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
• Article Data: 5

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

General Description

2,3-Dimethoxyphenylacetylene is a chemical compound with the molecular formula C10H10O2. It is a derivative of phenylacetylene, with two methoxy groups attached to the phenyl ring at the 2 and 3 positions. 2,3-Dimethoxyphenylacetylene is used in organic synthesis and as a building block for the construction of various organic molecules. It is often employed in the production of pharmaceuticals, agrochemicals, and other fine chemicals due to its versatile reactivity and ability to modify the properties of the resulting compounds. Additionally, 2,3-Dimethoxyphenylacetylene has potential applications in materials science and as a precursor for the synthesis of functional materials with unique electronic and optical properties.

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

• 171088-00-9 1,3-bis(2,3-dimethoxyphenyl)propyne 
• 175844-61-8 1,4-bis(2,3-dimethoxyphenylethynyl)-2,3-dimethoxybenzene 
• 299926-53-7 1-(2,3-dimethoxyphenyl)-2-(8-methoxyquinolin-7-yl)ethane 
• 299926-55-9 1-(2,3-dihydroxyphenyl)-2-(8-hydroxyquinolin-7-yl)ethane 
• 171088-06-5 3,3'-propane-1,3-diylbis(1,2-benzenediol) 
• 171088-01-0 1,3-bis(2,3-dimethoxyphenyl)propane 
• 175844-52-7 1,4-bis(2,3-dihydroxyphenyl)butane 
• 175844-60-7 1,4-bis(2,3-dimethoxyphenyl)butane 
• 175844-53-8 1,4-bis<2-(2,3-dihydroxyphenyl)ethyl>-2,3-dihydroxybenzene 
• 175844-62-9 1,4-bis[2-(2,3-dimethoxyphenyl)ethyl]-2,3-dimethoxybenzene 
• 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 

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.

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.

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

Keywords: Brenzkatechin; Komplexe mit Sauerstoffliganden; Selbstorganisation; Titanverbindungen