5721-21-1

Basic information

• Product Name: 2-(prop-2-en-1-yl)benzene-1,4-diol
• CAS NO: 5721-21-1
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.1745
• Mol File: 5721-21-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 305°C at 760 mmHg
• Flash Point: 151.4°C
• Density: 1.148g/cm³
• Vapor Pressure: 0.000467mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 2-(prop-2-en-1-yl)benzene-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(prop-2-en-1-yl)benzene-1,4-diol(5721-21-1)
• EPA Substance Registry System: 2-(prop-2-en-1-yl)benzene-1,4-diol(5721-21-1)

Safety Data

• Hazardous Substances Data: 5721-21-1(Hazardous Substances Data)

Usage

General Description

2-(prop-2-en-1-yl)benzene-1,4-diol, also known as hydroquinone, is an organic compound commonly used in skincare products as a skin-lightening agent. It is a derivative of benzene with two hydroxyl groups at the 1 and 4 positions, and a propenyl group attached to the benzene ring. Hydroquinone works by inhibiting the enzyme responsible for melanin production, thereby reducing the appearance of hyperpigmentation and dark spots on the skin. However,

Upstream product

• 6411-34-3 4-allyloxyphenol 
• 24850-33-7 allyltributylstanane 
• 106-51-4 p-benzoquinone 
• 106-95-6 allyl bromide 
• 762-72-1 allyl-trimethyl-silane 
• 58981-41-2 4-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-phenol 
• 137362-24-4 4-((2E,5E)-3,6,10-Trimethyl-undeca-2,5,9-trienyloxy)-phenol 
• 123-31-9 hydroquinone 
• 71318-55-3 4-hydroxy-3-allyl-benzoic acid 
• 19754-22-4 2-allyl-1,4-dimethoxybenzene 

Downstream Products

• 1706-71-4 2-propenyl-hydroquinone 
• 3731-95-1 2-allyl-1,4-benzoquinone 
• 19754-22-4 2-allyl-1,4-dimethoxybenzene 

Relevant articles and documents

Indium- and gallium-mediated carbon-carbon bond-forming reactions in organic synthesis

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A Monooxygenase from Boreostereum vibrans Catalyzes Oxidative Decarboxylation in a Divergent Vibralactone Biosynthesis Pathway

The oxidative decarboxylation of prenyl 4-hydroxybenzoate to prenylhydroquinone has been frequently proposed for the biosynthesis of prenylated (hydro)quinone derivates (sometimes meroterpenoids), yet no corresponding genes or enzymes have so far been reported. A FAD-binding monooxygenase (VibMO1) was identified that converts prenyl 4-hydroxybenzoate into prenylhydroquinone and is likely involved in the biosynthesis of vibralactones and other meroterpenoids in the basidiomycete Boreostereum vibrans. Feeding of 3-allyl-4-hydroxybenzylalcohol, an analogue of the vibralactone pathway intermediate 3-prenyl-4-hydroxybenzylalcohol, generated 20 analogues with different scaffolds. This demonstrated divergent pathways to skeletally distinct compounds initiating from a single precursor, thus providing the first insight into a novel biosynthetic pathway for 3-substituted γ-butyrolactones from a shikimate origin.

Bi(OTf)3-catalyzed allylation of quinones with allyltrimethylsilane

p-Quinones react smoothly with allyltrimethylsilane in the presence of 2 mol% of Bi(OTf)3 under mild reaction conditions to afford the corresponding allyl substituted benzene derivatives, p-allylquinols and allyl substituted 1,4-naphthoquinones in excellent yields with high regioselectivity. This method is very useful for the direct introduction of an allyl functionality onto a quinone moiety.