Diethyloxalat

Diethyl Oxalate

HCID 7268CAS 95-92-1

Grundinformationen

Standard-SMILES
CCOC(=O)C(=O)OCC
InChIKey
WYACBZDAHNBPPB-UHFFFAOYSA-N
Summenformel
C6H10O4
Durchschnittliche Molmasse
146,14 g/mol
Monoisotopische Masse
146,0579088

Überblick

Ethyl oxalate appears as a colorless liquid. Slightly denser than water and insoluble in water. Hence sinks in water. May irritate skin and mucous membranes; may be mildly toxic by ingestion; may emit irritating fumes in a fire. Vapors are much heavier than air. Used as a solvent for plastics and in the manufacture of perfumes and pharmaceuticals.

Namen und Bezeichner

Bevorzugter Name
Diethyl Oxalate
IUPAC
diethyl oxalate
Lokaler Name
Diethyloxalat
Englischer Name
Diethyl oxalate
Summenformel
C6H10O4
Molmasse
146.14

Namen und Synonyme

DIETHYL OXALATE95-92-1Ethyl oxalateOxalic etherEthyl oxalate (VAN)NSC 8851Diethylester kyseliny staveloveDTXSID2044472HSDB 2131EINECS 202-464-1UNII-860M3ZWF6JDiethyl ester of oxalic acid
Weitere Namen anzeigen
OXALIC ACID DIETHYL ESTERDEOiethyl oxalateCeftriaxone Impurity 5GKSWoxalicetherEthyIoxalateDiethyl oxate
UN2525Diethylester kyseliny stavelove [Czech]BRN 0606350860M3ZWF6JETHYL OXOLATENSC-8851C2H5OCOCOOC2H5Ethanedioic acid, 1,2-diethyl ester

Datenbank-Bezeichner

CAS
95-92-1
PubChem CID
7268
DTXSID
DTXSID2044472
ChEMBL
CHEMBL3183226
UNII
860M3ZWF6J
EC Number
202-464-1
Nikkaji
J43.379I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,6
Polarare Oberfläche (TPSA)
52,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
5
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Esters, Other

Flammable agents - 2nd degree

CosmeticsChelating; Plasticiser; Hair conditioning
SpringerMaterials PropertiesBoiling point
LogP0.56
OdorAROMATIC ODOR
Food AdditivesFood

Physikochemische Eigenschaften

Schmelzpunkt
-41 °C · -41 °C (lit.)
Siedepunkt
185 °C · 185 °C (lit.)
Dichte
1.076 g/mL · 1.076 g/mL at 25 °C (lit.)
Dampfdichte
5.03 · 5.03 (vs air)
Dampfdruck
1 mm · 1 mm Hg ( 47 °C)
Brechungsindex
20 · n20/D 1.410(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P337+P317, P363, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Ethanedioic acid, diethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanedioic acid, 1,2-diethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedioic acid, 1,2-diethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 28-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14261

Diethyl oxalate: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Oxalate esters (C1-C4): Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· Combustible material: may burn but does not ignite readily.

Fire Potential · 3 Einträge

MODERATE WHEN EXPOSED TO HEAT OR FLAME

THIS ESTER IS A COMBUSTIBLE LIQ, BUT IT DOES NOT PRODUCE A FLAMMABLE CONCN OF VAPOR @ ROOM TEMP.

SOME ESTERS WITH HIGHER FLASH POINTS, LIKE...ETHYL OXALATE, ARE NOT SO DANGEROUS AT ROOM TEMP. THEY ARE NEVERTHELESS READILY IGNITED AS FLAMMABLE LIQ, & SOURCE OF IGNITION MUST NOT BE ALLOWED TO COME IN CONTACT WITH THEM.

Health Hazards · 2 Einträge

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 Einträge

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresFOAM, CARBON DIOXIDE, DRY CHEMICAL
Storage Conditions · 2 Einträge

STORAGE TANKS CONTAINING FLAMMABLE ESTERS SHOULD BE SITUATED IN MOUNDED COMPOUND CONSTRUCTED TO RETAIN MAX QUANTITY OF LIQ THAT COULD ESCAPE FROM TANKS. /ESTERS/

...DRUMS & OTHER SMALLER RECEPTACLES CONTAINING ESTERS SHOULD BE KEPT IN /FIRE RESISTANT/ STOREROOM...WITH MOUNDED OR RAMPED DOORWAY TO PREVENT ESCAPE OF SPILLED LIQ. /ESTERS/

Toxikologische Informationen

Adverse EffectsNeurotoxin - Acute solvent syndrome
Human Toxicity Excerpts · 5 Einträge

...COMPLAINTS OF WEAKNESS, HEADACHE, AND NAUSEA, TOGETHER WITH EVIDENCE OF SOME SLIGHT ANEMIA AND LEUKOPENIA, NEUTROPENIA, AND EOSINOPHILIA WERE ENCOUNTERED IN WORKMEN WHO HAD BEEN EXPOSED FOR SEVERAL MONTHS TO CONCN OF 0.76 MG/L. ...SYMPTOMS REGRESSED WHEN EXPOSURE CEASED.

SYMPTOMATOLOGY: 1. BURNING PAIN IN THROAT, ESOPHAGUS, & STOMACH. ... 2. VOMITING...BURNING PAIN, SEVERE PURGING. 3. PULSE...WEAK, IRREGULAR... SOMETIMES IMPERCEPTIBLE. HYPOTENSION &...SIGNS OF CARDIOVASCULAR COLLAPSE APPEAR. 5. ...OLIGURIA, ALBUMINURIA, & HEMATURIA MAY PERSIST FOR WK. /OXALATE/

SYMPTOMATOLOGY: 4. IF DEATH IS DELAYED FOR FEW HR, NERVOUS OR NEUROMUSCULAR SYMPTOMS DEVELOP: HEADACHE, MUSCLE CRAMP (PARTICULARLY OF JAWS & EXTREMITIES), TETANY, SOMETIMES CONVULSIONS, STUPOR, COMA, & DEATH. /OXALATE/

WHILE EVIDENCE FOR TOXICITY...REMAINS OBSCURE, IT WOULD SEEM REASONABLE TO USE STRICT PRECAUTIONS TO AVOID PROLONGED INHALATION OR SKIN CONTACT...

STRONG IRRITANT TO SKIN AND MUCOUS MEMBRANES, ESP BY INGESTION.

Non-Human Toxicity Excerpts · 2 Einträge

DOSES OF 10 ML/KG ON GUINEA PIG SKIN CAUSED NO FATALITIES AND LITTLE IRRITATION.

RAT ORAL LD50 IS 0.4-1.6 G/KG WITH DISTURBANCE OF RESPIRATION AND MUSCLE TWITCHING NOTED AS PROMINENT SYMPTOMS. MASSIVE RENAL OXALATE DEPOSITS AND DILATATION OF TUBULES WERE SEEN AFTER ORAL DOSE OF 400 MG/KG IN RAT.

Probable Routes of Human ExposureNO CASES OF LETHAL POISONING FROM ETHYL OXALATE IN INDUSTRY ARE KNOWN, BUT ITS POTENTIAL TOXIC ACTION MUST BE TAKEN INTO CONSIDERATION.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 2525
hs_code
29171900
RTECS-Nr.
RO2800000
risk_code
22-36-68/21-48/25-35-61-60

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesETHYL OXALATE IS HYDROLYZED IN BODY TO FORM OXALIC ACID WHICH ACCOUNTS FOR ITS TOXIC ACTION.

Verwendung und Herstellung

Uses · 6 Einträge

Used to make pharmaceuticals, plastics, dyes, and dyestuff intermediates; Also used as a solvent for cellulose esters, ethers, resins, perfumes, and lacquers for electronics; [HSDB]

Semiconductor Manufacturing [Category: Industry]

MANUFACTURE OF PHENOBARBITAL, ETHYLBENZYL MALONATE, TRIETHYLAMINE, & SIMILAR CHEMICALS; MANUFACTURE OF PLASTICS, DYESTUFF INTERMEDIATES; SOLVENT FOR CELLULOSE ESTERS

ORGANIC SYNTHESES, ESP IN MFR OF PHARMACEUTICALS; SOLVENT FOR ETHERS & RESINS

RADIO TUBE CATHODE FIXING LACQUERS

SOLVENT FOR PERFUMES & FOR NATURAL & SYNTHETIC RESINS (CELLULOSE ESTERS); AGENT IN RADIO TUBE CATHODE FIXING LACQUERS; CHEM INT FOR PHARMACEUTICALS, PLASTICS & DYES

U.S. Exports · 2 Einträge

(1972) No Data

(1975) No Data

U.S. Imports · 2 Einträge

(1972) No Data

(1975) No Data

U.S. Production · 3 Einträge

2023: 70,547 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS

Industry UsesSoil amendments (fertilizers)
Methods of Manufacturing · 3 Einträge

ESTERIFICATION OF OXALIC ACID WITH ETHANOL

PREPN: CLARKE, DAVIS, ORG SYN 2, 23 (1922); COLL VOL I, 256; KENYON, COLL VOL I, 258 (P 261 IN 2ND ED).

ETHYL OXALATE IS PRODUCED BY STANDARD ESTERIFICATION PROCEDURE, USING ETHYL ALCOHOL AND OXALIC ACID.

Anwendungen · 1 Eintrag

VerwendenDiethyl oxalate is used to prepare active pharmaceutical ingredients (API), plastics and dyestuff intermediates. It is also used as a solvent for cellulose esters, ethers, resins, perfumes and lacquers for electronics. It is involved in the transesterification reaction with phenol to get dipheny oxalate. It is also involved in the Claisen condensation ketosteroids to prepare glyoxalyl derivatives. Further, it is used to prepare sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine. In addition to this, it is utilized in the microemulsion synthesis of zinc oxide nanoparticles.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Ethyl 1-methyl-5-propyl-1H-pyrazole-3-carboxylate5-tert-Butyl-1H-pyrazole-3-carboxylic acid3-Phenyl-1H-pyrazole-5-carboxamide ,97%Ethyl 3-(3-chlorophenyl)-1H-pyrazole-5-carboxylate ,97%5-(3-Chlorophenyl)-1H-pyrazole-3-carboxylic acidEthyl 5-(3-nitrophenyl)-1H-pyrazole-3-carboxylateEthyl 2,4-dioxoheptanoate5-Fluor-1H-indol-2-carbonsure3-(4-Methoxyphenyl)-1H-pyrazole-5-carboxamide ,97%1-Methyl-5-propyl-1H-pyrazole-3-carboxylic acid amide ,97%Ethyl 5-(2-furyl)-1H-pyrazole-3-carboxylateEthyl-5-methylisoxazol-3-carboxylat

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