22944-08-7

Basic information

• Product Name: Benzene, 2-ethynyl-1,4-diMethoxy-
• Synonyms: Benzene, 2-ethynyl-1,4-diMethoxy-;2-ethynyl-1,4-dimethoxybenzene
• CAS NO: 22944-08-7
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.1852
• Mol File: 22944-08-7.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzene, 2-ethynyl-1,4-diMethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 2-ethynyl-1,4-diMethoxy-(22944-08-7)
• EPA Substance Registry System: Benzene, 2-ethynyl-1,4-diMethoxy-(22944-08-7)

Safety Data

• Hazardous Substances Data: 22944-08-7(Hazardous Substances Data)

Usage

General Description

Benzene, 2-ethynyl-1,4-dimethoxy- is a chemical compound with the molecular formula C10H10O2. It is a derivative of benzene with two methoxy groups and an ethynyl group attached to the 2 and 4 positions, respectively. Benzene, 2-ethynyl-1,4-dimethoxy- is used in organic synthesis as a building block for the production of pharmaceuticals and agrochemicals. It is also utilized in the manufacturing of dyes and pigments. Additionally, its unique chemical structure and properties make it a valuable tool in academic and industrial research for the development of new materials and compounds. However, it is important to handle this compound with care as it is considered harmful if ingested and can cause skin and eye irritation.

Upstream product

• 104970-98-1 1-chloro-1-(2,5-dimethoxyphenyl)ethene 
• 531504-78-6 [(2,5-dimethoxyphenyl)ethynyl]trimethylsilane 
• 1201-38-3 2',5'-dimethoxyacetophenone 
• 3899-91-0 4-methoxyphenyl p-toluenesulfonate 
• 25245-35-6 1-iodo-2,4-dimethoxybenzene 
• 98279-45-9 3-iodo-4-methoxyphenol 
• 186134-37-2 3-iodo-4-methoxyphenyl 4-methylbenzenesulfonate 
• 150-78-7 1,4-dimethoxybezene 
• 25245-34-5 1-bromo-2,5-dimethoxybenzene 
• 22944-10-1 2-methyl-4-(2,5-dimethoxyphenyl)-3-butyn-2-ol 
• 1224168-51-7 2-(2,2-dibromoethenyl)-1,4-dimethoxybenzene 
• 558-13-4 carbon tetrabromide 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 75-20-7 calcium carbide 

Downstream Products

• 104971-15-5 1,4-Dimethoxy-2-oct-1-ynyl-benzene 
• 479546-83-3 N-[6-(2,5-dimethoxy-phenylethynyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl]-2,2-dimethyl-propionamide 
• 1070162-89-8 4-(2,5-dimethoxyphenylethynyl)-2,5-dimethoxybromobenzene 
• 861906-14-1 1-(2,5-Dimethoxy-phenylethynyl)-4-ethynyl-2,5-dimethoxy-benzene 
• 861906-15-2 C₃₀H₂₆O₆ 
• 873464-13-2 2-(2,5-dimethoxy-phenylethynyl)-6-ethynyl-pyridine 

Relevant articles and documents

Hydroquinone-pyrrole dyads with varied linkers

A series of pyrroles functionalized in the 3-position with p-dimethoxy benzene via various linkers (CH2, CH2CH2, CH=CH, C=C) has been synthesized. Their electronic properties have been deduced from 1H NMR, 13C NMR, and UV-vis spectra to detect possible interactions between the two aromatic subunits. The extent of conjugation between the subunits is largely controlled by the nature of the linker, with the largest conjugation found with the tmns-ethene linker and the weakest with the aliphatic linkers. DFT calculations revealed substantial changes in the HOMO-LUMO gap that correlated with the extent of conjugation found experimentally. The results of this work are expected to open up for use of the investigated compounds as components of redox-active materials in sustainable, organic electrical energy storage devices.

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.).

Iodine/Palladium approaches to the synthesis of polyheterocyclic compounds

Chemical Equation Represented A simple, straightforward strategy for the synthesis of polyheterocyclic compounds (PHCs) is reported, which involves iterative cycles of palladium-catalyzed Sonogashira coupling, followed by iodocyclization using I2 or ICI. A variety of heterocyclic units, including benzofurans, benzothiophenes, indoles, and isocoumarins, can be efficiently incorporated under mild reaction conditions. In addition, variations of this strategy afford a variety of linked and fused PHCs.