97-72-3

Usage

Chemical Properties

clear colorless liquid

Uses

Isobutyric anhydride was used in the synthesis of 4-O-isobutyryl derivative via reaction with octyl β-D-glucopyranoside in the presence of C2-symmetric chiral 4-pyrrolidinopyridine as a catalyst.

Definition

ChEBI: An acyclic carboxylic anhydride of isobutyric acid. Metabolite observed in cancer metabolism.

General Description

A colorless liquid. Flash point 139°F. Burns skin and eyes. Vapors are heavier than air.

Air & Water Reactions

Flammable. Reacts exothermically with water or moisture-containing materials to form isobutyric acid.

Reactivity Profile

Isobutyric anhydride reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with a cids, strong oxidizing agents, alcohols, amines, and bases.

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

InChI:InChI=1/C8H14O3/c1-5(2)7(9)11-8(10)6(3)4/h5-6H,1-4H3

Upstream product

• 78-84-2 isobutyraldehyde 
• 79-31-2 isobutyric Acid 
• 79-30-1 isobutyryl chloride 
• 14332-14-0 thallium(I) 2-methylpropanoate 
• 535-80-8 3-chlorobenzoate 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 75-65-0 tert-butyl alcohol 
• 108-24-7 acetic anhydride 
• 292638-85-8 acrylic acid methyl ester 
• 98-88-4 benzoyl chloride 
• 598-26-5 dimethylketene 
• 3908-04-1 tetrakis-isobutyryloxy-silane 
• 681-98-1 tetraisobutoxysilane 

Downstream Products

• 4208-53-1 2-methyl-1-(2-furyl)-1-propanone 
• 36448-60-9 2-methyl-1-thiophen-2-yl-propan-1-one 
• 92475-82-6 1-isobutyrylpyrrolidin-2-one 
• 32405-64-4 N-pyridin-3-yl-isobutyramide 
• 725266-70-6 6-ethyl-3-isobutyryl-pyran-2,4-dione 
• 133461-92-4 N-(2-acetylphenyl)isobutyramide 
• 34190-46-0 N-vanillyl-isobutyramide 
• 118728-63-5 α-isobutyrylamino-isobutyric acid 
• 1180-43-4 Cholesteryl-α-methylpropionate 
• 563-80-4 3-methyl-butan-2-one 
• 565-69-5 ethyl isopropyl ketone 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 23985-59-3 3-hydroxy-2,2-dimethyl-3-phenylpropanoic acid 
• 6395-29-5 2-(2-methyl-1-propenyl)phenol 

Relevant academic research and scientific papers

ADAMANTYLMETHYLAMINE DERIVATIVE AND USE THEREOF AS PHARMACEUTICAL

The present invention provides a pharmaceutical composition for treating or preventing a cognitive disease or disorder, comprising a compound represented by Formula (I), an enantiomer thereof, a diastereomer thereof, or a pharmaceutically acceptable salt thereof.

PROCESS FOR PREPARING 2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIOL

Disclosed is a method for preparing 2,2,4,4-tetramethyl-1,3-cyclobutanediol, which prepares (E) 2,2,4,4-tetramethyl-1,3-cyclobutanediol (CBDO) which is a final material by sequentially going through (A) methacrylic acid (MAA) as a raw material, and (B) isobutyric acid (IBA), (C) isobutyric anhydride (IBAN), and (D) 2,2,4,4-tetramethyl-1,3-cyclobutanedione (CBDK) as an intermediate. According to the present invention, the method for preparing 2,2,4,4-tetramethyl-1,3-cyclobutanediol which is economical and eco-friendly by optimizing preparation steps and maximizing the efficiency is provided.COPYRIGHT KIPO 2019

Anhydrides from aldehydes or alcohols via oxidative cross-coupling

A novel type of metal-free oxidative cross-coupling for the synthesis of symmetrical and mixed anhydrides from aldehydes or benzylic alcohols has been developed. The aldehydes or alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with an array of carboxylic acids. The methodology has a general applicability, and was successfully employed to prepare either aromatic or aliphatic symmetrical anhydrides and mixed anhydrides, which are very unstable compounds.

Metal-free oxidative self-coupling of aldehydes or alcohols to symmetric carboxylic anhydrides

A metal-free synthesis of symmetrical anhydrides has been developed starting from aldehydes, both aliphatic and aromatic or primary benzylic alcohols. The reaction occurs at room temperature and makes use of trichloroisocyanuric acid (TCCA) as an oxidant providing the desired carboxylic anhydrides in satisfactory yields.

Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification

We present an organocatalytic C-O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, m-CPBA as the oxidant, and N,N-diisopropylcarbodiimide as the activating agent. Racemic acyclic diols as well as trans-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols.

Epoxidation of olefins with O2 and isobutyraldehyde catalyzed by cobalt (II)-containing zeolitic imidazolate framework material

Co-containing zeolitic imidazolate framework material (Co-ZIF) was prepared and its catalytic performance in the aerobic epoxidation of olefins using isobutyraldehyde as reductant under mild conditions was first studied. Co-ZIF was characterized by XRD, FT-IR and X-ray single-crystal diffraction. It showed good performance in the epoxidation of olefins, with 100% conversion, 98.5% selectivity and 638.3 turnover frequency for the epoxidation of cyclooctene. Co-ZIF could be reused for 5 times without loss of its catalytic activity and the structure of the recovered catalyst was almost unchanged compared to that of the fresh one.

Domino catalysis in the direct conversion of carboxylic acids to esters

The combined use of high concentration conditions, auxiliary bases, and new catalysts allows for the rapid synthesis of sterically hindered carboxylic acid esters at room temperature. Mechanistic analysis indicates the intermediate formation of acid anhydrides and subsequent rate-limiting transformation to the ester products.

Reaction of dicarbonates with carboxylic acids catalyzed by weak Lewis acids: General method for the synthesis of anhydrides and esters

The reaction between carboxylic acids (RCOOH) and dialkyl dicarbonates [(R1OCO)2O], in the presence of a weak Lewis acid such as magnesium chloride and the corresponding alcohol (R1OH) as the solvent, leads to the esters RCOOR1 in excellent yields. The mechanism involves a double addition of the acid to the dicarbonate, affording a carboxylic anhydride [(RCO)2O], R1OH and carbon dioxide. The esters arise from the attack of the alcohols on the anhydrides. Exploiting the lesser reactivity of tert-butyl alcohol in comparison with other alcohols, a clean synthesis of both carboxylic anhydrides and esters has been set up. In the former reaction, an acid/Boc2O molecular ratio of 2:1 leads to the anhydride in good to excellent yields, depending on the stability of the resulting anhydride to the usual workup conditions. In the latter reaction, stoichiometric mixtures of the acid and Boc2O are allowed to react with a twofold excess of a primary alcohol, secondary alcohol or phenol (R 2OH) to give the corresponding esters (RCOOR2). Purification of the products is particularly easy since all byproducts are volatile or water soluble. A very easy chromatography is required only in the case of nonvolatile alcohols. A broad variety of sensitive functional groups is tolerated on both the acid and the alcohol, in particular a high chemoselectivity is observed. In fact, no transesterification processes occur with the acid-sensitive acetoxy group and methyl esters. Georg Thieme Verlag Stuttgart.

Process for the manufacture of isobutyric anhydride

This process for the manufacture of isobutyric anhydride by reacting acetic anhydride with isobutyric acid, distilling the acetic acid generated as it is formed, is characterized in that the reactor is initially loaded with at least a portion of one of the reagents and a portion of the other such that the reagents are in an excess molar ratio relative to the stoichiometry of one of the reagents, and the reaction is carried out while adding the remainder of the reagents as the reaction progresses and according to the place left free in the reactor by the distillation of the acetic acid produced by the reaction, until the desired overall molar ratio of the reagents is reached.