2445-78-5

Basic information

• Product Name: 2-Methylbutyl 2-methylbutyrate
• Synonyms: 2-methyl-butanoicaci2-methylbutylester;Butanoic acid, 2-methyl-, 2-methylbutyl ester;Butanoicacid,2-methyl-,2-methylbutylester;Butyric acid, 2-methyl-, 2-methylbutyl ester;METHYL-2-BUTYL-2-METHYLBUTYRATE;DL-2-METHYLBUTYRIC ACID 2-METHYLBUTYL ESTER;FEMA 3359;2-METHYLBUTYL DL-2-METHYLBUTYRATE
• CAS NO: 2445-78-5
• Molecular Formula: C₁₀H₂₀O₂
• Molecular Weight: 172.26
• EINECS: 219-497-2
• Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 2445-78-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 70-72 °C11 mm Hg(lit.)
• Flash Point: 153 °F
• Appearance: colorless liquid
• Density: 0.855 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00329mmHg at 25°C
• Refractive Index: n20/D 1.411-1.417(lit.)
• CAS DataBase Reference: 2-Methylbutyl 2-methylbutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylbutyl 2-methylbutyrate(2445-78-5)
• EPA Substance Registry System: 2-Methylbutyl 2-methylbutyrate(2445-78-5)

Safety Data

• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 2445-78-5(Hazardous Substances Data)

Usage

Description

2-Methylbutyl 2-methylbutyrate is like fruit, berry, and apple. May be prepared by esterification of 2-methylbutanoic acid with 2-methyl-1-butanol; by condensation of isobutyraldehyde at 120°C.

Chemical Properties

2-Methylbutyl-2-methyl butyrate has a fruity, berry, apple like aroma.

Occurrence

Reported found as a component in the essential oil of hops (Humulus lupulus); also as the odorous component in Vaccinium vitis-idaea and in cocoa beans. Also reported found in apple, apricot, feyoa fruit (Feijoa sellowiana), melon, peppermint oil, spearmint oil, filberts, lovage leaf, myrtle leaf and berry and Roman chamomile oil

Preparation

By esterification of 2-methylbutanoic acid with 2-methyl-1-butanol; by condensation of isobutyraldehyde at 120°C

Taste threshold values

Taste characteristics at 30 ppm: sweet, fruity, pineapple character, estery with green, waxy and woody nuances

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 4319, 1987 DOI: 10.1021/jo00228a032

InChI:InChI=1/C10H20O2/c1-5-7-8(3)10(4,6-2)9(11)12/h8H,5-7H2,1-4H3,(H,11,12)/p-1

Upstream product

• 137-32-6 (+/-)-2-methyl-1-butanol 
• 116-53-0 2-Methylbutanoic acid 
• 96-17-3 2-Methylbutyraldehyde 

Downstream Products

• 137-32-6 (+/-)-2-methyl-1-butanol 

Relevant articles and documents

Rhodium-catalyzed synthesis of imines and esters from benzyl alcohols and nitroarenes: Change in catalyst reactivity depending on the presence or absence of the phosphine ligand

The [Rh(COD)Cl]2/xantphos/Cs2CO3 system efficiently catalyzes the reductive N-alkylation of aryl nitro compounds with alcohols by a borrowing-hydrogen strategy to afford the corresponding imine products in good to excellent yields. In the absence of xantphos, the [Rh(COD)Cl]2/Cs2CO3 catalytic system behaves as an effective catalyst for the dehydrogenative coupling of alcohols to esters, with nitrobenzene as a hydrogen acceptor. The reactivity of the rhodium catalytic system can be easily manipulated to selectively afford the imine or ester.

Acceptorless dehydrogenative coupling of alcohols catalysed by ruthenium PNP complexes: Influence of catalyst structure and of hydrogen mass transfer

Base-free catalytic acceptorless dehydrogenative homo-coupling of alcohols to esters under neat conditions was investigated using a combined organometallic synthesis and kinetic modelling approach. The considered bifunctional ruthenium aliphatic PNP complexes are very active, affording TONs up to 15,000. Notably, gas mass transfer issues were identified, which allowed us to rationalize previous observations. Indeed, the reaction kinetics are limited by the rate of transfer from the liquid phase to the gas phase of the hydrogen co-produced in the reaction. Mechanistically speaking, this relates to the interconverting couple amido monohydride/amino bishydride. Overcoming this by switching into the chemical regime leads to an initial turnover frequency increase from about 2000 up to 6100?h?1. This has a significant impact when considering assessment of novel or reported catalytic systems in this type of reaction, as overlooking of these engineering aspects can be misleading.

Efficient dimeric esterification of alcohols with NBS in water using l-proline as catalyst

The L-proline-catalyzed oxidation of aliphatic primary alcohols with N-bromosuccimide (NBS) in water at room temperature to afford the corresponding dimeric esters in good to excellent yields was described. This pathway of dimeric esterification was proved to be very simple and environmentally friendly.