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
• Article Data: 14

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

Description

2-Isopropenylphenol, also known as Isoeugenol, is an organic compound that serves as a key intermediate in the chemical industry. It is characterized by its aromatic structure, which includes a phenol group and an isopropenyl side chain. This unique structure endows 2-Isopropenylphenol with versatile chemical properties, making it a valuable building block for the synthesis of various compounds.

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.

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.).

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.