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CAS No.: | 762-42-5 |
---|---|
Name: | Dimethyl acetylenedicarboxylate |
Article Data: | 40 |
Molecular Structure: | |
Formula: | C6H6O4 |
Molecular Weight: | 142.111 |
Synonyms: | Dimethyl acetylenedicarboxylic acid;1,2-Bis(methoxycarbonyl)acetylene;Dimethyl ethynedicarboxylate;Di(carbomethoxy)acetylene;Dimethyl butynedioate;2-Butynedioic acid, dimethyl ester;Bis(methoxycarbonyl)acetylene;dimethyl but-2-ynedioate;Dimethyl but-2-yndioate;But-2-ynedioic acid dimethyl ester;Dimethyl 2-butynedioate;1, 2-Bis(methoxycarbonyl)acetylene;Methyl acetylenedicarboxylate;Acetylenedicarboxylic acid, dimethyl ester;1,2-Bis(methoxycarbonyl)ethyne;Acetylenedicarboxylic acid dimethyl ester;Acetylenedicarboxylic acid, dimethyl ester (8CI); |
EINECS: | 212-098-4 |
Density: | 1.206 g/cm3 |
Melting Point: | -18 °C |
Boiling Point: | 204.309 °C at 760 mmHg |
Flash Point: | 86.111 °C |
Solubility: | Soluble in most organic solvents. Insoluble in water. |
Appearance: | clear colorless to light yellow liquid |
Hazard Symbols: | C |
Risk Codes: | 34-22 |
Safety: | 23-26-27-36/37/39-45 |
Transport Information: | UN 3265 8/PG 2 |
PSA: | 52.60000 |
LogP: | -0.66420 |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,2-dichloro-ethane; toluene Reflux; | 93% |
With sulfuric acid at 20℃; for 24h; Inert atmosphere; | 88% |
With sulfuric acid | |
With toluene-4-sulfonic acid |
trans-2,3-dibromobutenedioic acid dimethyl ester
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With zinc In tetrahydrofuran for 2h; Heating; | 93% |
With zinc In tetrahydrofuran for 2h; Heating; Yield given; |
A
bis(cyclopentadienyl)vanadium dichloride
B
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With chlorine In tetrachloromethane | A 68% B 37% |
With Cl2 In tetrachloromethane | A 68% B 37% |
3-methoxycarbonyl-5-pyrazolinone
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene In methanol 1.) -23 deg C, 45 min; 2.) rt, 1 h; | 59% |
dimethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate
A
dimethyl acetylenedicarboxylate
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
at 500℃; under 0.01 Torr; | A 59% B n/a |
at 500℃; under 0.001 - 0.1 Torr; for 1h; | A 59 % Spectr. B n/a |
methyl 7-oxo-2-phenyl-7H-[1,2,4]triazolo[3,2-b][1,3]thiazine-5-carboxylate
methanol
A
dimethyl acetylenedicarboxylate
B
3-phenyl-4,5-dihydro-1H-1,2,4-triazole-5-thione
Conditions | Yield |
---|---|
Stage #1: methyl 7-oxo-2-phenyl-7H-[1,2,4]triazolo[3,2-b][1,3]thiazine-5-carboxylate With potassium hydroxide In methanol; water for 48h; Stage #2: methanol at 20℃; for 96h; | A n/a B 59% |
(Z)-1-hydroperoxy-N-[(Z)-3-(methoxycarbonyl)-2-propenylidene]cyclohexylamine N-oxide
A
Maleinaldehydsaeure-methylester
B
cyclohexanone
C
dimethyl acetylenedicarboxylate
D
(Z)-4-[(E)-Hydroxyimino]-but-2-enoic acid methyl ester
Conditions | Yield |
---|---|
In benzene for 0.5h; Heating; Further byproducts given; | A 32% B 6% C 32% D n/a |
(Z)-1-hydroperoxy-N-[(Z)-3-(methoxycarbonyl)-2-propenylidene]cyclohexylamine N-oxide
A
cyclohexanone
B
dimethyl acetylenedicarboxylate
C
(Z)-anti-methyl 4-(hydroxyimino)but-2-enoate
D
(Z)-4-[(E)-Hydroxyimino]-but-2-enoic acid methyl ester
Conditions | Yield |
---|---|
In benzene for 0.5h; Heating; Further byproducts given. Title compound not separated from byproducts; | A 6% B 32% C n/a D n/a |
(1S,3aR)-1H-1,3a-Etheno-azulene-9,10-dicarboxylic acid dimethyl ester
A
dimethyl heptalene-4,5-dicarboxylate
B
dimethyl acetylenedicarboxylate
C
azulene
Conditions | Yield |
---|---|
In (2)H8-toluene at 60℃; under 750.06 Torr; for 30h; thermolyse, other pressure; |
2-(2-thienyl)-4,5-dimethoxycarbonyl-1,3-dithiole
methyl iodide
A
thiophene-2-carbodithioic acid methyl ester
B
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With n-butyllithium 1) 2 h -30 deg C THF hexane, 2) 2 h; Multistep reaction; |
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IUPAC Name: Dimethyl but-2-ynedioate
Molecular Formula: C6H6O4
Molecular Weight: 142.11 g/mol
Canonical SMILES: C(C(OC)=O)#CC(OC)=O
InChI: InChI=1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
EINECS: 212-098-4
Classification Code: Agricultural Chemical; Experimental pesticide; Unspecified / Unclassified pesticide
Product Categories: Aromatic Esters;Small molecule; Acetylenes; Acetylenic Carboxylic Acids & Their Derivatives
Sensitive: Light Sensitive
Surface Tension: 41.1 dyne/cm
Density: 1.205 g/cm3
Flash Point: 86.1 °C
Enthalpy of Vaporization: 44.05 kJ/mol
Boiling Point: 204.3 °C at 760 mmHg
Melting Point: -18 °C
Vapour Pressure of Dimethyl acetylenedicarboxylate (CAS NO.762-42-5): 0.265 mmHg at 25 °C
Dimethyl acetylenedicarboxylate (CAS NO.762-42-5) is mainly used in organic synthesis. It is is a lachrymator and a vesicant.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 550mg/kg (550mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA BEHAVIORAL: COMA | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(6), Pg. 55, 1984. |
rat | LDLo | oral | 50mg/kg (50mg/kg) | National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 13, 1953. |
Reported in EPA TSCA Inventory.
Poison by ingestion. A dienophile. Explosive reaction with 1-methylsilacyclopenta-2,4-diene at 150°C. Octakis(trifluorophosphine)dirhodium catalyzes explosive polymerization of the acid above 20°C. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: C
Risk Statements: 34-22
R34: Causes burns.
R22: Harmful if swallowed.
Safety Statements: 23-26-27-36/37/39-45
S23: Do not breathe vapour.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27: Take off immediately all contaminated clothing.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3265 8/PG 2
WGK Germany: 3
RTECS: ES0175000
F: 8-19
HazardClass: 8
PackingGroup of Dimethyl acetylenedicarboxylate (CAS NO.762-42-5): III
Dimethyl acetylenedicarboxylate (CAS NO.762-42-5), its Synonyms are Acetylenedicarboxylic acid dimethyl ester ; 2-Butynedioic acid, 1,4-dimethyl ester ; 2-Butynedioic acid, dimethyl ester ; 1,2-Bis(methoxycarbonyl)acetylene ; Bis(methoxycarbonyl)acetylene . It is clear colorless to light yellow liquid.