13991-37-2

Basic information

• Product Name: TRANS-2-PENTENOIC ACID
• Synonyms: (E)-pent-2-en-1-oicacid;2-Pentenoic acid, (E)-;2-Pentenoicacid,(E)-;2-PENTENOIC ACID;FEMA 4193;(E)-2-PENTENOIC ACID;BETA-ETHYL ACRYLIC ACID;TRANS-PENT-2-ENOIC ACID
• CAS NO: 13991-37-2
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 237-791-9
• Mol File: 13991-37-2.mol

Chemical Properties

• Melting Point: 9-11 °C(lit.)
• Boiling Point: 106 °C20 mm Hg(lit.)
• Flash Point: 102 °C
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.99 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 60g/l
• PKA: pK1:4.70 (25°C)
• Explosive Limit: 1.6%(V)
• BRN: 1720312
• CAS DataBase Reference: TRANS-2-PENTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2-PENTENOIC ACID(13991-37-2)
• EPA Substance Registry System: TRANS-2-PENTENOIC ACID(13991-37-2)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• RTECS: SB2750000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 13991-37-2(Hazardous Substances Data)

Usage

Chemical Description

Trans-2-pentenoic acid is an organic compound with the formula C5H8O2.

Uses

Used in Pharmaceutical Industry:
TRANS-2-PENTENOIC ACID is used as a key component in the preparation of new nonsteroidal human androgen receptor (hAR) agonists. These agonists are derived from an hAR antagonist pharmacophore, 2(1H)-piperidino[3,2-g]quinolinone, and have potential applications in the development of novel therapeutic agents for various medical conditions.
Used in Flavor and Fragrance Industry:
Due to its unique sour caramellic aroma and cheese-like odor, TRANS-2-PENTENOIC ACID can be utilized as a flavoring agent in the food and beverage industry. It can be added to various products to enhance their taste and aroma, providing a distinct and appealing sensory experience for consumers.
Used in Research and Development:
TRANS-2-PENTENOIC ACID can also be employed in research and development for the study of its chemical properties and potential applications in various fields. Its sour acetic buttery taste and medium strength odor make it an interesting compound for further investigation and potential use in the development of new products and technologies.

InChI:InChI=1/C5H8O2/c1-2-3-4-5(6)7/h3-4H,2H2,1H3,(H,6,7)/p-1/b4-3+

Upstream product

• 1576-86-9 2-pentenal 
• 141-82-2 malonic acid 
• 123-38-6 propionaldehyde 
• 64-19-7 acetic acid 
• 4436-74-2 hex-3-ene-1,6-dicarboxylic acid 
• 5963-77-9 pent-2-ynoic acid 
• 42482-20-2 3-hydroxyvaleric acid 
• 91-22-5 quinoline 
• 64-18-6 formic acid 
• 31844-98-1 (E)/(Z)-1-bromo-1-butene 
• 75-07-0 acetaldehyde 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 591-80-0 pent-4-enoic acid 
• 1576-96-1 (E)-2-penten-1-ol 

Downstream Products

• 31844-98-1 (E)/(Z)-1-bromo-1-butene 
• 33698-85-0 (E)-pent-2-enoyl chloride 
• 42482-20-2 3-hydroxyvaleric acid 
• 124-38-9 carbon dioxide 
• 7732-18-5 water 
• 802294-64-0 propionic acid 
• 34042-00-7 (2SR,3RS)-2-amino-3-hydroxypentanoic acid 
• 2076-43-9 (2SR,3SR)-2-amino-3-hydroxypentanoic acid 
• 2938-98-9 2-methyl-1,4-butandiol 

Relevant articles and documents

Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols

A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.

Regioselective Isomerization of Terminal Alkenes Catalyzed by a PC(sp3)Pincer Complex with a Hemilabile Pendant Arm

We describe an efficient protocol for the regioselective isomerization of terminal alkenes employing a previously described bifunctional Ir-based PC(sp3)complex (4) possessing a hemilabile sidearm. The isomerization, catalyzed by 4, results in a one-step shift of the double bond in good to excellent selectivity, and good yield. Our mechanistic studies revealed that the reaction is driven by the stepwise migratory insertion of Ir?H species into the terminal double bond/β-H elimination events. However, the selectivity of the reaction is controlled by dissociation of the hemilabile sidearm, which acts as a selector, favoring less sterically hindered substrates such as terminal alkenes; importantly, it prevents recombination and further isomerization of the internal ones.

Palladium catalyzed carbonylations of alkenyl halides with formic acid to get corresponding Α,Β-unsaturated carboxylic acids and esters

Palladium-catalysed carbonylation reactions have been developed in the presence of formic acid as carbon monoxide source. α,β-Unsaturated carboxylic acids and esters were synthesized by the transformation of alkenyl halides in moderate to good yields. The selection of the base proved to be crucial regarding the reaction outcome. A set of various substrates were proven under optimised reaction conditions. Compared to aliphatic alcohols, phenols showed excellent reactivity as O-nucleophiles.

Lithium perchlorate catalyzed electrophilic activation: A convenient one-pot synthesis of trans-cinnamic acids

Background: Currently perchlorate catalysts gain much attention in organic synthesis due to ease of operation, wide applicability, high yield, and economy. This is evident through increasing number of citation related to their application in industry as well as other allied fields. The aim of this paper is to describe a methodology using lithium perchlorate to catalyze the Knoevenagel condensation reaction for the synthesis of biologically active trans-cinnamic acid in good to excellent yield. Methods: We discuss herein an economic, user-friendly one-pot synthesis of trans-cinnamic acids by refluxing a mixture of a malonic acid with aryl aldehyde in pyridine. The product was easily isolated via filtration and thereafter washed and characterized by spectroscopic methods. Results: This method is robust, stereoselective and high yielding. It can be utilized to synthesize a wide array of trans-cinnamic acids in good to excellent yield using 20% of lithium perchlorate catalyst. It is also useful in the synthesis of aliphatic α,β-unsaturated carboxylic acid. Conclusion: The role of lithium perchlorate as a mild catalyst in the synthesis of trans-cinnamic acid was explored. The reactions afforded a good yield of various products with simpler isolation.

Selective Isomerization of Terminal Alkenes to (Z)-2-Alkenes Catalyzed by an Air-Stable Molybdenum(0) Complex

Positional and stereochemical selectivity in the isomerization of terminal alkenes to internal alkenes is observed using the cis-Mo(CO)4(PPh3)2 precatalyst. A p-toluenesulfonic acid (TsOH) cocatalyst is essential for catalyst activity. Various functionalized terminal alkenes have been converted to the corresponding 2-alkenes, generally favoring the Z isomer with selectivity as high as 8:1 Z:E at high conversion. Interrogation of the catalyst initiation mechanism by 31P NMR reveals that cis-Mo(CO)4(PPh3)2 reacts with TsOH at elevated temperatures to yield a phosphine-ligated Mo hydride (MoH) species. Catalysis may proceed via 2,1-insertion of a terminal alkene into a MoH group and stereoselective β-hydride elimination to yield the (Z)-2-alkene.

A CATALYST FOR THE CARBONYLATION OF ALKENES

The present application relates to a metal complex of Formula (I) and a catalyst composition for the carbonylation of alkenes comprising the metal complex, wherein the metal is a group 10 element such as palladium, platinum or nickel, and the complex comprises a bidentate phosphine ligand. The present invention also relates to a process for the preparation of a dicarboxylic acid or ester thereof from an alkenoic acid or ester thereof, or a process for the preparation of a carboxylic acid or ester thereof from an alkene or alkenoic acid with high selectivity and activity using said metal complex or catalyst composition. The present application also relates to a method of preparing Nylon 6-6 comprising the step of copolymerising adipic acid with hexamethylenediamine.

PROCESS FOR PREPARING MONO AND DICARBOXYLIC ACIDS

The present application relates to a process for preparing a dicarboxylic acid or dicarboxylic ester according to general formula (IV) R1OOC-(CH2)m-CH2CH2-(CH2)y-COOR4 (IV), comprising the steps of subjecting alkenoic acid or alkenoate of formula (II) R1OOC-(CH2)m-CH=CH-(CH2)x-H (II) to a metathesis reaction in the presence of a metathesis catalyst to form a longer-chain alkenoic acid or alkenoate of formula (III) R1OOC-(CH2)m-CH=CH-(CH2)y-H (III) where xa carbonylation reaction in the presence of a carbonylation catalyst and a carbonyl source to form said compound of Formula (IV). Alternative embodiments provide: a process for preparing an alkenoic acid or alkenoate comprising the step of subjecting a lactone to a ring opening reaction; a process for preparing a monocarboxylic acid or monocarboxylic ester according to general formula (XI) R1OOC-(CH2)m-CH2-(CH2)y-CH3 (XI) by subjecting an alkenoic acid or alkenoate to alkene hydrogenation; and a process for preparing an alcohol or ether according to general formula (XII) R1O-CH2-(CH2)m-CH2-(CH2)y-CH3 (XII) by subjecting an alkenoic acid or alkenoate to hydrogenation. The use of the respective mono/dicarboxylic acid, mono/dicarboxylic ester, ethers or alcohols in a variety of applications is also disclosed.

MANUFACTURING METHOD OF α,β-UNSATURATED CARBOXYLIC ACID

PROBLEM TO BE SOLVED: To provide a manufacturing method which can get α,β-unsaturated carboxylic acid at a high yield by liquid phase oxidation of α,β-unsaturated aldehyde by oxygen or air with a handy metal catalyst under a mild reaction condition. SOLUTION: Preferably under a presence of organic solvent, α,β-unsaturated carboxylic acid is manufactured by oxidation of α,β-unsaturated aldehydes and oxygen or air under a presence of an iron salt catalyst and a catalyst of alkali metal salt of carboxylic acid. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Iron-catalyzed selective oxidation of α,β-unsaturated aldehydes to α,β-unsaturated carboxylic acids by molecular oxygen

Selective oxidation of α,β-unsaturated aldehydes to α,β-unsaturated carboxylic acids was performed using O2 as the oxidant in the presence of a simple iron catalyst. The addition of an alkali metal carboxylate as a cocatalyst enhanced the selectivity for the desired product. Redox tuning of the iron catalyst via association with the alkali metal led to a controlled radical generation during the catalytic O2 oxidation.

Preparation and odour of cis- and trans-2-methyltetrahydrofuran-3-thiol acetates

The preparation of cis- and trans-2-methyltetrahydrofuran-3-thiol acetates from (E)-3-penten-1-ol is reported. The mesylate of (E)-3-penten-1-ol was converted into trans- or cis-2-methyl-3-hydroxytetrahydrofuran by oxidation with H2O2 and HCOOH or with KMnO4. cis- or trans-2-Methyltetrahydrofuran-3-thiol acetate was prepared by mesylation and an SN2 nucleophilic substitution with AcSH from trans- or cis-2-methyl-3-hydroxytetrahydrofuran respectively. The configuration of the products was confirmed by their synthesis. Olfactory evaluation of cis- and trans-2-methyltetrahydrofuran-3-thiol acetates indicated some differences both in odour feature and intensity.