6953-67-9

Basic information

• Product Name: 1-(3,4-dimethoxyphenyl)prop-2-yn-1-ol
• Synonyms: 1-(3,4-Dimethoxyphenyl)-2-propyn-1-ol
• CAS NO: 6953-67-9
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.2112
• Mol File: 6953-67-9.mol

Chemical Properties

• Boiling Point: 296.3°C at 760 mmHg
• Flash Point: 133°C
• Density: 1.138g/cm³
• Vapor Pressure: 0.000651mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: 1-(3,4-dimethoxyphenyl)prop-2-yn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-dimethoxyphenyl)prop-2-yn-1-ol(6953-67-9)
• EPA Substance Registry System: 1-(3,4-dimethoxyphenyl)prop-2-yn-1-ol(6953-67-9)

Safety Data

• Hazardous Substances Data: 6953-67-9(Hazardous Substances Data)

Usage

Type of compound

Propargyl alcohol derivative

Substitution on phenyl group

Two methoxy groups at the 3 and 4 positions

Common use

Reactant in organic synthesis

Specific applications

Formation of heterocycles and complex organic molecules

Biological properties

Potential antioxidant and anti-inflammatory effects

Relevance in pharmaceuticals

Development of new pharmaceuticals and chemical products

Unique features

Compound's structure and reactivity

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 1066-54-2 trimethylsilylacetylene 
• 74-86-2 acetylene 
• 70277-75-7 lithium acetylide 

Downstream Products

• 10548-83-1 1-(3,4-dimethoxyphenyl)propan-1-ol 
• 1297605-72-1 1-(3,4-dimethoxyphenyl)-2-[(2S,4S)-4-isopropyl-3-tosyloxazolidin-2-yl]ethanone 
• 1429048-82-7 methyl 2-(3,4-dimethoxyphenyl)pyrrolo[1,2-b]pyridazine-7-carboxylate 

Relevant articles and documents

Lipase/Oxovanadium Co-Catalyzed Dynamic Kinetic Resolution of Propargyl Alcohols: Competition between Racemization and Rearrangement

Quantitative conversion of racemic propargyl alcohols into optically active propargyl esters with up to 99% ee has been achieved by lipase/oxovanadium co-catalyzed dynamic kinetic resolution, which combines the lipase-catalyzed enantioselective esterification of the racemic substrates and the in situ racemization of the remaining enantiomers. The success is owed to our discovery of a magic solvent, (trifluoromethyl)benzene, that accelerated the racemization while sufficiently suppressing the common oxovanadium-catalyzed rearrangement of propargyl alcohols to irreversibly produce enals.

Synthesis and evaluation of novel fluorinated pyrazolo-1,2,3-triazole hybrids as antimycobacterial agents

A library of novel 3-trifluoromethyl pyrazolo-1,2,3-triazole hybrids (5-7) were accomplished starting from 5-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-amine (1) via key intermediate 2-azido-N-(5-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)acetamide (3) throu

Parallel synthesis of "Click" chalcones as antitubulin agents

It has been shown that some chalcones are able to inhibit tubulin polymerization, giving cytotoxicity and destruction of tumoral vasculature. A library of 180 novel chalcone analogs has been synthesized via click chemistry and screened for their cytotoxic

Diversity-oriented synthesis based on the dppp-catalyzed mixed double-michael reactions of electron-deficient acetylenes and β-amino alcohols

In this study, we prepared oxizolidines through 1,3-bis(diphenylphosphino)- propane (DPPP)-catalyzed mixed double-Michael reactions of β-amino alcohols with electron-deficient acetylenes. These reactions are very suitable for the diversity-oriented parallel syntheses of oxizolidines because: (i) they are performed under mild metal-free conditions and (ii) the products are isolated without complicated work-up. To demonstrate the applicability of mixed double-Michael reactions for the preparation of five-membered-ring heterocycles, we prepared 60 distinct oxazolidines from five β-amino alcohols and 12 electron-deficient acetylenes. We synthesized 36 of these 60 oxazolidines in enantiomerically pure form from proteinogenic amino acid-derived β-amino alcohols.

Rapid preparation of 3-deoxyanthocyanidins and novel dicationic derivatives: New insight into an old procedure

Common 3-deoxyanthocyanidins and original dicationic flavylium- benzopyrylium derivatives are easily and efficiently synthesized through reactions between the corresponding phenols and aryl ethynyl ketones in the presence of aqueous hexafluorophosphoric acid. The mechanism of the reaction is discussed and two competitive pathways are consistent with our results. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Straightforward synthesis of highly hydroxylated phloroglucinol-type 3-deoxyanthocyanidins

Phloroglucinol-type 3-deoxyanthocyanidins were synthesized through the interaction between phloroglucinol derivatives and arylethynylketones in acetic acid in the presence of aqueous hexafluorophosphoric acid. This methodology was applied to achieve the synthesis of natural apigeninidin, luteolinidin and tricetanidin with high yields. Georg Thieme Verlag Stuttgart.

Straightforward synthesis of highly hydroxylated phloroglucinol-type 3-deoxyanthocyanidins

Phloroglucinol-type 3-deoxyanthocyanidins were synthesized through the interaction between phloroglucinol derivatives and arylethynylketones in acetic acid in the presence of aqueous hexafluorophosphoric acid. This methodology was applied to achieve the synthesis of natural apigeninidin, luteolinidin and tricetanidin with high yields. Georg Thieme Verlag Stuttgart.

Synthesis and trypanocidal activity of 1,4-bis-(3,4,5-trimethoxy-phenyl)-1,4-butanediol and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol

Chagas' disease is endemic in Central and South American countries. Specific chemotherapy with nifurtimox or benznidazole has been recommended for treatment of recent infection but they have limited efficacy. The natural products veraguensin (1) and grand