762-42-5

Basic information

• Product Name: Dimethyl acetylenedicarboxylate
• Synonyms: 1,2-Bis(methoxycarbonyl)acetylene;1,2-Bis(methoxycarbonyl)ethyne;2-butynedioicacid,dimethylester;Bis(carbomethoxy)acetylene;Bis(methoxycarbonyl)acetylene;But-2-ynedioic acid dimethyl ester;but-2-ynedioicaciddimethylester;Butynedioic acid dimethyl ester
• CAS NO: 762-42-5
• Molecular Formula: C₆H₆O₄
• Molecular Weight: 142.11
• EINECS: 212-098-4
• Product Categories: Aromatic Esters;Small molecule;Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives
• Mol File: 762-42-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: -18 °C
• Boiling Point: 95-98 °C19 mm Hg(lit.)
• Flash Point: 187 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.156 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.265mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: Store at
• Water Solubility: Soluble in most organic solvents. Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 607063
• CAS DataBase Reference: Dimethyl acetylenedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl acetylenedicarboxylate(762-42-5)
• EPA Substance Registry System: Dimethyl acetylenedicarboxylate(762-42-5)

Safety Data

• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 23-26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: ES0175000
• F: 8-19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 762-42-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Dimethyl acetylenedicarboxylate as a versatile dienophile used in Diels-Alder reactions.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 6243, 1994 DOI: 10.1016/S0040-4039(00)73402-2

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3

Synthetic route

methanol (67-56-1) + Acetylenedicarboxylic acid (142-45-0) → dimethyl acetylenedicarboxylate (762-42-5)

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 (1114-20-1, 62675-22-3, 116631-94-8) → dimethyl acetylenedicarboxylate (762-42-5)

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

(C5H5)2VC2(CO2CH3)2 → bis(cyclopentadienyl)vanadium dichloride (12083-48-6) + dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
With chlorine In tetrachloromethane	A 68% B 37%
With Cl2 In tetrachloromethane	A 68% B 37%

3-methoxycarbonyl-5-pyrazolinone (86625-25-4) → dimethyl acetylenedicarboxylate (762-42-5)

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 (64995-84-2) → dimethyl acetylenedicarboxylate (762-42-5) + Triphenylphosphine oxide (791-28-6)

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 (68827-52-1) + methanol (67-56-1) → dimethyl acetylenedicarboxylate (762-42-5) + 3-phenyl-4,5-dihydro-1H-1,2,4-triazole-5-thione (3414-94-6)

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 (183586-23-4) → Maleinaldehydsaeure-methylester (57314-32-6) + cyclohexanone (108-94-1) + dimethyl acetylenedicarboxylate (762-42-5) + (Z)-4-[(E)-Hydroxyimino]-but-2-enoic acid methyl ester (183813-49-2)

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 (183586-23-4) → cyclohexanone (108-94-1) + dimethyl acetylenedicarboxylate (762-42-5) + (Z)-anti-methyl 4-(hydroxyimino)but-2-enoate (183586-28-9) + (Z)-4-[(E)-Hydroxyimino]-but-2-enoic acid methyl ester (183813-49-2)

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 (58150-95-1) → dimethyl heptalene-4,5-dicarboxylate (58150-88-2) + dimethyl acetylenedicarboxylate (762-42-5) + azulene (275-51-4)

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 (116935-20-7) + methyl iodide (74-88-4) → thiophene-2-carbodithioic acid methyl ester (2168-83-4) + dimethyl acetylenedicarboxylate (762-42-5)

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

Bicyclo[2.2.2]octa-2,5,7-triene-2,3,5,6-tetracarboxylic acid tetramethyl ester → phthalic acid dimethyl ester (131-11-3) + dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
With base

methanol (67-56-1) + dibromomaleic acid (608-37-7) → dimethyl acetylenedicarboxylate (762-42-5) + dimethylfumarate (624-49-7) + Dimethyl succinate (106-65-0)

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 (67-56-1) + meso-2,3-dibromosuccinic acid (916065-46-8) → dimethyl acetylenedicarboxylate (762-42-5) + dimethylfumarate (624-49-7) + Dimethyl succinate (106-65-0)

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 (194220-96-7) → 2-(2-chlorophenyl)furan (38527-56-9) + dimethyl acetylenedicarboxylate (762-42-5) + 2'-Chloro-4-hydroxy-biphenyl-2,3-dicarboxylic acid dimethyl ester + 5-[1-(2-Chloro-phenyl)-1-hydroxy-meth-(Z)-ylidene]-cyclopenta-1,3-diene-1,2-dicarboxylic acid dimethyl ester

Conditions	Yield
With hydrogenchloride; water In dichloromethane for 24h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; retro-Diels-Alder reaction; Heating;

methanol (67-56-1) + monopotassium salt of/the/ acetylenedicarboxylic acid → dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
With sulfuric acid at 25℃;
With sulfuric acid

methanol (67-56-1) + monopotassium-salt of/the/ butynedioic acid → dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
With sulfuric acid; sulfur trioxide; 1,2-dichloro-ethane

methanol (67-56-1) + sulfuric acid (7664-93-9) + Acetylenedicarboxylic acid (142-45-0) → 2-methoxyfumaric acid (2215-12-5) + 2-methoxy-2-butenedioic acid dimethyl ester (26579-97-5) + dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
Veresterung;

tetrakis(2-bromobenzoato)bis(dimethyl acetylenedicarboxylate)tetracopper(I) (121619-92-9) → tetrakis(2-bromobenzoato)(dimethyl acetylenedicarboxylate)tetracopper(I) + dimethyl acetylenedicarboxylate (762-42-5)

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) (121619-91-8) → tetrakis(2-chlorobenzoato)(dimethyl acetylenedicarboxylate)tetracopper(I) + dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
In (2)H8-toluene N2, NMR tube, T: 213 - 293 K; (1)H NMR spectroscopy;

tetrakisbenzoatobis(dimethyl acetylenedicarboxylate)tetracopper(I) (121619-90-7) → tetrakisbenzoato(dimethyl acetylenedicarboxylate)tetracopper(I) + dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
In (2)H8-toluene N2, NMR tube, T: 213 - 298 K; (1)H NMR spectroscopy;

1,1,2-tricarbonyl-μ-(dimethyl 2-butynedioate-μ-C(2),μ-C(3)3)(2-3-η-dimethyl 2-butynedioate)-μ-(1-5:1'-5'-.eta-fulvalene)-dimolybdenum (Mo-Mo) → (η5:η5-fulvalene)tetracarbonyl(dimethyl ethynedicarboxylate)dimolybdenum + dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
In toluene heating in toluene at 110°C; alkyne detected by NMR;

Pd2((C6H5)4P2CH2)2C2(CO2CH3)2I2 (77590-29-5) → Pd2I2(μ-bis(diphenylphosphino)methane)2 (67477-87-6) + dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
In dichloromethane Irradiation (UV/VIS); Exposure of a CH2Cl2-soln. to light from Hg lamp;;

1,3-bis(azidopropyl)tetramethyldisiloxane → dimethyl acetylenedicarboxylate (762-42-5)

dimethyl (2E)-2,3-diiodo-2-butenedioate (18434-84-9) → dimethyl acetylenedicarboxylate (762-42-5)

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 (51575-86-1) → dimethyl acetylenedicarboxylate (762-42-5)

Conditions	Yield
With potassium hydroxide In ethanol for 4h; Time; Reflux;

N-Methylpyrrole (96-54-8) + dimethyl acetylenedicarboxylate (762-42-5) → 1-methyl-1,7a-dihydro-indole-2,3,3a,4-tetracarboxylic acid tetramethyl ester (1444-11-7)

Conditions	Yield
In dichloromethane at 40℃; under 11250900 Torr; for 6h;	100%

dimethyl acetylenedicarboxylate (762-42-5) → hexamethyl benzenehexacarboxylate (6237-59-8)

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 (110-91-8) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl (Z)-2-(morpholino)-2-butenedioate (24432-42-6)

Conditions	Yield
at 20℃; for 0.05h; Michael addition;	100%
at 100℃; for 3h;
With water; potassium carbonate at 20℃; stereoselective reaction;

p-toluidine (106-49-0) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl (Z)-N-(4-methylphenyl)aminofumarate (24559-80-6)

Conditions	Yield
at 20℃; for 0.133333h; Michael addition;	100%
In benzene at 5 - 10℃;	70%
In diethyl ether

diethylamine (109-89-7) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl (2E)-2-(diethylamino)but-2-enedioate (996-85-0)

Conditions	Yield
In water at 20℃; for 2h; Michael-type addition;	100%
In diethyl ether

2-amino-phenol (95-55-6) + dimethyl acetylenedicarboxylate (762-42-5) → (2Z)-[2-oxo-2H-1,4-benzoxazine-3(4H)-ylidene]acetic acid methyl ester (66628-73-7)

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 (107-10-8) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl (Z)-2-(n-propylamino)fumarate (24559-78-2)

Conditions	Yield
at 20℃; for 0.05h; Michael addition;	100%
In diethyl ether

dimethyl acetylenedicarboxylate (762-42-5) + N-methylaniline (100-61-8) → 2-(methylphenylamino)but-2-enedioic acid dimethyl ester (125735-97-9)

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 (110-89-4) + dimethyl acetylenedicarboxylate (762-42-5) → 1,4-dimethyl (2E)-2-(piperidin-1-yl)but-2-enedioate (4596-77-4)

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 (110-91-8) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl α-morpholinomaleate (26138-59-0)

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 (625-86-5) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate (18063-93-9)

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 (625-86-5) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate (18063-93-9)

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;

(E)-2H-chromen-2-one oxime + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl (2H-<1>benzopyran-2-ylidenaminoxy)butenedioate

Conditions	Yield
With triethylamine In dichloromethane Ambient temperature;	100%

1-methyl-cis-2-benzoyl-3-phenylaziridine (6476-40-0) + dimethyl acetylenedicarboxylate (762-42-5) → (E)-2-[((E)-1-Benzoyl-2-phenyl-vinyl)-methyl-amino]-but-2-enedioic acid dimethyl ester (113405-17-7)

Conditions	Yield
for 24h; Ambient temperature;	100%

2-Hydroxy-4-methylanilin (2835-98-5) + dimethyl acetylenedicarboxylate (762-42-5) → (Z)-3-methoxycarbonylmethylene-7-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-one (104827-36-3)

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 (95-54-5) + dimethyl acetylenedicarboxylate (762-42-5) → (Z)-methyl 2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)acetate (53700-46-2)

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 (95-84-1) + dimethyl acetylenedicarboxylate (762-42-5) → (Z)-3-methoxycarbonylmethylene-6-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-one (70917-48-5)

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 (922-69-0) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 3,3-dimethoxycyclobutene-1,2-dicarboxylate (142645-55-4)

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 (74-90-8) + dimethyl acetylenedicarboxylate (762-42-5) → hexamethyl benzenehexacarboxylate (6237-59-8)

Conditions	Yield
With triphenyl phosphite; tetrakis(triphenylphosphite)nickel(0); zinc(II) chloride In toluene at 60℃; for 0.5h;	100%

1,1-dimethoxy-propene (5634-52-6) + dimethyl acetylenedicarboxylate (762-42-5) → 3,3-Dimethoxy-4-methyl-cyclobut-1-ene-1,2-dicarboxylic acid dimethyl ester (142645-56-5)

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 (99115-93-2) + dimethyl acetylenedicarboxylate (762-42-5) → 4-Ethyl-3,3-dimethoxy-cyclobut-1-ene-1,2-dicarboxylic acid dimethyl ester

Conditions	Yield
In chloroform at 18℃; for 3h;	100%

tris(methylseleno)borane (29634-51-3) + dimethyl acetylenedicarboxylate (762-42-5) → (Z)-2-Methylselanyl-but-2-enedioic acid dimethyl ester (132330-33-7) + (E)-2,3-Bis-methylselanyl-but-2-enedioic acid dimethyl ester (82849-75-0)

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 (29680-62-4) + dimethyl acetylenedicarboxylate (762-42-5) → Phenylselenoethylendicarbonsaeure-dimethylester (15642-80-5)

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	100%

ethyl N-hydroxyiminobenzoate (2446-52-8) + dimethyl acetylenedicarboxylate (762-42-5) → ethyl O-(2'-ethoxycarbonylvinyl)-N-hydroxyiminobenzoate (139172-68-2)

Conditions	Yield
With triethylamine In dichloromethane Ambient temperature;	100%

2-(methylamino)-N'-(2-phenylacetyl)benzohydrazide (30907-73-4) + dimethyl acetylenedicarboxylate (762-42-5) → 2-Methoxycarbonylmethyl-1-methyl-4-oxo-3-phenylacetylamino-1,2,3,4-tetrahydro-quinazoline-2-carboxylic acid methyl ester

Conditions	Yield
In methanol for 2h; Heating;	100%

<4.3.2>Propella-2,4,8-trien-7-one (124944-28-1) + dimethyl acetylenedicarboxylate (762-42-5) → C17H16O5

Conditions	Yield
at 80℃; for 12h;	100%

1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole (89241-38-3) + dimethyl acetylenedicarboxylate (762-42-5) → Dimethyl 1,4-Epoxy-1,4-dimethyl-1,4-dihydro-5-(phenylsulfonyl)-2,3-carbazoledicarboxylate (92399-38-7)

Conditions	Yield
In benzene 1.) 1h, room temp., 2.) 5h, reflux;	100%

3,4-di-tert-butyl-thiophene 1,1-dioxide (116375-45-2) + dimethyl acetylenedicarboxylate (762-42-5) → 4,5-Di-tert-butyl-phthalic acid dimethyl ester (116375-46-3)

Conditions	Yield
In 1,2-dichloro-benzene for 7h; Heating;	100%

<4.3.2>propella-2,4,7,10-tetraene (4473-99-8) + dimethyl acetylenedicarboxylate (762-42-5) → C17H16O4 (131236-31-2)

Conditions	Yield
at 70℃; for 3h;	100%

N-(diazoacetoacetyl)-N-phenyl-1-pyrrolidinecarboxamide (130935-28-3) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl 2-acetyl-5-pyrrolidine-3,4-furandicarboxylate (130935-29-4)

Conditions	Yield
rhodium(II) octanoate In benzene at 25℃; for 0.25h;	100%

Upstream product

• 58150-95-1 (1S,3aR)-1H-1,3a-Etheno-azulene-9,10-dicarboxylic acid dimethyl ester 
• 18434-84-9 dimethyl (2E)-2,3-diiodo-2-butenedioate 
• 51575-86-1 dimethyl 2,3-dibromobutane-1,4-dicarboxylate 
• 77590-29-5 Pd₂((C₆H₅)4P₂CH₂)2C₂(CO₂CH₃)2I₂ 
• 121619-90-7 tetrakisbenzoatobis(dimethyl acetylenedicarboxylate)tetracopper(I) 
• 121619-91-8 tetrakis(2-chlorobenzoato)bis(dimethyl acetylenedicarboxylate)tetracopper(I) 
• 121619-92-9 tetrakis(2-bromobenzoato)bis(dimethyl acetylenedicarboxylate)tetracopper(I) 
• 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 
• 7664-93-9 sulfuric acid 
• 142-45-0 Acetylenedicarboxylic acid 
• 194220-96-7 Dimethyl 1-(2-chlorophenyl)-7-oxabicyclo[2.2.1]heptadiene-2,3-dicarboxylate 
• 916065-46-8 meso-2,3-dibromosuccinic acid 
• 608-37-7 dibromomaleic acid 

Downstream Products

• 61957-99-1 methoxycarbonylmethylsulfanyl-fumaric acid dimethyl ester 
• 114188-10-2 2,2-bis-methoxycarbonylmethylsulfanyl-succinic acid dimethyl ester 
• 5556-24-1 dimethyl 3-hydroxythiophene-2,5-dicarboxylate 
• 1444-11-7 1-Methyl-3a,7a-dihydro-indol-2,3,3a,4-tetracarbonsaeure-tetramethylester 
• 857809-56-4 dimethyl 1-benzylindole-2,3-dicarboxylate 
• 14309-54-7 dimethyl cyclohexa-1,4-diene-1,2-dicarboxylate 
• 17254-22-7 (+/-)-6-trans-styryl-9aH-quinolizin-1,2,3,4-tetracarboxylic acid tetramethyl ester 
• 16135-22-1 5-oxo-2,3-dihydro-5H-imidazo[2,1-b][1,3]thiazine-7-carboxylic acid methyl ester 
• 61760-28-9 2-phenyl-8aH-thiazolo[3,2-a]pyridine-5,6,7,8-tetracarboxylic acid tetramethyl ester 
• 61760-30-3 2-phenyl-5H-thiazolo[3,2-a]pyridine-5,6,7,8-tetracarboxylic acid tetramethyl ester 
• 61760-29-0 2-phenyl-thiazolo[3,2-a]pyridine-6,7,8,8a-tetracarboxylic acid tetramethyl ester 
• 41126-48-1 4,5-dicarbomethoxy-3-phenyl-1,3-thiazoline-2-thione 
• 41126-72-1 4-phenyl-1,6-dithia-4-aza-spiro[4,5]deca-2,7,9-triene-2,3,7,8,9,10-hexacarboxylic acid hexamethyl ester 
• 41296-74-6 4-(4-bromo-phenyl)-1,6-dithia-4-aza-spiro[4.5]deca-2,7,9-triene-2,3,7,8,9,10-hexacarboxylic acid hexamethyl ester 

Relevant articles and documents

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Synthesis of dimethyl acetylenedicarboxylate

The invention discloses synthesis of dimethyl acetylenedicarboxylate. The synthesis steps comprise: (1) dissolving 2,3-dibromosuccinic acid in methanol, adding concentrated sulfuric acid to the reaction solution in a dropwise manner, continuously stirring, and carrying out a reaction for 2-3 h to obtain 2,3-methyl dibromosuccinate; and (2) dissolving the 2,3-methyl dibromosuccinate obtained in thestep (1) into ethanol, adding an alkali substance, stirring, carrying out a heating reflux reaction, and carrying out post-treatment to obtain dimethyl acetylenedicarboxylate. According to the present invention, the operation is simple, the requirement on the operation technology of the technician is not high, the production cost can be effectively saved, and the dimethyl acetylenedicarboxylate obtained through the method has the high purity and can be directly used for the next reaction.

Mechanism and scope of the base-induced dehalogenation of (E)-diiodoalkenes

A wide range of nucleophiles have induced the elimination of iodine from (E)-diiodoalkenes to form alkynes under surprisingly mild conditions. The iodide anion is particularly efficient, and can drive the reaction to completion in less than 1 hour at room temperature in a polar aprotic solvent. Detailed investigations have suggested the reaction has a bimolecular polar mechanism. The deiodination reaction can be driven to completion with 1 equiv. of nucleophile and is partially catalytic with substoichiometric amounts of deiodinating reagent. Kinetic analysis of the stoichiometric iodide-induced reaction indicated an overall pseudo-first-order behavior. The reaction exhibited strong solvent effects, with much slower reactions observed in protic solvents than in polar aprotic solvents. The substrate dimethyl (2E)-2,3-diiodo-butene-2-dioate demonstrated orthogonal reactivity for either elimination or hydrolysis, depending on the solvent and nucleophile used. This reaction is a major pathway for all the diiodoalkenes examined, and represents a challenge and an opportunity for using these substrates in organic synthesis.