1443-80-7

Basic information

• Product Name: 4-ACETYLBENZONITRILE
• Synonyms: 4'-Cyanoacetophenonele;4-Cyanophenyl methyl ketone;4-Cyanophenylmethylketone;Benzonitrile, p-acetyl-;Benzonitrile,4-acetyl-;Benzonitrile,p-acetyl-;Methylp-cyanophenylketone;Paracyanoacetophenone
• CAS NO: 1443-80-7
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 215-885-0
• Product Categories: Aromatic Nitriles;Benzonitriles (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 1443-80-7.mol
• Article Data: 263

Chemical Properties

• Melting Point: 56-59 °C(lit.)
• Boiling Point: 95-96°C 14mm
• Flash Point: 95-96°C/14mm
• Appearance: Light yellow to yellow-beige/Crystalline Mass or Crystalline Powder and Chunks
• Density: 1.1555 (rough estimate)
• Vapor Pressure: 0.00174mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform
• Water Solubility: Soluble in chloroform. Insoluble in water.
• BRN: 1932887
• CAS DataBase Reference: 4-ACETYLBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETYLBENZONITRILE(1443-80-7)
• EPA Substance Registry System: 4-ACETYLBENZONITRILE(1443-80-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 36-36/37/39-26-22
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1443-80-7(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to yellow-beige crystalline mass or crystalline powder and chunks

Uses

Different sources of media describe the Uses of 1443-80-7 differently. You can refer to the following data:
1. 4-Acetylbenzonitrile can be used in the preparation of antimalarial isonitriles.
2. 4-Acetylbenzonitrile is used in the preparation of antimalarial isonitriles. It is also used for synthetic API such as anesthetic agents and anti-allergic agents.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 1613, 1979 DOI: 10.1021/jo01324a006Tetrahedron Letters, 28, p. 1345, 1987 DOI: 10.1016/S0040-4039(00)95366-8

General Description

The relaxation-assisted two-dimensional infrared (RA 2DIR) spectroscopy of 4-acetylbenzonitrile was analyzed.

Flammability and Explosibility

Notclassified

Purification Methods

Recrystallise the nitrile from EtOH [Wagner et al. J Am Chem Soc 108 7727 1986]. [Beilstein 10 H 695, 10 III 3030.]

InChI:InChI=1/C9H7NO/c1-7(11)9-4-2-8(6-10)3-5-9/h2-5H,1H3

Synthetic route

4-Cyanophenacyl bromide (20099-89-2) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With AcrH2; perchloric acid; tris(2,2’-bipyridine)ruthenium(II) In acetonitrile at 298℃; for 8h; Irradiation;	100%
With AcrH2; perchloric acid; tris(2,2’-bipyridine)ruthenium(II) In acetonitrile at 298℃; for 8h; Quantum yield; Mechanism; Irradiation; Electron-Transfer Rate Constants ;;	100%
With ammonium chloride; zinc In ethanol at 80℃; for 0.00833333h; microwave irradiation;	99%

4-Iodoacetophenone (13329-40-3) + sodium cyanide (143-33-9) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With copper(l) iodide; tetrabutylammomium bromide In water at 170℃; under 10343.2 Torr; for 0.05h; microwave irradiation;	99%
With sodium tetrahydroborate; zinc(II) chloride; Na2{PdCl2(Ph2P(m-C6H4SO3))2} In n-heptane; water for 1h; Heating;	91%

nickel cyanide (557-19-7) + para-bromoacetophenone (99-90-1) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one; water at 200℃; under 10343 Torr; for 0.166667h; microwave irradiation;	99%

4-Iodoacetophenone (13329-40-3) + copper(l) cyanide → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With tetrabutylammomium bromide In water at 170℃; under 10343.2 Torr; for 0.05h; microwave irradiation;	99%

zinc(II) cyanide (557-21-1) + para-bromoacetophenone (99-90-1) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In tetrahydrofuran; water at 20℃; for 18h; Inert atmosphere;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; zinc(II) formate dihydrate In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere;	89%

sodium cyanide (773837-37-9) + para-bromoacetophenone (99-90-1) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With tri-tert-butyl phosphine; [Pd2(dba)5]; zinc In tetrahydrofuran; acetonitrile at 70℃; for 2h;	99%

4-oxiran-2-ylbenzonitrile (52695-39-3) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; copper(II) choride dihydrate In toluene at 80℃; for 24h; Meinwald Rearrangement; Inert atmosphere;	99%

para-chloroacetophenone (99-91-2) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With [Pd(cinnamyl)Cl]2; N-ethyl-N,N-diisopropylamine; XPhos In isopropyl alcohol at 80℃; for 2h; Inert atmosphere;	98%
With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; sodium carbonate; palladium diacetate In N,N-dimethyl acetamide at 140℃; for 21h;	89 % Chromat.

4-acetylphenyl mesylate (69497-83-2) + dicyanozinc (557-21-1) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With palladium diacetate; PS-triphenylphosphine In tetrahydrofuran at 120℃; for 1.5h;	98%

potassiumhexacyanoferrate(II) trihydrate + para-bromoacetophenone (99-90-1) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With potassium phosphate tribasic trihydrate; C38H28O4P2Pd In N,N-dimethyl-formamide at 130℃; for 12h;	98%
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 10h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	96%
With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; tert-butyl alcohol at 85℃; for 5h; Schlenk technique; Inert atmosphere;	95%

4-ethylbenzonitrile (25309-65-3) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With Oxone; potassium bromide In dichloromethane; water at 20℃; for 24h; visible light irradiation;	98%
Stage #1: 4-ethylbenzonitrile With cis-RuCl2(4,4'-di-tert-butyl-2,2'-bipyridine)2; acetic acid In water for 0.0333333h; Darkness; Stage #2: With periodic acid In water for 4h; Darkness; chemoselective reaction;	72%
Stage #1: 4-ethylbenzonitrile With dichlorobis(4,4'-di-tert-butyl-2,2'-bipyridine)ruthenium(II); acetic acid In water for 0.0333333h; Darkness; Stage #2: With periodic acid In water for 4h; Darkness;	72%

p-formylacetophenone (3457-45-2) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction; chemoselective reaction;	98%
Stage #1: p-formylacetophenone With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With potassium hydrogen difluoride; 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate In water at 20℃; for 3h;	95%
With hydroxylamine hydrochloride In methanol; water at 20℃; for 18h; Irradiation;	88%
With ferric(III) bromide; trimethylsilylazide In acetonitrile at 60℃; for 4h;	67%
With ammonia; oxygen In tert-Amyl alcohol at 40℃; under 750.075 Torr; for 24h; Green chemistry;	94 %Chromat.

4-(1-hydroxyethyl)benzonitrile (101219-69-6, 101219-71-0, 134679-06-4, 52067-35-3) + 3,3-dimethyldioxirane (74087-85-7) → 4-cyanophenyl methyl ketone (1443-80-7) + 2-hydroxy-1-(4-cyanophenyl)ethan-1-one (36776-32-6)

Conditions	Yield
In acetone at 25℃; for 3h;	A 97% B 2%
In acetone at 25℃; for 3h; Rate constant;	A 97% B 2%

4-Iodoacetophenone (13329-40-3) + potassium ferrocyanide → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With 10% Pd/C; sodium fluoride In water at 130℃; for 2h; Microwave irradiation;	97%
With copper(l) iodide; sodium carbonate In N,N-dimethyl acetamide for 2h; Reflux;	95%
With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.1h; Microwave irradiation;	93%

para-bromoacetophenone (99-90-1) + potassium ferrocyanide → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With dichlorobis(dibenzyl diisopropylphosphoramidite)palladium(II); sodium fluoride In N,N-dimethyl-formamide at 130℃; for 16h; Reagent/catalyst;	97%
With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 6h; Inert atmosphere;	94%
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 8h; Inert atmosphere; Sealed tube;	94%

potassium hexacyanoferrate(II) trihydrate + para-bromoacetophenone (99-90-1) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;	97%
With tetrabutylammomium bromide; copper(II) acetate monohydrate; potassium iodide In water at 20 - 140℃; Microwave irradiation;	32%
With sodium carbonate In N,N-dimethyl-formamide at 110℃; for 20h; Catalytic behavior; Sealed tube;	97 %Chromat.

tert-butylisonitrile (119072-55-8, 7188-38-7) + 4-Iodoacetophenone (13329-40-3) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 6h; Sealed tube; Inert atmosphere;	97%

para-bromoacetophenone (99-90-1) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
Stage #1: para-bromoacetophenone With copper(l) iodide; 1,10-Phenanthroline; potassium iodide In N,N-dimethyl-formamide at 110℃; for 6h; Stage #2: 2-hydroxy-2-methylpropanenitrile With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 60h;	96%
With 1,1'-bis-(diphenylphosphino)ferrocene; [(N,N,N',N'-tetramethylethylendiamine)NiCl(o-tolyl)]; N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 2h; Inert atmosphere;	86%
With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; sodium carbonate; palladium diacetate In N,N-dimethyl acetamide at 100℃; for 21h;	100 % Chromat.

zinc(II) cyanide (557-21-1) + para-chloroacetophenone (99-91-2) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
Stage #1: zinc(II) cyanide With aluminum oxide; Ni(xantphos)(o-tolyl)Cl for 1h; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: para-chloroacetophenone In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Schlenk technique; Inert atmosphere;	96%
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 8h; Schlenk technique; Inert atmosphere; Sealed tube;	81%
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 8h; Inert atmosphere; Sealed tube;	81%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; zinc(II) formate dihydrate In N,N-dimethyl acetamide at 120℃; for 12h; Inert atmosphere;	70%

4-Cyanophenacyl bromide (20099-89-2) → 4-cyanophenyl methyl ketone (1443-80-7) + (±)-4-(2-bromo-1-hydroxyethyl)benzonitrile (85554-13-8)

Conditions	Yield
With 9,10-dihydro-10-methylacridine; perchloric acid In acetonitrile at 61.9℃; Product distribution; Mechanism;	A 95% B n/a

potassiumhexacyanoferrate(II) trihydrate + para-chloroacetophenone (99-91-2) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With C46H62NO3PPdS(2-); potassium acetate; XPhos In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube;	95%
With potassium phosphate tribasic trihydrate; C38H28O4P2Pd In N,N-dimethyl-formamide at 130℃; for 16h; Catalytic behavior; Solvent; Reagent/catalyst;	93%
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In N,N-dimethyl acetamide at 120℃; for 10h;	63%

4-cyanophenylacetylene (3032-92-6) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With tetrakis(p-sulfonatophenyl)porphyrin cobalt(III) trisodium salt hexahydrate; water; bis(trifluoromethanesulfonyl)amide In methanol at 80℃; for 36h; Sealed tube;	95%
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I) In methanol; water at 120℃; for 6h; Schlenk technique; regioselective reaction;	92%
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water In methanol at 110℃; for 6h;	92%

zinc(II) cyanide (557-21-1) + 4-acetylphenyl p-toluenesulfonate (64101-67-3) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 12h; Sealed tube;	95%
With dmap; nickel(II) bromide dimethoxyethane; 1,4-di(diphenylphosphino)-butane; zinc In acetonitrile at 80℃; for 12h; Inert atmosphere;	94%

para-bromoacetophenone (99-90-1) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; palladium on activated charcoal; potassium carbonate; triphenylphosphine at 25 - 130℃; for 12.1667h;	95%

-butyl vinyl ether (111-34-2) + 4-cyanophenyl trifluoromethanesulfonate (66107-32-2) → 4-cyanophenyl methyl ketone (1443-80-7) + (Z)-1-Butoxy-2-(4-cyanophenyl)ethylene (127087-67-6) + (E)-1-Butoxy-2-(4-cyanophenyl)ethylene (127087-66-5)

Conditions	Yield
With triethylamine; Pd(Ac2O)2-DPPP In N,N-dimethyl-formamide at 80℃; for 3h; Yields of byproduct given;	A 94% B n/a C n/a

4-Iodoacetophenone (13329-40-3) + potassium cyanide (151-50-8) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In various solvent(s) at 60℃; for 2h;	94%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 1h; Substitution; Heating;

dicyanozinc (557-21-1) + para-bromoacetophenone (99-90-1) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; polymethylhydrosiloxane; palladium diacetate In water at 80℃; for 1.5h;	94%
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 5.5h;	91%
With water; tri tert-butylphosphoniumtetrafluoroborate; zinc; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In 1-methyl-pyrrolidin-2-one at 20℃; for 24h;	89%

-butyl vinyl ether (111-34-2) + 4-bromobenzenecarbonitrile (623-00-7) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
Stage #1: -butyl vinyl ether; 4-bromobenzenecarbonitrile With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine In various solvent(s) at 110℃; for 36h; Heck reaction; Stage #2: With hydrogenchloride Further stages.;	94%
With 1,3-bis-(diphenylphosphino)propane; diisopropylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate In dimethyl sulfoxide at 115℃; for 36h; Heck arylation;	88%
Stage #1: -butyl vinyl ether; 4-bromobenzenecarbonitrile With meso-2,4-bis(diphenylphosphino)pentane; triethylamine; palladium diacetate In dimethyl sulfoxide at 115℃; for 36h; Heck arylation; Stage #2: With hydrogenchloride In dimethyl sulfoxide at 20℃;	86%

4-(1-hydroxyethyl)benzonitrile (101219-69-6, 101219-71-0, 134679-06-4, 52067-35-3) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With oxygen; C26H21BrO In dichloromethane for 12h; Irradiation;	94%
With sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.166667h; Schlenk technique;	93%
With iodine; potassium carbonate; [bis(pyridine)iodine]+ tetrafluoroborate In acetonitrile at 60℃; for 21h;	85%

potassium hexacyanoferrate(III) trihydrate + 4-Iodoacetophenone (13329-40-3) → 4-cyanophenyl methyl ketone (1443-80-7)

Conditions	Yield
With potassium phosphate In N,N-dimethyl-formamide at 120℃; for 1.5h;	94%

4-cyanophenyl methyl ketone (1443-80-7) → 4-Cyanophenacyl bromide (20099-89-2)

Conditions	Yield
With bromine	100%
With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 25℃; Inert atmosphere;	72%
With bromine In chloroform at 20℃; for 20h; Inert atmosphere;	71%

4-cyanophenyl methyl ketone (1443-80-7) → 4-(1-hydroxyethyl)benzonitrile (101219-69-6, 101219-71-0, 134679-06-4, 52067-35-3)

Conditions	Yield
With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 0.666667h;	100%
With methanol; sodium tetrahydroborate at 0 - 25℃; for 5h; Inert atmosphere;	100%
With C15H13MnN3O3(1+)*Br(1-); potassium tert-butylate; isopropyl alcohol at 70℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;	99%

4-cyanophenyl methyl ketone (1443-80-7) → 4-(1,1-difluoroethyl)benzonitrile (55805-05-5)

Conditions	Yield
With diethylamino-sulfur trifluoride In dichloromethane at 50℃; for 20h;	100%
With (bis-(2-methoxyethyl)amino)sulfur trufluoride for 24h;	68.6%
With F6Mo; boron trifluoride In dichloromethane at -20 - 20℃;

4-cyanophenyl methyl ketone (1443-80-7) → 4,4′-(2,3-dihydroxybutane-2,3-diyl)dibenzonitrile (82491-64-3)

Conditions	Yield
With zinc(II) chloride; zinc In tetrahydrofuran; water for 3h; Ambient temperature;	100%
With CdS(x)Se(1-x) x:0-1;; para-thiocresol In hexane for 22h; Inert atmosphere; Irradiation;	99%
With CeI2 In tetrahydrofuran 1.) 2 h, 0 deg C, 2.) 12 h, room temp.;	91%
With tetrachlorosilane; zinc In dichloromethane at 20℃; for 20h;	62%
With ytterbium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 3h; Ambient temperature;	58%

4-cyanophenyl methyl ketone (1443-80-7) + ethylene glycol (107-21-1) → 4-(2-methyl-[1,3]dioxolan-2-yl)benzonitrile (14517-91-0)

Conditions	Yield
With zeolite HSZ-360 In toluene for 5h; Heating;	100%
With ammonium chloride In toluene Reflux; Dean-Stark;	94%
With N-Bromosuccinimide; trimethyl orthoformate at 25 - 65℃; for 12h;	92%

4-cyanophenyl methyl ketone (1443-80-7) + potassium cyanide (151-50-8) + ammonium carbonate (506-87-6) → 4-(R,S)-(4-cyanophenyl)-4-methyl-2,5-dioxoimidazolidine (169808-00-8)

Conditions	Yield
In ethanol at 60℃; for 72h;	100%

4-cyanophenyl methyl ketone (1443-80-7) → 4-oxoacetyl-benzonitrile hydrate (19010-28-7)

Conditions	Yield
With selenium(IV) oxide; water In 1,4-dioxane for 72h; Inert atmosphere; Reflux;	100%
With selenium(IV) oxide; water In 1,4-dioxane at 50 - 55℃; Reflux; Inert atmosphere; Schlenk technique;

4,7-dichloroisatin (18711-13-2) + 4-cyanophenyl methyl ketone (1443-80-7) → 4-(2-(4,7-dichloro-3-hydroxy-2-oxoindolin-3-yl)acetyl)benzonitrile (1467720-52-0)

Conditions	Yield
With diethylamine In methanol at 20℃;	100%
With diethylamine In methanol at 20℃;	100%
With diethylamine In methanol at 20℃;	64%

4-cyanophenyl methyl ketone (1443-80-7) + methyltrichlorotitanium (2747-38-8) → 4-(2-hydroxypropan-2-yl)benzenecarbonitrile (77802-22-3)

Conditions	Yield
at -5 - -4℃; for 1h; Solvent; Temperature; Large scale;	99.7%

4-cyanophenyl methyl ketone (1443-80-7) → 4-acetyl-benzoic acid (586-89-0)

Conditions	Yield
With phosphate buffer at 30℃; for 24h; rhodococcus rhodocrous AJ270, pH 7.0;	99%
With potassium phosphate buffer at 30℃; for 24h; Rhodococcus sp. AJ270 cells;	99.3%
With sulfuric acid

4-cyanophenyl methyl ketone (1443-80-7) → (S)-4-(1-hydroxyethyl)benzonitrile (101219-71-0)

Conditions	Yield
With (R)-2,2',6,6'-tetramethoxy-4,4'-bis(di-3,5-dimethylphenylphosphine)3,3'-bipyridine; phenylsilane; cobalt(II) diacetate tetrahydrate In toluene at 40℃; for 36h; Molecular sieve; Under air; optical yield given as %ee; enantioselective reaction;	99%
With triiron dodecarbonyl; C52H58N4P2; hydrogen; potassium hydroxide In methanol at 45℃; under 37503.8 Torr; for 10h; enantioselective reaction;	98%
Stage #1: 4-cyanophenyl methyl ketone With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at -20 - -12.8℃; for 3.33333h; Industry scale; Stage #2: With methanol In tetrahydrofuran; toluene at -1.5℃; for 0.55h;	95%

4-cyanophenyl methyl ketone (1443-80-7) → 1-(4-(1-H-tetrazol-5-yl) phenyl) ethanone (552846-23-8)

Conditions	Yield
With trimethylsilylazide; dibutyltin diacetate In benzene at 30℃; for 60h;	99%
With trimethylsilylazide; di(n-butyl)tin oxide In toluene at 90 - 120℃;	99%
With sodium azide; C32H25ClCuN6O9 In dimethyl sulfoxide at 110℃; for 5h; Reagent/catalyst;	98%

m-bromobenzoic aldehyde (3132-99-8) + 4-cyanophenyl methyl ketone (1443-80-7) → 4-[3-(3-bromophenyl)-1-oxo-2-propenyl]benzonitrile (1028801-04-8)

Conditions	Yield
With sodium hydroxide In methanol at 0 - 20℃; for 4h; Claisen-Schmidt condensation;	99%

4-cyanophenyl methyl ketone (1443-80-7) + diphenylsilane (775-12-2) → 4-(1-((diphenylsilyl)oxy)ethyl)benzonitrile (1265032-61-8)

Conditions	Yield
With C84H110N10Zn2 In neat (no solvent) at 20℃; for 12h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox;	99%
With iron(II) bis(trimethylsilyl)amide In benzene-d6 at 23℃; for 17h; Inert atmosphere;

trimethylsilyl cyanide (7677-24-9) + 4-cyanophenyl methyl ketone (1443-80-7) → C13H16N2OSi (69813-81-6)

Conditions	Yield
With C42H50Mg2N4 In benzene-d6 at 60℃; for 5h; Glovebox; Inert atmosphere;	99%
With C32H39Br2MgN2(1-)*C16H32LiO4(1+) In chloroform-d1 at 20℃; for 48h; Inert atmosphere; Glovebox; chemoselective reaction;	73%
With TBA8H2[(γ-SiYW10O36)2]*7H2O In 1,2-dichloro-ethane at 30℃; under 760.051 Torr; for 1h; Air atmosphere;	90 %Chromat.
With zinc(II) iodide In dichloromethane for 2h;

diethyl cyanophosphonate (2942-58-7) + 4-cyanophenyl methyl ketone (1443-80-7) + lithium cyanide (2408-36-8) → 1-cyano-1-(4-cyanophenyl)ethyl diethylphosphate

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.0833333h;	99%

4-cyanophenyl methyl ketone (1443-80-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-(1-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)ethyl)benzonitrile

Conditions	Yield
With C84H110N10Zn2 In neat (no solvent) at 20℃; for 6h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox;	99%
With C14H24N4Si(1+)*I(1-) In benzene-d6 at 90℃; for 1h; Catalytic behavior; Inert atmosphere; Schlenk technique; regioselective reaction;	90%
With C24H45MgNO2Si at 20℃; for 4h; Schlenk technique; Glovebox; Inert atmosphere;	99 %Spectr.

4-cyanophenyl methyl ketone (1443-80-7) + ketene t-butyldimethylsilyl methyl acetal (77086-38-5) → methyl 3-((tert-butyldimethylsilyl)oxy)-3-(4-cyanophenyl)butanoate

Conditions	Yield
Stage #1: 4-cyanophenyl methyl ketone With bis(trifluoromethanesulfonyl)amide In diethyl ether at -78 - 23℃; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere; Stage #2: ketene t-butyldimethylsilyl methyl acetal In diethyl ether at -20℃; for 0.5h; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere;	99%

4-cyanophenyl methyl ketone (1443-80-7) + diphenyl hydrogen phosphite (4712-55-4) → diphenyl (S)-(1-hydroxy-1-(4-cyanophenyl)ethyl)phosphonate

Conditions	Yield
With C39H50N6O In toluene at -60℃; for 68h; enantioselective reaction;	99%

4-cyanophenyl methyl ketone (1443-80-7) + 1-chloro-3,5-dimethoxybenzene (7051-16-3) → C17H15NO3

Conditions	Yield
With C56H48ClN3Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 4h; Reagent/catalyst;	99%

4-cyanophenyl methyl ketone (1443-80-7) → 4-acetylbenzamide (67014-02-2)

Conditions	Yield
With 4-(benzyloxy)-1-hydroxy-2,2,6,6-tetramethylpiperidine In dichloromethane at 50℃; for 65h;	98%
With [2,2]bipyridinyl; water; palladium diacetate at 70℃; for 24h; Schlenk technique; Sealed tube;	98%
With water at 140℃; for 1h; Inert atmosphere;	97%

4-cyanophenyl methyl ketone (1443-80-7) + benzaldehyde (100-52-7) → 4-(1-oxo-3-phenyl-2-propen-1-yl)benzonitrile (31083-73-5)

Conditions	Yield
With Co(II)-VP-St (crosslinked 4-vinylpyridine-styrene copolimer); N,N-dimethyl-formamide at 80℃; for 18h;	98%
With sodium hydroxide In ethanol; water at 20℃;	50%
With potassium hydroxide In water at 20℃; Claisen-Schmidt Condensation;	23%

Upstream product

• 623-26-7 terephthalonitrile 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 586-89-0 4-acetyl-benzoic acid 
• 105-07-7 4-cyanobenzaldehyde 
• 75-16-1 methylmagnesium bromide 
• 6068-72-0 4-cyanobenzoyl chlorIde 
• 143-33-9 sodium cyanide 
• 99-90-1 para-bromoacetophenone 
• 111-34-2 -butyl vinyl ether 
• 623-00-7 4-bromobenzenecarbonitrile 
• 101219-69-6 4-(1-hydroxyethyl)benzonitrile 
• 99-91-2 para-chloroacetophenone 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 33189-95-6 3-(2,4-dichlorophenyl)-1-(4'-cyanophenyl)-2-propen-1-one 
• 5758-03-2 4-Cyan-acetophenon-dimethylhydrazon 
• 139152-78-6 2-p-Cyanophenyl-1-iodopropan-2-ol 
• 131941-27-0 4-(5-nitropyridine-2-yl)benzonitrile 
• 123316-67-6 4-p-Cyanophenyl-1,2-diphenylbut-2-ene-1,4-dione 
• 60695-04-7 1--3-<4-cyanophenyl>-propen-(1)-on-(3) 
• 60979-61-5 4-{1-[(E)-3-tert-Butylamino-2-hydroxy-propoxyimino]-ethyl}-benzonitrile 
• 19956-03-7 2-(4-cyanophenyl)propene 
• 182058-00-0 4-(1-((Trimethylsilyl)oxy)vinyl)benzonitrile 
• 649557-55-1 ethyl 4-(4-cyanophenyl)-2,4-dioxobutanoate 

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