99-90-1

Basic information

• Product Name: 4'-Bromoacetophenone
• Synonyms: p-BROMOACETOPHENONE pure;4-Bromophenyl methyl ketone;p-Acetylbromobenzene;p-Bromphenyl methyl ketone;1-(4-Bromophenyl)ethane-1-one;Methyl 4-bromophenyl ketone;1-acytyl-4-bromobenzene;4′-Bromoacetophenone,1-Acetyl-4-bromobenzene
• CAS NO: 99-90-1
• Molecular Formula: C₈H₇BrO
• Molecular Weight: 199.04
• EINECS: 202-783-6
• Product Categories: Aromatics;Miscellaneous Reagents;ketone| alkyl bromide;Acetophenone Series;FINE Chemical & INTERMEDIATES;Aromatic Acetophenones & Derivatives (substituted);Adehydes, Acetals & Ketones;Bromine Compounds;Acetophenones (Building Blocks for Liquid Crystals);Bifunctional Compounds (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials
• Mol File: 99-90-1.mol
• Article Data: 580

Chemical Properties

• Melting Point: 108-110 °C(lit.)
• Boiling Point: 255 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to light yellow/Crystals or Crystalline Flakes
• Density: 1.64
• Refractive Index: 1.5540 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: methanol: 0.1 g/mL, clear
• Water Solubility: Soluble in Chloroform. Insoluble in water.
• Merck: 14,1403
• BRN: 386015
• CAS DataBase Reference: 4'-Bromoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Bromoacetophenone(99-90-1)
• EPA Substance Registry System: 4'-Bromoacetophenone(99-90-1)

Safety Data

• Hazard Codes: C,Xi,Xn
• Statements: 34-36/38-42/43-36/37/38-22
• Safety Statements: 26-36/37/39-45-22-36/37
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 2
• RTECS: AM6950000
• F: 19-21
• TSCA: Yes
• Hazardous Substances Data: 99-90-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystals. soluble in alcohol, ether, glacial acetic acid, benzene, carbon disulfide and petroleum ether, insoluble in water. Easy to volatilize with water vapor.

Uses

Different sources of media describe the Uses of 99-90-1 differently. You can refer to the following data:
1. 4'-Bromoacetophenone is an important organic synthesis intermediate, widely used in synthetic medicine, pesticides, dyes, flavors and fragrances, perfumes, Intermediates of Liquid Crystals etc.
2. Labeled 4?-Bromoacetophenone possess activity against positive phototaxis of Chlamydomonas cells. A fundamental starting material for organic synthesis.

Preparation

4'-Bromoacetophenone is synthesized by the reaction of bromobenzene and acetic anhydride in the presence of aluminum trichloride. Add bromobenzene and dry carbon disulfide into the reactor, put in powdered anhydrous aluminum trichloride, heat until it starts to reflux, stop heating, add acetic anhydride dropwise, and then reflux for 1 hour after adding, steam out carbon disulfide, and put it while it is still hot. The reactant was poured into the hydrochloric acid ice-water mixture, filtered to dryness, and distilled under reduced pressure to obtain p-bromoacetophenone.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 5400, 1986 DOI: 10.1021/jo00376a064Tetrahedron Letters, 26, p. 4657, 1985 DOI: 10.1016/S0040-4039(00)98778-1

Purification Methods

Crystallise it from EtOH, MeOH or from pet ether (b 80-100o). [Tanner J Org Chem 52 2142 1987, Beilstein 7 IV 647.]

Synthetic route

1-(4-bromophenyl)ethanol (5391-88-8) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With polymer-supported phenyliodine(III) diacetate; JandaJel-CH2O-TEMPO In 1,2-dichloro-ethane at 70℃; for 12h;	100%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; sodium hydrogencarbonate; gold(I) chloride In water at 100℃; under 38002.6 Torr; for 24h;	100%
With 1,1,1,3',3',3'-hexafluoro-propanol; 5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ5-benzo[d][1,2]-iodoxol-1-ol anion; trifluoroacetic acid at 20℃; for 0.25h;	100%

α-(benzoyloxy)-p-bromoacetophenone (7506-12-9) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole; azobisisobutyronitrile In acetonitrile at 61℃; for 48h; Rate constant; other temp., other reagents;	100%
With 4-methyl-morpholine; 1.3-propanedithiol; tetrabutyl ammonium fluoride In tetrahydrofuran for 0.0833333h; Ambient temperature;	74%

2-(4-bromophenyl)-2-methyl-1,3-dioxolane (4360-68-3) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With diiodosilane In chloroform at -42℃; for 0.0166667h; other reagent: iodotrimethylsilane (TMSI); other temp. and mol percent; other ketals and acetals;	99%
With diiodosilane In chloroform at -42℃; for 0.0166667h; other reagent: iodotrimethylsilane (TMSI);	99%
With caro's acid; silica gel In acetonitrile at 20℃; for 0.666667h;	95%

4-bromoacetophenone phenylhydrazone (10591-75-0) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With quinolinium dichromate(VI) In acetonitrile for 1h; Heating;	99%
With polumer-supported phenyliodine bis(trifluoroacetate); water In tetrahydrofuran for 0.75h;	85%
With manganese(IV) oxide; potassium permanganate In dichloromethane at 20℃; for 10h;	68%

4-bromo-1-ethynylbenzene (766-96-1) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With trifluorormethanesulfonic acid; silver trifluoromethanesulfonate; C75H52AuClN2O2 In methanol; dichloromethane; water at 20℃; for 20h;	99%
With water at 60℃; for 20h; Sealed tube;	99%
With 5,10,15-tris(pentafluorophenyl)corrole cobalt(III) triphenyl phosphine; sulfuric acid; water In methanol at 80℃; for 72h;	99%

1-bromo-4-(1,1-diethoxyethyl)benzene (61390-40-7) → para-bromoacetophenone (99-90-1)

Conditions	Yield
bismuth(III) iodide In water at 100℃; for 2h;	99%
With copper(II) sulfate; sodium iodide In acetone at 56℃; for 2.5h;	81%

1-(4-acetylphenyl)diazonium tetrafluoroborate (350-47-0) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With dibenzo-18-crown-6; potassium bromide; copper(ll) bromide; 1,10-Phenanthroline; copper(I) bromide In acetonitrile at 20℃; for 0.333333h; Sandmeyer bromination;	99%
With (triphenylphosphine)gold(I) chloride; sodium bromide In acetonitrile at 50℃; for 5h; Sandmeyer Reaction;	81%

2-(4-bromophenyl)propane (586-61-8) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With oxygen at 190℃; under 760.051 Torr; for 24h; Autoclave;	99%
With hydrogenchloride; sodium nitrite In water at 23℃; for 3h; Sealed tube;	50%

para-bromophenacyl bromide (99-73-0) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With sodium dithionite; potassium carbonate; 1,1′-dioctyl-4,4′-bipyridinium In water; toluene at 35℃; for 3h;	98%
With sodium tetrahydroborate; nickel dichloride In N,N-dimethyl-formamide for 0.25h;	98%
With Methyltrichlorosilane; sodium iodide In acetonitrile for 2h; Ambient temperature;	98%

piperidine (110-89-4) + bis(1-naphthoyl) telluride (107469-89-6) → (naphthalen-1-yl)(piperidin-1-yl)methanone (5454-14-8) + para-bromoacetophenone (99-90-1)

Conditions	Yield
With para-bromophenacyl bromide In toluene at 25℃; for 2h;	A 98% B 50%

p-bromoacetophenone oxime (59862-55-4, 73744-33-9, 5798-71-0) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With quinolinium dichromate(VI) In acetonitrile for 0.8h; Heating;	98%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 1h; Heating;	98%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In dichloromethane for 0.05h; microwave irradiation;	98%

1,2-bis-[1-(4-bromophenyl)ethylidene]hydrazine (56587-87-2, 21399-36-0) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 18h; Oxidation;	98%
With 2-phenyl-1,2-benzoisoselenazol-3(2H)-one; dihydrogen peroxide In methanol; water at 65℃; for 24h;	96%

1-(4-bromophenyl)-2-chloroethan-1-one (4209-02-3) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With bismuth(III) chloride; sodium tetrahydroborate; sodium iodide In acetone Ambient temperature;	98%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid for 3h; Irradiation; Inert atmosphere;	92%

[1-(4-Bromo-phenyl)-eth-(E)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine → para-bromoacetophenone (99-90-1)

Conditions	Yield
With water; oxalic acid In diethyl ether for 4h; Ambient temperature;	98%

1-(4-Bromo-phenyl)-1-{2-[1-(4-bromo-phenyl)-1-hydroxy-ethyl]-quinazolin-4-yl}-ethanol → para-bromoacetophenone (99-90-1) + 2-(α-methyl-α-hydroxy-p-bromobenzyl)quinazoline

Conditions	Yield
With tetra-n-butylammonium cyanide In tetrahydrofuran for 0.333333h; Heating;	A 89% B 98%

N'-[1-(4-Bromo-phenyl)-eth-(E)-ylidene]-N,N-dimethyl-hydrazine (5757-83-5) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With sodium perborate In acetic acid at 50 - 60℃; for 5h;	97%
With cerium(III) chloride; silica gel for 0.0833333h; Microwave irradiation;	90%

para-bromophenacyl bromide (99-73-0) + 4-Ethyltellanyl-butan-1-ol (189247-72-1) → para-bromoacetophenone (99-90-1) + 2-Bromo-2-ethyl-2λ4-[1,2]oxatellurane

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	A 97% B 63%

1-bromo-4-ethylbenzene (1585-07-5) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With tert.-butylhydroperoxide In water at 20℃; for 18h; Sealed tube;	97%
With Iron(III) nitrate nonahydrate; 1-hydroxy-pyrrolidine-2,5-dione; oxygen In benzonitrile at 90℃; for 30h;	97%
With Oxone; potassium bromide In nitromethane at 50℃; for 24h;	96%

4-acetylphenylboronic acid (149104-90-5) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 80℃; for 12h;	97%
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; Sealed tube;	87%
With sodium nitrite In acetonitrile at 80℃; for 10h; Sealed tube;	85%
With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide In N,N-dimethyl-formamide at 130℃; for 20h;	78%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sodium methylate In methanol; water; acetonitrile at 40℃; for 4h;	99 % Chromat.

3,3-dimethyldioxirane (74087-85-7) + 1-(4-bromophenyl)ethanol (5391-88-8) → 4-bromo-2-hydroxyacetophenone (3343-45-1) + para-bromoacetophenone (99-90-1)

Conditions	Yield
In acetone at 25℃; for 3h;	A 3% B 96%
In acetone at 25℃; for 3h; Thermodynamic data; Rate constant; Ea, ΔH(excit.), ΔS(excit.), ΔG(excit.);	A 3% B 96%

para-bromophenacyl bromide (99-73-0) + 3-(methyltellanyl)propan-1-ol (110851-05-3) → para-bromoacetophenone (99-90-1) + 2-Bromo-2-methyl-2λ4-[1,2]oxatellurolane

Conditions	Yield
In dichloromethane for 2.5h; Ambient temperature;	A 96% B 72%

1-(4-bromophenyl)-2-(phenylsulfonyl)ethanone (41024-55-9) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With formic acid; eosin Y bis(tetrabutyl ammonium salt) In acetonitrile at 20℃; Irradiation; Inert atmosphere;	96%
With samarium; acetic acid In ethanol at 20℃; for 3h;	75%

4-acetophenyl triflate (109613-00-5) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With [Cp*Ru(CH3CN)3]OTf; lithium bromide at 100℃; for 12h; Inert atmosphere;	96%
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; potassium bromide In 1,4-dioxane at 130℃; for 16h; Inert atmosphere;	79%

4'-bromoacetophenone semicarbazone (120445-88-7, 20576-97-0) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With (H2DABCO)2(HDABCO)2(Br)2(Br3)4 In water at 80℃; for 0.333333h;	95%
With tribromo-isocyanuric acid In acetonitrile at 20℃; for 6h;	94%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 2h; Heating;	93%

(1-(4-bromophenyl)ethoxy)trimethylsilane → para-bromoacetophenone (99-90-1)

Conditions	Yield
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.15h;	95%
With potassium dichromate; aluminium trichloride for 0.416667h;	90%

2-(4-bromophenyl)-2-methyl-1,3-dithiane (77464-23-4) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With quinolinium monofluorochromate(VI) In acetonitrile for 2.5h; Heating;	95%
With potassium permanganate; tungstate sulfuric acid In dichloromethane at 20℃; for 1.16667h;	95%
With silica gel; iodic acid at 20℃; for 0.0111111h;	93%

2-(p-bromo-α-methylbenzyloxy)tetrahydropyran (52779-71-2) → para-bromoacetophenone (99-90-1)

Conditions	Yield
With β‐cyclodextrin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetone at 20℃; for 0.666667h;	95%
With N-Bromosuccinimide; β‐cyclodextrin In acetone at 20℃; for 0.5h;	90%

1-bromo-4-ethenyl-benzene (2039-82-9) → para-bromoacetophenone (99-90-1) + 1-(4-bromophenyl)ethanol (5391-88-8)

Conditions	Yield
With triethylsilane; (1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyaninato)iron(II); oxygen In ethanol at 20℃; under 760.051 Torr; for 8.5h; Wacker Oxidation; Sealed tube; Green chemistry; chemoselective reaction;	A 95% B 3%

pyridine (110-86-1) + para-bromoacetophenone (99-90-1) → 1-(2-(4-bromophenyl)-2-oxoethyl)pyridin-1-ium iodide (6320-91-8)

Conditions	Yield
With iodine for 16h; Reflux; Inert atmosphere;	100%
With iodine at 80℃; for 6h;	78%
With iodine at 100℃; for 3h;	76%

para-bromoacetophenone (99-90-1) + ethylene glycol (107-21-1) → 2-(4-bromophenyl)-2-methyl-1,3-dioxolane (4360-68-3)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 39h; Heating;	100%
With p-toluenesulfonic acid monohydrate In benzene for 50h; Inert atmosphere; Reflux; Dean-Stark;	100%
With toluene-4-sulfonic acid In toluene at 160℃; for 16h; Dean-Stark; Inert atmosphere;	99%

para-bromoacetophenone (99-90-1) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With selenium (IV) oxide In 1,4-dioxane; water Heating;	100%
With copper(II) choride dihydrate In dimethyl sulfoxide at 80℃;	90%
With selenium(IV) oxide; water In ethanol for 8h; Reflux;	78%

para-bromoacetophenone (99-90-1) → 1-(4-bromophenyl)ethanol (5391-88-8)

Conditions	Yield
With zirconium dioxide hydrate; isopropyl alcohol at 130℃; for 0.366667h; Meerwein-Ponndorf-Verley Reduction;	100%
Stage #1: para-bromoacetophenone With C24H20Cl2F5NRuS; isopropyl alcohol at 82℃; for 0.166667h; Stage #2: With potassium hydroxide at 82℃; for 0.5h;	100%
With methanol; sodium tetrahydroborate at 0℃; for 0.166667h; Reagent/catalyst;	100%

para-bromoacetophenone (99-90-1) → p-bromoacetophenone oxime (59862-55-4, 73744-33-9, 5798-71-0)

Conditions	Yield
With hydroxylamine	100%
With hydroxylamine hydrochloride	100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;	100%

styrene (292638-84-7) + para-bromoacetophenone (99-90-1) → 4-acetylstilbene (3112-03-6)

Conditions	Yield
With cis-(N,N'-bis(2,2-diethoxyethyl)imidazolin-2-ylidene)dichlorotriphenylphosphinepalladium(II); tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 2h; Heck reaction;	100%
With 6F6P(1-)*C50H64N12Pd(6+); sodium acetate In N,N-dimethyl-formamide at 140℃; for 3h; Reagent/catalyst; Heck Reaction;	100%
With C28H28N4O2(2+)*2Cl(1-); palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 145℃; for 0.0833333h; Heck reaction; Microwave irradiation;	99%

4-fluoroboronic acid (1765-93-1) + para-bromoacetophenone (99-90-1) → 4'-fluoro-4-acetyl-1,1'-biphenyl (720-74-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate; palladium diacetate In acetone at 110℃; for 3.5h; Suzuki-Miyaura cross-coupling reaction;	100%
With potassium phosphate; [Pd(Ph2PCH2CH(CH3)O)2] In tetrahydrofuran; water at 20℃; for 8h; Suzuki cross-coupling reaction;	99%
With potassium phosphate; cis-bis((diphenylphosphino)acetate-κ2P,O)palladium(II) In tetrahydrofuran at 25 - 27℃; for 6h; Suzuki coupling;	99%

para-bromoacetophenone (99-90-1) + trimethylsilylacetylene (1066-54-2) → 4'-(2-trimethylsilylethynyl)acetophenone (75883-03-3)

Conditions	Yield
With copper diacetate; triethylamine; triphenylphosphine; palladium dichloride at 100℃; for 1.5h;	100%
With copper diacetate; triethylamine; triphenylphosphine; palladium dichloride at 100℃; for 1.5h;	100%
With copper(l) iodide; palladium diacetate; triethylamine; triphenylphosphine at 60℃; for 12h;	98%

tert-Butyl acrylate (1663-39-4) + para-bromoacetophenone (99-90-1) → (E)-tert-butyl 3-(4-acetylphenyl)prop-2-enoate (389091-50-3)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 120℃; for 15h; Heck cross-coupling reaction;	100%
With 1,3-disubstituted imidazolium bromide; potassium carbonate; 4-methylmorpholine N-oxide; palladium diacetate In 1-methyl-pyrrolidin-2-one at 120℃; for 2h; Heck reaction;	99%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Mizoroki-Heck reaction;	99%

para-bromoacetophenone (99-90-1) + phenylacetylene (536-74-3) → 4-(phenylethinyl)acetophenone (1942-31-0)

Conditions	Yield
With copper(l) iodide; 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 130℃; for 20h; Sonogashira cross-coupling;	100%
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 24h; Sonogashira reaction;	100%
With 1,4-diaza-bicyclo[2.2.2]octane; PdCl2[4,4'-bis(n-C10F21CH2OCH2)-2,2'-bipyridine] In N,N-dimethyl-formamide at 140℃; for 1h; Catalytic behavior; Sonogashira Cross-Coupling; Microwave irradiation;	100%

para-bromoacetophenone (99-90-1) + phenylboronic acid (98-80-6) → biphenyl-4-acetaldehyde (92-91-1)

Conditions	Yield
With potassium carbonate; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 In xylene at 130℃; for 13h; Suzuki-Miyaura cross-coupling reaction;	100%
With tetrabutylammomium bromide; potassium carbonate; quasi polymeric 4-pyridine-aldoxime Pd(II)-catalyst at 120℃; for 0.333333h; Suzuki-Miyaura reaction; microwave irradiation;	100%
With 3-tert-butyl-5-methyl-1-(2-(diphenylphosphino)phenyl)-1H-pyrazole; tris(dibenzylideneacetone)dipalladium (0) In toluene at 65℃; for 2h; Suzuki coupling;	100%

acrylic acid n-butyl ester (141-32-2) + para-bromoacetophenone (99-90-1) → (E)-3-(4-acetylphenyl)acrylic acid butyl ester (173464-57-8)

Conditions	Yield
With palladium diacetate; caesium carbonate In N,N-dimethyl acetamide at 100℃; for 3h; Product distribution; Further Variations:; Reagents; Heck reaction;	100%
With tributyl-amine In N,N-dimethyl-formamide at 150℃; for 1h; Heck reaction;	100%
With C29H33Cl2N5Pd; tetrabutylammomium bromide; sodium carbonate In N,N-dimethyl acetamide at 140℃; for 4h; Heck reaction; Inert atmosphere;	100%

styrene (292638-84-7) + para-bromoacetophenone (99-90-1) → 4-acetyl-trans-stilbene (20488-43-1, 3112-03-6, 20488-42-0)

Conditions	Yield
With sodium acetate; {1,1'-dibenzyl-3,3'-CH2-diimidazolin-2,2'-diylidene}PdBr2 In N,N-dimethyl acetamide at 165 - 175℃; for 1h; Heck coupling reaction;	100%
With [Pd2(1,2-bis(diphenylphosphino)ethane)2(SC6H4S)]2(OTf)4; sodium acetate In N,N-dimethyl acetamide; water at 120℃; for 16h; Catalytic behavior; Reagent/catalyst; Temperature; Heck Reaction; Inert atmosphere;	100%
With C180H144O4P8Pd4S4(4+)*4CF3O3S(1-); sodium acetate In N,N-dimethyl acetamide; water at 120℃; for 16h; Heck Reaction; Inert atmosphere;	100%

4-methylphenylboronic acid (5720-05-8) + para-bromoacetophenone (99-90-1) → 4-acetyl-4'-methylbiphenyl (5748-38-9)

Conditions	Yield
With C23H35N4O4Pd(1+)*Br(1-); potassium carbonate In water at 100℃; for 1h; Suzuki-Miyaura Coupling;	100%
With potassium phosphate In N,N-dimethyl-formamide at 120℃; for 5h; Suzuki Coupling;	100%
With potassium carbonate In water at 80℃; for 10.5h; Suzuki-Miyaura Coupling; Green chemistry;	100%

tributylphenylstannane (960-16-7) + para-bromoacetophenone (99-90-1) → biphenyl-4-acetaldehyde (92-91-1)

Conditions	Yield
{1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PCPh)PdI2 In toluene at 110℃; for 17h; Stille reaction;	100%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium hydroxide; poly(ethylene glycol)-400; palladium diacetate In water at 80℃; for 10h; Stille coupling;	100%
With potassium carbonate; trans-(1,3-di(1'-(R)-phenylethyl)imidazolin-2-ylidene)(tricyclohexylphosphine)palladium(II) diiodide In toluene at 110℃; for 17h; Stille cross coupling;	99%

morpholine (110-91-8) + para-bromoacetophenone (99-90-1) → 4-morpholinoacetophenone (39910-98-0)

Conditions	Yield
With 2-(dicyclohexylphosphino)-4'-(N,N-dimethylamino)-1,1'-biphenyl at 100℃;	100%
With potassium 2-methylbutan-2-olate In 1,2-dimethoxyethane at 80℃; for 3h; Hartwig-Buchwald amination; Inert atmosphere;	99%
With C30H25BrN3PPdS; potassium carbonate In iso-butanol at 100℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere;	94.7%

para-bromoacetophenone (99-90-1) → (R)-1-(4-bromophenyl)ethanol (5391-88-8, 25675-29-0, 76155-78-7, 100760-04-1)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C45H58NP; potassium tert-butylate; hydrogen In propan-1-ol at 25 - 30℃; under 4560.31 Torr; for 0.166667h; Autoclave; optical yield given as %ee; enantioselective reaction;	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 5h;	99.9%
With Geotrichum candidum IFO 5767 In water at 30℃; for 24h; aerobic conditions;	99%

acrylic acid n-butyl ester (141-32-2) + para-bromoacetophenone (99-90-1) → butyl 3-(4-acetylphenyl)acrylate

Conditions	Yield
With diethylene glycol dibutyl ether; [PdBr2]([Ph2PCH2C(Ph)=N(2,6-iPr2C6H3)]) In N,N-dimethyl acetamide at 130℃; for 20h; Product distribution; Further Variations:; Catalysts; Heck coupling;	100%
With water; potassium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Catalytic behavior; Heck Reaction;	99%
With tributyl-amine; Palladium bipyridyl complex anchored on nanosized MCM-41 In various solvent(s) at 170℃; for 16h; Heck reaction;	98%

2-Methylphenylboronic acid (16419-60-6) + para-bromoacetophenone (99-90-1) → 4-acetyl-2'-methylbiphenyl (56917-39-6)

Conditions	Yield
With potassium phosphate; water In toluene at 100℃; for 1h; Suzuki coupling reaction;	100%
With potassium carbonate; N,N-diethylaminopropyl-Al2O3-Pd(OAc)2 In ethanol; water at 80℃; for 2h; Suzuki-Miyaura reaction; microwave irradiation;	100%
With potassium carbonate In ethanol; water at 20℃; for 0.5h; Suzuki-Miyaura reaction; Inert atmosphere;	100%

4-methoxyphenylboronic acid (5720-07-0) + para-bromoacetophenone (99-90-1) → 1-(4'-methoxy-biphenyl-4-yl)-ethanone (13021-18-6)

Conditions	Yield
With sodium phosphate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 2h; Suzuki-Miyaura reaction;	100%
With potassium carbonate In water at 80℃; for 5h; Suzuki Coupling;	100%
With potassium carbonate In methanol at 25℃; for 1h; Wavelength; Suzuki-Miyaura Coupling; Inert atmosphere; Irradiation;	100%

para-bromoacetophenone (99-90-1) → (E)-1-(4-bromophenyl)ethan-1-one oxime (59862-55-4)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol Heating;	100%
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;	100%
With 3 A molecular sieve; hydroxylamine hydrochloride at 20℃; for 0.25h;	96%

2-Methoxyphenylboronic acid (5720-06-9) + para-bromoacetophenone (99-90-1) → 4-acetyl-2'-methoxybiphenyl (52807-17-7)

Conditions	Yield
With sodium carbonate; palladium on activated charcoal In ethanol at 20℃; for 4h; Suzuki-Miyaura cross-coupling;	100%
With potassium carbonate In ethanol; water at 60℃; for 12h; Suzuki Coupling; Green chemistry;	99%
With potassium carbonate In ethanol; water at 20℃; for 1.5h; Suzuki-Miyaura reaction; Inert atmosphere;	97%

4-trifluoromethylphenylboronic acid (128796-39-4) + para-bromoacetophenone (99-90-1) → 4-acetyl-4'-trifluoromethylbiphenyl (142557-76-4)

Conditions	Yield
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water at 60℃; for 2h; Inert atmosphere;	100%
With 1-dodecyl-2,3-dimethylimidazolium bis(2,4,4-trimethylpentyl)phosphinate; potassium carbonate; palladium dichloride In n-heptane; water at 80℃; for 1h; Catalytic behavior; Suzuki Coupling;	100%
With Br(1-)*C28H29BrN5O2Pd(1+); potassium carbonate In water at 100℃; for 3h; Suzuki-Miyaura coupling;	99%

para-bromoacetophenone (99-90-1) + 4-acetylphenylboronic acid (149104-90-5) → 4,4'-diacetylbiphenyl (787-69-9)

Conditions	Yield
With potassium carbonate; N,N-diethylaminopropyl-Al2O3-Pd(OAc)2 In ethanol; water for 0.0833333h; Suzuki-Miyaura reaction;	100%
With potassium carbonate; Pd(NH3)2Cl2 In water at 100℃; for 3h; Suzuki cross-coupling reaction;	99%
With iron(III) chloride; potassium fluoride In ethanol at 90℃; for 16h; Suzuki-Miyaura type coupling; sealed tube; air;	99%

para-bromoacetophenone (99-90-1) + oxalic acid diethyl ester (95-92-1) → ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate (40155-54-2)

Conditions	Yield
Stage #1: para-bromoacetophenone With sodium In ethanol at 0 - 10℃; for 1h; Stage #2: oxalic acid diethyl ester In ethanol for 1.5h;	100%
With sodium ethanolate In ethanol at 20℃; for 12h;	85%
Stage #1: oxalic acid diethyl ester With sodium ethanolate In benzene at 0℃; Inert atmosphere; Stage #2: para-bromoacetophenone In benzene at 0 - 20℃; for 14.5h; Inert atmosphere;	75%

1H-imidazole (288-32-4) + para-bromoacetophenone (99-90-1) → 4'-(imidazol-1-yl)acetophenone (10041-06-2)

Conditions	Yield
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride at 140 - 145℃; for 24h;	100%
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 24.5h;	99%
With potassium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 110℃; for 24h; Ullmann coupling reaction;	98%

1,2-bis(tert-butyldimethylsilyl)hydrazine (10000-20-1) + para-bromoacetophenone (99-90-1) → 4'-bromoacetophenone N-tert-butyldimethylsilylhydrazone (690275-01-5)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) at 0 - 23℃;	100%

dimethyl zinc(II) (544-97-8) + para-bromoacetophenone (99-90-1) → para-methylacetophenone (122-00-9)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 1h; Heating;	100%

Upstream product

• 5391-88-8 1-(4-bromophenyl)ethanol 
• 108-86-1 bromobenzene 
• 75-36-5 acetyl chloride 
• 4360-68-3 2-(4-bromophenyl)-2-methyl-1,3-dioxolane 
• 125763-64-6 2-(4-Bromo-phenyl)-2,4,5-trimethyl-[1,3]dioxolane 
• 201230-82-2 carbon monoxide 
• 594-27-4 tetramethylstannane 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 81815-13-6 3-methyl-3-(p-bromophenyl)-1,2-dioxetane 
• 99-73-0 para-bromophenacyl bromide 
• 56587-87-2 1,2-bis-[1-(4-bromophenyl)ethylidene]hydrazine 
• 41024-55-9 1-(4-bromophenyl)-2-(phenylsulfonyl)ethanone 
• 6888-79-5 4-bromo-α-methylstyrene 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 36715-58-9 (E)-1-(4-bromophenyl)-3-(furan-2-yl)-2-propen-1-one 
• 342017-91-8 2-(4-bromo-phenyl)-6-iodo-quinoline-4-carboxylic acid 
• 881850-14-2 3-(p-bromophenyl)-but-2-enal 
• 118559-25-4 1-[4-(4-Methyl-oxazol-2-yl)-phenyl]-ethanone 
• 132932-61-7 2-(p-acetylphenyl)benzofuran 
• 80827-31-2 1,3-Bis(p-bromophenyl)pyrido<1,2-a>benzinidazole 
• 116227-92-0 (Z)-1-(4-Bromo-phenyl)-3-(2-phenyl-thiazol-4-yl)-propenone 
• 54835-25-5 3-diethylaminopropionyl-4-bromobenzene 
• 78065-00-6 N-(p-bromo-α-methylbenzyl)pyrrolidine 
• 88875-43-8 [1-(4-Bromo-phenyl)-1-pyrrolidin-1-yl-meth-(Z)-ylidene]-phosphoramidic acid diphenyl ester 
• 66702-80-5 2-Oxo-2-<4-brom-phenyl>-ethylnitrat 
• 6940-50-7 4-bromo-DL-mandelic acid 
• 26245-53-4 1-(4-bromo-phenyl)-3-[4-(2,3,4-trihydroxy-phenyl)-thiazol-2-ylamino]-propan-1-one 
• 70619-19-1 4‐(N‐adamantan‐1‐yl)‐1‐[1‐(4‐bromophenyl)ethylidene]thiosemicarbazone 

Relevant articles and documents

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Visible light-mediated, high-efficiency oxidation of benzyl to acetophenone catalyzed by fluorescein

An environmentally friendly aerobic oxidation of benzyl C(sp3)-H bonds to ketones via selective oxidation catalysis was developed. Fluorescein is an efficient photocatalyst with excellent chemical selectivity. The reaction has a wide substrate scope, and a successful gram-scale experiment demonstrated its potential industrial utility.

One-Dimensional Organic Conjugated Polymers as Recyclable Heterogeneous Photocatalysts

Organic conjugated polymers with long-range conjugation generally have strong light absorption capacity in the visible light region and impressive performance in charge transfer, which endows them great application potential in the field of opto-electronic materials. However, there are few reports on their use in photocatalytic reactions. At present, it has been reported that a variety of donor-acceptor (D?A) type organic dyes can be used in efficient organic photocatalytic transformations. We designed and synthesized one-dimensional organic conjugated polymers pPhCzBP-Th and pPhCzBP-DTh with D?A structure, and proved that they are good heterogeneous photo-redox catalysts, which can photocatalyze hydrodehalogenation reduction of α-bromoacetophenone and its derivatives. Due to the strong reducibility of the excited state, pPhCzBP-Th can also efficiently reduce α-chloroacetophenone. Furthermore, by simply wrapping the catalyst powder, high-efficient separation of products and catalysts recycling can be achieved.