10277-93-7

Basic information

• Product Name: 2-Isopropenylphenol
• Synonyms: 2-Isopropenylphenol;2-(1-Methylethenyl)phenol;2-(2-Hydroxyphenyl)-1-propene;2-Hydroxy-alpha-methylstyrene;o-Hydroxy-alpha-methylstyrene;o-Isopropenylphenol;2-prop-1-en-2-ylphenol
• CAS NO: 10277-93-7
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.1751
• Product Categories: Aromatics, Intermediates
• Mol File: 10277-93-7.mol

Chemical Properties

• Boiling Point: 203-208 °C
• Appearance: /
• Density: 1.024 g/cm3(Temp: 23 °C)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform, DMSO
• PKA: 9.88±0.30(Predicted)
• CAS DataBase Reference: 2-Isopropenylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropenylphenol(10277-93-7)
• EPA Substance Registry System: 2-Isopropenylphenol(10277-93-7)

Safety Data

• Hazardous Substances Data: 10277-93-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Isopropenylphenol is used as a common intermediate for the synthesis of 2,4'-Bisphenol A (B519490). This application is due to its reactive functional groups that facilitate the formation of the desired product through a series of chemical reactions.
Used in Polymer Industry:
In the polymer industry, 2-Isopropenylphenol is utilized as a monomer for the production of various polymers, such as epoxy resins and polycarbonates. Its aromatic structure and reactive side chain contribute to the formation of polymers with specific properties, making it an essential component in the synthesis process.
Used in Pharmaceutical Industry:
2-Isopropenylphenol also finds application in the pharmaceutical industry, where it is used as a starting material for the synthesis of various drugs and pharmaceutical compounds. Its unique chemical properties allow for the development of new drugs with potential therapeutic benefits.
Used in Flavor and Fragrance Industry:
Due to its distinct aromatic properties, 2-Isopropenylphenol is employed in the flavor and fragrance industry as a key component in the creation of various scents and flavors. Its ability to impart specific olfactory characteristics makes it a valuable asset in the development of perfumes, cosmetics, and other fragrance products.

Upstream product

• 698-91-9 2-phenoxypropene 
• 3045-32-7 2-(1-hydroxy-1-methylethyl)phenol 
• 1129293-64-6 β-methyl-o-coumaric acid 
• 107-18-6 allyl alcohol 
• 108-95-2 phenol 
• 107-05-1 3-chloroprop-1-ene 
• 917-64-6 methyl magnesium iodide 
• 119-36-8 methyl salicylate 
• 13524-73-7 3-methyl-2,3-dihydrobenzofuran 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 917-54-4 methyllithium 
• 346433-44-1 2-(tert-butoxycarbonyloxy)acetophenone 
• 118-93-4 o-hydroxyacetophenone 

Downstream Products

• 88-69-7 2-(1-methylethyl)phenol 
• 5026-12-0 2-(2-hydroxyphenyl)-2,4,4-trimethylchroman 
• 860767-16-4 2,4-dibromo-6-(α,β,β'-tribromo-isopropyl)-phenol 
• 10278-02-1 2-(2-methoxyphenyl)propene 
• 3045-32-7 2-(1-hydroxy-1-methylethyl)phenol 
• 38865-54-2 <1-(2-Hydroxyphenyl)-1-methylethyl>-(2-isopropenylphenyl)-ether 
• 299465-78-4 1-isopropenyl-2-(1-benzyloxyallyloxy)benzene 
• 299465-81-9 2-benzyloxy-4-methyl-2H-chromene 
• 21022-73-1 2-(2'-methoxyphenyl)-2-propanol 
• 26307-50-6 4-bromo-2-isopropyl-phenol 
• 1365789-60-1 methyl 2-(2-(prop-1-en-2-yl)phenoxy)propanoate 
• 1365789-32-7 2-(1-(2-(prop-1-en-2-yl)phenoxy)ethyl)-4,5-dihydro-1H-imidazole 
• 1392836-25-7 2-((2S,4S)-1,2,3,4-tetrahydro-6-methoxy-4-methyl-2-(4-nitrophenyl)quinolin-4-yl)phenol 
• 1392836-29-1 2-((2S,4S)-6-ethoxy-1,2,3,4-tetrahydro-4-methyl-2-(4-nitrophenyl)quinolin-4-yl)phenol 

Relevant articles and documents

Synthesis of Benzofuranones via Palladium-Catalyzed Intramolecular Alkoxycarbonylation of Alkenylphenols

Herein, a new catalytic system to synthesize benzofuranones is reported. A palladium-catalyzed intramolecular alkoxycarbonylation is employed to generate 3-substituted-benzofuran-2(3H)-ones from alkenylphenols under mild reaction conditions, linked to an ex situ formation of CO from N-formylsaccharin. The carefully chosen catalytic system enables an efficient reaction with a novel functional group tolerance, despite the high polymerization tendency of the starting material.

Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions

Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.

Bichromatic Photosynthesis of Coumarins by UV Filter-Enabled Olefin Metathesis

Herein, we report on a two-step bichromatic synthesis of coumarins involving UV-A and UV-C light. The first step is a UV-A-photoinduced ruthenium-catalyzed cross-metathesis (CM) reaction of 2-nitrobenzyl-protected 2-hydroxystyrenes with acrylates, using an external solution of 1-pyrenecarboxaldehyde as a UV filter. Irradiation in the absence of the filter permanently inhibits the light-activated catalyst due to photocleavage of the photolabile protecting group (PPG) and ensuing phenolate chelation to the ruthenium. The simple removal of the external filter after CM allows further photochemical reactions with UV-C light to achieve more complex architectures, such as the coumarins presented in this work. (Figure presented.).

Lewis Acid Catalyzed Cyclization of Propargylic Alcohols with 2-Vinylphenol

An unprecedented Lewis acid catalyzed, protection-free, and high-efficiency synthesis of valuable 3,4-dihydro-2H-2,4-methanochromans via cycloaddition of propargylic alkynols with 2-vinylphenol is described. This cycloaddition protocol, which tolerates a

OH-directed alkynylation of 2-vinylphenols with ethynyl benziodoxolones: A fast access to terminal 1,3-enynes

The first direct alkynylation of 2-vinylphenols was developed. The rationally optimized hypervalent iodine reagent TIPS-EBX in combination with [(CpRhCl2)2] as a C-H-activating transition metal catalyst enables the construction of a variety of highly substituted 1,3-enynes in high yields of up to 98 %. This novel C-H activation method shows excellent chemoselectivity and exclusive (Z)-stereoselectivity, and it is also remarkably mild and tolerates a variety of functional groups. Furthermore, synthetic modifications of the resulting 1,3-enynes were demonstrated. To our knowledge, this is the first example for an OH-directed C-H alkynylation with hypervalent iodine reagents.

Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes

Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.

Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes

The dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under RhIII catalysis. These reactions are successful using Cu(OAc)2 or air as the stoichiometric oxi

Palladium(II)-catalyzed direct carboxylation of alkenyl C-H bonds with CO2

Pd-catalyzed direct carboxylation of alkenyl C-H bonds with carbon dioxide was realized for the first time. Treatment of 2-hydroxystyrenes and a catalytic amount of Pd(OAc)2 with Cs2CO3 under atmospheric pressure of CO2 afforded corresponding coumarins in good yield. Furthermore, isolation of the key alkenylpalladium intermediate via C-H bond cleavage was achieved. The reaction was proposed to undergo reversible nucleophilic addition of the alkenylpalladium intermediate to CO2.

Remarkable improvement achieved by imidazole derivatives in ruthenium-catalyzed hydroesterification of alkenes using formates

Imidazole derivatives are revealed to be effective ligands in the Ru-catalyzed hydroesterification of alkenes using formates, affording one-carbonelongated esters in high yields. Further, intramolecular hydroesterification was successfully performed to give lactones for the first time. Imidazole derivatives can contribute to promote the reaction as well as to suppress the undesired decarbonylation of formate. Toxic CO gas, a directing group, and large excess alkenes are not required.

Synthesis of coumarins via Pd-catalyzed oxidative cyclocarbonylation of 2-vinylphenols

Palladium-catalyzed oxidative cyclocarbonylation of 2-vinylphenols constitutes a simple, direct method for the synthesis of coumarins. The reaction conditions, employing low pressures of CO, and air or 1,4- benzoquinone as the oxidant, are attractive in terms of environmental considerations and operational simplicity. Coumarins with a variety of functional groups were prepared in yields up to 85%.