14309-54-7

Basic information

• Product Name: DIMETHYL 1,4-CYCLOHEXADIENE-1,2-DICARBOXYLATE
• Synonyms: TIMTEC-BB SBB008041;DIMETHYL 1,4-CYCLOHEXADIENE-1,2-DICARBOXYLATE;DIMETHYL 3,6-DIHYDROPHTHALATE
• CAS NO: 14309-54-7
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• Mol File: 14309-54-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 266.7°Cat760mmHg
• Flash Point: 127.9°C
• Appearance: /
• Density: 1.194g/cm³
• Vapor Pressure: 0.00849mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: DIMETHYL 1,4-CYCLOHEXADIENE-1,2-DICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 1,4-CYCLOHEXADIENE-1,2-DICARBOXYLATE(14309-54-7)
• EPA Substance Registry System: DIMETHYL 1,4-CYCLOHEXADIENE-1,2-DICARBOXYLATE(14309-54-7)

Safety Data

• Hazardous Substances Data: 14309-54-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2098, 1986 DOI: 10.1021/jo00361a031

InChI:InChI=1/C10H12O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-4H,5-6H2,1-2H3

Upstream product

• 18668-68-3 4-bromo-buta-1,2-diene 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 67969-82-8 tetrafluoroboric acid diethyl ether 
• 314082-92-3 [Os(k1-OC(O)CH₃)(-C=CHCH₂C(CO₂Me)=C(CO₂Me)CH₂-)(CO)2(P(i-Pr)3)2] 
• 4773-89-1 1,4-cyclohexadiene-1,2-dicarboxylic anhydride 
• 6012-81-3 (1S,2R)-1,2-Dichloro-3-vinyl-cyclobutane-1,2-dicarboxylic acid 
• 5680-13-7 dimethyl 3-vinyl-1,2-dichlorocyclobutane-1,2-dicarboxylate 
• 101774-07-6 dimethyl 3-vinylcyclobutene-1,2-dicarboxylate 
• 77-79-2 3-Sulfolene 
• 186581-53-3 diazomethane 
• 610-13-9 cyclohexa-1,4-diene-1,2-dicarboxylic acid 
• 106-99-0 buta-1,3-diene 

Downstream Products

• 4773-89-1 1,4-cyclohexadiene-1,2-dicarboxylic anhydride 
• 610-11-7 2,4-cyclohexadiene-1,2-dicarboxylic acid 
• 1515-23-7 cyclohexa-2,5-diene-1,2-dicarboxylic acid 
• 65774-75-6 1,2-bis(hydroxymethyl)-3,6-dihydrobenzene 
• 4336-19-0 1,2-dimethyl cyclohex-1-ene-1,2-dicarboxylate 
• 90295-61-7 (±)-dimethyl cyclohexa-2,4-diene-1,2-dicarboxylate 

Relevant articles and documents

Studies in sesquiterpene synthesis. The marasmic acid skeleton

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PYRIDAZINONE-BASED BROAD SPECTRUM ANTI-INFLUENZA INHIBITORS

The present invention relates to compounds of formula (I): (I) or pharmaceutically acceptable salts thereof, as well as processes for their manufacture, pharmaceutical compositions comprising them, and their use as medicaments.

The dihydride-osmium(IV) complex [OsH2(/c2-O2CCH3)(H2O)(PiPr3)2]BF4 as a precursor for carbon-carbon coupling reactions

The dihydride-osmium(IV) complex [OsH2(/c2-O2CCH3)(H2O)(PiPr3)2]BF4 (1) reacts with acetylene (1 atm) at 0 °C to give polyacetylene and the vinyl-carbyne derivative [Os(CH= CH2)(2-02CCH3)(=CCH3)(PiPr3)2]BF4 (2). Both polyacetylene and 2 can also be obtained by reaction of [OsH(K2-O2CCH3XCCH3XPiPr3)2]BF4 (3) with acetylene. Under an acetylene atmosphere, complex 2 yields polyacetylene in a slow but constant manner. Complex 2 reacts with carbon monoxide to give initially the carbene derivative [Os(/t2-O2CCH3){=C(CH= CH2)CH3}(CO)(PiPr3)2]BF4 (4), by migratory insertion of the carbyne ligand of 2 into the Os-vinyl bond. Under a carbon monoxide atmosphere, complex 2 is unstable and evolves into [Os(K2-O2CCH3)(CO)2(PiPr3)2]BF4 (5). Treatment of 2 with KOH in methanol produces the deprotonation of the carbyne ligand and the formation of the vinyl-vinylidene derivative Os(CH=CH2)(/c2-O2CCH3)(=C=CH2)(PiPr3)2 (6), which reacts with carbon monoxide to give the butadienyl compound Os{C(CH=CH2)=CH2}{1-OC(O)CH3}(CO)2(PiPr3)2 (7) by migratory insertion of the vinylidene ligand into the Os-vinyl bond. The structure of 7 has been determined by X-ray diffraction analysis. The geometry around the osmium atom can be rationalized as a distorted octahedron with the phosphine ligands occupying opposite positions. The remaining perpendicular plane is formed by the butadienyl ligand, the acetate, and the carbonyl groups mutually cis disposed. The Os-butadienyl distance is 2.195(5) A, whereas the torsion angle in the diene is 50.7(8)°. The butadienyl ligand of 7 acts as a diene in Diels-Alder reactions. Thus, the addition of dimethyl acetylenedicarboxylate and maleic anhydride to benzene solutions of 7 affords the corresponding cycloaddition products Os-{C=CHCH2C(CO2Me)=C(C02Me)CH2{1-OC(O)CH3}(CO)2(PiPr3)2 (8) and Os{C=CHCH2CH-[C(O)OC(0)]CHCH2}{1-OC(O)CH3}(CO)2(PiPr3)2 (9). Treatment of 8 with HBF4-OEt2 gives i 5 and dimethyl l,4-cyclohexadiene-l,2-dicarboxylate.