542-55-2

Basic information

• Product Name: Isobutyl formate
• Synonyms: 2-Methyl-1-propyl formate;2-methyl-1-propylformate;2-Methylpropylmethanoate;Formic acid, 2-methylpropyl ester;Formicacid,2-methylpropylester;formicacid2-methylpropylester;Isobutylester kyseliny mravenci;isobutylesterkyselinymravenci
• CAS NO: 542-55-2
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 208-818-1
• Product Categories: C2 to C5;Carbonyl Compounds;Esters;Alphabetical Listings;Flavors and Fragrances;I-L
• Mol File: 542-55-2.mol

Chemical Properties

• Melting Point: -96 °C
• Boiling Point: 98.4 °C(lit.)
• Flash Point: 50 °F
• Appearance: COLORLESS LIQUID
• Density: 0.885 g/mL at 25 °C(lit.)
• Vapor Density: 3.52 (vs air)
• Vapor Pressure: 38.2mmHg at 25°C
• Refractive Index: n20/D 1.385(lit.)
• Storage Temp.: Flammables area
• Explosive Limit: 8.9%
• Water Solubility: Soluble in water
• Merck: 14,5143
• CAS DataBase Reference: Isobutyl formate(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutyl formate(542-55-2)
• EPA Substance Registry System: Isobutyl formate(542-55-2)

Safety Data

• Hazard Codes: F,C,Xi
• Statements: 11-34-36/37
• Safety Statements: 16-26-33-36/37/39-45-24-9
• RIDADR: UN 2393 3/PG 2
• WGK Germany: 2
• RTECS: LQ8650000
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 542-55-2(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Isobutyl formate is used as a flavoring agent for its fruity, slightly sweet, and fresh taste. It is commonly used in fruit flavors such as pear, raspberry, and other berry flavors, with applications in beverages, ice cream, candy, and baked goods at concentrations of 2–18 ppm.
Used in Perfumery:
Isobutyl formate is also used as a solvent and in the production of perfumes due to its pleasant fruity odor.
Used in Food Industry:
Isobutyl formate is found in various food items such as pineapple, apple, vinegar, wheat bread, beer, cognac, and rum, contributing to their unique flavors and aromas.
Chemical Properties:
Isobutyl formate is a clear, colorless to light yellow liquid with a fruity, ether-like odor and a sweet taste reminiscent of rum. It is less dense than water and has a flash point of 60°F. Vapors of isobutyl formate are heavier than air and may be narcotic and irritating in high concentrations.
Storage:
Isobutyl formate should be stored in glass or tin containers to ensure its stability and prevent any potential reactions with other materials.

Preparation

From isobutyl alcohol and carbon monoxide in the presence of sodium isobutylate at 110°C and 400 atm

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Isobutyl formate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Biochem/physiol Actions

Taste at 10 ppm

Purification Methods

Wash the formate with saturated aqueous NaHCO3, in the presence of saturated NaCl solution until no further reaction occurs, then with saturated aqueous NaCl, dry (MgSO4) and fractionally distil it. [Beilstein 2 H 21, 2 I 18, 2 II 30, 2 III 41, 2 IV 29.]

InChI:InChI=1/C5H10O2/c1-5(2)3-7-4-6/h4-5H,3H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 78-83-1 2-methyl-propan-1-ol 
• 64-18-6 formic acid 
• 109-53-5 isobutyl vinyl ether 
• 107-31-3 Methyl formate 
• 110-05-4 di-tert-butyl peroxide 
• 76050-98-1 methoxyisobutoxymethane 
• 1749-19-5 phenyl(1-phenylethylidene)amine 
• 574-45-8 N-(diphenylmethylidene)phenylamine 
• 27126-13-2 N-tert-butyl-1,1-diphenylmethanimine 
• 590-86-3 isovaleraldehyde 
• 18296-01-0 triethylsilyl formate 
• 16754-49-7 triisobutyl orthoformate 
• 2051-90-3 Dichlorodiphenylmethane 

Downstream Products

• 10285-87-7 N-isopentyl-formamide 
• 110-19-0 2-methylpropyl acetate 
• 253185-03-4 tert-butylbenzene 
• 93-58-3 benzoic acid methyl ester 
• 120-50-3 isobutyl benzoate 
• 71-43-2 benzene 
• 60068-11-3 4-Isobutoxy-6,6-dimethyl-2-oxo-cyclohex-3-enecarbaldehyde 
• 60068-08-8 4-Isobutoxy-2-oxo-cyclohex-3-enecarbaldehyde 
• 60068-10-2 4-Isobutoxy-3-methyl-2-oxo-cyclohex-3-enecarbaldehyde 
• 1012-72-2 1,4-di-tert-butylbenzene 
• 64-18-6 formic acid 
• 78-83-1 2-methyl-propan-1-ol 
• 3085-54-9 N-(4-methylphenyl)formamide 
• 103-70-8 Formanilid 

Relevant articles and documents

PROCESS FOR MAKING FORMIC ACID UTILIZING LOWER-BOILING FORMATE ESTERS

Disclosed is a process for recovering formic acid from a formate ester of a C3 to C4 alcohol. Disclosed is also a process for producing formic acid by carbonylating a C3 to C4 alcohol, hydrolyzing the formate ester of the alcohol, and recovering a formic acid product. The alcohol may be dried and returned to the reactor. The process enables a more energy efficient production of formic acid than the carbonylation of methanol to produce methyl formate.

Method for preparing formate-type compound

The invention discloses a method for preparing a formate-type compound. The method comprises the following steps of: adopting an alcohol-type compound and 1,3-dihydroxyacetone as reaction raw materials, and under the existence of a composite catalyst and an oxidant, reacting for 2-48 hours in a reaction medium in a reactor at a reaction temperature of 25-100 DEG C so as to obtain the formate-typecompound. The method disclosed by the invention is simple, and is mild in reaction condition, and by the method, a target product can be obtained by low cost and high yield; the used catalyst has highcatalytic activity, and is easily separated from a reaction system to be repeatedly used; the whole process is environment-friendly, and the reaction raw material (1,3-dihydroxyacetone) is easily converted from a side product (glycerol) of biodiesel, so that the utilization of the glycerol is promoted.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

MONOMER, POLYMER, RESIST COMPOSITION, AND PATTERNING PROCESS

A polymer comprising recurring units derived from a (meth)acrylate monomer of tertiary ester type having branched alkyl on alicycle is used to form a resist composition. When subjected to exposure, PEB and organic solvent development, the resist composition is improved in dissolution contrast.

Nickel-catalyzed hydrosilylation of CO2 in the Presence of Et3B for the synthesis of formic acid and related formates

The reaction of CO2 with Et3SiH catalyzed by the nickel complex [(dippe)Ni(μ-H)]2 (1) afforded the reduction products Et3SiOCH2OSiEt3 (12%), Et 3SiOCH3 (3%), and CO, which were characterized by standard spectroscopic methods. Part of the generated CO was found as the complex [(dippe)Ni(CO)]2 (2), which was characterized by single-crystal X-ray diffraction. When the same reaction was carried out in the presence of a Lewis acid, such as Et3B, the hydrosilylation of CO2 efficiently proceeded to give the silyl formate (Et3SiOC(O)H) in high yields (85-89%), at 80 C for 1 h. Further reactivity of the silyl formate to yield formic acid, formamides, and alkyl formates was also investigated.

Hypervalent λ3-bromane strategy for Baeyer-Villiger oxidation: Selective transformation of primary aliphatic and aromatic aldehydes to formates, which is missing in the classical Baeyer-Villiger oxidation

A conceptually distinct, modern strategy for Baeyer-Villiger oxidation (BVO) was developed. Our novel method involves initial hydration of water to carbonyl compounds, followed by ligand exchange of hypervalent aryl-λ3-bromane on bromane(III) with the resulting hydrate, yielding a new type of activated Criegee intermediate. The intermediate undergoes BV rearrangement and produces an ester via facile reductive elimination of an aryl-λ3-bromanyl group, because of the hypernucleofugality. The novel strategy makes it possible to induce selectively the BV rearrangement of straight chain primary aliphatic as well as aromatic aldehydes, which is missing in the classical BVO: for instance, octanal and benzaldehyde afforded rearranged formate esters with high selectivity (>95%) under our conditions, while the attempted classical BVO produced only carboxylic acids. This firmly establishes the powerful nature of new methodology for BVO.

Oxidative C-C bond cleavage of primary alcohols and vicinal diols catalyzed by H5PV2Mo10O40 by an electron transfer and oxygen transfer reaction mechanism

Primary alcohols such as 1-butanol were oxidized by the H5PV2Mo10O40 polyoxometalate in an atypical manner. Instead of C-H bond activation leading to the formation of butanal and butanoic acid, C-C bond cleavage took place leading to the formation of propanal and formaldehyde as initial products. The latter reacted with the excess 1-butanol present to yield butylformate and butylpropanate in additional oxidative transformations. Kinetic studies including measurement of kinetic isotope effects, labeling studies with 18O labeled H5PV2Mo10O40, and observation of a prerate determining step intermediate by 13C NMR leads to the formulation of a reaction mechanism based on electron transfer from the substrate to the polyoxometalate and oxygen transfer from the reduced polyoxometalate to the organic substrate. It was also shown that vicinal diols such as 1,2-ethanediol apparently react by a similar reaction mechanism. Copyright

PROCESS FOR PREPARATION OF FORMATE ESTERS OR METHANOL AND CATALYST THEREFOR

A production process and a catalyst are provided, which can be less decreased in activity of the catalyst even when CO2, water and the like are present in the starting material and/or the reaction system, and which can produce a formic ester or a methanol at a low temperature and a low pressure. The present invention relates to a process for producing methanol, comprising reacting carbon monoxide with an alcohol in the presence of an alkali metal-type catalyst, and/or an alkaline earth metal-type catalyst to produce a formic ester, wherein a hydrogenolysis catalyst of formic ester and hydrogen are allowed to be present together in the reaction system to hydrogenate the produced formic ester and thereby obtain a methanol.

Preparation of optically active 2-halopropionic acids

The present invention relates to a process for the preparation of optically active 2--halopropionic acids, in which the corresponding optically active alkyl 2--halopropionates are caused to react with a carboxylic acid at elevated temperature in a transacylation reaction with the formation of the optically active 2--halopropionic acid and the alkyl carboxylate, and the optically active 2--halopropionic acid obtained is separated from the reaction mixture. The optically active products produced are important intermediates for the preparation of plant protectants and pharmaceuticals.