52130-14-0

Basic information

• Product Name: 4-(pent-4-en-1-yl)phenol
• Synonyms: 4-(pent-4-en-1-yl)phenol
• CAS NO: 52130-14-0
• Molecular Weight: 162.232
• Mol File: 52130-14-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-(pent-4-en-1-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(pent-4-en-1-yl)phenol(52130-14-0)
• EPA Substance Registry System: 4-(pent-4-en-1-yl)phenol(52130-14-0)

Safety Data

• Hazardous Substances Data: 52130-14-0(Hazardous Substances Data)

Upstream product

• 106-41-2 4-bromo-phenol 
• 7766-48-5 1-iodo-4-pentene 
• 99522-34-6 4-[(tetrahydro-2H-pyran-2-yl)oxy]iodobenzene 
• 14140-15-9 4-(2-bromoethyl)phenol 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 52130-13-9 2-(p-Trimethylsilyloxyphenyl)-ethylbromid 
• 106-95-6 allyl bromide 
• 540-38-5 p-Iodophenol 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 

Downstream Products

• 1240629-57-5 4-hydroxy-4-(pent-4-enyl)cyclohexa-2,5-dienone 

Relevant articles and documents

Mechanism of Iodine(III)-Promoted Oxidative Dearomatizing Hydroxylation of Phenols: Evidence for a Radical-Chain Pathway

The oxidative dearomatization of phenols with the addition of nucleophiles to the aromatic ring induced by hypervalent iodine(III) reagents and catalysts has emerged as a highly useful synthetic approach. However, experimental mechanistic studies of this important process have been extremely scarce. In this report, we describe systematic investigations of the dearomatizing hydroxylation of phenols using an array of experimental techniques. Kinetics, EPR spectroscopy, and reactions with radical probes demonstrate that the transformation proceeds by a radical-chain mechanism, with a phenoxyl radical being the key chain-carrying intermediate. Moreover, UV and NMR spectroscopy, high-resolution mass spectrometry, and cyclic voltammetry show that before reacting with the phenoxyl radical, the water molecule becomes activated by the interaction with the iodine(III) center, causing the Umpolung of this formally nucleophilic substrate. The radical-chain mechanism allows the rationalization of all existing observations regarding the iodine(III)-promoted oxidative dearomatization of phenols.

Liquid crystals

Compounds of the formula STR1 wherein n stands for the number 0 or 1; the rings A1, A2 and A3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; X1 represents a single covalent bond, --COO--, --OOC--, --CH2 CH2 --, p--C6 H4 --, --CH2 CH2 --p-- C6 H4 --, --CH2 CH2 --p--C6 H4 --CH2 CH2 -- or, insofar as the rings A1 and A2 represent 1,4-phenylene, also --NON--; R2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.