77336-36-8

Usage

Uses

Used in Pharmaceutical Industry:
Benzene, 1-ethynyl-2,4-dimethoxyis used as an intermediate in the production of pharmaceuticals for its ability to be synthesized into various medicinal compounds.
Used in Organic Compounds Synthesis:
This chemical is also utilized in the synthesis of a range of organic materials, including dyes, pigments, and fragrances, due to its reactive ethynyl and dimethoxy groups that can be further modified in chemical reactions.
It is important to handle Benzene, 1-ethynyl-2,4-dimethoxywith care, as it is classified as toxic and can cause skin and eye irritation upon contact. Prolonged exposure may also result in harmful effects on the liver and kidneys.

Upstream product

• 77336-35-7 1-(1-Iodo-vinyl)-2,4-dimethoxy-benzene 
• 146795-08-6 4-(2,4-dimethoxyphenylmethylidene)-3-methylisoxazol-5(4H)-one 
• 558-13-4 carbon tetrabromide 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 77336-34-6 2,4-Dimethoxyacetophenone Hydrazone 
• 20469-63-0 1-iodo-2,4-dimethoxybenzene 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 213459-61-1 1-(2,2-dibromovinyl)-2,4-dimethoxybenzene 
• 157953-17-8 4-(2,4-Dimethoxy-phenyl)-2-methyl-but-3-yn-2-ol 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 7314-44-5 2,4-dimethoxylbenzyl alcohol 

Downstream Products

• 4107-65-7 2,4-dimethoxybenzonitrile 

Relevant academic research and scientific papers

DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes

Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).

Photochemical Dual-Catalytic Synthesis of Alkynyl Sulfides

A photochemical dual-catalytic cross-coupling to form alkynyl sulfides via C(sp)?S bond formation is described. The cross-coupling of thiols and bromoalkynes is promoted by a soluble organic carbazole-based photocatalyst using continuous flow techniques. Synthesis of alkynyl sulfides bearing a wide range of electronically and sterically diverse aromatic alkynes and thiols can be achieved in good to excellent yields (50–96 %). The simple continuous flow setup also allows for short reaction times (30 min) and high reproducibility on gram scale. In addition, we report the first application of photoredox/nickel dual catalysis towards macrocyclization, as well as the first example of the incorporation of an alkynyl sulfide functional group into a macrocyclic scaffold.

Acetylenes from Aldehydes. Preparation of Ethynylphenols and Phenylacetylenes by Flash Vacuum Pyrolysis of Isoxazolones

The flash vacuum pyrolysis method of synthesis of acetylenes from aldehydes via isoxazolones is a convenient method for the preparation of a variety of derivatives, including kinetically unstable, sensitive compounds such as the ethynylphenols.

Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy

A gold-catalyzed intermolecular alkyne oxidation for the preparation of 3-coumaranones has been developed. Using 8-isopropylquinoline N-oxides as oxidants, the reactions of o-ethynylanisoles afford versatile 3-coumaranones in moderate to good isolated yields. The synthetic utility of this chemistry is also indicated by the synthesis of the natural product sulfuretin.

The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity

The dual role of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was demonstrated in a synthesis of terminal aryl- and styryl-acetylenes. Mechanistically, a tandem process involving elimination/Umpolung/protonation occurs in a single step to generate terminal aryl- and styryl-acetylenes from geminal dibromoalkenes. The key to the success of this transformation lies in the organobase-mediated generation of the acetylide from the 1-bromoalkynes at room temperature. The unique characteristics of DBU as an inherently safer reagent make it an attractive alternative to previous systems wherein required pyrophoric reagents and nonambient temperatures remain unsolved issues. The procedure does not work for the synthesis of alkyl-acetylenes.

2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzyl-pyrrolo[2,3-d] pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance

Gangjee et al. recently reported a novel series of 2-amino-4-methyl-5- phenylethyl substituted-7-benzyl-pyrrolo[2,3-d]pyrimidines, some of which exhibited two digit nanomolar antitumor and antimitotic activity and were not subject to P-glycoprotein (Pgp)

Electrophilic cyclization of 2-chalcogenealkynylanisoles: Versatile access to 2-chalcogen-benzo[b]furans

An efficient synthesis of 2-ehalcogen-3-substituted-benzo[b]furan compounds has been accomplished via electrophilic cyclization reaction of 2-chalcogenealkynyl anisoles using I2, ICl, Br2, and PhSeBr as electrophile sources. The product distributions were strongly dependent on the nature of substituents in the aromatic ring of anisole and on the chalcogen atom directly bonded to the triple bond. The 2-chalcogen-3-iodo- benzo[b]furans obtained smoothly underwent conversion to more complex structures of benzo-[b]furan derivatives via palladium- or copper-catalyzed cross-coupling reaction with thiols, diphenyl diselenides, and zincates.

One-pot conversion of activated alcohols into 1,1-dibromoalkenes and terminal alkynes using tandem oxidation processes with manganese dioxide

Approaches to the preparation of C1-homologated dibromoalkenes and terminal alkynes from activated alcohols using one-pot tandem oxidation processes (TOPs) with manganese dioxide are outlined. The conversion of alcohols into dibromoalkenes is described using dibromomethyltriphenylphosphonium bromide and the formation of terminal alkynes was achieved via a sequential one-pot, two-step process utilising the Bestmann-Ohira reagent.

One-pot conversion of activated alcohols into terminal alkynes using manganese dioxide in combination with the Bestmann-Ohira reagent

The direct conversion of activated primary alcohols into terminal alkynes through a sequential one-pot, two-step process involving oxidation with manganese dioxide and then treatment with the Bestmann-Ohira reagent is described. This transformation proceeds efficiently (59-99% yield) under mild reaction conditions with a range of benzylic, heterocyclic and propargylic alcohols. A tandem variant is also described, which is successful only with highly activated substrates.

Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones

The invention relates to the use of 1,3-bis-aromatic-prop-2-en-1-ones (chalcones), 1,3-bis-aromatic-propan-1-ones (dihydrochalcones), and 1,3-bis-aromatic-prop-2-yn-1-ones for the preparation of pharmaceutical compositions for the treatment or prophylaxis of a number of serious diseases including i) conditions relating to harmful effects of inflammatory cytokines, ii) conditions involving infection by Helicobacter species, iii) conditions involving infection by viruses, iv) neoplastic disorders, and v) conditions caused by microorganisms or parasites. The invention also relates to novel chalcones and dihydrochalcones (especially alkoxy substituted variants) having advantageous substitution patterns with respect to their effect as drug substances, and to methods of preparing them, as well as to pharmaceutical compositions comprising the novel chalcones. Moreover, the present invention relates to a method for the isolation of Leishmania fumarate reductase, QSAR methodologies for selecting potent compounds for the above-mentioned purposes.