6622-76-0

Basic information

• Product Name: Methyl tiglate
• Synonyms: TIGLIC ACID METHYL ESTER;METHYL E-2,3-DIMETHYLACRYLATE;METHYL-TRANS-2-METHYL-2-BUTENOATE;METHYL TIGLATE;(E)-2-Methyl-but-2-enoicacidmethylester;2-Butenoic acid, 2-methyl-, methyl ester, (E)-;2-Butenoicacid,2-methyl-,methylester,(2E)-;2-Carbomethoxy-2-butene, (E)-
• CAS NO: 6622-76-0
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• EINECS: 229-575-8
• Product Categories: Aromatic Esters
• Mol File: 6622-76-0.mol
• Article Data: 37

Chemical Properties

• Melting Point: 37.22°C (estimate)
• Boiling Point: 137-138 °C758 mm Hg(lit.)
• Flash Point: 95 °F
• Appearance: colourless liquid
• Density: 0.95 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.436(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Soluble in alcohol, water 3813 mg/L @ 25°C (est).
• Stability: Stable. Flammable. Incompatible with strong oxidising agents.
• Merck: 14,9433
• BRN: 1720455
• CAS DataBase Reference: Methyl tiglate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl tiglate(6622-76-0)
• EPA Substance Registry System: Methyl tiglate(6622-76-0)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 2
• RTECS: EM9254600
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 6622-76-0(Hazardous Substances Data)

Usage

Description

Methyl tiglate is an organic compound that serves as a valuable reactant in the synthesis of conjugated alkenes through a process initiated by the insertion into a vinylic C-H bond. This characteristic makes it a versatile component in various chemical reactions and applications.

Uses

Used in Chemical Synthesis:
Methyl tiglate is used as a reactant for the elaboration of conjugated alkenes, which are essential in the synthesis of various organic compounds. Its ability to insert into a vinylic C-H bond allows for the formation of new chemical bonds and the creation of complex molecular structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, methyl tiglate may be utilized as a building block for the development of new drugs or drug candidates. Its role in the synthesis of conjugated alkenes can contribute to the discovery of novel therapeutic agents with unique properties and potential applications in medicine.
Used in Material Science:
Methyl tiglate can also be employed in material science for the development of advanced materials with specific properties. The synthesis of conjugated alkenes using methyl tiglate can lead to the creation of new polymers, coatings, or other materials with improved characteristics for various applications.

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 3016, 1986 DOI: 10.1021/ja00271a034

InChI:InChI=1/C6H10O2/c1-4-5(2)6(7)8-3/h4H,1-3H3/b5-4+

Upstream product

• 91-22-5 quinoline 
• 815-75-8 3-chloro-2-methyl-butyric acid methyl ester 
• 82504-42-5 methyl (2-chloromethyl)butanoate 
• 67-56-1 methanol 
• 80-59-1 Tiglic acid 
• 6028-38-2 (E)-2-methyl-2-butenamide 
• 64-17-5 ethanol 
• 3586-58-1 2-methylenebutyric acid 
• 74-88-4 methyl iodide 
• 5953-76-4 methyl angelate 
• 39847-91-1 (Z)-methyl 2-hydroxy-4-oxopent-2-enoate 
• 4111-08-4 2-hydroxy-2-methyl-butyronitrile 
• 99968-60-2 methyl (E)-4-bromo-2-methylbut-2-enoate 
• 1237706-56-7 1,3-bis-(2,4,6-trimethylphenyl)-4,6-diketo-5,5-dimethylpyrimidin-2-ylidene 

Downstream Products

• 104286-59-1 4--2-methylbut-2-en-4-olide 
• 73213-61-3 methyl boninenalate 
• 23009-73-6 trans-1-chloro-2-methylbut-2-ene 
• 72450-34-1 methyl 2-hydroxy-2-methyl-3-oxobutanoate 
• 104286-63-7 4-(p-formylphenoxy)-2-methylbut-2-en-4-olide 
• 104286-61-5 methyl (Z)-4-(p-formylphenoxy)-2-methylbut-2-enoate 
• 104286-60-4 methyl (E)-4-(p-formylphenoxy)-2-methylbut-2-enoate 
• 5058-17-3 2-methyl-4-deoxy-DL-threonic acid 
• 953786-91-9 (R)-3-(p-methoxyphenyl)-2-methylene-butyric acid methyl ester 
• 92186-72-6 methyl 5-hydroxy-2-methyl-5-phenyl-2-pentenoate 
• 108733-47-7 methyl 2-methyl-5-hydroxy-5-(4-nitrophenyl)-2-pentenoate 
• 114996-10-0 erythro-methyl 2-methyl-2-(α-hydroxy-p-nitrobenzyl)-3-butenoate 
• 114996-10-0 threo-methyl 2-methyl-2-(α-hydroxy-p-nitrobenzyl)-3-butenoate 

Relevant articles and documents

Lewis Acid Catalysis of the Ene Addition of Chloral and Bromal to Olefins; Stereochemical and Mechanistic Studies

The Lewis acid catalysed ene additions of chloral and bromal to alkenes are completely regiospecific, moderately regioselective, and often highly stereoselective.Diastereoselectivity in the addition to (-)-β-pinene was a function of the Lewis acid, and with TiCl4 essentially quantitative asymmetric induction was observed.The stereochemical phenomena are explained satisfactory by assuming the active enophiles possess transoid structures such as (1), that a concerted or rapid stepwise mechanism operates, and that product formation occurs predominantly through the least hindered encounter complex of the olefin and (1).In the case of 2-methylbut-2-ene, however, there is some evidence for an additional stereoelectronic contribution, the 'cis-effect'.Stereochemical assignements are supported by X-ray structural data.Ketones, hydrohalogenated ene adducts, or rearrangement products are formed (mainly in the addition to olefins of moderate reactivity) indicating the participation of Friedel-Crafts type dipolar intermediates.The ene adducts themselves could be formed via dipolar intermediates or in competing 'concerted' reactions; the stepwise mechanism must operate in some reactions because of the observation of Wagner-Meerwein rearrangements.Olefin reactivity over the series, measured by the competitive technique, towards chloral-AlCl3 showed a ca. 900-fold variation in rate; 'ene' reactivity decreases more steeply.

Gastric cytoprotective activity of 2-cyclopenten-1-one and related compounds

The cytoprotective activity of the isolated functional groups of several sesquiterpene lactones is reported. Among them the highest activity is shown by α-methylen-γ-butyrolactone and 2-cyclopenten-1-one. The activity shown by those Michael acceptors with a β carbon hindered by an alkyl substituent was always lower or almost null. A three-way mechanism of action is proposed: a) reduced glutathione synthesis, b) prostaglandin synthesis and c) mucosal glycoprotein synthesis.

Second-Generation meta-Phenolsulfonic Acid-Formaldehyde Resin as a Catalyst for Continuous-Flow Esterification

A second-generation m-phenolsulfonic acid-formaldehyde resin (PAFR II) catalyst was prepared by condensation polymerization of sodium m-phenolsulfonate and paraformaldehyde in an aqueous H2SO4 solution. This reusable, robust acid resin catalyst was improved in both catalytic activity and stability, maintaining the characteristics of the previous generation catalyst (p-phenolsulfonic acid-formaldehyde resin). PAFR II was applied in the batchwise and continuous-flow direct esterification without water removal and provided higher product yields in continuous-flow esterification than any other commercial ion-exchanged acid catalyst tested.

BIPOLAR TRANS CAROTENOID SALTS AND USES THEREOF

PROBLEM TO BE SOLVED: To provide compounds useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans. SOLUTION: There is provided a compound which has a structure represented by YZ-TCRO-ZY and is not trans sodium crocetinate [where, Y is a cation; Z is a polar group which is associated with the cation; and TCRO is trans carotenoid skeleton], and preferably, Y is a monovalent metal ion selected from the group consisting of Na+, K+ and Li+, or is an organic cation selected from the group consisting of R4 N+ and R3S+ [R is H, or CnH2n+1(n is 1 to 10)]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.