23326-27-4

Basic information

• Product Name: METHYL 2-BUTYNOATE
• Synonyms: TETROLIC ACID METHYL ESTER;METHYL TETROLATE;METHYL 2-BUTYNOATE;2-BUTYNOIC ACID METHYL ESTER;Methyl-2-Butynaote97%;Methyl2-butynoate=Methyltetrolate;Methyl 2-butynoate,97%;Methyl 2-butynoate, 97% 5GR
• CAS NO: 23326-27-4
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.1
• Product Categories: Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives
• Mol File: 23326-27-4.mol

Chemical Properties

• Boiling Point: 76-77 °C (80 mmHg)
• Flash Point: 45 °C
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.98
• Vapor Pressure: 6mmHg at 25°C
• Refractive Index: 1.436-1.438
• Storage Temp.: Flammables area
• CAS DataBase Reference: METHYL 2-BUTYNOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-BUTYNOATE(23326-27-4)
• EPA Substance Registry System: METHYL 2-BUTYNOATE(23326-27-4)

Safety Data

• Hazard Codes: Xn
• Statements: 10-36/37/38-20/21/22
• Safety Statements: 16-36/37/39-26
• RIDADR: 1993
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 23326-27-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2-BUTYNOATE is used as a synthetic intermediate for the preparation of phenanthrenes and benzoindolyl carboxylates, which are important compounds in the development of pharmaceuticals. These compounds have potential applications in the treatment of various diseases and disorders.
Used in Chemical Synthesis:
METHYL 2-BUTYNOATE is used as a key building block in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure and reactivity make it a valuable asset in the development of new and innovative products.
Used in Research and Development:
METHYL 2-BUTYNOATE is employed as a research compound in academic and industrial laboratories, where it is used to explore new reaction pathways and develop novel synthetic methods. Its versatility and unique properties make it an essential tool in the advancement of chemical science and technology.

Synthesis Reference(s)

Synthesis, p. 1100, 1982 DOI: 10.1055/s-1982-30090

InChI:InChI=1/C5H6O2/c1-3-4-5(6)7-2/h1-2H3

Upstream product

• 1743-62-0 [acetyl(methoxycarbonyl)methylene]triphenylphosphorane 
• 186581-53-3 diazomethane 
• 590-93-2 2-Butynoic acid 
• 4344-87-0 1,2-dihydro-5-methyl-3H-pyrazol-3-one 
• 67-56-1 methanol 
• 74-99-7 prop-1-yne 
• 79-22-1 methyl chloroformate 
• 201230-82-2 carbon monoxide 
• 108-26-9 3-methyl-2-pyrazoline-5-one 

Downstream Products

• 50983-22-7 1-Carbomethoxy-2-methylcyclohexa-1,4-dien 
• 27948-31-8 (E)-methyl 3-methyl-5-phenyl-2-penten-4-ynoate 
• 70134-71-3 3,4-dibromo-1,2,5-oxadiazole 2-oxide 
• 188686-98-8 3-Bromo-5-methyl-isoxazole-4-carboxylic acid methyl ester 
• 4525-27-3 β-acetoxy-crotonic acid methyl ester 
• 139615-87-5 3,6-bis(methoxycarbonyl)-2-methylspiro<4.5>dec-2-en-1-one 
• 4660-19-9 5-hydroxy-5-phenyl-pent-2-ynoic acid methyl ester 
• 476170-47-5 2-methoxycarbonyl-3-methyl-6,N-bis(trisopropylsilyl)aniline 
• 476170-70-4 [4-13C]-2-methoxycarbonyl-3-methyl-6,N-bis(trisopropylsilyl)aniline 
• 476170-59-9 [1-13C]-2-methoxycarbonyl-3-methyl-6,N-bis(trisopropylsilyl)aniline 
• 135462-51-0 4-Methoxy-6-methyl-1-phenyl-2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene-5-carboxylic acid methyl ester 
• 135462-54-3 methyl 5-hydroperoxy-2,2-dimethoxy-4-methyl-5-phenyl-2,5-dihydrofuran-3-carboxylate 
• 947505-31-9 1-(4-methoxybenzyl)-5-methyl-1H-[1,2,3]|triazole-4-carboxylic acid methyl ester 
• 947505-32-0 3-(4-methoxybenzyl)-5-methyl-3H-[1,2,3]triazole-4-carboxylic acid methyl ester 

Relevant articles and documents

The detection of PHIP effects allows new insights into the mechanism of olefin isomerisation during catalytic hydrogenation

PHIP (parahydrogen-induced polarisation) effects in the 1H NMR spectra of the products of Rh-complex-catalysed alkyne hydrogenation brings to light the fact that the cis-trans isomerisation of the formed olefin occurs through the formation of a σ-bonded intermediate stabilised by the reversible addition of a hydrogen molecule at the metal centre. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of trisubstituted alkenes by Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters

A method for Ni-catalyzed hydroalkylation of internal alkynes with cycloketone oxime esters was developed. The reaction has a broad substrate scope. This hydroalkylation shows excellent regio-and stereo-selectivity. This method enables readily available starting materials to be used to access a range of cyano-substituted single-configuration trisubstituted alkenes. These are valuable feedstock chemicals and are widely used in synthetic and medicinal chemistry.

Copper-Catalyzed Domino Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidin-4(10H)-ones using Cyanamide as a Building Block

An efficient and practical copper-catalyzed domino synthesis of benzo[4,5]imidazo[1,2-a]pyrimidin-4(10H)-ones has been developed. The protocol uses N-(2-halophenyl)-3-alkylpropiolamides and cyanamide as the starting materials, inexpensive copper(I) iodide and pipecolinic acid as the catalyst and ligand, and the corresponding products were obtained in moderate to good yields.

A new strategy for the synthesis of chiral β-alkynyl esters via sequential palladium and copper catalysis

A new strategy for the synthesis of chiral β-alkynyl esters which relies on sequential Pd and Cu catalysis is reported. Terminal alkynes bearing aryl, alkyl, and silyl groups can be employed without prior activation yielding a wide range of important chiral building blocks. The reaction sequence utilizes a robust Pd(II)-catalyzed hydroalkynylation of ynoates with terminal alkynes providing geometrically pure ynenoates which are readily reduced by CuH. In contrast to previous reports, where additions to ynenoates proceed with marginal preference for the 1,6-pathway, this conjugate reduction occurs with high 1,4-selectivity yielding β-alkynyl esters with excellent levels of enantioselectivity. Importantly, the method tolerates a wide range of functionality, including allylic carbonates and carbamates, and thus allows for rapid elaboration of the β-alkynyl esters into a variety of chiral, substituted heterocycles.

Synthesis and spectroscopic characterization of 1-13C- and 4-13C-plastoquinone-9

This paper presents the synthesis of 1-13C- and 4-13C-plastoquinone-9 and their characterization with NMR spectroscopy and mass spectrometry. The synthetic scheme has been further adapted to introduce 13C-labeled plastoquinones on all individual and on each combination of positions in the quinone ring. Also a two-step scheme is disclosed to prepare unlabeled plastoquinone-9. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Hypervalent Iodine Oxidation of 5-Substituted and 4,5-Disubstituted Pyrazol-3(2H)-ones: A Facile Synthesis of Methyl-2-alkynoates and Methyl 2,3-alkadienoates

Hypervalent iodine oxidation of various 5-substituted pyrazol-3(2H)-ones (1a-h) with iodobenzene diacetate or iodosobenzene in methanol results in fragmentative loss of molecular dinitrogen to yield methyl 2-alkynoates (2a-h).However, 5-methyl-4-substituted pyrazol-3(2H)-ones (3a-d) under similar conditions yield methyl 2,3-allenic esters (4a-d).Methyl 2,3-cycloalkadienoates (6a-e) are obtained by the oxidative cleavage of 4,5-polymethylene pyrazol-3(2H)-ones (5c-e) using iodobenzene diacetate or iodosobenzene in methanol. 5-Methyl-4,4-disubstituted pyrazol-3(2H)-ones (7a-b) were found not to undergo raction under similar conditions.The scope and mechanism of these reactions are discussed.

Hypervalent Iodine Oxidation of 5-Substituted and 5-Methyl-4-substituted Pyrazol-3(2H)-ones. A Facile Synthesis of 2-Alkynoic and 2,3-Allenic Esters

PhI(OAc)2-MeOH causes oxidation of 5-substituted pyrazol-3(2H)-ones to the 2-alkynoic methyl ester and 5-methyl-4-substituted pyrazol-3(2H)-ones to the 2,3-allenic methyl ester.