615-81-6

Usage

Uses

Used in Pharmaceutical Industry:
Diisopropyl oxalate is used as a reagent and intermediate in the synthesis of pharmaceuticals for its versatility and reactivity in organic synthesis.
Used in Agrochemical Industry:
Diisopropyl oxalate is used as a reagent and intermediate in the synthesis of agrochemicals for its ability to facilitate the creation of various organic compounds.
Used in Adhesives and Coatings Industry:
Diisopropyl oxalate is used as a plasticizer and a coupling agent in the formulation of adhesives and coatings, contributing to the flexibility and bonding properties of these products.
Overall, diisopropyl oxalate has a range of industrial and laboratory applications due to its versatility and reactivity in organic synthesis.

InChI:InChI=1/C8H14O4/c1-5(2)11-7(9)8(10)12-6(3)4/h5-6H,1-4H3

Upstream product

• 144-62-7 oxalic acid 
• 67-63-0 isopropyl alcohol 
• 95-92-1 oxalic acid diethyl ester 
• 79-37-8 oxalyl dichloride 
• 553-90-2 Dimethyl oxalate 
• 75-30-9 2-iodo-propane 
• 40227-15-4 N,N'-diacetyl-oxalamide 
• 201230-82-2 carbon monoxide 
• 50624-94-7 oxalic acid tert-butyl ester ethyl ester 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 39061-59-1 t-butoxalyl chloride 

Downstream Products

• 6830-62-2 isopropyl 2-cyclohexyl-2-hydroxyacetate 
• 36983-28-5 isopropyl 2,4-dioxovalerate 
• 553-90-2 Dimethyl oxalate 
• 623-61-0 isopropyl glycolate 
• 15804-19-0 quinoxaline-2,3-dione 
• 107846-82-2 isopropyl bis-(pentachlorophenyl)acetate 
• 112312-95-5 (isopropoxycarbonyl)bis(pentachlorophenyl)methyl radical 
• 107846-84-4 bis(pentachlorophenyl)ketene methyl isopropyl acetal 
• 107846-83-3 sodium 1-isopropoxy-2,2-bis(pentachlorophenyl)ethenolate 
• 106675-70-1 N¹,N²-dimethoxy-N¹,N²-dimethyloxalamide 
• 112312-95-5 C₁₇H₇Cl₁₀O₂^(1-) 
• 150884-36-9 isopropyl α-(pentamethylphenyl)pentachlorophenylacetate 

Relevant academic research and scientific papers

PROCESSES FOR THE PREPARATION OF ALPHA-HYDROXY ESTERS VIA GRIGNARD COUPLING AND THIOLATION REACTIONS

The present disclosure provides processes for preparing an alpha-hydroxy ester by addition of a vinyl Grignard reagent to an oxalate ester and thiolation of the resulting double bond. Also provided are alpha-hydroxy esters and synthetic intermediates prepared according to processes disclosed herein and compositions comprising the alpha-hydroxy esters.

Copper-catalyzed asymmetric methylation of fluoroalkylated pyruvates with dimethylzinc

The catalytic asymmetric methylation of fluoroalkylated pyruvates is shown with dimethylzinc as a methylating reagent in the presence of a copper catalyst bearing a chiral phosphine ligand. This is the first catalytic asymmetric methylation to synthesize various α-fluoroalkylated tertiary alcohols with CF3, CF2H, CF2Br, and n-CnF2n+1 (n = 2, 3, 8) groups in good-to-high yields and enantioselectivities. Axial backbones and substituents on phosphorus atoms of chiral phosphine ligands critically influence the enantioselectivity. Moreover, the methylation of simple perfluoroalkylated ketones is found to be facilitated by only chiral phosphines without copper.

Cationic Chiral Pd-Catalyzed “Acetylenic” Diels–Alder Reaction: Computational Analysis of Reversal in Enantioselectivity

The highly enantioselective Diels–Alder reaction of acetylenic dienophiles is shown to be effectively catalyzed by cationic chiral palladium complexes. Not only the degree but also the sense of enantioselectivity critically depends on the steric demand of ligands. Computational analyses indicate that the steric demand does not affect the endo/exo-selectivity but the enantioface selectivity of dienes.

Template-free sol–gel synthesis of high surface area mesoporous silica based catalysts for esterification of di-carboxylic acids

High surface area mesoporous silica based catalysts have been prepared by a simple hydrolysis/sol–gel process without using any organic template and hydrothermal treatment. A controlled hydrolysis of ethyl silicate-40, an industrial bulk chemical, as a silica precursor, resulted in the formation of very high surface area (719?m2/g) mesoporous (pore size 67?? and pore volume 1.19?cc/g) silica. The formation of mesoporous silica has been correlated with the polymeric nature of the ethyl silicate-40 silica precursor which on hydrolysis and further condensation forms long chain silica species which hinders the formation of a close condensed structure thus creating larger pores resulting in the formation of high surface mesoporous silica. Ethyl silicate-40 was used further for preparing a solid acid catalyst by supporting molybdenum oxide nanoparticles on mesoporous silica by a simple hydrolysis sol–gel synthesis procedure. The catalysts showed very high acidity as determined by NH3-TPD with the presence of Lewis as well as Br?nsted acidity. These catalysts showed very high catalytic activity for esterification; a typical acid catalyzed organic transformation of various mono- and di-carboxylic acids with a range of alcohols. The in situ formed silicomolybdic acid heteropoly-anion species during the catalytic reactions were found to be catalytically active species for these reactions. Ethyl silicate-40, an industrial bulk silica precursor, has shown a good potential for its use as a silica precursor for the preparation of mesoporous silica based heterogeneous catalysts on a larger scale at a lower cost.

Palladium catalyzed oxidative carbonylation of alcohols: Effects of diphosphine ligands

The catalytic activity of a series of palladium diphosphine complexes of the type [PdX2(P∩P)] has been studied in the oxidative carbonylation of i-PrOH with p-benzoquinone as an oxidant. Diphosphine ligands have been chosen in order to cover a wide range of bite angles and electronic and steric parameters. Their properties have been correlated with the catalytic activity and selectivity of the reaction. The best catalytic performance has been achieved with weakly coordinating anions as well as non-bulky and electron-donating P∩P ligands with a relatively wide bite angle yet capable of maintaining a cis-coordination, such as cis-[Pd(OTs)2(pMeO-dppf)]. These results and those on the reactivity of dicarboalkoxy species of the type cis-[Pd(COOMe)2(P∩P)] toward reductive elimination, which is a crucial step in oxalate formation, suggest that the slow step of the catalysis depends on the nature of the P∩P ligand.

Efficient oxidative carbonylation of iPrOH to oxalate catalyzed by Pd(II)-PPh3 complexes using benzoquinone as a stoichiometric oxidant

The catalytic system trans-[PdBr2(PPh3) 2]/NEt3/PPh3/LiBr is highly active and selective in the oxidative carbonylation of iPrOH to the corresponding oxalate using benzoquinone (BQ) as a stoichiometric oxidant. The oxalate is formed together with minor amounts of carbonate and acetone. The influence of each component in the catalytic system is discussed together with the influence of the concentration of BQ, reaction time, temperature and CO pressure. NEt3 neutralizes the acid released in the catalytic cycle, thus favouring the formation of a dicarboalkoxy intermediate. Added PPh 3 reacts with benzoquinone giving betaine, which is a base that contributes to a further enhancement of the catalytic activity. The Br - anion might coordinate the Pd(0) which is formed in the product forming step thus stabilizing it against decomposition and making its reoxidation easier and reentering into the catalytic cycle. The catalytic activity depends slightly only on the concentration of BQ, suggesting that either uncoordinated BQ is not involved in the slow step of the catalytic cycle or that BQ is strongly coordinated in these species. The catalytic activity toward oxalate increases upon increasing the concentrations of NEt3 and PPh3, whereas the selectivity toward carbonate and the formation of acetone remains practically constant. The increase of the pressure of CO has a similar effect, except that the formation of acetone is suppressed. It is suggested that at relatively high pressure of CO, a pentacoordinated species may be formed so that there is no place for any interaction between palladium and the C-H bond before the β-H elimination. Instead there is a nucleophilic intrasphere attack of the alkoxy ligand onto a CO ligand. After catalysis the precursor trans-[PdBr2(PPh3)2] has been detected, together with trans-[PdBr(COOiPr)(PPh3) 2] and [Pd(BQ)(PPh3)2]. PPh3 remains coordinated to the palladium centre during catalysis. A BQ- and halides-assisted catalytic cycle is proposed. In this cycle, the reoxidation occurs through the release of a proton from an ammonium salt or a phosphonium salt, which are formed during the catalysis, with reformation of the catalyst precursor.

Esterification in dry media using ferric perchlorate adsorbed on silica gel

Adsorption of Fe(ClO4)3(H2O)6 onto chromatographic grade silica gel in the presence of alcohol ( to be used for esterification ) produces a supported reagent, Fe(ClO4)3(ROH)6/SiO2. This reagent, has been found effective for the rapid and high yield of esters, on grinding in the presence of carboxylic acids using pestle and mortar in the solid state.

Synthesis and reactivity of bis(alkyloxalyl) and alkoxycarbonyl alkyloxalyl iron complexes and (R, R'=Me or Et): evidence for reductive elimination of oxalate

The new complexes cis- (R=Me or Et) and cis- (R,R'=Me, Et or i-Pr) have been synthesized.The bis-(alkyloxalyl) complexes decarbonylate at +12 deg C to their alkoxycarbonyl alkyloxalyl homologues.The latter decompo

Surface-mediated reactions. 3. Hydrohalogenation of alkenes

Appropriately prepared silica gel and alumina have been found to mediate the addition of HCl, HBr, and HI to alkenes. The technique has been rendered even more convenient by the use of various organic and inorganic halides that undergo hydrolysis in the presence of silica gel or alumina to generate hydrogen halides in situ. Under these conditions alkenes such as cycloheptene (1), 1-octene (7), and 3,3-dimethyl-1-butene (15), which react with HCl only very slowly in solution, underwent rapid addition. 1-Octene (7) underwent ionic addition of HBr without competing radical addition. 1,2-Dimethylcyclohexane (24) afforded the syn addition product 25c, which underwent equilibration with the thermodynamically more stable isomer 25t. A mechanism for surface-mediated addition/elimination is proposed involving a stepwise transfer of H+ and X- from or to the surface in syn fashion, as shown in Scheme II.

Method of preparation of oxalic acid esters and amides

A new process is described for the preparation of oxalic acid esters and amides of general formula (I) STR1 wherein Z designates an --OR or --NR1 R2 group, wherein R represents substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, or aryl-alkyl, R1 is hydrogen or substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, or aryl-alkyl, R2 represents substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, or aryl-alkyl, or R1 and R2 taken together with the adjacent nitrogen atom represent a saturated 5-, 6-, 7-, or 8-membered heterocyclic ring, which may contain an additional heteroatom selected from --O--, --S--, and --N(H, Alkyl)--, and optionally bear one or more alkyl or alkenyl substituents, and Z1 designates an --OR or --NR1 R2 group, wherein R, R1, and R2 are as defined before, or a group --NHCOCH3, which comprises the base-catalysed reaction of diacetyloxamide with an alcohol ROH or/and an amine HNR1 R2. The compounds of formula (I) have many industrial utilities, mainly as intermediates and stabilizers in the polymer field.