53774-20-2

Basic information

• Product Name: 2-METHYL-3-BUTENOIC ACID
• Synonyms: CH2=CHCH(CH3)COOH;3-Butenoic acid, 2-Methyl-;2-Methyl-3-butenoie acid
• CAS NO: 53774-20-2
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.115820
• Mol File: 53774-20-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 20.44°C (estimate)
• Boiling Point: 42-43 °C/0.1 mmHg(lit.)
• Flash Point: 76 °C
• Appearance: /
• Density: 0.968 g/mL at 20 °C
• Vapor Pressure: 0.512mmHg at 25°C
• Refractive Index: n20/D 1.424
• Storage Temp.: 2-8°C
• PKA: 4.36±0.10(Predicted)
• CAS DataBase Reference: 2-METHYL-3-BUTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-3-BUTENOIC ACID(53774-20-2)
• EPA Substance Registry System: 2-METHYL-3-BUTENOIC ACID(53774-20-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 1760
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 53774-20-2(Hazardous Substances Data)

Usage

General Description

2-Methyl-3-butenoic acid, also known as alpha-isopropylacrylic acid, is a colorless to light yellow liquid with a fruity odor. It is a carboxylic acid with the chemical formula C5H8O2. 2-METHYL-3-BUTENOIC ACID is used in the manufacture of flavors and fragrances, as well as in the production of polymers and pharmaceuticals. It is also known for its potential use as a precursor to synthesize other chemicals, such as pharmaceutical intermediates and natural products. 2-Methyl-3-butenoic acid is known to be a skin and eye irritant and should be handled with caution in a controlled laboratory environment.

InChI:InChI=1/C5H8O2/c1-3-4(2)5(6)7/h3-4H,1H2,2H3,(H,6,7)

Upstream product

• 106-98-9 1-butylene 
• 1822-71-5 n-pentylsodium 
• 109-66-0 pentane 
• 107-01-7 butene-2 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 124-38-9 carbon dioxide 
• 106-99-0 buta-1,3-diene 
• 1617-32-9 (E)-3-pentenoic acid 
• 4894-61-5 trans-but-2-enyl chloride 
• 563-52-0 2-chloro-3-butene 
• 12087-70-6 (η3-crotyl)bis(cyclopentadienyl)titanium 
• 201230-82-2 carbon monoxide 
• 80-59-1 Tiglic acid 
• 78-76-2 s-butyl bromide 

Downstream Products

• 80-59-1 Tiglic acid 
• 115476-39-6 (3S,5S)-3-Methyl-5-((E)-styryl)-dihydro-furan-2-one 
• 115476-39-6 (3R,5S)-3-Methyl-5-((E)-styryl)-dihydro-furan-2-one 
• 37526-85-5 benzyl 2-methylbut-3-enoate 
• 24560-24-5 2-methyl-3-butenoic acid chloride 
• 4516-90-9 2-methyl-3-buten-1-ol 
• 80188-12-1 2-methyl-N-phenylbut-3-enamide 
• 182699-77-0 (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one 
• 182699-81-6 (3S,3aS,7aS)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one 
• 182699-80-5 (3S,3aR,7aS)-3,6-dimethyl-3a,4,5,7a-tetrahydro-1-benzofuran-2(3H)-one 
• 182699-78-1 (3R,3aR,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one 
• 51037-05-9 2-methyl-4-(p-tolyl)butanoic acid 
• 32231-50-8 (R)-2-methylbutyric acid 
• 1730-91-2 (S)-2-Methylbutyric acid 

Relevant articles and documents

Nickel-catalyzed electrocarboxylation of allylic halides with CO2

Nickel-catalyzed regioselective electrocarboxylation of allylic halides with CO2at atmospheric pressure has been developed by adjusting reaction parameters, including catalyst, solvent, temperature and additive. β,γ-Unsaturated carboxylic acids were obtained in moderate to good yields and with high chain selectivity. This reaction shows tolerance to functional groups. In addition, cyclic voltammetry was performed to provide the possible mechanism of nickel-catalyzed CO2allylation.

By using a palladium amidocarbonyl manufacturing method

The present invention relates to a process for the preparation of beta- or gamma-unsaturated or saturated carboxylic acids. It relates more particularly to the hydroxycarbonylation of an organic compound comprising a conjugated unsaturation, such as butadiene, by the action of carbon monoxide and water in the presence of a palladium-based catalyst. The carboxylic acids thus obtained are preferably pentenoic acids. According to the invention, the reaction medium after the end of the hydroxycarbonylation stage is treated with hydrogen to reduce the palladium present in the 2+ oxidation state to palladium in the zero oxidation state and the precipitated palladium is recovered.

Conjugate addition of organolithium reagents to α,β-unsaturated carbocyclic acids

Conjugate addition of primary, secondary, tertiary alkyi and phenyl lithium reagents to 2-alkenoic acids affords good yields of branched saturated carboxylic acids. Methyl groups at the α- and β-carbon of the 2-alkenoic acid decrease reactivity as acceptors, and foster deprotonation, respectively. The lithium enediolate resulting from the conjugate addition can react with electrophiles. PM3 calculations are in agreement with the substituent effects.