1128-92-3

Basic information

• Product Name: o-Prenylphenol
• Synonyms: 2-(3-Methyl-2-butenyl)phenol;2-Prenylphenol;o-Prenylphenol;Phenol, 2-(3-methyl-2-buten-1-yl)-
• CAS NO: 1128-92-3
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• Mol File: 1128-92-3.mol

Chemical Properties

• Boiling Point: 254.3°C at 760 mmHg
• Flash Point: 114.2°C
• Appearance: /
• Density: 0.991g/cm³
• Vapor Pressure: 0.0109mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: o-Prenylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: o-Prenylphenol(1128-92-3)
• EPA Substance Registry System: o-Prenylphenol(1128-92-3)

Safety Data

• Hazardous Substances Data: 1128-92-3(Hazardous Substances Data)

Usage

Uses

Used in Cosmetic and Personal Care Industry:
o-Prenylphenol is used as a fragrance ingredient for its sweet, fruity odor, enhancing the sensory experience of cosmetic and personal care products.
Used in Antimicrobial Applications:
o-Prenylphenol is used as an antimicrobial agent due to its demonstrated antibacterial and antifungal activity, making it a potential candidate for use in products designed to combat microbial growth.
Used in Biotechnology Research:
o-Prenylphenol is used as a starting material in the synthesis of novel bioactive compounds, leveraging its unique chemical structure for the development of new pharmaceuticals or other bioactive substances.

InChI:InChI=1/C11H14O/c1-9(2)7-8-10-5-3-4-6-11(10)12/h3-7,12H,8H2,1-2H3

Upstream product

• 139-02-6 sodium phenoxide 
• 870-63-3 prenyl bromide 
• 78-79-5 isoprene 
• 108-95-2 phenol 
• 2513-25-9 2,2-dimethyl-2H-chromene 
• 34125-70-7 ((2-methylbut-3-en-2-yl)oxy)benzene 
• 100-99-2 triisobutylaluminum 
• 14309-15-0 phenyl prenyl ether 
• 76240-29-4 2-(3-chloro-3-methylbutyl)phenol 
• 598-25-4 Dimethylallene 
• 115-18-4 2-methyl-3-buten-2-ol 
• 865-58-7 3-bromo-3-methyl-but-1-ene 
• 157953-28-1 Benzoic acid 2-(3-methyl-but-2-enyl)-phenyl ester 
• 503-60-6 3,3-dimethyl-allyl chloride 

Downstream Products

• 1198-96-5 2,2-dimethylchroman 
• 17235-13-1 1-(2-acetoxyphenyl)-3-methylbut-2-ene 
• 5032-03-1 (3-methyl-butyl)-phenol 
• 93727-54-9 2,4-Bis-(2-hydroxy-phenyl)-2-methyl-butan 
• 91969-55-0 4-hydroxy-1,1-dimethylindane 
• 4957-17-9 1-methoxy-2-(3-methylbut-2-en-1-yl)benzene 
• 1427302-19-9 C₂₀H₂₀O 
• 1452898-23-5 C₁₁H₁₃FO 
• 1265882-36-7 5-cyclohexyl-2-(3-methylbutyl)phenol 
• 1265882-34-5 6-cyclohexyl-4-hydroxy-1,1-dimethylindane 
• 102016-86-4 (4-nitro-phenyl)-carbamic acid-(2-isopentyl-phenyl ester) 
• 72446-43-6 1-(2-acetoxyphenyl)-2,3-epoxy-3-methylbutane 
• 76240-34-1 2-(3-methylbut-3-enyl)phenyl acetate 

Relevant articles and documents

Montmorillonite clays in organic synthesis: A one-pot conversion of phenols to 2,2-dimethylbenzopyrans

2,2-Dimethylbenzopyran derivatives were generated through a one-pot Montmorillonite K10 clay-catalyzed condensation of substituted phenols with prenyl bromide.

Investigation of the Montmorillonite clay-catalyzed [1,3] shift reaction of 3-methyl-2-butenyl phenyl ether

The [1,3] shift reaction of 3-methyl-2-butenyl phenyl ether was catalyzed more effectively by Montmorillonite K10 clay than Montmorillonite KSF clay, and proceeded with greatest ortho-selectivity in carbon tetrachloride at room temperature.

Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin

The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids

Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol, α-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.

Alkylation of Phenol And Hydroquinone by Prenol in the Presence of Organoaluminum Catalysts

Prenylphenols and 2,2-dimethylbenzopyrans were synthesized via alkylation of phenol and hydroquinone with prenol in the presence of organoaluminum catalysts, i.e., aluminum phenoxide and isopropoxide. Reaction products were isolated and characterized. Sev

Catalytic, Enantioselective, Intramolecular Sulfenofunctionalization of Alkenes with Phenols

The catalytic, enantioselective, cyclization of phenols with electrophilic sulfenophthalimides onto isolated or conjugated alkenes affords 2,3-disubstituted benzopyrans and benzoxepins. The reaction is catalyzed by a BINAM-based phosphoramide Lewis base c

Synthesis of isobavachalcone and some organometallic derivatives

Isobavachalcone [2′,4,4′-trihydroxy-3′-(3″-methyl- 2″-butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of 190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium-catalysed Stille coupling of 3-iodo-2,4-bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen-Schmidt condensation with 4-(methoxymethoxy)benzaldehyde to form the triply MOM-protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy) benzaldehyde used in the Claisen-Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5-formylcyclopentadienyl) (η4-tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.

InIII-catalysed tandem C-C and C-O bond formation between phenols and allylic acetates

Indium triflate catalysed tandem allylation-intramolecular hydroalkoxylation was efficiently carried out by using 1 mol-% of the catalyst under mild conditions to afford the dihydrobenzopyran ring system (chroman-type structure) in good yields. Kinetic, mechanistic and theoretical studies are also presented. Tandem allylation-intramolecular hydroalkoxylation carried out in the presence of an indium catalyst (1 mol-%) under mild conditions provides the dihydrobenzopyranring system in good yields. Kinetic, mechanistic and theoretical studies are presented.

Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst

N,N-Diphenylguanidinium ion associated with the noncoordinating BArF counterion is shown to be an effective catalyst for the [3,3]-sigmatropic rearrangement of a variety of substituted allyl vinyl ethers. Highly enantioselective catalytic Claisen rearrangements of ester-substituted allyl vinyl ethers are then documented using a new C2-symmetric guanidinium ion derivative. Copyright