615-81-6

Basic information

• Product Name: diisopropyl oxalate
• Synonyms: Oxalic acid diisopropyl ester;dipropan-2-yl ethanedioate;dipropan-2-yl oxalate
• CAS NO: 615-81-6
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.2
• EINECS: 210-448-0
• Mol File: 615-81-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 190°C (estimate)
• Flash Point: 75.3°C
• Appearance: /
• Density: 1.0020
• Vapor Pressure: 0.339mmHg at 25°C
• Refractive Index: 1.4100 (estimate)
• CAS DataBase Reference: diisopropyl oxalate(CAS DataBase Reference)
• NIST Chemistry Reference: diisopropyl oxalate(615-81-6)
• EPA Substance Registry System: diisopropyl oxalate(615-81-6)

Safety Data

• Hazardous Substances Data: 615-81-6(Hazardous Substances Data)

Usage

General Description

Diisopropyl oxalate, also known as bis(isopropyl)oxalate or oxalic acid diisopropyl ester, is an organic compound with the formula (CH3)2CHOC(O)C(O)OCH(CH3)2. It is a colorless, odorless liquid that is insoluble in water but soluble in organic solvents. Diisopropyl oxalate is primarily used as a reagent and intermediate in the synthesis of pharmaceuticals, agrochemicals, and various other organic compounds. It is also utilized as a plasticizer and a coupling agent in the formulation of adhesives and coatings. The compound is considered to be relatively stable and is generally handled and stored under normal laboratory conditions. However, it may react violently with strong oxidizing agents and is flammable in its liquid form. 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 
• 75-30-9 2-iodo-propane 
• 201230-82-2 carbon monoxide 
• 39061-59-1 t-butoxalyl chloride 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 50624-94-7 oxalic acid tert-butyl ester ethyl ester 
• 40227-15-4 N,N'-diacetyl-oxalamide 
• 553-90-2 Dimethyl oxalate 

Downstream Products

• 114894-30-3 2,4,6-trimethyl-mandelic acid-isopropyl ester 
• 6830-62-2 isopropyl 2-cyclohexyl-2-hydroxyacetate 
• 36983-28-5 isopropyl 2,4-dioxovalerate 
• 553-90-2 Dimethyl oxalate 
• 112312-91-1 isopropyl decachlorobenzilate 
• 623-61-0 isopropyl glycolate 
• 1027493-60-2 2-{2-[4-(2-furan-2-yl-5-methyl-oxazol-4-ylmethoxy)-3-methoxy-phenyl]-ethyl}-3-oxo-succinic acid diisopropyl ester 
• 106675-70-1 N¹,N²-dimethoxy-N¹,N²-dimethyloxalamide 
• 112312-95-5 C₁₇H₇Cl₁₀O₂^(1-) 

Relevant articles and documents

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.

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.

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.