171087-99-3

Basic information

• Product Name: 2,3-Dimethoxyphenylacetylene
• Synonyms: 2,3-Dimethoxyphenylacetylene;2,3-Dimethoxy-1-ethynylbenzene;2,3-DiMethoxyphenylacetylen
• CAS NO: 171087-99-3
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.1852
• Mol File: 171087-99-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3-Dimethoxyphenylacetylene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethoxyphenylacetylene(171087-99-3)
• EPA Substance Registry System: 2,3-Dimethoxyphenylacetylene(171087-99-3)

Safety Data

• Hazardous Substances Data: 171087-99-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3-Dimethoxyphenylacetylene is utilized as a building block in organic synthesis for the construction of a wide range of organic molecules. Its reactivity allows for the creation of diverse chemical structures, making it a valuable component in the synthesis process.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,3-Dimethoxyphenylacetylene is used as a key intermediate in the production of various drugs. Its ability to modify the properties of resulting compounds contributes to the development of new and improved pharmaceuticals.
Used in Agrochemical Production:
Similarly, in agrochemicals, 2,3-Dimethoxyphenylacetylene serves as an essential component in the synthesis of different agrochemicals, enhancing their effectiveness and properties.
Used in Materials Science:
2,3-Dimethoxyphenylacetylene has potential applications in materials science, where it can be employed as a precursor for the synthesis of functional materials with unique electronic and optical properties. Its versatility in this field opens up opportunities for the development of advanced materials with specific characteristics.

Upstream product

• 171087-98-2 [2-(2,3-dimethoxyphenyl)ethynyl]trimethylsilane 
• 91-16-7 1,2-dimethoxybenzene 
• 25245-33-4 1-iodo-2,3-dimethoxybenzene 
• 5424-43-1 3-bromoveratrole 
• 60190-80-9 dimethyl (1-diazo-2-oxo-2-phenylethyl)phosphonate 
• 86-51-1 2,3-dimethyoxybenzaldehyde 

Downstream Products

• 1004754-45-3 2,8-bis(2,3-dimethoxybenzene-1-ylethynyl)-4,10-dimethyl-6H,12H-5,11-methanodibenzodiazocine 
• 1450594-61-2 1-benzyl-4-(2,3-dimethoxyphenyl)-1H-1,2,3-triazole 
• 175844-62-9 1,4-bis[2-(2,3-dimethoxyphenyl)ethyl]-2,3-dimethoxybenzene 
• 175844-53-8 1,4-bis<2-(2,3-dihydroxyphenyl)ethyl>-2,3-dihydroxybenzene 
• 175844-60-7 1,4-bis(2,3-dimethoxyphenyl)butane 
• 175844-52-7 1,4-bis(2,3-dihydroxyphenyl)butane 
• 171088-01-0 1,3-bis(2,3-dimethoxyphenyl)propane 
• 171088-06-5 3,3'-propane-1,3-diylbis(1,2-benzenediol) 
• 299926-55-9 1-(2,3-dihydroxyphenyl)-2-(8-hydroxyquinolin-7-yl)ethane 
• 299926-53-7 1-(2,3-dimethoxyphenyl)-2-(8-methoxyquinolin-7-yl)ethane 
• 175844-61-8 1,4-bis(2,3-dimethoxyphenylethynyl)-2,3-dimethoxybenzene 
• 171088-00-9 1,3-bis(2,3-dimethoxyphenyl)propyne 

Relevant articles and documents

A convenient reagent for aldehyde to alkyne homologation

A convenient reagent for the one-carbon homologation of an aldehyde to the corresponding alkyne is reported. This reagent allows this conversion to conveniently be carried out on a large scale under ambient conditions.

Synthesis of bis(catechol) ligands derived from Troeger's base and their dinuclear triple-stranded complexes with titanium(IV) ions

Bis(catechol) ligands derived from 2,8-disubstituted analogues of Troeger's base and monofunctionalized MOM-protected or unprotected catechols bearing both rigid and flexible spacers were synthesized, which gave rise to dissymmetric oxygen donor ligands w

Macrotricyclic Steroid Receptors by Pd°-Catalyzed Cross-Coupling Reactions: Dissolution of Cholesterol in Aqueous Solution and Investigations of the Principles Governing Selective Molecular Recognition of Steroidal Substrates

Three double-decker cyclophane receptors, (±)-2,(±)-3, and (±)-4 with 11-13-A deep hydrophobic cavities were prepared and their steroid-binding properties investigated in aqueous and methanolic solutions. Pd°-Catalyzed cross-coupling reactions were key steps in the construction of these novel macrotricyclic structures. In the synthesis of D2-symmetrical (±)-2, the double-decker precursor (±)-7 was obtained in 14% yield by fourfold Stille coupling of equimolar amounts of bis(tributylstannyl)acetylene with dibromocyclophane 5 (Scheme 1). For the preparation of the macrotricyclic precursor (±)-15 of D2-.symmetrical (±)-3, diiodocylophane 12 was dialkynylated with Me3SiC≡CH to give 13 using the Sonogoshira cross-coupling reaction; subsequent alkyne deprotection yielded the diethynylated cyclophane 14, which was transformed in 42% yield into (±)-15 by Glaser-Hay macrocyclization (Scheme 2). The synthesis of the C2-symmetrical conical receptor (±)-4 was achieved via the macrotricyclic precursor (±)-25, which was prepared in 20% yield by the Hiyama cross-coupling reaction between the diiodo[6.1.6.1]paracyclophane 19 and the larger, dialkynylated cyclophane 17 (Scheme 4). Solid cholesterol was efficiently dissolved in water through complexation by (±)-2 and (±)-3, and the association constants of the formed 1:1 inclusion complexes were determined by solid-liquid extraction as Ka = 1.1 × 106 and 1.5 × 105 1 mol-1, respectively (295 K) (Table 1). The steroid-binding properties of the three receptors were analyzed in detail by 1H-NMR binding titrations in CD3OD. Observed steroid-binding selectivities between the two structurally closely related cylindrical receptors (±)-2 and (±)-3 (Table 2) were explained by differences in cavity width and depth, which were revealed by computer modeling (Fig. 4). Receptor (±)-2, with two ethynediyl tethers linking the two cyclophanes, possesses a shallower cavity and, therefore, is specific for flatter steroids with a C(5)=C(6) bond, such as cholesterol. In contrast, receptor (±)-3. constructed with longer buta-1,3-diynediyl linkers, has a deeper and wider hydrophobic cavity and prefers fully saturated steroids with an aliphatic side chain, such as 5α-cholestane (Fig. 7). In the 1:1 inclusion complexes formed by the conical receptor (±)-4 (Table 3), testosterone or progesterone penetrate the binding site from the wider cavity side, and their flat A ring becomes incorporated into the narrower [6.1.6.1]paracyclophane moiety. In contrast, cholesterol penetrates (±)-4 with its hydrophobic side chain from the wider rim of the binding side. This way, the side chain is included into the narrower cavity section shaped by the smaller [6.1.6.1]paracyclophane, while the A ring protrudes with the OH group at C(3) into the solvent on the wider cavity side (Fig. 8). The molecular-recognition studies with the synthetic receptors (±)-2, (±)-3, and (±)-4 complement the X-ray investigations on biological steroid complexes in enhancing the understanding of the principles governing selective molecular recognition of steroids.

Synthesis of linear oligo(catechol) ligands for the metal directed self-assembling of helicates

The synthesis of the oligo(catechol) systems 1-4 with different substituents, length of the connecting spacer, and number of catechol units is achieved by the use of various coupling reactions (e.g. Wurtz, Glaser-Eglinton, Stephens-Castro). In order to do this methods of preparing the building blocks, 2,3-dimethoxybenzyl bromides 5, 2,3-dimethoxyphenylacetylene (17), or 1,4-dibromo-2,3-dimethoxybenzene (23) have been developed starting with simple catechol (benzene-1,2-diol) derivatives.

Bildung eines "meso-Helicats" durch Selbstorganisation von drei Bis(brenzkatechinat)-Liganden und zwei Titan(IV)-Ionen

Keywords: Brenzkatechin; Komplexe mit Sauerstoffliganden; Selbstorganisation; Titanverbindungen