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611-73-4

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611-73-4 Usage

Chemical Properties

white to light yellow adhering crystals,

Uses

Different sources of media describe the Uses of 611-73-4 differently. You can refer to the following data:
1. Phenylglyoxylic Acid (cas# 611-73-4) is a compound useful in organic synthesis.
2. Phenylglyoxylic acid can be used as a precursor in the synthesis of: O-acyl acetanilides by decarboxylative o-acylation of acetanilides using Pd catalyst.Phenylhydroxycarbene by high-vacuum flash pyrolysis.2-arylbenzothiazoles by reacting with o-aminothiophenol using ammonium niobium oxalate (ANO) as a catalyst.3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones by treating with o-aminophenol in the presence of ammonium niobium oxalate catalyst.2-aryl benzothiazoles through potassium persulfate (K2S2O8)-mediated oxidative condensation of benzothiazoles.

Definition

ChEBI: A 2-oxo monocarboxylic acid that is glyoxylic acid in which the aldehyde hydrogen is substituted by a phenyl group.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 26, p. 1631, 1983 DOI: 10.1021/jm00365a015Organic Syntheses, Coll. Vol. 1, p. 241, 1941Tetrahedron Letters, 17, p. 3735, 1976 DOI: 10.1016/S0040-4039(00)93096-X

Synthesis

The synthesis of Benzoylformic acid is as follows:Acetophenone (120 g, 1 mol) was dissolved in 2000 ml of pyridine, and 165 g (1.5 mol) of selenium dioxide was added under stirring.The mixture was refluxed for 3 hours and left to cool overnight.Filter through celite, wash the filter cake with xylene, and combine the filtrate and washings with azeotropic evaporation.The evaporated residue was dissolved in 1 L of ethyl acetate and washed with 300 ml of 10% dilute hydrochloric acid.The organic layer was washed with 400 ml of 5% sodium hydroxide solution, and the washed aqueous layer was adjusted to pH 2-3 with 10% dilute hydrochloric acid.A white solid precipitates, is filtered, the filter cake is washed with water, and dried to obtain 120 g of a white solid.Yield: 87%, purity: 99.2%.

Purification Methods

If the sample is oily, then it may contain H2O. In this case dry it in a vacuum desiccator over P2O5 or KOH until crisp. For further purification dissolve 5.5g in hot CCl4 (750mL), add charcoal (2g, this is necessary otherwise the acid may separate as an oil), filter, cool in ice-water until crystallisation is complete. Filter the acid off, and the solvent on the crystals is removed by keeping the acid (4.5g) in a vacuum desiccator for 2 days. Slightly yellow crystals are obtained. It can be recrystallised also from *C6H6/pet ether, and can be distilled in a vacuum. The acid is estimated by titration with standard NaOH. The phenylhydrazone is recrystallised from EtOH, m 163-164o, and the semicarbazone acid has m 259o(dec) (from EtOH). The methyl ester distils at 137o/14mm, 110-111o/2mm, n 20 1.5850. [Baert & Kates J Am Chem Soc 67 1482 1945, Schaffer & Corey J Org Chem 24 1825 1959, Beilstein 10 H 654, 10 IV 2737.]

Check Digit Verification of cas no

The CAS Registry Mumber 611-73-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 1 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 611-73:
(5*6)+(4*1)+(3*1)+(2*7)+(1*3)=54
54 % 10 = 4
So 611-73-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)

611-73-4 Well-known Company Product Price

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  • Alfa Aesar

  • (L00648)  Phenylglyoxylic acid, 98%   

  • 611-73-4

  • 5g

  • 383.0CNY

  • Detail
  • Alfa Aesar

  • (L00648)  Phenylglyoxylic acid, 98%   

  • 611-73-4

  • 25g

  • 1245.0CNY

  • Detail

611-73-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name phenylglyoxylic acid

1.2 Other means of identification

Product number -
Other names Benzeneacetic acid, α-oxo-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:611-73-4 SDS

611-73-4Synthetic route

methyl 2-oxo-2-phenylacetate
15206-55-0

methyl 2-oxo-2-phenylacetate

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With water; sodium hydroxide100%
With water; sodium hydroxide In dichloromethane100%
With water; sodium hydroxide at 20℃; for 2h;99.2%
tert-butyl phenylglyoxylate
7332-98-1

tert-butyl phenylglyoxylate

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;100%
With trifluoroacetic acid at 0℃; for 1h;57%
With trifluoroacetic acid at 0℃; for 5h;
benzalacetophenone
94-41-7

benzalacetophenone

A

Benzoylformic acid
611-73-4

Benzoylformic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 - 912.061 Torr; for 48h; chemoselective reaction;A 91%
B 99%
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate; ruthenium trichloride; potassium peroxymonosulfate / acetonitrile; water; ethyl acetate / 0.3 h
2: iron(II) perchlorate hexahydrate; tetramethylammonium hydroxide pentahydrate / acetonitrile; water / 12 h / Inert atmosphere
View Scheme
Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With sodium bromate In acetonitrile for 52h; Heating;98%
With oxalyl dichloride; methyl dodecyl sulfoxide; triethylamine In dichloromethane at -60 - 20℃; Swern oxidation;96%
With oxalyl dichloride; methyl dodecyl sulfoxide; triethylamine In dichloromethane at -60 - 20℃; Swern oxidation;96%
5-hydroxy-N,N',5-triphenylimidazolidine-2,4-dione
1352131-39-5

5-hydroxy-N,N',5-triphenylimidazolidine-2,4-dione

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 20 - 50℃; for 1h;98%
2-(hydroxyimino)-2-phenylacetonitrile
825-52-5

2-(hydroxyimino)-2-phenylacetonitrile

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With sulfuric acid at 100 - 120℃; for 5h;96.6%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iron(III) chloride; thymidyl acetic acid In decane; acetonitrile at 80℃; for 6h;96%
With Oxone; 2-Iodobenzoic acid In water; acetonitrile at 70℃; for 6h;94%
With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide In methanol at 20℃; for 15h; In air;91%
With potassium permanganate; acetic acid; Tris(3,6-dioxaheptyl)amine In dichloromethane for 4h; Ambient temperature;71%
aqua(2,2'-bipyridine)(2,2':6',2''-terpyridine)ruthenium(II)(2+) In phosphate buffer for 6h; pH=7.2; Electrolysis;47%
2-Bromo-1-phenylethanol
2425-28-7

2-Bromo-1-phenylethanol

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With tetramethoxytitanium; β-Propiolactone at 60℃; for 2h; Temperature;96%
Multi-step reaction with 5 steps
1.1: hydrogen bromide; dihydrogen peroxide / water / 4.5 h / 25 - 90 °C
2.1: toluene-4-sulfonic acid; benzene / water / 36 h / 85 °C
3.1: tetrabutylammomium bromide; sodium ethanolate / water / 23 h / 105 °C
4.1: oxalic acid / dichloromethane; water / 5 h / 25 °C
5.1: tetrabutylammomium bromide; hydrogen bromide / water / 0.02 h
5.2: 5 h / 25 - 90 °C
View Scheme
2-hydroxy-4-methyl-2-phenylmorpholin-3-one

2-hydroxy-4-methyl-2-phenylmorpholin-3-one

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;94%
(R)-Mandelic Acid
611-71-2

(R)-Mandelic Acid

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With phosphotungstic acid; ferric nitrate at 55 - 60℃; for 0.166667h;93%
With D-lactate oxidase from Gluconobacter oxydans 621H; oxygen; catalase In aq. buffer at 30℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;
With NAD at 30℃; for 48h; pH=9.5; Kinetics; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction;
Na2S2O3·5H2O

Na2S2O3·5H2O

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hypobromide; sodium thiosulfate In dichloromethane; water91%
1-phenyl-2-hydroxyethanone
582-24-1

1-phenyl-2-hydroxyethanone

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide In water at 25 - 65℃; for 5h; Reagent/catalyst; Time;90.1%
With hydrogen bromide; dihydrogen peroxide In water Temperature; Reflux;79.3%
Stage #1: 1-phenyl-2-hydroxyethanone With tetrabutylammomium bromide; hydrogen bromide In water for 0.0166667h;
Stage #2: With dihydrogen peroxide In water at 25 - 90℃; for 5h;
83 %Chromat.
With hydrogen bromide; dihydrogen peroxide In water at 90℃; for 7h;
3,4-diphenyl-4-hydroxy-2-isoxazolin-5-one
80490-41-1

3,4-diphenyl-4-hydroxy-2-isoxazolin-5-one

A

benzonitrile
100-47-0

benzonitrile

B

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With triethylamine In benzene for 3h; Heating;A n/a
B 89.3%
With hydrogenchloride; sodium hydroxide; water Mechanism;
epoxide of α,β-difluoro-β-chlorostyrene
134918-42-6

epoxide of α,β-difluoro-β-chlorostyrene

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate for 0.5h;89%
acetophenone
98-86-2

acetophenone

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With pyridine; selenium(IV) oxide at 120℃; for 18h; Inert atmosphere;87%
With pyridine; selenium(IV) oxide for 3h; Reflux;87%
With pyridine; selenium(IV) oxide at 90℃; for 5h; Inert atmosphere;87%
phenylglycin
2835-06-5

phenylglycin

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With potassiuim nitrosodisulfonate In water for 60h; pH 10.0;82%
With ω-transaminase
2,2,2-Tris-benzotriazol-1-yl-1-phenyl-ethanone
130749-19-8

2,2,2-Tris-benzotriazol-1-yl-1-phenyl-ethanone

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 50℃; for 48h;81%
3,5-diphenyl-4,4-dichloro-5-hydroxy-Δ2-isoxazoline
79344-05-1

3,5-diphenyl-4,4-dichloro-5-hydroxy-Δ2-isoxazoline

A

benzonitrile
100-47-0

benzonitrile

B

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With potassium hydroxide In water for 2.5h; Heating;A 75.4%
B 80%
phenylglyoxal hydrate
1074-12-0

phenylglyoxal hydrate

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
Stage #1: phenylglyoxal hydrate With silver perchlorate; sodium hydroxide In water at 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water Inert atmosphere;
78%
bei der Einw. von gaerender Hefe;
Multi-step reaction with 2 steps
1: 26.5 percent Spectr. / Et3N, pyridine, O2, 3-Angstroem sieves / Cu(NO3)2py2 / methanol / 12 h / 25 °C / 1748 Torr
2: 68.6 percent Spectr. / Et3N, pyridine, O2, H2O / Cu(NO3)2py2 / methanol / 12 h / 25 °C / 1748 Torr
View Scheme
carbon dioxide
124-38-9

carbon dioxide

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With chloro-trimethyl-silane; magnesium In N,N-dimethyl-formamide at 20℃; Temperature; Solvent;75%
oxo-phenyl-acetaldehyde oxime
532-54-7

oxo-phenyl-acetaldehyde oxime

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With hydrogenchloride; water; sodium nitrite at 80℃; for 4h;73.5%
With acetic anhydride bei der Destillation u. Verseifen mit Salzsaeure;
carbon dioxide
124-38-9

carbon dioxide

benzaldehyde
100-52-7

benzaldehyde

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; benzaldehyde With potassium cyanide In N,N-dimethyl-formamide at 12℃; for 1h; Schlenk technique;
Stage #2: With titanium(IV)isopropoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 40℃; for 18h; Schlenk technique;
72%
diphenacyl sulfide
2461-80-5

diphenacyl sulfide

A

C16H10O4S
1522397-30-3

C16H10O4S

B

(3-phenylthiophene-2,5-diyl)bis(phenylmethanone)
595565-17-6

(3-phenylthiophene-2,5-diyl)bis(phenylmethanone)

C

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane for 2h; Reflux;A n/a
B 10%
C 71%
4-hydroxy-3-methyl-4-phenylisoxazoline-5-one
80490-51-3

4-hydroxy-3-methyl-4-phenylisoxazoline-5-one

A

Benzoylformic acid
611-73-4

Benzoylformic acid

B

acetonitrile
75-05-8

acetonitrile

Conditions
ConditionsYield
With 2,6-dichloro-benzonitrile In benzene for 0.5h; Heating;A 70%
B n/a
benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

carbon dioxide
124-38-9

carbon dioxide

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With chloro-trimethyl-silane; magnesium In N,N-dimethyl-formamide at 20℃;69%
2-nitroacetophenone
614-21-1

2-nitroacetophenone

A

Benzoylformic acid
611-73-4

Benzoylformic acid

B

benzoic acid
65-85-0

benzoic acid

C

3,4-dibenzoyl-1,2,5-oxadiazole-N-oxide
6635-54-7

3,4-dibenzoyl-1,2,5-oxadiazole-N-oxide

Conditions
ConditionsYield
With nitric acid; sodium nitrite In nitromethane; water at 60℃; for 0.5h;A 9.7%
B 4.4%
C 68.4%
With nitric acid; sodium nitrite In nitromethane; water at 60℃; for 0.5h; Product distribution; Mechanism; variation of solvents, reactants;A 9.7%
B 4.4%
C 68.4%
iodobenzene
591-50-4

iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

B

Benzoylformic acid
611-73-4

Benzoylformic acid

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With methyl iodide; sodium tetrahydroborate In 1,4-dioxane; water at 20℃; for 20h;A 3%
B 68%
C 5%
With methyl iodide; sodium tetrahydroborate In 1,4-dioxane; water at 20℃; for 20h;A 3%
B 64%
C 13%
With calcium hydroxide; water; dichlorobis(dimethylphenylphosphine)palladium(II) In isopropyl alcohol at 100℃; for 12h; P(CO) = 150 atm at room temperature; further catalysts, solvents and hydroxide;A 69.0 % Chromat.
B 3.8 % Chromat.
C 9.3 % Chromat.
With calcium hydroxide; water; bis(benzonitrile)palladium(II) dichloride In isopropyl alcohol at 100℃; for 12h; P(CO) = 150 atm at room temperature; further catalysts, solvents and hydroxide;A 46.0 % Chromat.
B 8.7 % Chromat.
C 25.5 % Chromat.
With sodium sulfide; CoCl2 In 1,4-dioxane; water at 20℃; for 20h; Product distribution; other reag.; other solvent;A 3 % Chromat.
B 62 % Chromat.
C 5 % Chromat.
phenylacetylene
536-74-3

phenylacetylene

A

phenylacetic acid
103-82-2

phenylacetic acid

B

Benzoylformic acid
611-73-4

Benzoylformic acid

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane for 48h;A 21%
B 68%
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetone for 48h;A 65%
B 11%
2-methylsulfonyl-1-phenylethanone
3708-04-1

2-methylsulfonyl-1-phenylethanone

A

Benzoylformic acid
611-73-4

Benzoylformic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; oxygen In acetonitrile at 60℃;A 26%
B 65%

A

Benzoylformic acid
611-73-4

Benzoylformic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile at 20℃; for 3h;A 63%
B 30%
Benzoylformic acid
611-73-4

Benzoylformic acid

phenylglyoxylyl chloride
25726-04-9

phenylglyoxylyl chloride

Conditions
ConditionsYield
With Dichloromethyl methyl ether at 50℃; for 0.5h;100%
With Dichloromethyl methyl ether In dichloromethane at 15 - 20℃; for 1h; Inert atmosphere;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane95%
pyrrolidine
123-75-1

pyrrolidine

Benzoylformic acid
611-73-4

Benzoylformic acid

1-thiobenzoylpyrrolidine
15563-45-8

1-thiobenzoylpyrrolidine

Conditions
ConditionsYield
With sulfur In benzene at 80℃; for 0.166667h;100%
With sulfur In benzene for 0.166667h; Heating;100%
piperidine
110-89-4

piperidine

Benzoylformic acid
611-73-4

Benzoylformic acid

N-thiobenzoylpiperidine
15563-40-3

N-thiobenzoylpiperidine

Conditions
ConditionsYield
With sulfur In benzene at 80℃; for 0.75h;100%
With sulfur In benzene at 80℃; for 1h;
morpholine
110-91-8

morpholine

Benzoylformic acid
611-73-4

Benzoylformic acid

Thiobenzmorpholid
2032-36-2

Thiobenzmorpholid

Conditions
ConditionsYield
With sulfur In benzene at 80℃; for 0.75h;100%
1,4-pyrazine
290-37-9

1,4-pyrazine

Benzoylformic acid
611-73-4

Benzoylformic acid

phenyl(pyrazin-2-yl)methanone
3430-09-9

phenyl(pyrazin-2-yl)methanone

Conditions
ConditionsYield
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h;100%
Stage #1: 1,4-pyrazine; Benzoylformic acid With ammonium peroxydisulfate; sulfuric acid; silver nitrate In dichloromethane; water at 50℃; for 2h;
Stage #2: With water; sodium hydrogencarbonate In dichloromethane
91%
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide In dichloromethane; water at 40℃; Minisci Aromatic Substitution;74%
With ammonium peroxydisulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water at 60℃; for 3h;68%
With dipotassium peroxodisulfate; silver orthophosphate In dichloromethane; water at 40℃; for 24h;26%
methyl (4-pyridyl) ketone
1122-54-9

methyl (4-pyridyl) ketone

Benzoylformic acid
611-73-4

Benzoylformic acid

1-(2-benzoylpyridin-4-yl)-ethanone
132883-96-6

1-(2-benzoylpyridin-4-yl)-ethanone

Conditions
ConditionsYield
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h;100%
33%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Benzoylformic acid
611-73-4

Benzoylformic acid

2-benzoylisonicotinonitrile

2-benzoylisonicotinonitrile

Conditions
ConditionsYield
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h;100%
2,3-diethynylquinoxaline
91-19-0

2,3-diethynylquinoxaline

Benzoylformic acid
611-73-4

Benzoylformic acid

phenyl(quinoxalin-2-yl)methanone
13481-33-9

phenyl(quinoxalin-2-yl)methanone

Conditions
ConditionsYield
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h;100%
With dipotassium peroxodisulfate In water; acetonitrile at 20 - 37℃; for 15h; Irradiation; Green chemistry; regioselective reaction;80%
With dipotassium peroxodisulfate; silver orthophosphate In dichloromethane; water at 40℃; for 24h;58%
2-furoic acid hydrazide
3326-71-4

2-furoic acid hydrazide

Benzoylformic acid
611-73-4

Benzoylformic acid

[(Furan-2-carbonyl)-hydrazono]-phenyl-acetic acid

[(Furan-2-carbonyl)-hydrazono]-phenyl-acetic acid

Conditions
ConditionsYield
100%
1,2,3,4-tetrahydroisoquinoline
91-21-4

1,2,3,4-tetrahydroisoquinoline

Benzoylformic acid
611-73-4

Benzoylformic acid

(3,4-dihydroisoquinoline-2(1H)-yl)(phenyl)methanethione
122709-96-0

(3,4-dihydroisoquinoline-2(1H)-yl)(phenyl)methanethione

Conditions
ConditionsYield
With sulfur In benzene at 80℃; for 0.25h;100%
With sulfur In benzene at 80℃; for 0.25h;
Benzoylformic acid
611-73-4

Benzoylformic acid

benzylamine
100-46-9

benzylamine

N-benzylidene benzylamine
780-25-6

N-benzylidene benzylamine

Conditions
ConditionsYield
In dichloromethane at 40℃; for 3h;100%
oxalyl dichloride
79-37-8

oxalyl dichloride

Benzoylformic acid
611-73-4

Benzoylformic acid

diallylamine
124-02-7

diallylamine

1-phenyl-2-(diallylamino)ethane-1,2-dione

1-phenyl-2-(diallylamino)ethane-1,2-dione

Conditions
ConditionsYield
Stage #1: oxalyl dichloride; Benzoylformic acid With copper diacetate; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
Stage #2: diallylamine With triethylamine In dichloromethane
100%
(1S,2R)-(1-methyl-2-phenyl-2-hydroxy)ethyltrimethylammonium iodide
64868-20-8

(1S,2R)-(1-methyl-2-phenyl-2-hydroxy)ethyltrimethylammonium iodide

Benzoylformic acid
611-73-4

Benzoylformic acid

[(1R,2S)-N,N-dimethylephedrinium][phenylglyoxylate]
1639366-24-7

[(1R,2S)-N,N-dimethylephedrinium][phenylglyoxylate]

Conditions
ConditionsYield
With Dowex Inert atmosphere;100%
1-acetoxy-1,2-benziodoxol-3-one
1829-26-1

1-acetoxy-1,2-benziodoxol-3-one

Benzoylformic acid
611-73-4

Benzoylformic acid

C15H9IO5

C15H9IO5

Conditions
ConditionsYield
In chloroform for 0.5h; Inert atmosphere; Reflux;100%
In chloroform for 0.5h; Inert atmosphere; Reflux;100%
2-oxo-imidazolidine-1-ethanol
3699-54-5

2-oxo-imidazolidine-1-ethanol

Benzoylformic acid
611-73-4

Benzoylformic acid

PhGA-HEI

PhGA-HEI

Conditions
ConditionsYield
In water; acetone100%
4-hydrazino-quinazoline

4-hydrazino-quinazoline

Benzoylformic acid
611-73-4

Benzoylformic acid

phenyl[(3H-quinazolin-4-ylidene)hydrazono]acetic acid

phenyl[(3H-quinazolin-4-ylidene)hydrazono]acetic acid

Conditions
ConditionsYield
In isopropyl alcohol for 1h; Heating;99.2%
Benzoylformic acid
611-73-4

Benzoylformic acid

phenylacetic acid
103-82-2

phenylacetic acid

Conditions
ConditionsYield
With chlorobenzene In methanol at 40℃; for 5h; Sealed tube; Green chemistry; chemoselective reaction;99%
With phosphonic Acid; methanesulfonic acid; sodium iodide In water at 95℃; for 48h; Inert atmosphere;94.3%
With hydrazine hydrate anschliessend Erhitzen mit KOH;
With phosphorus; hydrogen iodide at 160℃;
(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Benzoylformic acid
611-73-4

Benzoylformic acid

Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester
88002-15-7

Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;99%
With toluene-4-sulfonic acid In toluene at 130℃; for 2h; Dean-Stark;25%
With hydrogen cation
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

Benzoylformic acid
611-73-4

Benzoylformic acid

N-methoxy-N-methyl-α-oxo-benzeneacetamide
141694-25-9

N-methoxy-N-methyl-α-oxo-benzeneacetamide

Conditions
ConditionsYield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In acetonitrile at 20℃; for 1.5h;99%
Stage #1: Benzoylformic acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0℃; for 0.25h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 1h; chemoselective reaction;
75%
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane for 0.75h; Heating;53%
Benzoylformic acid
611-73-4

Benzoylformic acid

(1R,2R)-1,2-diphenyl-2-(4-trifluoromethylbenzyloxy)ethanol
415919-99-2

(1R,2R)-1,2-diphenyl-2-(4-trifluoromethylbenzyloxy)ethanol

(1R,2R)-1,2-diphenyl-2-(4-trifluoromethylbenzyloxy)ethyl phenylglyoxylate
415920-05-7

(1R,2R)-1,2-diphenyl-2-(4-trifluoromethylbenzyloxy)ethyl phenylglyoxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃;99%
(1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethanol
866457-05-8

(1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethanol

Benzoylformic acid
611-73-4

Benzoylformic acid

oxophenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester
866457-10-5

oxophenylacetic acid (1R,2S)-2-(1,1-dimethylethoxy)-1,2-diphenylethyl ester

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;99%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;
(1R,2S)-1-(2-methoxyethoxy)-1,2-bis-(2-methoxyphenyl)-ethanol
916525-75-2

(1R,2S)-1-(2-methoxyethoxy)-1,2-bis-(2-methoxyphenyl)-ethanol

Benzoylformic acid
611-73-4

Benzoylformic acid

oxophenylacetic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester
916525-80-9

oxophenylacetic acid (1R,2S)-2-(2-methoxyethoxy)-1,2-bis(2-methoxyphenyl)ethyl ester

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h;99%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h;
diallylcarbonate
15022-08-9

diallylcarbonate

Benzoylformic acid
611-73-4

Benzoylformic acid

(E)-1-phenyl-2-buten-1-one
35660-91-4, 35845-66-0, 495-41-0

(E)-1-phenyl-2-buten-1-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); Tri(p-tolyl)phosphine In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;99%
Benzoylformic acid
611-73-4

Benzoylformic acid

2-thiocresol
137-06-4

2-thiocresol

S-(o-tolyl) benzothioate

S-(o-tolyl) benzothioate

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water; acetonitrile at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;99%
With ammonium peroxydisulfate; copper(II) oxide In water; dimethyl sulfoxide at 80℃; for 12h;73%
para-thiocresol
106-45-6

para-thiocresol

Benzoylformic acid
611-73-4

Benzoylformic acid

A

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

B

S-(4-methylphenyl) thiobenzoate
10371-42-3

S-(4-methylphenyl) thiobenzoate

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water; acetonitrile at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;A 5.5%
B 99%
para-thiocresol
106-45-6

para-thiocresol

Benzoylformic acid
611-73-4

Benzoylformic acid

S-(4-methylphenyl) thiobenzoate
10371-42-3

S-(4-methylphenyl) thiobenzoate

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water; acetonitrile at 70℃; for 24h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Schlenk technique; Sealed tube;99%
phenylhydrazine
100-63-0

phenylhydrazine

Benzoylformic acid
611-73-4

Benzoylformic acid

phenyl-((Z)-phenylhydrazono)-acetic acid
74470-05-6

phenyl-((Z)-phenylhydrazono)-acetic acid

Conditions
ConditionsYield
With acetic acid In ethanol for 3h; Reflux;99%

611-73-4Relevant articles and documents

-

Banholzer,Schmid

, p. 548,553 (1956)

-

Biosynthesis of Phenylglyoxylic Acid by LhDMDH, a Novel d -Mandelate Dehydrogenase with High Catalytic Activity

Tang, Cun-Duo,Shi, Hong-Ling,Xu, Jian-He,Jiao, Zhu-Jin,Liu, Fei,Ding, Peng-Ju,Shi, Hong-Fei,Yao, Lun-Guang,Kan, Yun-Chao

, p. 2805 - 2811 (2018)

d-Mandelate dehydrogenase (DMDH) has the potential to convert d-mandelic acid to phenylglyoxylic acid (PGA), which is a key building block in the field of chemical synthesis and is widely used to synthesize pharmaceutical intermediates or food additives.

One-Pot Synthesis of Phenylglyoxylic Acid from Racemic Mandelic Acids via Cascade Biocatalysis

Tang, Cun-Duo,Ding, Peng-Ju,Shi, Hong-Ling,Jia, Yuan-Yuan,Zhou, Mao-Zhi,Yu, Hui-Lei,Xu, Jian-He,Yao, Lun-Guang,Kan, Yun-Chao

, p. 2946 - 2953 (2019)

Phenylglyoxylic acid (PGA) are key building blocks and widely used to synthesize pharmaceutical intermediates or food additives. However, the existing synthetic methods for PGA generally involve toxic cyanide and complex processes. To explore an alternati

Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives

Sun, Bin,Shi, Rongcheng,Zhang, Kesheng,Tang, Xiaoli,Shi, Xiayue,Xu, Jiayun,Yang, Jin,Jin, Can

supporting information, p. 6050 - 6053 (2021/06/21)

A novel and green strategy for the synthesis of acylated quinazolinone derivativesviaphoto-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without any external photocatalyst, additive or oxidant, and could be easily scaled-up in flow conditions with sunlight irradiation.

Novel peptidomimetic peptide deformylase (PDF) inhibitors of Mycobacterium tuberculosis

Gokhale, Kunal M.,Telvekar, Vikas N.

, p. 148 - 156 (2020/08/26)

Emergence of MDR-TB and XDR-TB led to the failure of available anti-tubercular drugs. In order to explore, identify and develop new anti-tubercular drugs, novel peptidomimetic series of Mtb–peptide deformylase (PDF) inhibitors was designed and synthesized. In vitro antimycobacterial potential of compounds was established by screening of compounds against Mycobacterium tuberculosis H37Rv strain using MABA. Among them, ester series of compounds 4a, 4b, 4c, 4d, and 4e were found most active, with compound 4c being highly active and exhibiting minimum inhibitory concentration of 6.25?μg/ml against M.?tb H37Rv strain. Additionally, the compounds were docked to determine the probable binding interactions and understand the mechanism of action of most active molecules on Mtb-peptide deformylase (PDF), which is involved in the mycobacterium protein synthesis.

K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins

Laha, Joydev K.,Hunjan, Mandeep Kaur

, p. 664 - 673 (2021/06/03)

The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.

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