13329-40-3

Basic information

• Product Name: 4'-Iodoacetophenone
• Synonyms: 1-(4-IODOPHENYL)ETHANONE;4'-IODOACETOPHENONE;4-IODOACETOPHENONE;Ethanone, 1-(4-iodophenyl)-;p-Iodoacetophenone;(4-Acetylphenyl) iodide;4-Acetylphenyl iodide;Methyl(4-iodophenyl) ketone
• CAS NO: 13329-40-3
• Molecular Formula: C₈H₇IO
• Molecular Weight: 246.05
• EINECS: 236-372-8
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);API intermediates;Adehydes, Acetals & Ketones;Iodine Compounds;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 13329-40-3.mol
• Article Data: 85

Chemical Properties

• Melting Point: 82-84 °C(lit.)
• Boiling Point: 279.9 °C at 760 mmHg
• Flash Point: 123.1 °C
• Appearance: Pale brown to brown/Crystalline Powder
• Density: 1.7411 (estimate)
• Vapor Pressure: 0.0039mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: Store below +30°C.
• Water Solubility: Easily soluble in water.
• Sensitive: Light Sensitive
• BRN: 1857412
• CAS DataBase Reference: 4'-Iodoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Iodoacetophenone(13329-40-3)
• EPA Substance Registry System: 4'-Iodoacetophenone(13329-40-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13329-40-3(Hazardous Substances Data)

Usage

Chemical Properties

Pale brown to brown crystalline powder

Uses

Synthesis of quinoline-based potential anticancer agents. Substrate for palladium-catalyzed coupling reactions

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 5106, 1972 DOI: 10.1021/ja00769a066The Journal of Organic Chemistry, 48, p. 4394, 1983 DOI: 10.1021/jo00171a050

General Description

Pd(0)-catalyzed cross coupling reaction of 4′-iodoacetophenone with siloxane has been reported. Heck-Mizoroki reactions of 4′-iodoacetophenone with styrene catalyzed by Pd nanoparticles in the flow reactor has been reported.

InChI:InChI=1/C8H7IO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,1H3

Synthetic route

1-(4-iodophenyl)ethanol (68120-56-9, 104013-25-4, 53207-29-7) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With silica-supported Jones reagent In dichloromethane for 0.00269444h;	99.6%
With 1,10-Phenanthroline; iron(III)-acetylacetonate; potassium carbonate In toluene for 48h; Reflux; Green chemistry;	94%
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II) In toluene at 120℃; for 12h; Glovebox; Schlenk technique; Inert atmosphere;	94%

1-ethynyl-4-iodobenzene (766-99-4) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With tetrakis(p-sulfonatophenyl)porphyrin cobalt(III) trisodium salt hexahydrate; water; bis(trifluoromethanesulfonyl)amide In methanol at 80℃; for 12h; Sealed tube;	97%

4-Aminoacetophenone (99-92-3) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
Stage #1: p-aminobenzophenone With hydrogenchloride In water at 0 - 5℃; for 0.166667h; Stage #2: With 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]ethyl)-1H-imidazol-3-ium dinitrite In water for 0.166667h; Stage #3: With potassium iodide In water at 20℃; for 0.166667h; Ionic liquid;	95%
With toluene-4-sulfonic acid; sodium iodide In water; acetonitrile at 10 - 20℃; for 2h; Inert atmosphere;	94%
With N-iodo-succinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 4h; Reagent/catalyst; Temperature; Solvent;	92%

1-(p-acetophenyl)-3,3-diethyl-1-triazene (86452-55-3) → 4-Iodoacetophenone (13329-40-3) + benzene (71-43-2)

Conditions	Yield
With sulfonic acid resin (H+ form, Bio-Rad AG 50W-12); sodium iodide In acetonitrile at 75℃; for 0.133333h;	A 95% B n/a

1-(3,4-Diiodocyclohexa-1,3-dienyl)ethanone (85972-28-7) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene	95%

1,2,2-triphenyl-1-iodoethylene (22021-09-6) + 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With thallium(I) acetate; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) In toluene; acetonitrile at 90℃; for 8h;	95%

4-acetophenyl triflate (109613-00-5) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With [Cp*Ru(CH3CN)3]OTf; sodium iodide at 120℃; for 12h; Inert atmosphere;	95%
With iodine; lithium fluoride; sodium iodide In acetonitrile at 25℃; for 24h; Inert atmosphere; UV-irradiation; Schlenk technique;	20%
Multi-step reaction with 2 steps 1: KOAc / PdCl2(dppf) / dimethylsulfoxide / 3 h / 80 °C 2: 30 percent / aq. NaI; chloramine-T / tetrahydrofuran / 6 h View Scheme

1-(p-acetophenyl)-3,3-diethyl-1-triazene (86452-55-3) → 4-Iodoacetophenone (13329-40-3) + acetophenone (98-86-2)

Conditions	Yield
With cation exchange resin BioRad AG 50W-X12 (H+); sodium iodide In acetonitrile at 75℃; Product distribution; further solvent: THF, DMSO;	A 94% B 6%

para-bromoacetophenone (99-90-1) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With copper(I) oxide; L-proline; potassium iodide In ethanol at 110℃; for 30h; Schlenk technique; Inert atmosphere; Sealed tube;	92%
With tributylphosphine; potassium iodide; nickel dibromide In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide at 50℃; for 1.5h;	66%
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; potassium iodide at 150 - 160℃; for 5h;	60%

1-(p-acetophenyl)-3,3-diethyl-1-triazene (86452-55-3) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In acetonitrile at 60℃; for 0.0833333h;	92%

4-acetylphenylboronic acid (149104-90-5) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With iodine; potassium carbonate In acetonitrile at 80℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube;	91%
With sodium nitrite In acetonitrile at 80℃; for 5h; Sealed tube;	86%
With 1,10-Phenanthroline; oxygen; potassium iodide; copper(ll) bromide In N,N-dimethyl-formamide at 80℃; for 20h;	76%

1-(4-acetylphenyl)diazonium tetrafluoroborate (350-47-0) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With N-iodo-succinimide; sodium nitrite In dimethyl sulfoxide at 20℃; for 2.5h;	90%
With diiodomethane; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;	87%

iodobenzene (591-50-4) + 4-(phenylethynyl)nitrobenzene (1942-30-9) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With thallium(I) acetate; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) In toluene; acetonitrile at 90℃; for 8h;	89%

1-iodo-4-(prop-1-en-2-yl)benzene (561023-21-0) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With sodium tetrafluoroborate; [Cu(salicylate)2(NCMe)]2; tetrabutyl-ammonium chloride; oxygen In tetrahydrofuran at 60℃; for 12h;	85%

carbon monoxide (201230-82-2) + para-diiodobenzene (624-38-4) + methylmercury(II) iodide (143-36-2) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); tetra-(n-butyl)ammonium iodide In N,N,N,N,N,N-hexamethylphosphoric triamide under 760 Torr; for 5.5h; Ambient temperature;	83%

4-Aminoacetophenone (99-92-3) + bis(trifluoromethanesulfonyl)amide (82113-65-3) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
Stage #1: bis(trifluoromethanesulfonyl)amide With tert.-butylnitrite; acetic acid In ethanol Cooling with ice; Stage #2: p-aminobenzophenone With tetraethylammonium iodide In water at 20℃;	81%

carbon monoxide (201230-82-2) + tetramethylstannane (594-27-4) + 4-iodobenzenediazonium tetrafluoroborate (1514-50-7) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
palladium diacetate In acetonitrile under 6619.6 Torr; for 1.5h; Heating;	79%
With palladium diacetate In acetonitrile for 0.5h; Ambient temperature;	79%

4-(2-methyl-[1,3]dioxolan-2-yl)-phenylamine (19073-16-6) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With N-iodo-succinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 4h;	75%
Multi-step reaction with 2 steps 1: sodium nitrite; N-iodo-succinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2: sodium nitrite; N-iodo-succinimide / N,N-dimethyl-formamide / 4 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sodium nitrite; N-iodo-succinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2: tert.-butylnitrite / water; ethanol / 2 h / 0 - 20 °C 3: sodium nitrite; N-iodo-succinimide / dimethyl sulfoxide / 2.5 h / 20 °C View Scheme

4-ethyl-1-iodobenzene (25309-64-2) → 4-Iodoacetophenone (13329-40-3) + 1-(4-iodophenyl)ethanol (68120-56-9, 104013-25-4, 53207-29-7)

Conditions	Yield
With 1-hydroxy-1,2-benzodioxol-3-(1H)-one; tris(2,2'-bipyridyl)ruthenium dichloride; water at 30℃; for 10h; Reagent/catalyst; Irradiation; Inert atmosphere;	A 8% B 71%

2-(4-iodophenyl)propan-2-ol (60514-82-1) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate; dipotassium peroxodisulfate; silver nitrate In water at 30℃; for 24h; Inert atmosphere; Green chemistry;	71%

4-ethyl-1-iodobenzene (25309-64-2) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With tert.-butylhydroperoxide; C26H23ClN8ORu In water at 20℃; for 2h; Catalytic behavior; Schlenk technique;	66%
With tert.-butylhydroperoxide at 90℃; for 5h; Neat (no solvent);
With calcined praseodymium incorporated AlPO-5 molecular sieves ((Al+P)/Pr = 25); air In neat liquid at 120℃; for 6h; Green chemistry;
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation; Green chemistry;	96 %Chromat.

1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + 1-(4-(dichloro-λ3-iodanyl)phenyl)ethan-1-one (92527-07-6) → 4-Iodoacetophenone (13329-40-3) + Hexafluoroacetone (684-16-2)

Conditions	Yield
In dichloromethane-d2 at 20℃; for 20h; Inert atmosphere;	A 65% B n/a

4-(2-methyl-[1,3]dioxolan-2-yl)-phenylamine (19073-16-6) → 4-Iodoacetophenone (13329-40-3) + 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With N-iodo-succinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 4h;	A 31% B 62%

4-acetyl-benzoic acid (586-89-0) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 1-iodo-butane; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; chloro-N,N,N',N'-bis(tetramethylene)formamidinium hexafluorophosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 120℃; for 16h; Sealed tube; Inert atmosphere;	62%

potassium 4-acetylphenyltrifluoroborate → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With chloroamine-T; sodium iodide In tetrahydrofuran; water at 20℃; for 1.5h;	60%

α-(benzoyloxy)-p-iodoacetophenone (135774-36-6) → 4-Iodoacetophenone (13329-40-3) + phenacyl benzoate (33868-50-7)

Conditions	Yield
With 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole; azobisisobutyronitrile In acetonitrile at 61℃; for 19h; Rate constant;	A 19.6% B 35%

1-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)ethan-1-one (460088-33-9) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With chloroamine-T; sodium iodide In tetrahydrofuran for 6h;	30%

iodobenzene (591-50-4) + acetyl chloride (75-36-5) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
With carbon disulfide; aluminium trichloride
With aluminium trichloride
With aluminum (III) chloride In dichloromethane at 40℃; for 24h; Friedel-Crafts Acylation; Sealed tube; Inert atmosphere;

methyllithium (917-54-4) + 4-iodobenzoic acid chloride (1711-02-0) → 4-Iodoacetophenone (13329-40-3)

Conditions	Yield
(i) CuI, Et2O, (ii) /BRN= 774718/, MeOH; Multistep reaction;

iodobenzene (591-50-4) → 4-Iodoacetophenone (13329-40-3)

4-Iodoacetophenone (13329-40-3) → 2-bromo-1-(4-iodophenyl)ethanone (31827-94-8)

Conditions	Yield
With bromine In 1,4-dioxane at 20℃; for 1h;	100%
With bromine In 1,4-dioxane at 0 - 20℃; for 1 - 1.66667h; Product distribution / selectivity;	100%
With bromine In chloroform at 20℃; for 4h;	94%

4-Iodoacetophenone (13329-40-3) + 4-methoxy-benzaldehyde (123-11-5) → (E)-1-(4-iodophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (92855-02-2)

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; for 4.25h; Cooling with ice;	100%
With sodium hydroxide In methanol at 0 - 20℃; for 4h; Claisen-Schmidt condensation;	91%
With SiO2-H3PO4 Aldol Condensation; Microwave irradiation;	88%

4-Iodoacetophenone (13329-40-3) → 1-(4-iodophenyl)ethanol (68120-56-9, 104013-25-4, 53207-29-7)

Conditions	Yield
With zirconium dioxide hydrate; isopropyl alcohol at 130℃; for 0.366667h; Meerwein-Ponndorf-Verley Reduction;	100%
With C9H8BrMnN2O3; potassium tert-butylate In isopropyl alcohol at 30℃; for 168h; Inert atmosphere; Schlenk technique; Glovebox;	99%
With sodium tetrahydroborate In ethanol for 5h;	98.7%

4-Iodoacetophenone (13329-40-3) → acetophenone (98-86-2)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 36h; Inert atmosphere;	100%
With triethylamine In toluene at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;	83.4%
With tris-(trimethylsilyl)silane In acetonitrile Schlenk technique; Inert atmosphere; Irradiation;	80%

4-Iodoacetophenone (13329-40-3) + phenylacetylene (536-74-3) → 4-(phenylethinyl)acetophenone (1942-31-0)

Conditions	Yield
With tetrabutylammonium acetate; copper aluminum In N,N-dimethyl-formamide at 110℃; for 24h; Sonogashira coupling;	100%
With copper(l) iodide; triethylamine; triphenylphosphine In water at 60℃; for 24h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;	100%
With sodium phosphate dodecahydrate In water; isopropyl alcohol at 80℃; for 1h; Reagent/catalyst; Sonogashira Cross-Coupling; Inert atmosphere;	100%

4-Iodoacetophenone (13329-40-3) + acrylic acid methyl ester (292638-85-8) → methyl (2E)-3-(4-acetylphenyl)acrylate (71348-24-8, 71348-27-1)

Conditions	Yield
With PdCl2[4,4'-bis(n-C10F21CH2OCH2)-2,2'-bipyridine]; triethylamine In N,N-dimethyl-formamide at 145℃; for 0.167h; Catalytic behavior; Reagent/catalyst; Heck Reaction; Microwave irradiation;	100%
With trihexyl(tetradecyl)phosphonium chloride; sodium acetate; palladium diacetate In water at 50℃; for 2h; Heck reaction;	99%
With C42H50Cl2N6Pd; sodium formate; triethylamine In N,N-dimethyl-formamide at 80℃; Heck Reaction; diastereospecific reaction;	99%

4-Iodoacetophenone (13329-40-3) + tetrabutylammonium triphenyldifluorosilicate → biphenyl-4-acetaldehyde (92-91-1)

Conditions	Yield
bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 95℃; for 21h;	100%

4-Iodoacetophenone (13329-40-3) → (R)-(+)-1-(4-iodophenyl)ethanol (220089-24-7)

Conditions	Yield
With magnesium chloride In isopropyl alcohol at 25℃; pH=7; Catalytic behavior;	100%
With (S,S)-RuCl2(2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl)(1,1-dianisyl-2-isopropyl-1,2-ethylenediamine); potassium tert-butylate; hydrogen In isopropyl alcohol at 26 - 30℃; under 6080 Torr; for 4h;	99.7%
With C37H40MnN2O2P2(1+)*Br(1-); sodium t-butanolate In isopropyl alcohol at 50℃; for 3h; Inert atmosphere; Schlenk technique; enantioselective reaction;	98%

4-Iodoacetophenone (13329-40-3) + (E)-2-pyridyldimethyl-(2-thien-2-ylethenyl)silane (321155-45-7) → (E)-1-(4-acetyl)phenyl-2-(2-thienyl)ethene (63483-65-8)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; Hiyama coupling;	100%

acrylic acid n-butyl ester (141-32-2) + 4-Iodoacetophenone (13329-40-3) → (E)-3-(4-acetylphenyl)acrylic acid butyl ester (173464-57-8)

Conditions	Yield
With C29H33Cl2N5Pd; tetrabutylammomium bromide; sodium carbonate In N,N-dimethyl acetamide at 140℃; for 3h; Heck reaction; Inert atmosphere;	100%
With tributyl-amine; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In 1-methyl-pyrrolidin-2-one at 140℃; for 15h; Heck Reaction; Inert atmosphere;	100%
With phenyl carbamate; potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 130℃; for 2h; Heck-type reaction;	99%

4-Iodoacetophenone (13329-40-3) + 2-Methoxyphenylboronic acid (5720-06-9) → 4-acetyl-2'-methoxybiphenyl (52807-17-7)

Conditions	Yield
With trihexyl(tetradecyl)phosphonium chloride; potassium phosphate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In toluene at 50℃; for 1h; Suzuki cross-coupling;	100%
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Suzuki cross-coupling reaction; Heating;

4-Iodoacetophenone (13329-40-3) + phenylboronic acid (98-80-6) → biphenyl-4-acetaldehyde (92-91-1)

Conditions	Yield
With trihexyl(tetradecyl)phosphonium chloride; potassium phosphate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In toluene at 50℃; for 1h; Suzuki cross-coupling;	100%
Stage #1: 4-Iodoacetophenone With tetrakis(triphenylphosphine) palladium(0) In 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide at 20 - 110℃; Suzuki coupling; Inert atmosphere; Ionic liquid; Stage #2: phenylboronic acid With triethylamine In 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide; water at 20 - 110℃; Suzuki coupling; Ionic liquid; Inert atmosphere;	100%
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Suzuki-Miyaura reaction; in air;	100%

4-Iodoacetophenone (13329-40-3) + 2-methyl-but-3-yn-2-ol (115-19-5) → 1-(4-acetylphenyl)-3-methyl-1-butyn-3-ol (95785-28-7)

Conditions	Yield
With copper(l) iodide; 1-isobutyl-2,2,6,6-tetramethyl-phosphorinane*HBF4; diisopropylamine; bis(benzonitrile)palladium(II) dichloride In 1,4-dioxane at 20℃; for 6h; Sonogashira reaction;	100%
With piperidine; copper(l) iodide; polystyrene-N(CH2PPh2)2PdCl2 In 1,4-dioxane at 60℃; for 2h; Sonogashira coupling reaction;	94%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;	90%

4-Iodoacetophenone (13329-40-3) + 4-Ethynylaniline (14235-81-5) → 4-((4-aminophenyl)ethynyl)acetophenone (123770-68-3)

Conditions	Yield
With triethylamine In water at 80℃; for 0.5h; Sonogashira Cross-Coupling;	100%
With triethylamine; Nd2.04Cu0.95Pd0.05O4 In N,N-dimethyl-formamide at 120℃; for 16h; Sonogashira reaction;	92%
With Pd/SiO2; triethylamine In diethyl ether; water at 20℃; for 10h; Sonogashira Cross-Coupling;	86%

4-Iodoacetophenone (13329-40-3) → 4-Hydroxyacetophenone (99-93-4)

Conditions	Yield
With sodium hydroxide; copper(l) iodide; L-proline In water at 20 - 300℃; microwave irradiation;	100%
Stage #1: 4-Iodoacetophenone With copper(l) iodide; tetra(n-butyl)ammonium hydroxide In water at 60℃; for 24h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; for 2h; Inert atmosphere; chemoselective reaction;	96%
With copper(l) iodide; potassium hydroxide In water at 100℃; Inert atmosphere;	96%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + 4-Iodoacetophenone (13329-40-3) + bis(dibenzylideneacetone)-palladium(0) (32005-36-0) → PdI(4-MeCOC6H4)(N,N,N',N'-tetramethylethylenediamine) (191667-17-1)

Conditions	Yield
In not given byproducts: dibenzylideneacetone; N2-atmosphere; according to Markies, A. J. et al.: J. Organomet. Chem. 482 (1994) 191; elem. anal.;	100%

tert-Butyl acrylate (1663-39-4) + 4-Iodoacetophenone (13329-40-3) → (E)-tert-butyl 3-(4-acetylphenyl)prop-2-enoate (389091-50-3)

Conditions	Yield
With tetrabutyl ammonium fluoride; palladium dichloride at 40℃; for 3h; Heck reaction; Inert atmosphere; neat (no solvent);	100%
With tributyl-amine In N,N-dimethyl-formamide at 120℃; Heck-Mizoroki reaction;	99%
With di-μ-iodobis(tri-tert-butylphosphino)dipalladium(l); N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 15h; Heck Reaction; Inert atmosphere; Sealed tube; Glovebox;	99%

4-Iodoacetophenone (13329-40-3) + acrylic acid methyl ester (292638-85-8) → methyl 4-acetylcinnamate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.25h; Heck Reaction;	100%
With triethylamine In water; acetonitrile at 120℃; for 3h; Heck Reaction; Green chemistry;	99%
With 3C22H14N3O2(1-)*Ho(3+)*Pd(2+)*2Cl(1-); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Heck Reaction;	99%

(4-methylphenyl)gold(triphenylphosphine) (40667-81-0) + 4-Iodoacetophenone (13329-40-3) → 1-{4-[2-(4-methylphenyl)ethynyl]phenyl}ethanone (123770-66-1)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; diisopropylamine; 1,2-bis-(diphenylphosphino)ethane In toluene at 130℃; for 16h; Sonogashira coupling; Inert atmosphere;	100%

4-Iodoacetophenone (13329-40-3) + 4,4-dimethyl-1-phenyl-1-(pyridin-2-yl)pent-2-yn-1-ol (1046337-99-8) → 2-(4-acetylphenyl)-3-tert-butyl-8a-phenylindolizin-1(8aH)-one (1227746-69-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In acetonitrile at 90℃; for 13h;	100%

4-Iodoacetophenone (13329-40-3) + 3-phenyl-1,1-di(pyridin-2-yl)prop-2-yn-1-ol (87446-01-3) → 2-(4-acetylphenyl)-3-phenyl-8a-(pyridin-2-yl)indolizin-1(8aH)-one (1383711-44-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In acetonitrile at 90℃; for 13h;	100%

4-Iodoacetophenone (13329-40-3) → 1-(4-iodophenyl)ethan-1-one oxime (27760-43-6)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃;	100%
With hydroxylamine hydrochloride; sodium hydroxide In methanol at 20℃; Green chemistry;	78%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 1h; Reflux;

4-Iodoacetophenone (13329-40-3) + m-tolylboronic acid (17933-03-8) → 4-acetyl-3'-methylbiphenyl (76650-29-8)

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 0.333333h; Suzuki-Miyaura Coupling; Green chemistry;	100%
With potassium carbonate In water at 25℃; for 2h; Suzuki Coupling; Schlenk technique;	98%
With potassium carbonate In water at 20℃; for 4h; Catalytic behavior; Suzuki-Miyaura Coupling;	100 %Chromat.

4,7-dichloroisatin (18711-13-2) + 4-Iodoacetophenone (13329-40-3) → 4,7-dichloro-3-hydroxyl-3-[2-(4-iodophenyl-2-oxoethyl)]-1,3-dihydroindol-2-one (1037184-42-1)

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

4-Iodoacetophenone (13329-40-3) + 2-(2-(4-bromophenyl)-4-(4-ethylphenyl)-5-(4-methoxyphenyl)furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 1-(4-(2-(4-bromophenyl)-4-(4-ethylphenyl)-5-(4-methoxyphenyl)furan-3-yl)phenyl)ethan-1-one

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Schlenk technique;	100%

4-Iodoacetophenone (13329-40-3) → 4,4'-diacetylbiphenyl (787-69-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; [2-(Pd-Cl)-4,4'-dichlorobenzophenone oxime]2 In decane; N,N-dimethyl-formamide at 110℃; for 5h; Ullmann homocoupling;	99%
With potassium iodide; nickel dibromide; zinc In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide at 50℃; for 3h;	98%
With potassium phosphate In water at 110℃; for 48h; Ullmann Condensation;	98%

n-butyllithium (109-72-8, 29786-93-4) + 4-Iodoacetophenone (13329-40-3) → 2-(4-iodophenyl)-2-hexanol (84735-52-4)

Conditions	Yield
With cerium(III) triiodide In tetrahydrofuran; hexane at -65℃; for 3h;	99%
Stage #1: n-butyllithium With cerium(III) chloride at -78℃; Stage #2: 4-Iodoacetophenone at -78℃;	93%
With cerium(III) triiodide in THF, 1) -65 deg C, 30 min., 2) -65 deg C, 3h; Yield given. Multistep reaction;

ethanol (64-17-5) + 4-Iodoacetophenone (13329-40-3) + carbon monoxide (201230-82-2) → ethyl-4-acetylbenzoate (38430-55-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate at 20 - 125℃; under 7500.75 - 22502.3 Torr; for 0.333333h; microwave irradiation;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate at 125℃; under 7757.43 Torr; for 0.333333h; microwave irradiation;	97%
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere;	96%

4-Iodoacetophenone (13329-40-3) + acrylic acid (79-10-7) → 4-acetylcinnamic acid (18910-24-2)

Conditions	Yield
With potassium hydroxide In water at 90℃; for 5h; Mizoroki-Heck reaction;	99%
With potassium hydroxide In methanol at 80℃; for 24h; Heck reaction;	65%
With sodium carbonate; palladium dichloride In water at 100℃; Yield given;
With palladium diacetate; potassium carbonate In water at 120℃; for 0.416667h; Heck reaction; Microwave irradiation;
With potassium carbonate In water at 90℃; for 12h; Heck Reaction; Inert atmosphere;

Upstream product

• 109-89-7 Diethylamine 
• 99-92-3 4-Aminoacetophenone 
• 75-77-4 Chlorotrimethylsilane 
• 7681-11-0 Potassium iodide 

Downstream Products

• 1332-94-1 Vitamin 
• 133294-12-9 dioctadecylamidospermine 
• 133294-33-4 Piperidine, 2-(2-propenyl)-, (S)- (9CI) 
• 1332-96-3 FERRIC PYROPHOSPHATE 
• 1332965-90-8 Diisononyl Phthalate-d4 
• 1332965-96-4 7-Methyl-1-Octanol Phthalate-d4 
• 13329-66-3 ALUMINUM HYDROXYSTEARATE 
• 13329-67-4 sodium 12-hydroxyoctadecanoate 
• 133296-75-0 1-naphthyl 3-methoxybenzoate 
• 13329-69-6 [[6-[(hydroxymethyl)amino]-1,3,5-triazine-2,4-diyl]dinitrilo]tetrakismethanol 
• 13329-70-9 tris(hydroxymethyl)urea 
• 13329-71-0 N-isopropyloctadecylamine 
• 13329-78-7 decane-2,4-dione 
• 13329-82-3 O-(4-bromo-2,5-dichlorophenyl) O-methyl hydrogen phosphorothioate 

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