109-19-3

Basic information

• Product Name: Butyl isovalerate
• Synonyms: butyl3-methylbutyrate;n-Butyl 3-methylbutanoate;n-Butyl isopentanoate;n-butylisopentanoate;N-BUTYL ISOVALERATE;ISOVALERIC ACID BUTYL ESTER;BUTYL-3-METHYLBUTANOATE;BUTYL ISOPENTANOATE
• CAS NO: 109-19-3
• Molecular Formula: C₉H₁₈O₂
• Molecular Weight: 158.24
• EINECS: 203-654-7
• Product Categories: A-B;Alphabetical Listings;Flavors and Fragrances;BI - BZAnalytical Standards;Fatty AcidsAnalytical Standards;A-BAlphabetic;Alpha Sort;B;Chemical Class;EstersOther Lipid Related Products;Lipid Analytical Standards;Solvents;Volatiles/ Semivolatiles;A-BFlavors and Fragrances;Certified Natural Products
• Mol File: 109-19-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: -92.8°C (estimate)
• Boiling Point: 175 °C(lit.)
• Flash Point: 145 °F
• Appearance: /
• Density: 0.858 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.09mmHg at 25°C
• Refractive Index: n20/D 1.409(lit.)
• BRN: 1752803
• CAS DataBase Reference: Butyl isovalerate(CAS DataBase Reference)
• NIST Chemistry Reference: Butyl isovalerate(109-19-3)
• EPA Substance Registry System: Butyl isovalerate(109-19-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 1993
• WGK Germany: 2
• RTECS: NY1502000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 109-19-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 109-19-3 differently. You can refer to the following data:
1. Butyl Isovalerate is a clear liquid.
2. Butyl isovalerate has an odor reminiscent of the isobutyl ester with a sweet, apple-like taste.

Occurrence

Reported found in the oil from leaves of Eriostemon coxii and Phebalium dentatum; also in apricot, banana, cheeses, olive and plum.

Preparation

By prolonged boiling of the acid with n-butyl alcohol in benzene in the presence of concentrated H2SO4.

Taste threshold values

Taste characteristics at 5 ppm: fruity, sweet, pineapple, ripe, musty and green with a slight cheesy nuance.

Potential Exposure

May be used as a specialty solvent; food additive

Shipping

UN3272 Ethers, n.o.s., Hazard class: 3; Labels: 3—Flammable liquid. UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3—Flammable liquid, Technical Name Required

Incompatibilities

Vapor may form explosive mixture with air. Reaction, possibly violent, on contact with oxidizers. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur)

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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

Upstream product

• 108-12-3 isopentanoyl chloride 
• 71-36-3 butan-1-ol 
• 201230-82-2 carbon monoxide 
• 115-11-7 isobutene 
• 109-65-9 1-bromo-butane 
• 503-74-2 3-methylbutyric acid 

Downstream Products

• 1351987-32-0 (2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate 
• 325154-22-1 2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid 
• 945462-61-3 (R)-methyl 2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate 
• 173433-57-3 (2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]-methyl}-3-methylbutyric acid 
• 910546-52-0 (S)-methyl-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate 
• 1351987-21-7 methyl-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate 
• 172900-71-9 (R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid 
• 173334-57-1 (2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide 
• 173338-07-3 tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate 

Relevant articles and documents

Catalytic synthesis of butyl isovalerate by br?nsted acidic ionic liquid under microwave irradiation

Butyl isovalerate was synthesized from isovaleric acid and butanol with ionic liquid as catalysts under microwave irradiation. The systematic study was investigated including of the effects of molar ratio of acid to alcohol, microwave power, amount of catalyst, microwave time and microwave temperature on the process. The optimum operation conditions were as follows: n(butanol):n(isovaleric acid) = 1.6:1, microwave power 500 W, amount of catalyst of 6 wt % to isovaleric acid, microwave time of 0.5 h and microwave temperature of 110 °C. The yield of butyl isovalerate could reach 92.1 % under the optimal operation conditions mentioned above. The excellent durability and recycle ability of ionic liquids were also addressed even after five times reused.

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.

Hydroalkoxycarbonylation of olefins in the presence of palladium phosphine complexes: High activity and regioselectivity

Several types of catalyst systems were examined in the olefin hydroalkoxycarbonylation reaction. The systems contained Pd(PPh 3)4, PdCl2(PPh3)2, or some other palladium compounds as a principal component. The second component (promoter) was p-toluenesulfonic acid or diphenyl(m-sulfophenyl)phosphine, which combines both the ligand and promoter functions. An important feature of these systems is their high activity in the hydroalkoxycarbonylation of ethylene and a high regioselectivity (83-100%) in the hydroalkoxycarbonylation of α-olefins with respect to linear products. Thus, it was unnecessary to introduce additional stabilizing ligands to augment the catalyst and promoter. The esters obtained can find application in the pharmaceutical industry and perfumery, as well as in other industries. Nauka/Interperiodica 2006.