547-63-7

Basic information

• Product Name: Methyl isobutyrate
• Synonyms: Propanoicacid,2-methyl-,methylester;METHYL ISOBUTYRATE 99+%;Methyl #niso-butyrate;Methylisobutyrate,98%;methylmethylpropanoate,methyl2-methylpropanoate;ISOBUTRYIC METHYL ESTER;METHYL ISOBUTYRATE, NATURAL;2-Methylpropionic acid methyl
• CAS NO: 547-63-7
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 208-929-5
• Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N;C2 to C5;Carbonyl Compounds;Esters
• Mol File: 547-63-7.mol
• Article Data: 97

Chemical Properties

• Melting Point: -85--84 °C
• Boiling Point: 90 °C(lit.)
• Flash Point: 38 °F
• Appearance: Clear colorless/Liquid
• Density: 0.891 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.384(lit.)
• Storage Temp.: Flammables area
• Solubility: alcohol: miscible
• Water Solubility: slightly soluble
• Merck: 14,6088
• BRN: 1740720
• CAS DataBase Reference: Methyl isobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl isobutyrate(547-63-7)
• EPA Substance Registry System: Methyl isobutyrate(547-63-7)

Safety Data

• Hazard Codes: F,Xi,Xn
• Statements: 11-36/37/38-20-2017/11/20
• Safety Statements: 16-37/39-26-24/25
• RIDADR: UN 1237 3/PG 2
• WGK Germany: 3
• RTECS: NQ5425000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 547-63-7(Hazardous Substances Data)

Usage

Description

Methyl isobutyrate, also known as isobutyric acid methyl ester, is a naturally occurring organic compound that is found in various fruits and beverages. It is a clear, colorless liquid with a fruity (apple-pineapple) odor and a sweet flavor reminiscent of apricot. Methyl isobutyrate is soluble in water and miscible in common organic solvents, and it has a role as a metabolite.

Uses

1. Flavoring Agent:
Methyl isobutyrate is used as a flavoring agent in the food and beverage industry due to its sweet, ethereal, fruity, and juicy fruit taste characteristics at 35 ppm. It is commonly found in Russian champagnes and among the volatile components of strawberry juice, as well as in apple juice, banana, kumquat peel oil, blueberry, melon, papaya, pineapple, fried potato, starfruit, dill herb, cherimoya, kiwifruit, loquat, naranjilla fruit, and cape gooseberry.
2. Solvent and Organic Synthesis:
Methyl isobutyrate can be used as a solvent and in organic synthesis processes due to its chemical properties and solubility in common organic solvents.
3. Gas Chromatography Standard:
Methyl isobutyrate is used as a standard for gas chromatography, a technique used to separate and analyze volatile compounds in a mixture.
4. Mass Spectrometry Studies:
Radiofrequency-induced plasmas of methyl isobutyrate have been studied using mass spectrometry, which is a technique used to identify and quantify compounds based on their mass-to-charge ratio.

Preparation

Methyl isobutyrate can be synthesized by direct esterification of methanol with isobutyric acid.

Carcinogenicity

Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA.

InChI:InChI=1/C5H10O2/c1-4(2)5(6)7-3/h4H,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 2736-37-0 isobutyryl bromide 
• 67-56-1 methanol 
• 78-83-1 2-methyl-propan-1-ol 
• 74-96-4 ethyl bromide 
• 24985-51-1 (Z)-4-methoxy-5-methyl-hex-3-en-2-one 
• 60-29-7 diethyl ether 
• 1068-55-9 isopropylmagnesium chloride 
• 79-22-1 methyl chloroformate 
• 80-62-6 methacrylic acid methyl ester 
• 79-31-2 isobutyric Acid 
• 107-31-3 Methyl formate 
• 2589-57-3 dimethyl 2,2'-azobis(isobutyrate) 
• 71-43-2 benzene 

Downstream Products

• 78-82-0 Isobutyronitrile 
• 292638-85-8 acrylic acid methyl ester 
• 5162-48-1 2,2,4-trimethyl-3-pentanol 
• 59742-51-7 methyl 2,4-dimethyl-3-oxopentanoate 
• 34553-37-2 methyl 5-methyl-4-oxohexanoate 
• 594-60-5 2,3-dimethylbutan-2-ol 
• 54775-01-8 4-isopropyl-2,6-dimethyl-heptan-4-ol 
• 563-83-7 ISOPROPYLAMIDE 
• 22779-89-1 isobutyrohydroxamic acid 
• 80-62-6 methacrylic acid methyl ester 
• 68039-27-0 methyl 2-ethyl-3-oxohexanoate 
• 59906-54-6 2,5-dimethyl-4-nitro-3-hexanone 
• 13851-07-5 2,4,6,9-tetramethyldec-8-en-3,5-dione 
• 32998-99-5 5-isopropyl-4-phenyl-oxazole 

Relevant articles and documents

Boosting homogeneous chemoselective hydrogenation of olefins mediated by a bis(silylenyl)terphenyl-nickel(0) pre-catalyst

The isolable chelating bis(N-heterocyclic silylenyl)-substituted terphenyl ligand [SiII(Terp)SiII] as well as its bis(phosphine) analogue [PIII(Terp)PIII] have been synthesised and fully characterised. Their reaction with Ni(cod)2(cod = cycloocta-1,5-diene) affords the corresponding 16 VE nickel(0) complexes with an intramolecularη2-arene coordination of Ni, [E(Terp)E]Ni(η2-arene) (E = PIII, SiII; arene = phenylene spacer). Due to a strong cooperativity of the Si and Ni sites in H2activation and H atom transfer, [SiII(Terp)SiII]Ni(η2-arene) mediates very effectively and chemoselectively the homogeneously catalysed hydrogenation of olefins bearing functional groups at 1 bar H2pressure and room temperature; in contrast, the bis(phosphine) analogous complex shows only poor activity. Catalytic and stoichiometric experiments revealed the important role of the η2-coordination of the Ni(0) site by the intramolecular phenylene with respect to the hydrogenation activity of [SiII(Terp)SiII]Ni(η2-arene). The mechanism has been established by kinetic measurements, including kinetic isotope effect (KIE) and Hammet-plot correlation. With this system, the currently highest performance of a homogeneous nickel-based hydrogenation catalyst of olefins (TON = 9800, TOF = 6800 h?1) could be realised.

Iron-catalysed 1,2-aryl migration of tertiary azides

1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.

Process for the production of esters

A process for making methyl esters in high yields. The process comprises contacting aliphatic or aromatic aldehydes and methanol with a homogeneous dimeric ruthenium catalyst, to catalyze the dehydrogenative coupling between aliphatic or aromatic aldehydes and methanol. The reaction is highly selective (99.9%) toward the formation of methyl esters over homoesters and alcohols and operates at temperatures of less than 100° C. for 2-8 hours.