1076-96-6

Basic information

• Product Name: METHYL 4-VINYLBENZOATE
• Synonyms: METHYL 4-VINYLBENZOATE;4-VINYL-BENZOIC ACID METHYL ESTER;4-Styrenecarboxylic acid methyl ester;p-Vinylbenzoic acid methyl ester;Benzoic acid, 4-ethenyl-, methyl ester;4-ethenyl-Benzoic acid Methyl ester;Methyl p-vinylbenzoate;Methyl 4-vinylbenzoate 97%
• CAS NO: 1076-96-6
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Product Categories: Aromatic Esters;C10;Carbonyl Compounds;Carboxylic Acids
• Mol File: 1076-96-6.mol
• Article Data: 105

Chemical Properties

• Melting Point: 32-36 °C(lit.)
• Boiling Point: 89-90℃ (2 Torr)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.058g/cm³
• Vapor Pressure: 0.0186mmHg at 25°C
• Refractive Index: 1.5568 (589.3 nm 25℃)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 4-VINYLBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-VINYLBENZOATE(1076-96-6)
• EPA Substance Registry System: METHYL 4-VINYLBENZOATE(1076-96-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 1076-96-6(Hazardous Substances Data)

Usage

Uses

Methyl 4-vinylbenzoate is used as a fluid component for enhancing ink stability in printing and also in preparing vinyl substituted beta-diketones. Further, it is used as an organic intermediate for pharmaceuticals.

InChI:InChI=1/C10H10O2/c1-3-8-4-6-9(7-5-8)10(11)12-2/h3-7H,1H2,2H3

Upstream product

• 67-56-1 methanol 
• 1075-49-6 4-ethenylbenzoic acid 
• 88393-08-2 α-methyl-p-carbomethoxybenzyl phenyl sulfoxide 
• 1571-08-0 methyl 4-formylbenzoate 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 108-05-4 vinyl acetate 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 873869-19-3 1-(tert-butyl)-5-(methylsulfonyl)-1H-tetrazole 

Downstream Products

• 64-19-7 acetic acid 
• 792-74-5 4,4'-biphenyldicarboxylic acid dimethyl ester 
• 183058-01-7 (S)-methyl 4-(1,2-dihydroxyethyl)benzoate 
• 3609-53-8 methyl 4-acetylbenzoate 
• 1571-08-0 methyl 4-formylbenzoate 
• 863892-37-9 5-[2-(4-methylcarboxyphenyl)ethenyl]-1,1,3,3-tetramethylisoindolin-2-yloxyl 
• 106918-32-5 4-carbomethoxyphenylacetaldehyde 

Relevant articles and documents

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Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands

The synthesis of a series of N-(2-methoxyphenyl)piperazine and N-(2,3-dichlorophenyl)piperazine analogs and their in vitro binding affinities for dopamine D2, D3, D4 are presented. A series of N-(2-methoxyphenyl)piperazine

Improved Julia-Kocienski conditions for the methylenation of aldehydes and ketones

The scope of the methylenation of aldehydes and ketones under optimized Julia-Kocienski conditions is broadened by using 1-tert-butyl-1H-tetrazol-5- ylmethyl sulfone. Two different Barbier-type procedures are applied with NaHMDS at -78 °C or Cs2CO3 at 70 °C. The latter conditions are also adapted for the preparation of 1,2-disubstituted olefins and intramolecular olefination reactions.

One-pot Suzuki-Heck relay to prepare industrially valuable intermediates using the Pd-Cy?Phine catalyst system

A rare example of a one-pot, palladium-catalyzed Suzuki-Heck sequence has been developed with applicability to APIs and organoelectronic materials. High throughput screening was used to expedite development and survey strategies. Interchangeability of the coupling partners and the avoidance of intermediate isolation gives operational flexibility, which can be used to improve process efficiency and suppress by-product formation.

Discovery of 5-{2-[5-Chloro-2-(5-ethoxyquinoline-8-sulfonamido)phenyl]ethynyl}-4-methoxypyridine-2-carboxylic Acid, a Highly Selective in Vivo Useable Chemical Probe to Dissect MCT4 Biology

Due to increased lactate production during glucose metabolism, tumor cells heavily rely on efficient lactate transport to avoid intracellular lactate accumulation and acidification. Monocarboxylate transporter 4 (MCT4/SLC16A3) is a lactate transporter that plays a central role in tumor pH modulation. The discovery and optimization of a novel class of MCT4 inhibitors (hit 9a), identified by a cellular screening in MDA-MB-231, is described. Direct target interaction of the optimized compound 18n with the cytosolic domain of MCT4 was shown after solubilization of the GFP-tagged transporter by fluorescence cross-correlation spectroscopy and microscopic studies. In vitro treatment with 18n resulted in lactate efflux inhibition and reduction of cellular viability in MCT4 high expressing cells. Moreover, pharmacokinetic properties of 18n allowed assessment of lactate modulation and antitumor activity in a mouse tumor model. Thus, 18n represents a valuable tool for investigating selective MCT4 inhibition and its effect on tumor biology.

A new class of nifuroxazide analogues: Synthesis of 5-nitrothiophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus

Hospital-acquired methicillin-resistant Staphylococcus aureus (MRSA) has been an increasing problem worldwide since the initial reports over 40 years ago. To examine new drug leads with potential antibacterial activities, 14 p-substituted benzoic acid [(5-nitro-thiophen-2-yl)-methylene]-hydrazides were designed, synthesized, and tested against standard and multidrug-resistant S. aureus strains by serial dilution tests. All compounds exhibited significant bacteriostatic activity and some of them also showed bactericidal activity. The results confirmed the potential of this class of compounds as an alternative for the development of selective antimicrobial agents.

Pyrene-benzoylthiophene exciplexes as selective catalysts for the [2+2] cycloaddition between cyclohexadiene and styrenes

Efficient intramolecular fluorescence quenching in pyrene-benzoylthiophene systems leads to formation of exciplexes. These species interact with 1,3-cyclohexadiene (or styrenes), leading to reactive excited triplexes. The overall process affords [2+2] cro

Catalytic α-Selective Deuteration of Styrene Derivatives

We report an operationally simple protocol for the catalytic α-deuteration of styrenes. This process proceeds via the base-catalyzed reversible addition of methanol to styrenes in DMSO-d6 solvent. The concentration of methanol is shown to be critical for high yields and selectivities over multiple competing side reactions. The synthetic utility of α-deuterated styrenes for accessing deuterium-labeled chiral benzylic stereocenters is demonstrated.

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan

The hydrosulfamoylation of diverse aryl olefins provides facile access to alkylsulfonamides. Here we report a novel protocol utilizing radical-mediated addition and a thiol-assisted strategy to achieve the hydrosulfamoylation of diverse styrenes in modest to excellent yields under mild and economic reaction conditions. The methodology was found to provide an efficient and convenient approach for the synthesis of the anti-migraine drug naratriptan and it also can be used for the late-stage functionalization of natural products or medicines.