10548-83-1

Basic information

• Product Name: 1-(3',4'-Dimethoxyphenyl)-1-propanol
• Synonyms: 1-Veratryl Propanol;Ethylveratrylcarbinol;α-Ethyl-3,4-diMethoxybenzyl Alcohol;α-Ethylveratryl Alcohol;1-(3,4-diMethoxyphenyl)propan-1-ol
• CAS NO: 10548-83-1
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.25
• Product Categories: Aromatics
• Mol File: 10548-83-1.mol

Chemical Properties

• Melting Point: 36-38 °C
• Boiling Point: 300.6 °C at 760 mmHg
• Flash Point: 135.6 °C
• Appearance: /
• Density: 1.06 g/cm³
• PKA: 14.25±0.20(Predicted)
• CAS DataBase Reference: 1-(3',4'-Dimethoxyphenyl)-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3',4'-Dimethoxyphenyl)-1-propanol(10548-83-1)
• EPA Substance Registry System: 1-(3',4'-Dimethoxyphenyl)-1-propanol(10548-83-1)

Safety Data

• Hazardous Substances Data: 10548-83-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(3',4'-Dimethoxyphenyl)-1-propanol is used as a synthetic building block for the creation of various organic compounds. Its chemical structure, featuring a propanol group with a dimethoxyphenyl moiety, allows it to serve as a versatile intermediate in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
The compound's red oil appearance is indicative of its potential reactivity and utility in organic reactions, where it can be employed to introduce specific functional groups or structural elements into target molecules. Its uses in organic synthesis are diverse, reflecting the broad scope of applications for compounds that serve as synthetic intermediates.

Upstream product

• 1835-04-7 ethyl 3,4-dimethoxyphenyl ketone 
• 31706-95-3 1'-Hydroxymethyleugenol 
• 93-16-3 Methylisoeugenol 
• 121-33-5 vanillin 
• 74-96-4 ethyl bromide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 6953-67-9 1-(3,4-dimethoxyphenyl)prop-2-yn-1-ol 
• 925-90-6 ethylmagnesium bromide 
• 10467-10-4 ethylmagnesium iodide 

Downstream Products

• 191112-94-4 N-(2,2-Dimethoxy-ethyl)-N-[1-(3,4-dimethoxy-phenyl)-propyl]-C-phenyl-methanesulfonamide 
• 1835-04-7 ethyl 3,4-dimethoxyphenyl ketone 
• 5888-52-8 4-propyl-1,2-dimethoxybenzene 
• 93-16-3 Methylisoeugenol 
• 75513-68-7 3,4-bis-(3',4'-dimethoxyphenyl)-hex-3-ene 
• 191113-00-5 1-Ethyl-6,7-dimethoxy-2-phenylmethanesulfonyl-1,2-dihydro-isoquinoline 
• 69125-76-4 1-(3',4'-dimethoxyphenyl)-1,1-dideuteriopropane 
• 6380-24-1 (Z)-1,2-dimethoxy-4-(prop-1-en-1-yl)benzene 
• 6379-72-2 1,2-dimethoxy-4-(E)-propenylbenzene 
• 4974-97-4 1,2-Dimethoxy-4-(1-methoxy-propyl)-benzol 
• 4483-47-0 (+-)-1r-ethyl-3c-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2t-methyl-indan 

Relevant articles and documents

An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity

A series of nine methyl sulphones (3a-3i) starting from the aldehydes (1a-1i) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols (2a-2i) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF3.Et2O in acetic acid medium at room temperature for about 2-3 h. The reaction conditions are simple, yields are high (85%-95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1H, 13C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.

In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes

Thirty-four arylpropanoids and related compounds were evaluated in vitro for antifungal properties. Among them, 22 phenyl-, 4 naphthyl-, and 4 phenanthrylpropanoids; naphthalene; phenanthrene; and 2-chloro-1-hexyl-1- propanone were tested against dermatop

Oxygenation of styrenes catalyzed by N-doped carbon incarcerated cobalt nanoparticles

NCI-Co catalyzed olefin oxygenation reactions were investigated. Among the metals examined, including noble metals, the reaction proceeded specifically on Co catalysts, and nitrogen dopant was crucial for the catalytic activity. The presence of NaBH4 as a hydride source, the corresponding alcohols were obtained in high yields. The substrates bearing a reductant-sensitive functional group were made tolerant by changing the reductant and using an additive, and furthermore, the corresponding ketones were accessed by changing reaction conditions. A preliminary examination of other SOMOphiles suggested that the heterogeneous catalyst systems have the potential to be applied to more general hydrofunctionalization of olefins to form various kinds of bonds. Several mechanistic studies suggested that the reaction proceeded in a heterogeneous manner and formed a radical intermediate on cobalt nanoparticle species.

Unexpected formation of aryl dialkyl carbinol as a side product from the reaction of methoxyarylaldehydes with Grignard reagents

In the attempted formation of secondary aryl alkyl carbinols from the reaction of methoxyarylaldehydes with Grignard reagents, aryl dialkyl carbinols were formed as unexpected side products. A mechanism for their formation is proposed.

Methoxy-substituted stilbenes, styrenes, and 1-arylpropenes: Photophysical properties and photoadditions of alcohols

The photochemistry of trans-stilbene and four methoxy-substituted stilbene derivatives has been investigated in a variety of solvents. The fluorescence of all five trans isomers was quenched by 2,2,2-trifluoroethanol (TFE). Upon irradiation of the five substrates in TFE, the products derived from photoaddition of the solvent were detected. Nuclear magnetic resonance spectroscopy of the products formed by irradiation in TFE-OD indicated that the proton and nucleophile are attached to two adjacent atoms of the original alkene double bond. Irradiation of the corresponding methoxy-substituted styrenes and trans-1-arylpropenes in TFE produced the analogous solvent adducts. The photoaddition of TFE proceeded with the general order of reactivity: styre > trans-1-arylpropenes > trans-stilbenes. Transient carbocation intermediates were observed following laser flash photolysis of the stilbenes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The results are consistent with a mechanism that involves photoprotonation of the substrates by TFE or HFIP, followed by nucleophilic trapping of short-lived carbocation intermediates. Compared to the other stilbene derivatives, trans-3,5-dimethoxystilbene displayed a large quantum yield of fluorescence and a low quantum yield of trans-cis isomerization in polar organic solvents. The unique photophysical properties of trans-3,5-dimethoxystilbene are attributed to formation of a highly polarized charge-transfer excited state (μe = 13.2 D).

Mechanism of isomerization of 4-propyl-o-quinone to its tautomeric p- quinone methide

In previous work, we showed that o-quinones (3,5-cyclohexadiene-1,2- diones) can isomerize to p-quinone methides (4-alkyl-2,5-cyclohexadien-1- one) at rates which depend on the type of substituent at the para position [Iverson, S. L., Hu, L. Q., Vukomanovic, V., and Bolton, J. L. (1995) Chem. Res. Toxicol. 8, 537-544]. In the present investigation, we explored the mechanism of this isomerization reaction using 4-propyl-3,5-cyclohexadiene- 1,2-dione (PQ) and its benzyl dideuterio analog 4-(1',1'-dideuteriopropyl)- 3,5-cyclohexadiene-1,2-dione (DPQ). The results show that the isomerization reaction is general base-catalyzed, which suggests that amino acids on proteins with basic side chains could catalyze the reaction in vivo. The Bronsted β value was determined to be 0.23 ± 0.02, consistent with the transfer of a proton in the rate-determining step. The rate/pH profile generated from the buffer dilution plots showed dependence on hydroxide ion concentration from pH 7.8 to 9, indicative of base catalysis. From pH 6 to 7.8, the reaction was independent of pH, suggesting that other processes compete at low buffer concentration in this pH region. Substitution of the benzyl CH2 group with CD2 dramatically slows the isomerization reaction. The kinetic deuterium isotope effect on quinone methide formation was determined by measuring the amount of quinone methide trapped as GSH conjugates from PQ compared with DPQ. The isotope effect on product formation was 5.5 ± 0.6, 37 °C. These data provide further evidence that formation of these electrophilic quinone methides from o-quinones could be catalyzed by basic residues in vivo and that the reaction could be inhibited by deuterium substitution at the benzyl methylene group.

SYNTHESIS OF METABOLIC INTERMEDIATES OF DIETHYLSTILBESTROL

This report details the synthesis of 1) 3,4,4'-trihydroxy-α,α'-diethyl-trans-stilbene; 2) 3,4-bis-(p-hydroxyphenyl)-trans-3-hexenol; 3) 3,4-bis-(p-hydroxyphenyl)-2,4-cis,cis-hexadienol; 4) 3,4-bis-(3'-methoxy-4'-hydroxyphenyl)-trans-3-hexene; 5) 3,4-bis-(3',4'-dimethoxyphenyl)-trans-3-hexene.These compounds are suspected metabolites of diethylstilbestrol.