Product Name

  • Name

    Glyoxylic acid monohydrate

  • EINECS 206-058-5
  • CAS No. 563-96-2
  • Article Data6
  • CAS DataBase
  • Density 1.33 g/mL at 20 °C
  • Solubility water: 0.1 g/mL, clear
  • Melting Point 49-52 °C(lit.)
  • Formula C2H4O4
  • Boiling Point 300.934 °C at 760 mmHg
  • Molecular Weight 92.0514
  • Flash Point 150.027 °C
  • Transport Information UN 3265 8/PG 2
  • Appearance white to light yellow crystalline powder
  • Safety 26-36/37/39-45-37/39-24-27
  • Risk Codes 34-43-41
  • Molecular Structure Molecular Structure of 563-96-2 (Glyoxylic acid monohydrate)
  • Hazard Symbols CorrosiveC,IrritantXi
  • Synonyms 2,2-dihydroxyacetate;Glyoxylic acid 1-hydrate;
  • PSA 63.60000
  • LogP -0.79440

Synthetic 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%

Glyoxylic Acid Monohydrate Chemical Properties

Molecular Formula: C2H4O4  
Molecular Weight: 92.05
IUPAC Name: oxaldehydic acid hydrate
Synonyms: Dihydroxyacetic acid ; Formylformic acid ; Oxoethanoic acid ; Formylformic acid monohydrate ; Oxoethanoic acid monohydrate
Melting Point: 49-52 °C (lit.)
Boiling Point: 100°C (lit.)
Density of Glyoxylic acid monohydrate (563-96-2) : 1.33 g/mL at 20 °C
Refractive index: n20/D 1.414
Flash Point: >230 °F
Storage temp.: 2-8 °C
Sensitive: Hygroscopic
Enthalpy of Vaporization: 62.76 kJ/mol
Vapour Pressure: 0.000107 mmHg at 25 °C
Solubility of Glyoxylic acid monohydrate (563-96-2): H2O: 0.1 g/mL, clear
Chemical Properties: Glyoxylic acid monohydrate (563-96-2) is a white to light yellow crystalline powder or chunks

Glyoxylic Acid Monohydrate Uses

In industrial field, Glyoxylic acid monohydrate (563-96-2) is used as a basic chemical for the synthesis of other chemical products of acids, esters, cyclic compounds.

Glyoxylic Acid Monohydrate Toxicity Data With Reference

 Carcinogenicity: Glyoxylic acid - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Water - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.

Other: The toxicological properties have not been fully investigated. See actual entry in RTECS for complete information.
 

Glyoxylic Acid Monohydrate Safety Profile

Hazard Codes: CorrosiveC,IrritantXi
Risk Statements: 34-43-41
34: Causes burns
43: May cause sensitization by skin contact
41: Risk of serious damage to eyes 
Safety Statements: 26-36/37/39-45-37/39-24-27
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
37/39: Wear suitable gloves and eye/face protection
24: Avoid contact with skin
27: Take off immediately all contaminated clothing
RIDADR: UN 3265 8/PG 2
WGK Germany: 1
RTECS: MD4550000
F: 3: Hygroscopic
HazardClass: 8
PackingGroup: III

Glyoxylic Acid Monohydrate Standards and Recommendations

Assay: 98.0% min

Glyoxylic Acid Monohydrate Specification

 Glyoxylic Acid Monohydrate, its cas register number is 563-96-2. It also can be called Dihydroxyacetic acid; Formylformic acid; Oxoethanoic acid, and its IUPAC name is (oxaldehydic acid hydrate.  L-serine (CAS NO.56-45-1) is hygroscopic, it can absorbs moisture or water from the air. And it is incompatible with strong oxidizing agents,strong bases. L-serine's  hazardous decomposition products are carbon monoxide, formaldehyde and carbon dioxide.Glyoxylic acid monohydrate (563-96-2) is a white to light yellow crystalline powder or chunks. In industrial field, Glyoxylic acid monohydrate (563-96-2) is used as a basic chemical for the synthesis of other chemical products of acids, esters, cyclic compounds. It should keep container tightly closed and  keep container in a cool, well-ventilated area.

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