504-85-8

Basic information

• Product Name: 4-METHYL-3-PENTENOIC ACID
• Synonyms: 4-methyl-3-pentenoicaci;RARECHEM AL BO 1803;4-METHYL-3-PENTENOIC ACID;3-Pentenoic acid, 4-methyl-;4-METHYLPENT-3-ENOICACID;Pyroterebic acid;4,4-Dimethyl-3-butenoic acid;4-Methyl-3-penten-1-oic acid
• CAS NO: 504-85-8
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Mol File: 504-85-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 98 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 208℃
• Flash Point: 105℃
• Appearance: /
• Density: 0.987
• Vapor Pressure: 0.0906mmHg at 25°C
• Refractive Index: 1.454
• PKA: pK1:4.60 (25°C)
• CAS DataBase Reference: 4-METHYL-3-PENTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-3-PENTENOIC ACID(504-85-8)
• EPA Substance Registry System: 4-METHYL-3-PENTENOIC ACID(504-85-8)

Safety Data

• Hazardous Substances Data: 504-85-8(Hazardous Substances Data)

Usage

Description

4-Methyl-3-Pentenoic Acid, an organic compound with the molecular formula C6H10O2, is a carboxylic acid characterized by a five-carbon chain with a methyl group and a carboxylic acid functional group. This colorless liquid at room temperature, with a molecular weight of 114.14 g/mol, is flammable and requires careful handling and adherence to safety precautions in laboratory or industrial settings.

Uses

Used in Pharmaceutical Industry:
4-Methyl-3-Pentenoic Acid is used as a precursor in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex organic molecules that can have medicinal properties.
Used in Agrochemical Industry:
4-Methyl-3-Pentenoic Acid is used as a precursor in the synthesis of agrochemicals, playing a role in the development of compounds that can be used in agricultural applications such as pesticides or herbicides.
Used in Industrial Chemical Production:
4-Methyl-3-Pentenoic Acid is utilized in the production of various industrial chemicals, highlighting its versatility and importance in the chemical industry for creating a range of end products.

InChI:InChI=1/C6H10O2/c1-5(2)3-4-6(7)8/h3H,4H2,1-2H3,(H,7,8)

Upstream product

• 5980-21-2 3-hydroxy-4-methylpentanoic acid 
• 141-82-2 malonic acid 
• 78-84-2 isobutyraldehyde 
• 115-18-4 2-methyl-3-buten-2-ol 
• 201230-82-2 carbon monoxide 
• 467-72-1 trans-isohumulone 
• 147-85-3 L-proline 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 26472-41-3 humulone 
• 2938-48-9 3,3-dimethyl glutaric acid anhydride 
• 7446-70-0 aluminium trichloride 
• 67-66-3 chloroform 
• 78-79-5 isoprene 
• 79353-05-2 1-diethylamino-1-piperidino-4-methyl-1,3-pentadiene 

Downstream Products

• 141-82-2 malonic acid 
• 75-07-0 acetaldehyde 
• 67-64-1 acetone 
• 3123-97-5 dihydro-5,5-dimethyl-2(3H)-furanone 
• 23203-48-7 4-methyl-4-(p-methoxyphenyl)pentanoic acid 
• 141484-12-0 (+)-(1R)-N,4-dimethyl-N-(4-methyl-3-cyclohexenyl)-3-pentenamide 
• 141484-04-0 (-)-(1S)-N,4-dimethyl-N-(4-methyl-3-cyclohexenyl)-3-pentenamide 
• 132280-00-3 dihydro-4-acetoxy-5,5-dimethyl-2(3H)-furanone 
• 68258-20-8 2-(2,2-dimethylcyclopropyl)acetic acid 
• 3568-90-9 deoxylapachol 
• 5594-02-5 2-(3-methyl-2-buten-1-yl)-2,5-cyclohexadiene-1,4-dione 
• 57620-99-2 2-acetyllapachol 
• 646-07-1 4-Methylpentanoic acid 
• 114475-19-3 4-methyl-3-pentenoic acid phenylamide 

Relevant articles and documents

Palladium-Catalyzed Low Pressure Carbonylation of Allylic Alcohols by Catalytic Anhydride Activation

A direct carbonylation of allylic alcohols has been realized for the first time with high catalyst activity at low pressure of CO (10 bar). The procedure is described in detail for the carbonylation of E-nerolidol, an important step in a new BASF-route to (?)-ambrox. Key to high activities in the allylic alcohol carbonylation is the finding that catalytic amounts of carboxylic anhydride activate the substrate and are constantly regenerated with carbon monoxide under the reaction conditions. The identified reaction conditions are transferrable to other substrates as well.

Oxidation of isohumulones induces the formation of carboxylic acids by hydrolytic cleavage

The degradation of isohumulones in mechanistic experiments was investigated. Incubation of trans-isohumulone in the presence of l-proline led to the formation of carboxylic acids and their corresponding proline amides. In the context of isohumulones unknown amides were verified first in model incubations and then in beer for the first time by comparison with authentic reference standards via LC-MS analyses. Carboxylic acids and amides were formed preferably under oxidative conditions and increasing pH. Stable isotope experiments excluded the incorporation of molecular oxygen into carboxylic acids, strongly indicating a hydrolytic mechanism via β-dicarbonyl cleavage. The proposed mechanism includes oxidation and thereby incorporation of molecular oxygen to the isohumulone ring structure followed by hydrolytic cleavage leading to acids and amides.

SiO2 catalysed expedient synthesis of [E]-3-alkenoic acids in dry media

Aliphatic aldehydes with α-hydrogens and malonic acid undergo decarboxylative condensation on the surface of SiO2 when subjected to microwave irradiation generating βγ-unsaturated acids in high yields.