1-ethynyl-4-methoxybenzene

• ChemBase ID: 69907
• Molecular Formular: C9H8O
• Molecular Mass: 132.15922
• Monoisotopic Mass: 132.05751488
• SMILES: COc1ccc(cc1)C#C
• Canonical SMILES: COc1ccc(cc1)C#C
• InChI: InChI=1S/C9H8O/c1-3-8-4-6-9(10-2)7-5-8/h1,4-7H,2H3
• InChIKey: KBIAVTUACPKPFJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethynyl-4-methoxybenzene
• IUPAC Traditional name: 1-ethynyl-4-methoxybenzene
• Synonyms: 4-Ethynylanisole; 1-Ethynyl-4-methoxybenzene; 4-Ethynylanisole; 4-Methoxyphenylacetylene; 1-eth-1-ynyl-4-methoxybenzene; 4-Methoxyphenylacetylene; 4-Ethynylanisole; 1-Ethynyl-4-methoxy-benzene; 1-ethynyl-4-methoxybenzene; p-Methoxyphenylethyne; p-Ethynylanisole; 4-Methoxy-1-ethynylbenzene; 4-Methoxyphenylethyne; Anisylacetylene; NSC 71091; 1-乙炔-4-甲氧基苯; 4-乙炔基苯甲醚; 4-甲氧基苯乙炔

Database IDs

• CAS Number: 768-60-5
• MDL Number: MFCD00168815
• PubChem SID: 24852402; 162035632
• PubChem CID: 251020

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.9664098
• LogD (pH = 7.4): 1.9664098
• Log P: 1.9664098
• Molar Refractivity: 37.6935 cm^3
• Polarizability: 15.433258 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Hexane; Methanol
• Apperance: Pale Yellow Oil
• Melting Point: 27-29°C; 28 - 29°C; 28-29 °C(lit.); 28-29°C
• Boiling Point: 60-65°C/1.5mmHg; 87-91 °C/11 mmHg(lit.); 87-91°C/11mm; 87-91°C/11mm
• Flash Point: 179.6 °F; 180 °F; 82 °C; 82°C; 82°C(180°F)
• Density: 1.019; 1.019 g/mL at 25 °C(lit.)
• Refractive Index: 1.563; n20/D 1.563(lit.)
• Hydrophobicity(logP): 2.331

Safety Information

• Storage Warning: IRRITANT; Irritant/Light Sensitive/Keep Cold/Store under Argon; Light and Temperature Sensitive
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 95+%; 97%; 98%; 99%
• Linear Formula: CH3OC6H4C≡CH

DETAILS

Sigma Aldrich - 206490

Application
1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes affords functionalized cyclopentenes in good yields.1
Forms the corresponding propargyl aldehyde in good yield directly from DMF-dimethyl acetal without the need for making an acetylide salt.
Used together with an arylboronic acid and sodium azide in a copper-catalyzed, three-component synthesis of trisubstituted 1,2,4-triazoles. Employed in a study of a gold (III)-catalyzed hydroamination of alkynes leading to N-vinylindoles.
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 520055

Legal Information
Manufactured by CB Research and Development

Toronto Research Chemicals - M265805

Intermediate in the synthesis of histamine H3-receptor antagonists. Also utilized to prepare its luminescent copper complex.

REFERENCES

• Krause, M., et al.: J. Med. Chem., 41, 4171 (1998)
• Yam, V.W.-W., et al.: Organomettalics, 17, 3293 (1998)