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563-96-2

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563-96-2 Usage

Uses

Different sources of media describe the Uses of 563-96-2 differently. You can refer to the following data:
1. Occurs in unripe fruit and in young green leaves; has also been found in very young sugar beets.
2. Glyoxylic acid is a reagent for sulfinylmaleate synthesis. It is one of the chemicals used in the Hopkins Cole reaction. It is involved to check the presence of tryptophan in proteins. It is condensed with urea and 1,2-diaminobenzene to form heterocycles. It also undergoes Friedel-Crafts and cyclocondensation reactions to form bis(pentamethylphenyl) acetic acid and a beta-carboline respectively. It is employed in the synthesis of a sulfinylmaleate, which serves as an efficient dienophile for enantioselective Diels-Alder cycloadditions.

Check Digit Verification of cas no

The CAS Registry Mumber 563-96-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,6 and 3 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 563-96:
(5*5)+(4*6)+(3*3)+(2*9)+(1*6)=82
82 % 10 = 2
So 563-96-2 is a valid CAS Registry Number.
InChI:InChI=1/C2H4O4/c3-1(4)2(5)6/h1,3-4H,(H,5,6)/p-1

563-96-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A16058)  Glyoxylic acid monohydrate, 97%   

  • 563-96-2

  • 25g

  • 300.0CNY

  • Detail
  • Alfa Aesar

  • (A16058)  Glyoxylic acid monohydrate, 97%   

  • 563-96-2

  • 100g

  • 801.0CNY

  • Detail

563-96-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Glyoxylic acid monohydrate

1.2 Other means of identification

Product number -
Other names oxaldehydic acid,hydrate

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:563-96-2 SDS

563-96-2Synthetic route

Glyoxilic acid
298-12-4

Glyoxilic acid

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

Conditions
ConditionsYield
at 25℃; Kinetics; in wss. Loesungen vom pH 8.27 bis pH 9.97;
With water In water-d2 at 20℃;
Glyoxilic acid
298-12-4

Glyoxilic acid

(4S,5S)-4,5-Dihydroxy-[1,3]dioxolane-2-carboxylic acid
98480-38-7

(4S,5S)-4,5-Dihydroxy-[1,3]dioxolane-2-carboxylic acid

B

(2,2-Dihydroxy-acetoxy)-hydroxy-acetic acid

(2,2-Dihydroxy-acetoxy)-hydroxy-acetic acid

C

(Carboxy-hydroxy-methoxy)-hydroxy-acetic acid
98453-07-7, 98453-08-8

(Carboxy-hydroxy-methoxy)-hydroxy-acetic acid

D

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

Conditions
ConditionsYield
With water at 45℃; Product distribution; effect of the concentration;
sulfuric acid
7664-93-9

sulfuric acid

water
7732-18-5

water

Glyoxilic acid
298-12-4

Glyoxilic acid

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

Conditions
ConditionsYield
at 25℃; Kinetics;
acetamide
60-35-5

acetamide

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

N-acetyl-α-hydroxyglycine
63327-49-1

N-acetyl-α-hydroxyglycine

Conditions
ConditionsYield
In acetone for 20h; Heating;100%
In acetone
1-(2-hydroxy-4-methoxyphenyl)ethanone
552-41-0

1-(2-hydroxy-4-methoxyphenyl)ethanone

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-Hydroxy-4-(2-hydroxy-4-methoxy-phenyl)-4-oxo-butyric acid
117379-73-4

2-Hydroxy-4-(2-hydroxy-4-methoxy-phenyl)-4-oxo-butyric acid

Conditions
ConditionsYield
at 95℃; under 50 Torr; for 3h;100%
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

rac-allylglycine
1069-48-3, 7685-44-1

rac-allylglycine

Conditions
ConditionsYield
Stage #1: 2,2-dihydroxyacetic acid With ammonium hydroxide In ethanol at 20℃; for 0.5h;
Stage #2: 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In ethanol at 20℃; for 3h;
100%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

N-benzyloxycarbonyl-glycine
79002-45-2

N-benzyloxycarbonyl-glycine

Conditions
ConditionsYield
In toluene at 40℃;100%
In toluene at 40℃; for 3.5h;100%
In toluene at 40℃; for 3.5h; Large scale reaction;96%
In diethyl ether at 20℃; for 10h;
inden-1-one
83-33-0

inden-1-one

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

1-oxoindan-Δ2,α-acetic acid
114915-75-2

1-oxoindan-Δ2,α-acetic acid

Conditions
ConditionsYield
With sulfuric acid Inert atmosphere;100%
2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

A

oxalic acid
144-62-7

oxalic acid

B

Glyoxilic acid
298-12-4

Glyoxilic acid

Conditions
ConditionsYield
With oxygen; ethylenediamine; Flavin mononucleotide In water at 15℃; under 4350.3 Torr; for 77h; glycolate oxidase, Aspergillus niger catalase, pH 8-9;A 0.2%
B 99.8%
1-iodocyclohexane
626-62-0

1-iodocyclohexane

O-benzylhydoxylamine hydrochloride
2687-43-6

O-benzylhydoxylamine hydrochloride

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-(benzyloxyamino)-2-cyclohexylethanoic acid

2-(benzyloxyamino)-2-cyclohexylethanoic acid

Conditions
ConditionsYield
Stage #1: O-benzylhydoxylamine hydrochloride; 2,2-dihydroxyacetic acid In water at 20℃; for 3h; Condensation;
Stage #2: Cyclohexyl iodide With triethyl borane In hexane; water at 20℃; for 1h; Addition; Further stages.;
99%
benzylurea
538-32-9

benzylurea

Glyoxilic acid
298-12-4

Glyoxilic acid

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

A

1-benzyl-5-hydroxy-hydantoin
110668-56-9

1-benzyl-5-hydroxy-hydantoin

B

1-benzyl-4-hydroxy-hydantoin

1-benzyl-4-hydroxy-hydantoin

Conditions
ConditionsYield
Stage #1: benzylurea; Glyoxilic acid; 2,2-dihydroxyacetic acid With acetic acid In water at 100℃; for 1h;
Stage #2: With acetic acid In dichloromethane; water at 25℃; for 12h;
A 97.2%
B 2.8%
4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)semicarbazide
71397-61-0

4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)semicarbazide

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

Glyoxyilic acid (E)-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)semicarbazone
82206-54-0

Glyoxyilic acid (E)-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)semicarbazone

Conditions
ConditionsYield
In methanol for 0.5h; Ambient temperature;97%
2-iodo-propane
75-30-9

2-iodo-propane

O-benzylhydoxylamine hydrochloride
2687-43-6

O-benzylhydoxylamine hydrochloride

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-(benzyloxyamino)-3-methylbutanoic acid
54837-19-3

2-(benzyloxyamino)-3-methylbutanoic acid

Conditions
ConditionsYield
Stage #1: O-benzylhydoxylamine hydrochloride; 2,2-dihydroxyacetic acid In water at 20℃; for 3h; Condensation;
Stage #2: 2-iodo-propane With triethyl borane In hexane; water at 20℃; for 1h; Addition; Further stages.;
97%
cyclopentyl iodide
1556-18-9

cyclopentyl iodide

O-benzylhydoxylamine hydrochloride
2687-43-6

O-benzylhydoxylamine hydrochloride

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-(benzyloxyamino)-2-cyclopentylacetic acid

2-(benzyloxyamino)-2-cyclopentylacetic acid

Conditions
ConditionsYield
Stage #1: O-benzylhydoxylamine hydrochloride; 2,2-dihydroxyacetic acid In water at 20℃; for 3h; Condensation;
Stage #2: cyclopentyl iodide With triethyl borane In hexane; water at 20℃; for 1h; Addition; Further stages.;
97%
p-toluidine
106-49-0

p-toluidine

diphenylphosphane
829-85-6

diphenylphosphane

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

A

α-(diphenylphosphanyl)-N-(p-tolyl)glycine
1221419-06-2

α-(diphenylphosphanyl)-N-(p-tolyl)glycine

B

N-tolylammonium (diphenylphosphanyl)glycolate
1221419-10-8

N-tolylammonium (diphenylphosphanyl)glycolate

Conditions
ConditionsYield
In diethyl ether Inert atmosphere;A 97%
B n/a
1,2-bishydroxylamino-2-methyl-1-phenylpropane
140133-91-1

1,2-bishydroxylamino-2-methyl-1-phenylpropane

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

1,3-dihydroxy-4,4-dimethyl-5-phenylimidazolidine-2-carboxylic acid

1,3-dihydroxy-4,4-dimethyl-5-phenylimidazolidine-2-carboxylic acid

Conditions
ConditionsYield
In ethanol at 20℃; for 2h; Cyclization;95%
2-butyl iodide
513-48-4, 52152-71-3

2-butyl iodide

O-benzylhydoxylamine hydrochloride
2687-43-6

O-benzylhydoxylamine hydrochloride

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

α-N-benzyloxyamino-γ-methylpentanoic acid
115220-56-9

α-N-benzyloxyamino-γ-methylpentanoic acid

Conditions
ConditionsYield
Stage #1: O-benzylhydoxylamine hydrochloride; 2,2-dihydroxyacetic acid In water at 20℃; for 3h; Condensation;
Stage #2: 2-butyl iodide With triethyl borane In hexane; water at 20℃; for 1h; Addition; Further stages.;
95%
allyl bromide
106-95-6

allyl bromide

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-hydroxypent-4-enoic acid
67951-43-3

2-hydroxypent-4-enoic acid

Conditions
ConditionsYield
With bismuth(III) chloride; zinc95%
dimethyl 2-ferrocenyl-2-oxoethylphosphonate

dimethyl 2-ferrocenyl-2-oxoethylphosphonate

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

(E)-4-ferrocenyl-4-oxobut-2-enoic acid

(E)-4-ferrocenyl-4-oxobut-2-enoic acid

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.333333h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;95%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Horner-Wadsworth-Emmons Olefination; stereoselective reaction;95%
acetophenone
98-86-2

acetophenone

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-hydroxy-4-oxo-4-phenyl-butyric acid
65245-10-5

2-hydroxy-4-oxo-4-phenyl-butyric acid

Conditions
ConditionsYield
With indium(III) chloride at 30℃; for 72h; sonication;94%
diethylamine
109-89-7

diethylamine

diphenylphosphane
829-85-6

diphenylphosphane

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

diethylammonium diphenylphosphinoglycolate
1384754-29-3

diethylammonium diphenylphosphinoglycolate

Conditions
ConditionsYield
Stage #1: diethylamine; 2,2-dihydroxyacetic acid In diethyl ether Inert atmosphere;
Stage #2: diphenylphosphane In tetrahydrofuran Heating; Inert atmosphere;
94%
(S)-dimethyl 4,8-dimethyl-2-oxonon-7-enylphosphonate

(S)-dimethyl 4,8-dimethyl-2-oxonon-7-enylphosphonate

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

(S,E)-6,10-dimethyl-4-oxoundeca-2,9-dienoic acid

(S,E)-6,10-dimethyl-4-oxoundeca-2,9-dienoic acid

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -20℃; for 1h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;93%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Horner-Wadsworth-Emmons Olefination; stereoselective reaction;93%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

benzamide
55-21-0

benzamide

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-(1H-benzotriazol-1-yl)-2-(benzoylamino)acetic acid
125453-17-0

2-(1H-benzotriazol-1-yl)-2-(benzoylamino)acetic acid

Conditions
ConditionsYield
In toluene for 3h; Heating;92%
tert-butylamine
75-64-9

tert-butylamine

diphenylphosphane
829-85-6

diphenylphosphane

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

tert-butylamino(diphenylphosphanyl)acetic acid
843664-57-3

tert-butylamino(diphenylphosphanyl)acetic acid

Conditions
ConditionsYield
In diethyl ether at 20℃; for 24h;92%
ethanolamine
141-43-5

ethanolamine

2-(1-azulenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane
620634-44-8

2-(1-azulenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-(azulen-1-yl)-N-(2-hydroxyethyl)glycine

2-(azulen-1-yl)-N-(2-hydroxyethyl)glycine

Conditions
ConditionsYield
In methanol at 20℃; for 3h; Petasis Reaction; Inert atmosphere;92%
acetamide
60-35-5

acetamide

4-Methylanisole
104-93-8

4-Methylanisole

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

Acetylamino-(2-methoxy-5-methyl-phenyl)-acetic acid

Acetylamino-(2-methoxy-5-methyl-phenyl)-acetic acid

Conditions
ConditionsYield
With sulfuric acid In formic acid for 72h; Ambient temperature;91%
piperidine
110-89-4

piperidine

2-(1-azulenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane
620634-44-8

2-(1-azulenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-(azulen-1-yl)-2-(piperidin-1-yl)acetic acid

2-(azulen-1-yl)-2-(piperidin-1-yl)acetic acid

Conditions
ConditionsYield
In methanol at 20℃; for 4h; Petasis Reaction; Inert atmosphere;91%
2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-amino-2-hydroxyacetic acid
4746-62-7

2-amino-2-hydroxyacetic acid

Conditions
ConditionsYield
With ammonium acetate In water at 0℃; for 2.75h;90.3%
With ammonia
morpholine
110-91-8

morpholine

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

morpholinohydroxyethanoic acid
78920-08-8

morpholinohydroxyethanoic acid

Conditions
ConditionsYield
In ethanol at 4℃; for 3h;90%
Ethyl diethoxyacetate
6065-82-3

Ethyl diethoxyacetate

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: Ethyl diethoxyacetate; 2,2-dihydroxyacetic acid With toluene-4-sulfonic acid at 90℃; for 27h;
Stage #2: With phosphorus pentoxide at 90 - 100℃; for 2h;
90%
2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid
59132-30-8

1,2,3,4-tetrahydro-β-carboline-1,3-dicarboxylic acid

Conditions
ConditionsYield
In sulfuric acid for 12h;89%
2-indanone
615-13-4

2-indanone

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

2-(2-oxo-indan-1-yl)-2-hydroxyacetic acid
318472-09-2

2-(2-oxo-indan-1-yl)-2-hydroxyacetic acid

Conditions
ConditionsYield
for 0.133333h; microwave irradiation;88.5%
2-thiophenylcarboxamide
5813-89-8

2-thiophenylcarboxamide

1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

benzotriazol-1-yl-[(thiophene-2-carbonyl)-amino]-acetic acid
368870-43-3

benzotriazol-1-yl-[(thiophene-2-carbonyl)-amino]-acetic acid

Conditions
ConditionsYield
In toluene for 3h; Heating;88%

563-96-2Relevant articles and documents

Efficient photodegradation of 2-chloro-4-nitrophenol over Fe-doped BiOCl nanosheets with oxygen vacancy

Liu, Xiangming,Wu, Haoyuan,Xu, Hua,Yang, Xinmin,Ye, Jinhua

, p. 5119 - 5124 (2021/08/16)

Photodegradation of organic pollutants emerged as a promising route for environmental remediation. Due to abundant localized electrons, oxygen vacancies (OVs) over BiOCl could promote the adsorption of organic pollutants and activation of oxygen to produce more reactive oxygen species (ROS) during the photocatalytic reaction. Considering the high oxidation potential (E0 = 1.8-2.7 V vs. NHE) of the hydroxyl radicals (OH), we introduced Fe dopant in the OV-associated BiOCl system (Fe-BOC) to build Fenton-like catalysts, which converted the H2O2 generated in the photoreaction to produce more OH for the photodegradation of 2-chloro-4-nitrophenol. Experimental results revealed that the concentration of H2O2 in the undoped BiOCl (BOC) photoreaction system was higher, while much more OH was detected in Fe-BOC, indicating that the Fenton-like reaction occurred for the conversion of H2O2 into OH over Fe-BOC. In addition, the better charge separation of Fe-BOC could motivate more surface e- for O2 activation into O2-. Thus, the more reactive oxygen species (OH and O2-) produced over Fe-BOC resulted in 3.1 times higher photocatalytic activity in contrast to that of BOC.

Etude de la composition de solutions aqueuses d'acide glyoxylique en RMN de 13C

Chastrette, Francine,Bracoud, Corinne,Chastrette, Maurice,Mattioda, Georges,Christidis, Yani

, p. 66 - 74 (2007/10/02)

In order to determine the composition of aqueous solutions of glyoxylic acid, we studied the 13C nmr spectra of variously concentrated solutions (20 to 60 percent).The two well-separated regions (acids and esters on one side, acetals, hemiacetals and hydrates on the other) display not directly related intensities owing to the relaxation times of carbonyl carbons.Nevertheless, by plotting the relative intensity of each line in its own region, we were able to associate signals coming from the same species.Aside from the two prominent lines of monomeric hydrate, we identified two other pairs with intensity increasing with total concentration.Apart from a small line due to glyoxal and some other very small lines, we observed four lines of equal and slightly increasing intensity, three of acetal type and one of acid or ester type.In order to establish the structures of the species present, we determined the chemical shifts of a series of related molecules to be used as models (reported on table 2): first esters, acids, acetals, hemiacetals and hydrates of monomeric strukture, then dimers and trimers of acetaldehyde, ethyl glyoxylate and glyoxal.We were thus able to establish increments and correlations which allowed us to estimate the values of chemical shifts for possible dimers and trimers of glyoxylic acid: it was easy to see that two of the entities present in the solution are dimeric hemiacetals-acids, the erythro and threo isomers (figure 3).The fourth species is necessarily a combination of acid with glyoxal and the inspection of models led us to identify it as dihydroxy-4,5 dioxolan-1,3 carboxylic acid (figure 4).Its concentration was shown to increase with that of glyoxal in glyoxylic acid, and furthermore, some of its derivatives could be isolated.The acetalization and esterification of glyoxylic acid by ethanol in acidic medium, effected with remowal of water, provided a mixture of esters-acetals which was analysed by coupled VPC-mass spectrometry and VPC-chemical ionization (with ammonia).The analysis confirmed the existence of the above monomer and dimers in proportions related to the composition of the aqueous solution; moreover a small amount of a cyclic dimer is observed.No more than 5 percent of higher oligomers was evidenced.As for the combinations between glyoxal and glyoxylic acid, the principal one can be accompanied by many others, of various stoechiometries, when more glyoxal is initially present in the glyoxylic acid solution.Thus it is shown that glyoxylic acid in aqueous solution is mostly in the form of monomeric hydrate (69 to 88 percent)) and dimeric hemiacetals-acids (2,5 to 12 percent).Higher oligomers never exceed 5 percent in concentrated solutions, but glyoxal, if present, easily combines with glyoxylic acid, to form various compounds, the major one accounting for up to 12 percent of the material in some concentrated mixture of glyoxal and glyoxylic acid.

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