ChemicalBook--->CAS DataBase List--->924-44-7

924-44-7

924-44-7 Structure

924-44-7 Structure
IdentificationMore
[Name]

Ethyl glyoxalate
[CAS]

924-44-7
[Synonyms]

ETHYL GLYOXALATE
ETHYL GLYOXYLATE
ETHYL GLYOXYLATE POLYMER FORM
ETHYL OXOACETATE
ETHYL OXOACETATE POLYMER FORM
GLYOXALIC ACID ETHYL ESTER POLYMER FORM
GLYOXYLIC ACID ETHYL ESTER
GLYOXYLIC ACID ETHYL ESTER POLYMER FORM
ethylglyoxalatesolution
oxo-aceticaciethylester
Ethyl oxoacetate~Glyoxylic acid ethyl ester~Oxoacetic acid ethyl ester
ETHYL GLYOXALATE SOLUTION, ~50% IN TOLUE NE
Ethyl glycolate(probably 50% solution in toluene)
GLYOXYLIC ACID ETHYL ESTER, POLYMER FORM: 45-50% IN TOLUENE
Ethyl oxoacetate, tech
Ethyl glyoxylate, ca 50% soln. in toluene
Ethyl Glyoxylate Polymer form (47% in Toluene)
Ethyl 2-oxoacetate
2-Oxoacetic acid ethyl ester
Formylformic acid ethyl ester
[EINECS(EC#)]

213-105-3
[Molecular Formula]

C4H6O3
[MDL Number]

MFCD00044009
[Molecular Weight]

102.09
[MOL File]

924-44-7.mol
Chemical PropertiesBack Directory
[Appearance]

Clear colorless to slightly yellow solution
[Boiling point ]

110°C
[density ]

1.03 g/mL at 20 °C
[refractive index ]

1.4750
[Fp ]

7°C
[storage temp. ]

Refrigerator
[solubility ]

Chloroform, Ethyl Acetate
[form ]

Oil
[color ]

Clear Colorless
[Water Solubility ]

Immiscible with water.
[Sensitive ]

Air Sensitive
[BRN ]

1209486
[InChI]

InChI=1S/C4H6O3/c1-2-7-4(6)3-5/h3H,2H2,1H3
[InChIKey]

DBPFRRFGLYGEJI-UHFFFAOYSA-N
[SMILES]

C(OCC)(=O)C=O
[CAS DataBase Reference]

924-44-7(CAS DataBase Reference)
[EPA Substance Registry System]

924-44-7(EPA Substance)
Questions And AnswerBack Directory
[Synthesis]

462 g of ethanol was added to 421.4 g of 50% glyoxylic acid (2.85 mol). After adding 40 g (0.406 mol) of concentrated hydrochloric acid, the mixture was heated to 55 °C over 20 minutes. The reaction mixture was then mixed with 111 g (0.80 mol) of potassium carbonate. The degree of esterification can be calculated based on the amount of potassium carbonate required for neutralization. This was 57.89%. To separate the formed potassium carbonate, an additional 400 g of ethanol was added to reduce the solubility of the salt, which was then filtered off. Finally, Ethyl glyoxalate was distilled off. The synthetic route is shown in the figure.

Synthetic Route of Ethyl glyoxalate

Figure: Synthetic Route of Ethyl glyoxalate

Safety DataBack Directory
[Symbol(GHS) ]

Flame (GHS02)Exclamation Mark (GHS07)Health Hazard (GHS08)
GHS02,GHS07,GHS08
[Signal word ]

Danger
[Hazard statements ]

H225-H315-H317-H361d
[Precautionary statements ]

P280-P308+P313
[Hazard Codes ]

F,Xn
[Risk Statements ]

R11:Highly Flammable.
R38:Irritating to the skin.
R43:May cause sensitization by skin contact.
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R63:Possible risk of harm to the unborn child.
R65:Harmful: May cause lung damage if swallowed.
R67:Vapors may cause drowsiness and dizziness.
[Safety Statements ]

S36/37:Wear suitable protective clothing and gloves .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
[RIDADR ]

UN 1294 3/PG 2
[WGK Germany ]

3
[TSCA ]

Yes
[REACH Registrations]

Active
[HazardClass ]

3
[PackingGroup ]

II
[HS Code ]

29183000
Raw materials And Preparation ProductsBack Directory
[Preparation Products]

Methyl-2-chlorooxazole-5-carboxylate-->2-Chloroquinoxaline-->2-Bromoquinoxaline-->5-amino-1,3,4-thiadiazole-2-carboxylic acid-->2-Quinoxalinethiol-->5-Amino-1,3,4-thiadiazole-2-carboxylic acid ethyl ester-->Ethyl oxazole-5-carboxylate-->Monoethyl fumarate-->1H-Benzoimidazole-2-carboxylic acid ethyl ester-->Methyl 5-oxazolecarboxylate-->7-Nitro-2(1H)-quinoxalinone-->Diethyl malate-->Ethyl 3-phenyl-2-(piperidin-1-yl)propanoate-->5-Chloro-2-benzothiazolecarboxylic acid ethyl ester-->2,3-Dichloro-α-(2,3-dichloro-4-Methoxyphenyl)-4-Methoxy-benzeneacetic Acid Ethyl Ester
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Ethyl oxoacetate(924-44-7).msds
Hazard InformationBack Directory
[Chemical Properties]

Clear colorless to slightly yellow solution
[Uses]

Ethyl glyoxylate is widely used as an intermediate in the synthesis of pharmaceuticals (high reactivity of aldehyde function). It is used in the synthesis of a biodegradable polymer, poly(ethyl glyoxylate). It is actively involved in the Friedel-Crafts alkylation reactions with thiophenes to give the corresponding secondary alcohols.
[Definition]

ChEBI: The ethyl ester of glyoxylic acid.
[Synthesis Reference(s)]

Tetrahedron Letters, 24, p. 2223, 1983 DOI: 10.1016/S0040-4039(00)81889-4
Spectrum DetailBack Directory
[Spectrum Detail]

Ethyl glyoxalate(924-44-7)FT-IR
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

Ethyl glyoxylate, ca 50% soln. in toluene(924-44-7)
[Sigma Aldrich]

924-44-7(sigmaaldrich)
[TCI AMERICA]

Ethyl Glyoxylate Polymer form  (47% in Toluene)(924-44-7)
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