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

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 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.

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

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

Downstream Products

• 56934-59-9 isopropyl oxalmonoanilide 
• 114894-30-3 2,4,6-trimethyl-mandelic acid-isopropyl ester 
• 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 
• 15804-19-0 quinoxaline-2,3-dione 
• 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 
• 623-61-0 isopropyl glycolate 

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.

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.

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.