15706-73-7

Basic information

• Product Name: FEMA 3393
• Synonyms: N-BUTYL 2-METHYLBUTYRATE;METHYL-2-BUTYL-BUTYRATE;BUTYL METHYL 2 BUTYRATE;BUTYL 2-METHYLBUTYRATE;FEMA 3393;2-METHYLBUTYRIC ACID BUTYL ESTER;2-methyl-butanoicacibutylester;Butanoic acid, 2-methyl-, butyl ester
• CAS NO: 15706-73-7
• Molecular Formula: C₉H₁₈O₂
• Molecular Weight: 158.24
• EINECS: 256-973-9
• Product Categories: A-B;Alphabetical Listings;Flavors and Fragrances;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 15706-73-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 174-176 °C
• Boiling Point: 173-176 °C730 mm Hg(lit.)
• Flash Point: 140 °F
• Appearance: Clear colourless liquid
• Density: 0.863 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.09mmHg at 25°C
• Refractive Index: n20/D 1.409(lit.)
• BRN: 1702551
• CAS DataBase Reference: FEMA 3393(CAS DataBase Reference)
• NIST Chemistry Reference: FEMA 3393(15706-73-7)
• EPA Substance Registry System: FEMA 3393(15706-73-7)

Safety Data

• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 15706-73-7(Hazardous Substances Data)

Usage

Description

FEMA 3393, also known as n-Butyl-2-methylbutyrate, is a clear colorless liquid with a fruity odor and cocoa undertones. It is a naturally occurring compound that can be found in various fruits such as strawberry, fresh apple, apple juice, apricot, banana, sweet cherry, and melon.

Uses

Used in Flavor Industry:
FEMA 3393 is used as a flavoring agent for its fruity aroma with cocoa undertones. It is commonly utilized in the creation of various food and beverage products to enhance their flavor profile.
Used in Fragrance Industry:
FEMA 3393 is also used as a fragrance ingredient due to its pleasant and distinctive scent. It can be found in a variety of personal care and cosmetic products, such as perfumes, colognes, and body lotions, to provide a unique and appealing fragrance.
Aroma Threshold Values:
The detection threshold of FEMA 3393 is between 17 to 87 parts per billion (ppb), indicating that it can be detected at very low concentrations, making it an effective ingredient in both the flavor and fragrance industries.

InChI:InChI=1/C9H18O2/c1-4-6-7-11-9(10)8(3)5-2/h8H,4-7H2,1-3H3/t8-/m1/s1

Synthetic route

2-Methylbutanoic acid (116-53-0, 600-07-7) + butan-1-ol (71-36-3) → n-butyl 2-methylbutanoate (15706-73-7)

Conditions	Yield
With pyridine; dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3.5h;	69.6%

1-bromo-butane (109-65-9) + 2-Methylbutanoic acid (116-53-0, 600-07-7) → n-butyl 2-methylbutanoate (15706-73-7)

Conditions	Yield
With ISOPROPYLAMIDE; tetra(n-butyl)ammonium hydroxide at 100℃; for 1h; 1) pH 10 - 12;

tetramethylammonium phenyltrimethylborate + 2-methyl-butyl acrylate (97-88-1) → n-butyl 2-methylbutanoate (15706-73-7)

Conditions	Yield
With benzophenone In acetonitrile; benzene at 25℃; Irradiation; Yield given;

(E)-but-2-enol (504-61-0) + 2-Methylbutyraldehyde (96-17-3, 57456-98-1) → 2-Methyl-butyric acid (E)-but-2-enyl ester + n-butyl 2-methylbutanoate (15706-73-7)

Conditions	Yield
With potassium carbonate; bis(1,5-cyclooctadiene)diiridium(I) dichloride In toluene at 20℃; for 12h;

carbon monoxide (201230-82-2) + tri-sec-butylindium (101749-61-5) + butan-1-ol (71-36-3) → n-butyl 2-methylbutanoate (15706-73-7)

Conditions	Yield
With 6,6'-bis(diphenylphosphanyl)-2,2',3,3'-tetrahydro-5,5'-bi-1,4-benzodioxin; bis-triphenylphosphine-palladium(II) chloride; Desyl chloride at 60℃; under 2585.81 Torr; for 36h;	60 %Chromat.

Upstream product

• 109-65-9 1-bromo-butane 
• 116-53-0 2-Methylbutanoic acid 
• 97-88-1 2-methyl-butyl acrylate 
• 504-61-0 (E)-but-2-enol 
• 96-17-3 2-Methylbutyraldehyde 
• 201230-82-2 carbon monoxide 
• 101749-61-5 tri-sec-butylindium 
• 71-36-3 butan-1-ol 

Relevant articles and documents

Nematicidal activity of natural ester compounds and their analogues against pine wood nematode, bursaphelenchus xylophilus

In this study, we evaluated the nematicidal activity of natural ester compounds against the pine wood nematode, Bursaphelenchus xylophilus, to identify candidates for the development of novel, safe nematicides. We also tested the nematicidal activity of synthesized analogues of these ester compounds to determine the structure-activity relationship. Among 28 ester compounds tested, isobutyl 2-methylbutanoate, 3-methylbutyl 2-methylbutanoate, 3-methylbutyl tiglate, 3-methyl-2-butenyl 2- methylbutanoate, and pentyl 2-methylbutanoate showed strong nematicidal activity against the pine wood nematode at a 1 mg/ mL concentration. The other ester compounds showed weak nematicidal activity. The LC50 values of 3-methylbutyl tiglate, isobutyl 2-methylbutanoate, 3-methylbutyl 2-methylbutanoate, 3-methyl-2-butenyl 2-methylbutanoate, and pentyl 2- methylbutanoate were 0.0218, 0.0284, 0.0326, 0.0402, and 0.0480 mg/mL, respectively. The ester compounds described herein merit further study as potential nematicides for pine wood nematode control.

Iridium-catalyzed oxidative esterification reaction of aliphatic aldehydes and olefinic alcohols with precoordination of the double bond of alcohols to iridium

A novel iridium-catalyzed oxidative esterification reaction of aliphatic aldehydes and olefinic alcohols in toluene was found under mild conditions of [IrCl(cod)]2 (5 mol %) in combination with K2CO 3 (10 mol %) at rt.

Quarternary Ammonium Salts for Butylation and Mass Spectral Identification of Volatile Organic Acids

The esterification method described by Greeley (J.Chromatogr. 1974, 88, 229) was modified to overcome the problem of volatile acid evaporation during sample workup procedures.After solvent extraction from an aqueous sample, the acids were converted to their butyl ester derivatives in a two step process.Firstly, an involatile quarternary ammonium salts was formed which allowed concentration by solvent evaporation without loss of volatile acids.The acid salts were then converted to butyl esters by heating in the presence of n-butyl bromide and the esters were separated on a support- coated open tabular (SCOT) OV17 capillary column.The recovery and butylation yield were shown to be quantitative for isobutyric acid and the linearities and limits of detection are given for the five C4-C5 aliphatic acids.The mass spectra of butyl esters contain abundant rearrangement ions not present in methyl, ethyl, trimethylsilyl, or aryl esters which enable their rapid identification.The method was applied to the analysis of volatile urinary acids from a patient with Maple Syrup Urine Disease and showed conclusively the presence of both 2-methylbutyric and isovaleric acids.