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; |
Conditions | Yield |
---|---|
With base |
methanol
dibromomaleic acid
A
dimethyl acetylenedicarboxylate
B
dimethylfumarate
C
Dimethyl succinate
Conditions | Yield |
---|---|
With samarium; sulfuric acid 1) MeOH, 24 h, RT, 2) reflux; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
methanol
meso-2,3-dibromosuccinic acid
A
dimethyl acetylenedicarboxylate
B
dimethylfumarate
C
Dimethyl succinate
Conditions | Yield |
---|---|
With samarium; sulfuric acid 1) MeOH, 24 h, Rt, 2) reflux; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Dimethyl 1-(2-chlorophenyl)-7-oxabicyclo[2.2.1]heptadiene-2,3-dicarboxylate
A
2-(2-chlorophenyl)furan
B
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With hydrogenchloride; water In dichloromethane for 24h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; retro-Diels-Alder reaction; Heating; |
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; | |
With sulfuric acid |
Conditions | Yield |
---|---|
With sulfuric acid; sulfur trioxide; 1,2-dichloro-ethane |
methanol
sulfuric acid
Acetylenedicarboxylic acid
A
2-methoxyfumaric acid
B
2-methoxy-2-butenedioic acid dimethyl ester
C
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
Veresterung; |
tetrakis(2-bromobenzoato)bis(dimethyl acetylenedicarboxylate)tetracopper(I)
B
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In (2)H8-toluene N2, NMR tube, T: 213 - 293 K; (1)H NMR spectroscopy; |
tetrakis(2-chlorobenzoato)bis(dimethyl acetylenedicarboxylate)tetracopper(I)
B
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In (2)H8-toluene N2, NMR tube, T: 213 - 293 K; (1)H NMR spectroscopy; |
tetrakisbenzoatobis(dimethyl acetylenedicarboxylate)tetracopper(I)
B
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In (2)H8-toluene N2, NMR tube, T: 213 - 298 K; (1)H NMR spectroscopy; |
B
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In toluene heating in toluene at 110°C; alkyne detected by NMR; |
Pd2((C6H5)4P2CH2)2C2(CO2CH3)2I2
A
Pd2I2(μ-bis(diphenylphosphino)methane)2
B
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In dichloromethane Irradiation (UV/VIS); Exposure of a CH2Cl2-soln. to light from Hg lamp;; |
dimethyl acetylenedicarboxylate
dimethyl (2E)-2,3-diiodo-2-butenedioate
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In nitrobenzene-d5 at 45℃; for 40h; Inert atmosphere; Darkness; |
dimethyl 2,3-dibromobutane-1,4-dicarboxylate
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 4h; Time; Reflux; |
N-Methylpyrrole
dimethyl acetylenedicarboxylate
1-methyl-1,7a-dihydro-indole-2,3,3a,4-tetracarboxylic acid tetramethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 40℃; under 11250900 Torr; for 6h; | 100% |
Conditions | Yield |
---|---|
[Rh(CO)Cl(1,2-bis(diphenylphosphino)ethane)] In tetrahydrofuran-d8 at 65℃; for 1h; cyclotrimerization; | 100% |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (R)-(+)-2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl In dichloromethane at 20℃; for 1h; | 100% |
Rh[C60(PhCH2)2Ph](cod) In 1,2-dichloro-benzene at 60℃; for 24h; | 99% |
morpholine
dimethyl acetylenedicarboxylate
dimethyl (Z)-2-(morpholino)-2-butenedioate
Conditions | Yield |
---|---|
at 20℃; for 0.05h; Michael addition; | 100% |
at 100℃; for 3h; | |
With water; potassium carbonate at 20℃; stereoselective reaction; |
p-toluidine
dimethyl acetylenedicarboxylate
dimethyl (Z)-N-(4-methylphenyl)aminofumarate
Conditions | Yield |
---|---|
at 20℃; for 0.133333h; Michael addition; | 100% |
In benzene at 5 - 10℃; | 70% |
In diethyl ether |
diethylamine
dimethyl acetylenedicarboxylate
dimethyl (2E)-2-(diethylamino)but-2-enedioate
Conditions | Yield |
---|---|
In water at 20℃; for 2h; Michael-type addition; | 100% |
In diethyl ether |
2-amino-phenol
dimethyl acetylenedicarboxylate
(2Z)-[2-oxo-2H-1,4-benzoxazine-3(4H)-ylidene]acetic acid methyl ester
Conditions | Yield |
---|---|
at 20℃; for 0.0666667h; Michael addition; | 100% |
In neat (no solvent) at 20℃; for 0.166667h; regioselective reaction; | 98% |
In ethanol at 0℃; for 3h; | 94% |
propylamine
dimethyl acetylenedicarboxylate
dimethyl (Z)-2-(n-propylamino)fumarate
Conditions | Yield |
---|---|
at 20℃; for 0.05h; Michael addition; | 100% |
In diethyl ether |
dimethyl acetylenedicarboxylate
N-methylaniline
2-(methylphenylamino)but-2-enedioic acid dimethyl ester
Conditions | Yield |
---|---|
In water at 20℃; for 2h; Michael-type addition; | 100% |
In water at 20℃; | 71% |
In water at 0 - 20℃; for 2h; | 69% |
In diethyl ether |
piperidine
dimethyl acetylenedicarboxylate
1,4-dimethyl (2E)-2-(piperidin-1-yl)but-2-enedioate
Conditions | Yield |
---|---|
In water at 20℃; for 2h; Michael-type addition; | 100% |
With silica gel for 0.0833333h; Neat (no solvent); optical yield given as %de; chemoselective reaction; | 82% |
In 1,4-dioxane at 80℃; for 10h; | 60% |
In diethyl ether | |
In diethyl ether at 0℃; |
morpholine
dimethyl acetylenedicarboxylate
dimethyl α-morpholinomaleate
Conditions | Yield |
---|---|
In water at 20℃; for 2h; Michael-type addition; | 100% |
In diethyl ether for 24h; Ambient temperature; | 86% |
With silica gel for 0.0833333h; Neat (no solvent); optical yield given as %de; chemoselective reaction; | 84% |
In diethyl ether for 15h; Ambient temperature; | 70% |
2,5-dimethylfuran
dimethyl acetylenedicarboxylate
dimethyl 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
Conditions | Yield |
---|---|
In 1,4-dioxane at 103℃; | 100% |
In dichloromethane under 7500600 Torr; for 20h; Ambient temperature; | 95% |
In 1,4-dioxane at 101℃; for 17.5h; | 81% |
2,5-dimethylfuran
dimethyl acetylenedicarboxylate
dimethyl 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
Conditions | Yield |
---|---|
at 100℃; for 21h; | 100% |
at 100℃; for 2h; Sealed tube; | 78% |
In 1,4-dioxane at 100℃; for 24h; Diels-Alder reaction; | |
In toluene at 150℃; Diels-Alder reaction; Microwave irradiation; |
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane Ambient temperature; | 100% |
1-methyl-cis-2-benzoyl-3-phenylaziridine
dimethyl acetylenedicarboxylate
(E)-2-[((E)-1-Benzoyl-2-phenyl-vinyl)-methyl-amino]-but-2-enedioic acid dimethyl ester
Conditions | Yield |
---|---|
for 24h; Ambient temperature; | 100% |
2-Hydroxy-4-methylanilin
dimethyl acetylenedicarboxylate
(Z)-3-methoxycarbonylmethylene-7-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-one
Conditions | Yield |
---|---|
at 20℃; for 0.0333333h; Michael addition; | 100% |
In ethanol at 0℃; for 3h; | 92% |
In methanol Ambient temperature; | 88.89% |
1,2-diamino-benzene
dimethyl acetylenedicarboxylate
(Z)-methyl 2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate
Conditions | Yield |
---|---|
at 20℃; for 0.0166667h; Michael addition; | 100% |
for 0.0833333h; microwave irradiation; | 90% |
In methanol Heating; | |
at 20℃; for 0.0833333h; Milling; |
3-amino-4-hydroxytoluene
dimethyl acetylenedicarboxylate
(Z)-3-methoxycarbonylmethylene-6-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-one
Conditions | Yield |
---|---|
at 20℃; for 0.0333333h; Michael addition; | 100% |
In ethanol at 0℃; for 3h; | 93% |
In methanol Ambient temperature; | 92.27% |
1,1-dimethoxyethylene
dimethyl acetylenedicarboxylate
dimethyl 3,3-dimethoxycyclobutene-1,2-dicarboxylate
Conditions | Yield |
---|---|
In chloroform at 18℃; for 3h; | 100% |
In toluene at 28 - 32℃; for 15h; | 93% |
In acetonitrile at 18 - 22℃; for 3h; | 53% |
hydrogen cyanide
dimethyl acetylenedicarboxylate
hexamethyl benzenehexacarboxylate
Conditions | Yield |
---|---|
With triphenyl phosphite; tetrakis(triphenylphosphite)nickel(0); zinc(II) chloride In toluene at 60℃; for 0.5h; | 100% |
1,1-dimethoxy-propene
dimethyl acetylenedicarboxylate
3,3-Dimethoxy-4-methyl-cyclobut-1-ene-1,2-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
In chloroform at 18℃; for 3h; | 100% |
In acetonitrile at 18 - 22℃; for 3h; Product distribution; Mechanism; other solvents, other temperatures, other times, other acetylenic ester; other 1,1-dimethoxyalkenes; | 58% |
In acetonitrile at 18 - 22℃; for 3h; | 58% |
1,1-dimethoxy-but-1-ene
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In chloroform at 18℃; for 3h; | 100% |
tris(methylseleno)borane
dimethyl acetylenedicarboxylate
A
(Z)-2-Methylselanyl-but-2-enedioic acid dimethyl ester
B
(E)-2,3-Bis-methylselanyl-but-2-enedioic acid dimethyl ester
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; Ambient temperature; | A 100% B n/a |
In dichloromethane for 0.5h; Ambient temperature; Yields of byproduct given; | A 75% B n/a |
Tris(phenylseleno)borane
dimethyl acetylenedicarboxylate
Phenylselenoethylendicarbonsaeure-dimethylester
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; Ambient temperature; | 100% |
ethyl N-hydroxyiminobenzoate
dimethyl acetylenedicarboxylate
ethyl O-(2'-ethoxycarbonylvinyl)-N-hydroxyiminobenzoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane Ambient temperature; | 100% |
2-(methylamino)-N'-(2-phenylacetyl)benzohydrazide
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In methanol for 2h; Heating; | 100% |
Conditions | Yield |
---|---|
at 80℃; for 12h; | 100% |
1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole
dimethyl acetylenedicarboxylate
Dimethyl 1,4-Epoxy-1,4-dimethyl-1,4-dihydro-5-(phenylsulfonyl)-2,3-carbazoledicarboxylate
Conditions | Yield |
---|---|
In benzene 1.) 1h, room temp., 2.) 5h, reflux; | 100% |
3,4-di-tert-butyl-thiophene 1,1-dioxide
dimethyl acetylenedicarboxylate
4,5-Di-tert-butyl-phthalic acid dimethyl ester
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene for 7h; Heating; | 100% |
<4.3.2>propella-2,4,7,10-tetraene
dimethyl acetylenedicarboxylate
C17H16O4
Conditions | Yield |
---|---|
at 70℃; for 3h; | 100% |
N-(diazoacetoacetyl)-N-phenyl-1-pyrrolidinecarboxamide
dimethyl acetylenedicarboxylate
dimethyl 2-acetyl-5-pyrrolidine-3,4-furandicarboxylate
Conditions | Yield |
---|---|
rhodium(II) octanoate In benzene at 25℃; for 0.25h; | 100% |
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.
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