5195-29-9

Basic information

• Product Name: (4-BROMO-PHENYL)-OXO-ACETALDEHYDE
• Synonyms: (4-BROMO-PHENYL)-OXO-ACETALDEHYDE;Benzeneacetaldehyde, 4-broMo-.alpha.-oxo-;2-(4-broMophenyl)-2-oxoacetaldehyde;Benzeneacetaldehyde, 4-broMo-a-oxo-
• CAS NO: 5195-29-9
• Molecular Formula: C₈H₅BrO₂
• Molecular Weight: 213.03
• Mol File: 5195-29-9.mol
• Article Data: 71

Chemical Properties

• Boiling Point: 271.2°Cat760mmHg
• Flash Point: 105.9°C
• Appearance: /
• Density: 1.584g/cm³
• Vapor Pressure: 0.00653mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (4-BROMO-PHENYL)-OXO-ACETALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-BROMO-PHENYL)-OXO-ACETALDEHYDE(5195-29-9)
• EPA Substance Registry System: (4-BROMO-PHENYL)-OXO-ACETALDEHYDE(5195-29-9)

Safety Data

• Hazardous Substances Data: 5195-29-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 6562, 1957 DOI: 10.1021/ja01581a057

InChI:InChI=1/C8H5BrO2/c9-7-3-1-6(2-4-7)8(11)5-10/h1-5H

Synthetic route

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-bromophenacyl bromide (99-73-0) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
In water; dimethyl sulfoxide at 20℃;	91%
With dimethyl sulfoxide
With dimethyl sulfoxide In water at 20℃; for 24h; Oxidation;
Multi-step reaction with 2 steps 1: n-Bu4N(+)NO3(-) / diethyl ether / 7 h / Ambient temperature 2: Et3N / diethyl ether View Scheme
Multi-step reaction with 2 steps 1: diethyl ether; ethanol 2: bromine; acetic acid View Scheme

1-(4-bromo-phenyl)-2,2-dichloro-ethanone (7716-86-1) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With water; sodium carbonate Heating;	75%

1-(4-bromophenyl)-2-chloroethan-1-one (4209-02-3) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With 2-Pyridone at 20℃;	55%

1-[2-(4-bromophenyl)-2-oxoethyl]quinolinium bromide (75613-95-5) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With bromine; acetic acid

2-Oxo-2-<4-brom-phenyl>-ethylnitrat (66702-80-5) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With triethylamine In diethyl ether Yield given;

3-(4-bromophenyl)-1-(4-nitrophenylmethyl)-2-propoxy-1,2-dihydroquinoxaline (91736-69-5) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 0.5h;

<4-dimethylamino-phenyl>-<4-bromo-phenacyliden>-amine oxide → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With sulfuric acid

bromobenzene (108-86-1) + potassium ferro cyanide → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / AlCl3 / 0 - 5 °C 2: 75 percent / Na2CO3, H2O / Heating View Scheme

1-bromo-4-ethenyl-benzene (2039-82-9) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere;
With iodine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 80℃; for 3.5h;

4-bromo-2-hydroxyacetophenone (3343-45-1) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 80℃; for 2h;

1-(4-bromo-phenyl)-2-iodo-ethanone (81585-72-0) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With iodine; potassium hydroxide In water; dimethyl sulfoxide at 100℃; Kornblum Aldehyd Synthesis;

1-(4-bromophenyl)-1,2-propanedione (10557-20-7) → 4-bromophenylglyoxal (5195-29-9)

Conditions	Yield
With selenium(IV) oxide

4-bromophenylglyoxal (5195-29-9) → 1-(4-bromophenyl)ethane-1,2-diol (92093-23-7)

Conditions	Yield
With sodium tetrahydroborate In ethanol for 1h;	100%

4-bromophenylglyoxal (5195-29-9) + 2-(2-chlorophenyl)but-1-en-1-one (1070793-26-8) → C18H14BrClO3 (1070793-48-4)

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃;	99%

methanol (67-56-1) + 4-bromophenylglyoxal (5195-29-9) → 4-methoxycarbonylphenyl bromide (619-42-1)

Conditions	Yield
With oxone at 65℃; for 30h;	98%

4-bromophenylglyoxal (5195-29-9) + ethanol (64-17-5) → Ethyl 4-bromobenzoate (5798-75-4)

Conditions	Yield
With oxone at 65℃; for 30h;	98%

4-bromophenylglyoxal (5195-29-9) + (Z)-1-(4-chlorophenyl)-2-hydroxyamino-1-hydroxyiminopropane (948908-05-2) → 6-(4-bromobenzoyl)-3-(4-chlorophenyl)-5-hydroxy-4-methyl-5,6-dihydro-4H-1,2,5-oxadiazine (1068654-59-0)

Conditions	Yield
With trifluoroacetic acid In methanol for 48h;	97%

4-bromophenylglyoxal (5195-29-9) + methyl phosphite (96-36-6, 868-85-9) → dimethyl (2-(4-bromophenyl)-1-hydroxy-2-oxoethyl)phosphonate

Conditions	Yield
In neat (no solvent) at 80℃; for 0.333333h;	97%

4-bromophenylglyoxal (5195-29-9) + thiourea (17356-08-0) + 1,3-dimethylthiobarbituric acid (3158-63-2) → 5-(4-bromobenzoyl)-1,3-dimethyl-2,7-dithioxo-2,3,5,6,7,8-hexahydropyrimido[4,5-d]pyrimidin-4(1H)-one

Conditions	Yield
With zirconyl chloride octahydrate In water at 50℃; for 2h; Reagent/catalyst; Biginelli Pyrimidone Synthesis; Green chemistry; regioselective reaction;	97%

4-bromophenylglyoxal (5195-29-9) + 2,4-imidazolidinedione (461-72-3) → (Z)-5-(2-(4-bromophenyl)-2-oxoethylidene)imidazolidine-2,4-dione

Conditions	Yield
With copper(II)-Para-aminobenzoic acid complex supported on Fe3O4 Magnetic nanoparticle In ethanol for 1.48333h; Aldol Condensation; Reflux; Green chemistry;	97%

4-bromophenylglyoxal (5195-29-9) + 2-Methoxypropene (116-11-0) → 1-(4-bromophenyl)-2-hydroxy-4-methoxypent-4-en-1-one

Conditions	Yield
With C43H64N4O4; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 30℃; Molecular sieve; optical yield given as %ee; enantioselective reaction;	96%

4-bromophenylglyoxal (5195-29-9) + 1,3-dimethylbarbituric acid (769-42-6) + thiourea (17356-08-0) → 5-(4-bromobenzoyl)-1,3-dimethyl-7-thioxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

Conditions	Yield
With zirconyl chloride octahydrate In water at 50℃; for 2h; Biginelli Pyrimidone Synthesis; Green chemistry; regioselective reaction;	96%

4-bromophenylglyoxal (5195-29-9) + 2-(2-amino-5-bromophenyl)acetonitrile (882855-95-0) → (5-bromo-1H-indol-2-yl)(4-bromophenyl)methanone (89671-79-4)

Conditions	Yield
With 1-(diphenylphosphino)ferrocene-1-(di-tert-butylphosphino)ferrocene; 1-cyanopropyl-3-methylimidazolium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; tin(IV) iodide; cerium triflate In ethylene glycol at 85℃; for 11h; Reagent/catalyst;	95.5%

4-bromophenylglyoxal (5195-29-9) + isopropenylbenzene (98-83-9) → 1-(4-bromophenyl)-2-hydroxy-4-phenylpent-4-en-1-one

Conditions	Yield
With C39H60N4O4; nickel(II) tetrafluoroborate hexahydrate In 1,2-dichloro-ethane at 60℃; for 24h; optical yield given as %ee;	95%

4-bromophenylglyoxal (5195-29-9) + isopropenylbenzene (98-83-9) → (S)-2-hydroxy-1-(4-bromophenyl)-4-phenyl-4-penten-1-one

Conditions	Yield
With C39H60N4O4; nickel(II) tetrafluoroborate hexahydrate In dichloromethane at 35℃; for 48h; enantioselective reaction;	95%

4-bromophenylglyoxal (5195-29-9) + dimedone (126-81-8) + urea (57-13-6) → 4-(4-bromophenyl)-5-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-1H-imidazol-2-one (1175008-67-9)

Conditions	Yield
at 20℃; for 0.0833333h; Solvent; Temperature; Time; Biginelli Pyrimidone Synthesis; Ionic liquid;	95%

4-bromophenylglyoxal (5195-29-9) + ethylenediamine (107-15-3) → 2-(4-bromophenyl)pyrazine (143526-49-2)

Conditions	Yield
Stage #1: 4-bromophenylglyoxal; ethylenediamine In methanol; water at 20℃; for 1h; Stage #2: With potassium tert-butylate In methanol; water for 24h;	95%

4-bromophenylglyoxal (5195-29-9) + 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid (70458-96-7) → 7-(4-(2-(4-bromophenyl)-2-oxoethanethioyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
With sulfur; sodium sulfide In N,N-dimethyl-formamide at 110℃; for 7h; Willgerodt-Kindler Rearrangement;	95%

4-bromophenylglyoxal (5195-29-9) + 2,4-thiazolidinedion (2295-31-0) → (Z)-5-(2-(4-bromophenyl)-2-oxoethylidene)thiazolidine-2,4-dione

Conditions	Yield
With copper(II)-Para-aminobenzoic acid complex supported on Fe3O4 Magnetic nanoparticle In ethanol for 1.51667h; Aldol Condensation; Reflux; Green chemistry;	95%
With urea/choline chloride eutectic salt In neat (no solvent) at 80℃; Aldol Condensation; Green chemistry;	94%

4-bromophenylglyoxal (5195-29-9) + 1,3-cylohexanedione (504-02-9) + urea (57-13-6) → 4-(4-bromophenyl)-5-(2-hydroxy-6-oxocyclohex-1-enyl)-1H-imidazol-2-one (1421471-35-3)

Conditions	Yield
at 20℃; for 0.2h; Biginelli Pyrimidone Synthesis; Ionic liquid;	94%

4-bromophenylglyoxal (5195-29-9) + 1,3-dimethylthiobarbituric acid (3158-63-2) → 3-(4-bromophenyl)-6,8-dimethyl-7-thioxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H)-one

Conditions	Yield
With hydrazine hydrate In ethanol at 20℃; for 0.466667h; Green chemistry;	94%
With hydrazine dihydrochloride In ethanol at 50℃; for 0.75h; regioselective reaction;	80%

4-bromophenylglyoxal (5195-29-9) + Thien-3-ylboronic acid (6165-69-1) → 1-(4-bromophenyl)-2-(thiophen-3-yl)ethane-1,2-dione

Conditions	Yield
With pyrrolidine In toluene at 20℃; for 4.5h;	94%

4-bromophenylglyoxal (5195-29-9) + Cyclohexyl isocyanide (931-53-3) + H-Gpn-OH (60142-96-3) → 3-(4-bromophenyl)-N-cyclohexyl-3-oxo-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)propanamide

Conditions	Yield
In ethanol at 50℃; Ugi Condensation;	94%

4-bromophenylglyoxal (5195-29-9) + cycl-isopropylidene malonate (2033-24-1) + 2-Chlorobenzonitrile (873-32-5) + p-toluidine (106-49-0) → 5-(5-(4-bromophenyl)-2-(2-chlorophenyl)-1-(p-tolyl)-1H-imidazol-4-yl)-6-hydroxy-2,2-dimethyl-4H-1,3-dioxin-4-one

Conditions	Yield
Stage #1: 2-Chlorobenzonitrile; p-toluidine at 120℃; for 1h; Stage #2: 4-bromophenylglyoxal; cycl-isopropylidene malonate In ethanol at 20℃; for 1.5h;	94%

4-bromophenylglyoxal (5195-29-9) + N-(4-chlorophenyl)benzamidine (7035-69-0) + malononitrile (109-77-3) → 2-(5-(4-bromophenyl)-1-(4-chlorophenyl)-2-phenyl-1H-imidazol-4-yl)-2-cyanoacetamide

Conditions	Yield
With triethylamine In acetonitrile for 2h; Reflux;	94%

4-bromophenylglyoxal (5195-29-9) → 4-bromobenzoyl cyanide (6048-21-1)

Conditions	Yield
With 1-amino-2-oxo-4,6-diphenylpyridine In toluene at 110℃; for 6h;	93%

4-bromophenylglyoxal (5195-29-9) + 2-phenyl-5-methylene-4,5-dihydrooxazole (146896-52-8) → 1-(4-bromophenyl)-2-hydroxy-3-(2-phenyloxazol-5-yl)propan-1-one (1616777-91-3)

Conditions	Yield
With C39H60N4O4*Ni(2+)*2BF4(1-)*6H2O In dichloromethane at 30℃; for 24h; enantioselective reaction;	93%

4-bromophenylglyoxal (5195-29-9) + benzyl alcohol (100-51-6) → benzyl 2-(4-bromophenyl)-2-oxoacetate (887641-65-8)

Conditions	Yield
With iodine; potassium carbonate In toluene at 20℃; for 2.5h; Green chemistry;	93%

4-bromophenylglyoxal (5195-29-9) + 2-thioxo-4-thiazolidinone (141-84-4) → (Z)-5-(2-(4-bromophenyl)-2-oxoethylidene)-2-thioxothiazolidin-4-one

Conditions	Yield
With urea/choline chloride eutectic salt In neat (no solvent) at 80℃; Aldol Condensation; Green chemistry;	93%

4-bromophenylglyoxal (5195-29-9) + isobutyraldehyde (78-84-2) → (S)-4-(4-bromophenyl)-3-hydroxy-2,2-dimethyl-4-oxobutanal

Conditions	Yield
Stage #1: isobutyraldehyde With NH2-Tle-(D-Pro)-Gly-Leu-OH; sodium sulfate In acetonitrile at 0℃; for 0.166667h; Aldol Addition; Green chemistry; Stage #2: 4-bromophenylglyoxal In acetonitrile at 0 - 20℃; for 24h; Aldol Addition; Green chemistry; enantioselective reaction;	93%

4-bromophenylglyoxal (5195-29-9) + phenyl carbamate (64-10-8) → 5-(4-bromophenyl)-1-phenylhydantoin (37932-71-1)

Conditions	Yield
With polyphosphoric ester for 0.05h; microwave irradiation;	92%
With hydrogenchloride; acetic acid for 4h; Heating;	60%

Upstream product

• 99-90-1 para-bromoacetophenone 
• 10557-20-7 1-(4-bromophenyl)-1,2-propanedione 
• 81585-72-0 1-(4-bromo-phenyl)-2-iodo-ethanone 
• 3343-45-1 4-bromo-2-hydroxyacetophenone 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 108-86-1 bromobenzene 
• 91736-69-5 3-(4-bromophenyl)-1-(4-nitrophenylmethyl)-2-propoxy-1,2-dihydroquinoxaline 
• 4209-02-3 1-(4-bromophenyl)-2-chloroethan-1-one 
• 66702-80-5 2-Oxo-2-<4-brom-phenyl>-ethylnitrat 
• 7716-86-1 1-(4-bromo-phenyl)-2,2-dichloro-ethanone 
• 99-73-0 para-bromophenacyl bromide 
• 75613-95-5 1-[2-(4-bromophenyl)-2-oxoethyl]quinolinium bromide 

Downstream Products

• 586-76-5 4-Bromobenzoic acid 
• 1172616-53-3 dimethyl 5-(4-bromophenyl)-1-(4-methylphenyl)-pyrrole-2,3-dicarboxylate 
• 1172616-54-4 diethyl 5-(4-bromophenyl)-1-(4-methylphenyl)-pyrrole-2,3-dicarboxylate 
• 1172616-57-7 dimethyl 5-(4-bromophenyl)-1-(4-chlorophenyl)-pyrrole-2,3-dicarboxylate 
• 1172616-56-6 diethyl 5-(4-bromophenyl)-1-(4-methoxyphenyl)-pyrrole-2,3-dicarboxylate 
• 1384521-94-1 diethyl 4-(4-bromobenzoyl)isoxazole-3,5-dicarboxylate 
• 1394973-48-8 (4-bromophenyl)(5-chlorobenzo[d]thiazol-2-yl)methanone 
• 30565-47-0 isopropyl-2-(4-bromophenyl)-2-oxoacetate 
• 887641-65-8 benzyl 2-(4-bromophenyl)-2-oxoacetate 
• 14547-83-2 4-bromo-N-(pyridin-2-yl)benzamide 

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