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1-Phenoxy-4-(2-propenyl)benzene, also known as isoeugenol, is an organic compound with the chemical formula C15H16O. It is a colorless to pale yellow liquid with a strong, spicy odor. This molecule consists of a phenyl group (C6H5) attached to a propenyl group (C3H5) at the para position (4th carbon) and a phenoxy group (C6H5O) at the ortho position (1st carbon). Isoeugenol is widely used in the flavor and fragrance industry, particularly in the production of vanillin, as well as in the synthesis of various pharmaceuticals and agrochemicals. It is also found in trace amounts in some essential oils, such as clove oil and basil oil. Due to its potential health risks, including its classification as a possible human carcinogen, isoeugenol is subject to regulatory restrictions in certain applications.

2653-93-2

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2653-93-2 Usage

Uses

Safrole is used primarily in the manufacture of perfumes, soaps, and flavorings, as well as in some pesticide formulations.

Recreational Drug Production

Safrole is an intermediate in the production of the recreational drug MDMA (ecstasy).

Potential Carcinogenicity

The use of safrole in food and drugs is strictly regulated due to concerns about its potential carcinogenicity.

Illegal Drug Synthesis

Safrole has been identified as a precursor in the synthesis of the illegal drugs MDA (3,4-methylenedioxyamphetamine) and MDEA (3,4-methylenedioxyethylamphetamine).

Banned or Restricted

Due to its potential health risks and connections to illegal drug production, safrole has been banned or heavily restricted in many countries.

Check Digit Verification of cas no

The CAS Registry Mumber 2653-93-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,5 and 3 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2653-93:
(6*2)+(5*6)+(4*5)+(3*3)+(2*9)+(1*3)=92
92 % 10 = 2
So 2653-93-2 is a valid CAS Registry Number.
InChI:InChI=1/C15H14O/c1-2-6-13-9-11-15(12-10-13)16-14-7-4-3-5-8-14/h2-5,7-12H,1,6H2

2653-93-2Relevant academic research and scientific papers

Palladium-catalyzed prenylation of (hetero)aryl boronic acids

Leister, Jeffrey,Chao, Darrian,Billingsley, Kelvin L.

supporting information, (2021/02/09)

Prenyl or dimethylallyl groups are common structural motifs in natural products and small molecule therapeutics. In this report, we describe a palladium-catalyzed method for the cross-coupling of aryl and heteroaryl boronic acids with prenyl alcohol. Catalyst systems based on dialkylbiaryl phosphines were highly active for this transformation. These supporting ligands provided opportunities for tuning the efficiency and regioselectivity of carbon–carbon bond formation. In addition, this method was further extended to the cross-coupling of symmetrical allylic alcohols with aryl boronic acids.

Design, synthesis and cytotoxicity of 7-deoxy aryl discodermolide analogues

Burlingame, Mark A.,Shaw, Simon J.,Sundermann, Kurt F.,Zhang, Dan,Petryka, Joseph,Mendoza, Esteban,Liu, Fenghua,Myles, David C.,LaMarche, Matthew J.,Hirose, Tomoyasu,Freeze, B. Scott,Smith III, Amos B.

, p. 2335 - 2338 (2007/10/03)

A series of 7-deoxy discodermolide analogues in which the lactone fragment 'C' was replaced by aryl substituents were designed, synthesized, and evaluated for cytotoxicity.

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