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Dimethyl acetylenedicarboxylate

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Name

Dimethyl acetylenedicarboxylate

EINECS 212-098-4
CAS No. 762-42-5 Density 1.206 g/cm3
PSA 52.60000 LogP -0.66420
Solubility Soluble in most organic solvents. Insoluble in water. Melting Point -18 °C
Formula C6H6O4 Boiling Point 204.309 °C at 760 mmHg
Molecular Weight 142.111 Flash Point 86.111 °C
Transport Information UN 3265 8/PG 2 Appearance clear colorless to light yellow liquid
Safety 23-26-27-36/37/39-45 Risk Codes 34-22
Molecular Structure Molecular Structure of 762-42-5 (Dimethyl acetylenedicarboxylate) Hazard Symbols CorrosiveC
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);

Article Data 40

Dimethyl acetylenedicarboxylate Synthetic route

67-56-1

methanol

142-45-0

Acetylenedicarboxylic acid

762-42-5

dimethyl acetylenedicarboxylate

Conditions
ConditionsYield
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
1114-20-1, 62675-22-3, 116631-94-8

trans-2,3-dibromobutenedioic acid dimethyl ester

762-42-5

dimethyl acetylenedicarboxylate

Conditions
ConditionsYield
With zinc In tetrahydrofuran for 2h; Heating;93%
With zinc In tetrahydrofuran for 2h; Heating; Yield given;

(C5H5)2VC2(CO2CH3)2

A

12083-48-6

bis(cyclopentadienyl)vanadium dichloride

B

762-42-5

dimethyl acetylenedicarboxylate

Conditions
ConditionsYield
With chlorine In tetrachloromethaneA 68%
B 37%
With Cl2 In tetrachloromethaneA 68%
B 37%
86625-25-4

3-methoxycarbonyl-5-pyrazolinone

762-42-5

dimethyl acetylenedicarboxylate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In methanol 1.) -23 deg C, 45 min; 2.) rt, 1 h;59%
64995-84-2

dimethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate

A

762-42-5

dimethyl acetylenedicarboxylate

B

791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
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
68827-52-1

methyl 7-oxo-2-phenyl-7H-[1,2,4]triazolo[3,2-b][1,3]thiazine-5-carboxylate

67-56-1

methanol

A

762-42-5

dimethyl acetylenedicarboxylate

B

3414-94-6

3-phenyl-4,5-dihydro-1H-1,2,4-triazole-5-thione

Conditions
ConditionsYield
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%
183586-23-4

(Z)-1-hydroperoxy-N-[(Z)-3-(methoxycarbonyl)-2-propenylidene]cyclohexylamine N-oxide

A

57314-32-6

Maleinaldehydsaeure-methylester

B

108-94-1

cyclohexanone

C

762-42-5

dimethyl acetylenedicarboxylate

D

183813-49-2

(Z)-4-[(E)-Hydroxyimino]-but-2-enoic acid methyl ester

Conditions
ConditionsYield
In benzene for 0.5h; Heating; Further byproducts given;A 32%
B 6%
C 32%
D n/a
183586-23-4

(Z)-1-hydroperoxy-N-[(Z)-3-(methoxycarbonyl)-2-propenylidene]cyclohexylamine N-oxide

A

108-94-1

cyclohexanone

B

762-42-5

dimethyl acetylenedicarboxylate

C

183586-28-9

(Z)-anti-methyl 4-(hydroxyimino)but-2-enoate

D

183813-49-2

(Z)-4-[(E)-Hydroxyimino]-but-2-enoic acid methyl ester

Conditions
ConditionsYield
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
58150-95-1

(1S,3aR)-1H-1,3a-Etheno-azulene-9,10-dicarboxylic acid dimethyl ester

A

58150-88-2

dimethyl heptalene-4,5-dicarboxylate

B

762-42-5

dimethyl acetylenedicarboxylate

C

275-51-4

azulene

Conditions
ConditionsYield
In (2)H8-toluene at 60℃; under 750.06 Torr; for 30h; thermolyse, other pressure;
116935-20-7

2-(2-thienyl)-4,5-dimethoxycarbonyl-1,3-dithiole

74-88-4

methyl iodide

A

2168-83-4

thiophene-2-carbodithioic acid methyl ester

B

762-42-5

dimethyl acetylenedicarboxylate

Conditions
ConditionsYield
With n-butyllithium 1) 2 h -30 deg C THF hexane, 2) 2 h; Multistep reaction;

Dimethyl acetylenedicarboxylate Chemical Properties


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 Uses

 Dimethyl acetylenedicarboxylate (CAS NO.762-42-5) is mainly used in organic synthesis. It is is a lachrymator and a vesicant.

Dimethyl acetylenedicarboxylate Toxicity Data With Reference

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.

Dimethyl acetylenedicarboxylate Consensus Reports

Reported in EPA TSCA Inventory.

Dimethyl acetylenedicarboxylate Safety Profile

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: CorrosiveC
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 Specification

 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.

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