868-57-5

Basic information

• Product Name: Methyl 2-methylbutyrate
• Synonyms: 2-METHYLBUTYRIC ACID METHYL ESTER;METHYL METHYLETHYLACETATE;METHYL DL-2-METHYLBUTYRATE;METHYL-2-METHYLBUTANOATE;METHYL 2-METHYLBUTYRATE;DL-METHYLBUTYRIC ACID METHYL ESTER;DL-2-METHYLBUTYRIC ACID METHYL ESTER;FEMA 2719
• CAS NO: 868-57-5
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• EINECS: 212-778-0
• Product Categories: Organics;C6 to C7;Carbonyl Compounds;Esters;Certified Natural ProductsFlavors and Fragrances;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 868-57-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: -91°C (estimate)
• Boiling Point: 115 °C(lit.)
• Flash Point: 90 °F
• Appearance: /Liquid
• Density: 0.88 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.393(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1720409
• CAS DataBase Reference: Methyl 2-methylbutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-methylbutyrate(868-57-5)
• EPA Substance Registry System: Methyl 2-methylbutyrate(868-57-5)

Safety Data

• Statements: 10-11
• Safety Statements: 16-23-33-29-7/9
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 2
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 868-57-5(Hazardous Substances Data)

Usage

Description

Methyl 2-methylbutyrate has a pungent, fruity odor with a sweet, fruity, apple-like taste at low levels. May be prepared from a mixture of esters including methyl 2-methylbutyrate; is obtained from isobutene, CO, and methanol under pressure, or from butene, CO, and an acid catalyst under pressure.

Chemical Properties

Methyl-2-methylbutyrate has a sweet, fruity, apple-like odor and an apple-like taste at low concentrations.

Occurrence

The levorotatory and the racemic forms are known. Reported found in fresh strawberry juice, apple, apricot, sour cherry, melon, pineapple, peas, baked potato, peppermint oil, spearmint oil, thymus, durian (Durio zibethinus), olive, mushroom, starfruit, prickly pear, dill herb, cashew apple, cherimoya, loquat, mountain papaya, cape gooseberry and rooibus tea (Aspalathus linearis). bilberry, strawberry, and cheeses

Preparation

A mixture of esters including methyl-2-methylbutyrate is obtained from isobutene, CO and methanol under pressure, or from butene, CO and an acid catalyst under pressure.

Aroma threshold values

Detection: 0.92 to 4.4 ppb

Taste threshold values

Taste characteristics at 7.5 ppm: sweet, berry, pineapple, etherial, lifting, fruity, tutti-fruitti and ripe with a fatty, green nuance

General Description

Methyl 2-methylbutyrate is an important odor-active constituent of pineapple, apple, cantaloupe, cucumber and strawberries.

InChI:InChI=1/C6H12O2/c1-4-5(2)6(7)8-3/h5H,4H2,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 124-38-9 carbon dioxide 
• 78-76-2 s-butyl bromide 
• 41725-90-0 methyl 2-methylbut-2-enoate 
• 590-18-1 (Z)-2-Butene 
• 201230-82-2 carbon monoxide 
• 624-64-6 trans-2-Butene 
• 67-56-1 methanol 
• 116-53-0 2-Methylbutanoic acid 
• 5856-79-1 iso-butyl chloroformate 
• 17042-21-6 2-chloro-3-pentanone 
• 124-41-4 sodium methylate 
• 86659-57-6 2-methylbutanoyl fluoride 
• 106-98-9 1-butylene 

Downstream Products

• 13851-08-6 3,5,7,10-tetramethylundec-9-en-4,6-dione 
• 18641-70-8 2,4-Dimethyl-3-pentanone 
• 32444-33-0 methyl 2-ethyl-3-methylbutyrate 
• 5296-70-8 methyl 2-ethyl-2-methylbutyrate 
• 41487-73-4 Methyl-2-ethyl-2-methyloctanoat 
• 3234-80-8 methyl 2-ethyl-2-methylhexanoate 
• 91008-82-1 2-Isopropyl-capronsaeure-methylester 
• 137-32-6 (+/-)-2-methyl-1-butanol 
• 82504-42-5 methyl (2-chloromethyl)butanoate 
• 13888-03-4 methyl 4-chloro-2-methylbutanoate 
• 58308-68-2 methyl 2-chloro-2-methylbutanoate 
• 82504-44-7 chloromethyl 2-methylbutanoate 
• 815-75-8 methyl erythro-3-chloro-2-methylbutanoate 
• 815-75-8 methyl threo-3-chloro-2-methylbutanoate 

Relevant articles and documents

Synthesis and pyrolysis of two novel pyrrole ester flavor precursors

In order to develop the high-temperature-released pyrrole aroma, two novel flavors precursors of methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate and methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate were synthesized using glucosamine hydrochloride and methyl acetoacetate as raw materials through cyclization, oxidation, alkylation, reduction, and esterification. The target compounds were characterized by nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). Thermogravimetry (TG), differential scanning calorimeter (DSC) and the pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) methods were used to analyze the heating-stability of the target compounds, and the pyrolysis mechanism was inferred. Py-GC/MS results indicated that some fragrance compounds were formed during?thermal degradation such as 2-methylbutyric acid, 2-methylbutyrate, alkylpyrroles, and benzoic acid, which were important aroma components or flavor additives. This provided a theoretical reference for the application of pyrrole ester in cigarette and heat-processed food flavoring.

mCPBA-mediated dioxygenation of unactivated alkenes for the synthesis of 5-imino-2-tetrahydrofuranyl methanol derivatives

A mCPBA-mediated, metal-free, intramolecular dioxygenation reaction of unactivated alkenes is reported. In the presence of m-chlorobenzoic peracid, different unsaturated amide substrates could be cyclized via epoxide intermediates, producing the corresponding 5-imino-2-tetrahydrofuranyl methanol products in up to 94% yield at room temperature.

Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand

The invention discloses a method for preparing organic carboxylic ester by combined catalysis of an aryl bidentate phosphine ligand. The method comprises the following steps: under the action of a palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, carrying out a hydrogen esterification reaction on terminal olefin, carbon monoxide and alcohol so as to generate theorganic carboxylic ester with one more carbon than olefin. According to the invention, by adoption of the palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, good catalytic activity and selectivity for the hydrogen esterification reaction of the olefin are achieved, and olefin carbonylation to synthesize organic carboxylic ester can be efficiently catalyzed. Thearyl bidentate phosphine ligand has a rigid skeleton structure of a rigid ligand and the flexibility of a flexible ligand, so the aryl bidentate phosphine ligand has proper flexibility due to the characteristic that the aryl bidentate phosphine ligand is soft and rigid, and a most favorable coordination mode and a stable active structure in space are favorably formed. In addition, the aryl bidentate phosphine ligand has the advantages of high stability, simple and convenient synthesis method and the like; and a novel industrial technology is provided for production of organic carboxylate compounds.