666667h;	97%
Stage #1: E-3-nitrobenzaldoxime With 2-chloro-1-methyl-pyridinium iodide In dichloromethane at 20℃; for 0.166667h; Stage #2: With triethylamine In dichloromethane at 20℃; for 1h;	91%
With palladium diacetate; triphenylphosphine In acetonitrile for 3h; Reflux;	81%

m-iodonitrobenzene (645-00-1) + potassium ferrocyanide → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique;	97%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique;	97%
With mesoporous silica SBA-15 supported Cu2O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Green chemistry;	94%
With CuO-supported Pd(0) nanoparticles In N,N-dimethyl-formamide at 120℃; for 13h;	60%
With 3% Pd/CeO2; sodium hydroxide In ethanol; N,N-dimethyl-formamide at 55℃; for 10h; Irradiation;	40%

potassium hexacyanoferrate(II) + m-iodonitrobenzene (645-00-1) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Green chemistry;	97%

3-nitrobenzoic acid (121-92-6) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide at 55 - 60℃; for 2h;	96%
With hydroxyammonium sulfate; zinc for 0.45h; Microwave irradiation;	87%
With aluminum oxide; aminosulfonic acid; urea for 0.1h; Irradiation;	81%
With ammonium hydroxide; thionyl chloride 2.) dioxane, 3.) reflux; Multistep reaction;

3-Bromonitrobenzene (585-79-5) + potassium ferrocyanide → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique;	96%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique;	96%
With 3% Pd/ZrO2; sodium acetate In N,N-dimethyl-formamide; isopropyl alcohol at 55℃; for 12h; Irradiation;	60%
With 1-methyl-pyrrolidin-2-one; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate at 120℃; for 12h; Schlenk technique; Inert atmosphere;

3-Bromonitrobenzene (585-79-5) + N-cyano-N-phenyl-p-toluenesulfonamide (55305-43-6) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With silver hexafluoroantimonate; bis(1,5-cyclooctadiene)iridium(I) tetrafluoroborate; ammonium cerium (IV) nitrate; lanthanum(lll) triflate; XPhos at 100℃; for 8h;	95.1%

trimethylsilyl cyanide (7677-24-9) + m-nitrobenzene boronic acid (13331-27-6) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With copper(I) oxide; oxygen; N,N`-dimethylethylenediamine In acetonitrile at 25℃; for 12h; Schlenk technique;	95%
With potassium phosphate; copper(l) iodide In 1-methyl-pyrrolidin-2-one at 60℃; for 2h;	67%

C14H10N2O4 → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 0.116667h; Schlenk technique;	94%

3,6,6-Trimethyl-4-{[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amino}-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester (117227-33-5) → 3-nitro-benzaldehyde (99-61-6) + 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With sodium methylate In ethanol for 3h; Product distribution; Heating;	A 4% B 93%

3-nitrothiobenzamide (70102-34-0) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With triphenyl bismuth (2+); dichloride; triethylamine In dichloromethane at 20℃; for 0.25h;	93%

potassium hexacyanoferrate(II) + 3-Bromonitrobenzene (585-79-5) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Green chemistry;	93%

benzonitrile (100-47-0) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With magnesium(II) perchlorate; 2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide In [D3]acetonitrile at 85℃; for 5h; Inert atmosphere; Sealed tube;	92%
With tetrammine copper(II) sulphate; nitric acid In dichloromethane; water at 20℃; for 2.5h; regioselective reaction;	84%
With magnesium(II) nitrate hexahydrate; AMA at 20℃; for 24h; Neat (no solvent);	82%

3-nitro-benzaldehyde (99-61-6) → 3-nitrobenzonitrile (619-24-9) + 3-nitrobenzamide (645-09-0)

Conditions	Yield
With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate In water at 100℃; for 7h; Reagent/catalyst; Inert atmosphere; Sealed tube; Green chemistry;	A n/a B 92%

m-cyanoaniline → bis(3-cyanophenyl)diazene oxide (17197-24-9, 71298-00-5) + 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With selenium(IV) oxide; dihydrogen peroxide In methanol; water at 20℃; for 24h;	A 91% B 3%

potassiumhexacyanoferrate(II) trihydrate + 3-Bromonitrobenzene (585-79-5) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; Schlenk technique;	90%
With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; tert-butyl alcohol at 85℃; for 5h; Schlenk technique; Inert atmosphere;	80%
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In N,N-dimethyl acetamide at 120℃; for 11h;	67%

acetonitrile (75-05-8) + 3-nitrobenzoic acid (121-92-6) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
at 350℃; under 48754.9 Torr; for 0.416667h; Supercritical conditions; Flow reactor;	90%

3-nitro-benzaldehyde (99-61-6) + potassium ferrocyanide → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With Aloe vera mediated silver nanoparticles In water at 50℃; for 0.75h; Green chemistry;	90%

3-nitrobenzamide (645-09-0) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With diethyl chlorophosphate at 120℃; for 0.25h; Neat (no solvent);	89%
With di-morpholin-4-yl-phosphinic acid chloride; triethylamine In dichloromethane at 20℃; for 4h;	72%
With lead acetate In dichloromethane for 12h; Reflux;	71%

3-Methyl-4-{[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amino}-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid diethyl ester (117227-24-4) → 3-nitro-benzaldehyde (99-61-6) + 3-Methyl-4H-cyclopenta-1,2,4-triazin-5,7-dicarbonsaeure-diethylester (117227-45-9) + 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With ethanol Heating;	A 56% B 89% C 15%
In ethanol Product distribution; Heating;	A 56% B 89% C 15%

4-chlorophenyl thiocyanate (3226-37-7) + m-nitrobenzene boronic acid (13331-27-6) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With N,N,N-trimethyl-2-(sulfooxy)ethanaminium palladium(II) chloride; sodium carbonate In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; water for 2h;	89%

m-nitrobenzene boronic acid (13331-27-6) + 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With silver (II) carbonate; copper(II) bis(trifluoromethanesulfonate); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 20h;	88%

m-nitrobenzene boronic acid (13331-27-6) + ethyl (ethoxymethylene)cyanoacetate (94-05-3) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) iodide In N,N-dimethyl-formamide at 130℃; for 24h;	88%

3-iodobenzonitrile (69113-59-3) → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
With 1,10-Phenanthroline; iron(II) sulfate; potassium nitrate In dimethyl sulfoxide at 20℃; for 48h; UV-irradiation; Inert atmosphere;	88%

tetra-n-butylammonium cyanide (10442-39-4) + 3-nitrobenzenediazonium o-benzenedisulfonimide → 3-nitrobenzonitrile (619-24-9)

Conditions	Yield
In acetonitrile at 22℃; for 0.75h; Sandmeyer Reaction;	87%

3-nitrobenzonitrile (619-24-9) → 5-(3-nitrophenyl)-1H-tetrazole (21871-44-3)

Conditions	Yield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 120℃; for 4h;	100%
Stage #1: 3-nitrobenzonitrile With sodium azide In N,N-dimethyl-formamide at 120℃; for 36h; Stage #2: With hydrogenchloride In water; ethyl acetate for 0.0833333h;	98%
With aluminum (III) chloride; sodium azide In 1-methyl-pyrrolidin-2-one at 200℃; for 0.05h; Microwave irradiation;	98%

3-nitrobenzonitrile (619-24-9) → m-nitrobenzamide oxime (5023-94-9)

Conditions	Yield
With hydroxylamine In ethanol; water at 80℃; for 5h;	100%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 85℃; for 2h; Inert atmosphere;	99%
With hydroxylamine hydrochloride; triethylamine In methanol at 20℃; Reflux;	93%

3-nitrobenzonitrile (619-24-9) → 5-(3-nitrophenyl)-2H-tetrazole (21871-44-3)

Conditions	Yield
With aluminum (III) chloride; sodium azide In 1-methyl-pyrrolidin-2-one at 200℃; for 0.0833333h; Microwave irradiation;	100%
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 16℃; Reflux;	97%
With sodium azide; zinc dibromide In water for 51h; Reflux;	94%

acetic anhydride (108-24-7) + 3-nitrobenzonitrile (619-24-9) → N-(3-cyanophenyl)acetamide (58202-84-9)

Conditions	Yield
With indium; acetic acid In methanol at 20℃; for 1.5h;	100%

3-nitrobenzonitrile (619-24-9) → m-cyanoaniline (2237-30-1)

Conditions	Yield
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; Microwave irradiation; Green chemistry;	99%
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; for 0.0333333h; Microwave irradiation; chemoselective reaction;	99%
With maghemite; methylhydrazine In ethanol at 60℃; for 0.2h; Sealed tube; Inert atmosphere; chemoselective reaction;	99%

3-nitrobenzonitrile (619-24-9) → 3-nitrobenzamide (645-09-0)

Conditions	Yield
With cobalt(II,III) oxide; water at 140℃; for 24h;	99%
With potassium tert-butylate In tert-butyl alcohol at 20℃; for 12h; Solvent; Temperature; Inert atmosphere;	99%
With manganese(IV) oxide; water In isopropyl alcohol at 100℃; under 5171.62 Torr; for 0.25h;	98%

Cysteamine (60-23-1) + 3-nitrobenzonitrile (619-24-9) → 2-(3-nitrophenyl)-4,5-dihydro-1,3-thiazole (96159-88-5)

Conditions	Yield
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.0333333h; chemoselective reaction;	98%
With 1-butyl-3-methylimidazolium tribromide at 100℃; for 0.1h;	88%
With tribromomelamine at 100℃; for 0.0833333h; Neat (no solvent);	87%
In ethanol for 5h; Heating;	63%

ethanol (64-17-5) + 3-nitrobenzonitrile (619-24-9) → 3-nitrobenzenecarboximidic acid ethyl ester monohydrochloride (57508-53-9)

Conditions	Yield
With hydrogenchloride In ethanol	98%
With hydrogenchloride In benzene Cooling with ice;
With hydrogenchloride In 1,4-dioxane

3-nitrobenzonitrile (619-24-9) → 5-(3-hydroxyphenyl)-1H-tetrazole (96859-34-6)

Conditions	Yield
With sodium azide at 120℃; for 2.16667h; Suzuki Coupling;	97%

3-nitrobenzonitrile (619-24-9) + benzyl alcohol (100-51-6) → 3-(benzylideneamino)benzonitrile (50338-03-9)

Conditions	Yield
With caesium carbonate In toluene at 150℃; for 24h; Inert atmosphere; Sealed tube;	96%

ethylenediamine (107-15-3) + 3-nitrobenzonitrile (619-24-9) → 2-(3-nitrophenyl)-2-imidazoline (31659-42-4)

Conditions	Yield
With sodium sulfide In methanol for 8h; Reflux;	95.3%
With sodium monohydrogen sulfide x-hydrate at 110℃; for 48h;	60%
With sulfur In methanol at 67℃; for 24h; Large scale;

3-nitrobenzonitrile (619-24-9) → 3-(hydroxyamino)benzonitrile (24171-82-2)

Conditions	Yield
With ammonium formate; zinc In acetonitrile at 25 - 30℃; for 1.66667h; sonification;	95%
With methyldiazene In acetonitrile at 28℃; for 1.66667h; Irradiation; Sealed tube; Inert atmosphere;	93%
With sulfuric acid In ethanol at 20℃; (electrochemical reduction);
With ammonium chloride; zinc at 60 - 80℃;
With ammonium chloride; zinc In ethanol

3-nitrobenzonitrile (619-24-9) → 3-fluoro-5-nitrobenzonitrile (110882-60-5)

Conditions	Yield
With fluorine In acetonitrile at 0 - 10℃;	95%
With fluorine In acetonitrile at 90℃; under 1500.15 Torr; for 1h; Sealed tube;	345 g

3-nitrobenzonitrile (619-24-9) → N-Cyan-(3-nitro-benzamidin) (23275-42-5)

Conditions	Yield
Stage #1: 3-nitrobenzonitrile With sodium methylate In methanol at 20℃; for 4h; Stage #2: With CYANAMID In methanol at 20℃;	95%

3-nitrobenzonitrile (619-24-9) → 3-nitrothiobenzamide (70102-34-0)

Conditions	Yield
With diammonium sulfide; 1,6-bis(3-methylimidazolium-1-yl)hexane dichloride at 70℃; for 0.1h;	94%
Stage #1: 3-nitrobenzonitrile With Lawessons reagent; boron trifluoride diethyl etherate In diethyl ether; toluene at 50℃; for 14h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In diethyl ether; toluene at 20℃; for 0.333333h; Inert atmosphere;	88%
With triethanolamine; hydrogen sulfide In ethanol

(S)-valinol (2026-48-4) + 3-nitrobenzonitrile (619-24-9) → (4S)-4-isopropyl-2-(3-nitrophenyl)-4,5-dihydrooxazole

Conditions	Yield
With zinc(II) chloride In chlorobenzene for 21h; Inert atmosphere; Reflux;	94%

(4S)-1-benzyl-4,5-dihydroxypyrrolidin-2-one (192987-90-9) + 3-nitrobenzonitrile (619-24-9) → (3aR,6aS)-4-benzyl-2-(3-nitrophenyl)-3a,4,6,6a-tetrahydro-5H-pyrrolo[2,3-d]oxazol-5-one

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; Ritter Amidation; Inert atmosphere; diastereoselective reaction;	94%

Upstream product

• 3717-30-4 3-nitrobenzaldoxime 
• 541-41-3 chloroformic acid ethyl ester 
• 684-78-6 O,N-bis-(trifluoroacetyl)-hydroxylamine 
• 99-61-6 3-nitro-benzaldehyde 
• 3459-99-2 3-nitrobenzamidine 
• 117227-44-8 4-Amino-4,6-dihydro-3-methyl-1H-cyclopenta-1,2,4-triazin-5,7-dicarbonsaeure-diethylester 
• 60415-44-3 3-nitrosobenzonitrile 
• 12402-46-9 3-Nitrobenzonitrile radical anion 
• 123-91-1 1,4-dioxane 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 110-86-1 pyridine 
• 7664-93-9 sulfuric acid 
• 20199-04-6 Thiobenzamide S-oxide 

Downstream Products

• 116313-68-9 3-nitro-benzimidic acid methyl ester; hydrochloride 
• 618-95-1 methyl 3-nitrobenzoate 
• 618-98-4 ethyl 3-nitrobenzoate 
• 831-65-2 ethyl 3-nitrobenzenecarboximidate 
• 70102-34-0 3-nitrothiobenzamide 
• 102178-43-8 5-hexyl-2,4-dihydroxy-3'-nitro-benzophenone 
• 121-92-6 3-nitrobenzoic acid 
• 21871-44-3 5-(3-nitrophenyl)-1H-tetrazole 
• 7409-18-9 3-nitrobenzylamine 
• 5023-94-9 m-nitrobenzamide oxime 
• 2237-30-1 m-cyanoaniline 
• 645-09-0 3-nitrobenzamide 
• 17420-30-3 5-nitroanthranilonitrile 
• 87331-46-2 2-amino-3-nitrobenzonitrile 

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