947409-39-4

Basic information

• Product Name: 2-chloro-6-nitrophenyl acetylene
• Synonyms: 2-chloro-6-nitrophenyl acetylene
• CAS NO: 947409-39-4
• Molecular Weight: 181.578
• Mol File: 947409-39-4.mol

Chemical Properties

• CAS DataBase Reference: 2-chloro-6-nitrophenyl acetylene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-6-nitrophenyl acetylene(947409-39-4)
• EPA Substance Registry System: 2-chloro-6-nitrophenyl acetylene(947409-39-4)

Safety Data

• Hazardous Substances Data: 947409-39-4(Hazardous Substances Data)

Upstream product

• 83-42-1 6-chloro-2-nitrotoluene 
• 6361-22-4 2-chloro-6-nitrobenzaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 

Downstream Products

• 947513-72-6 C₂₆H₂₁NO₄ 
• 1057483-30-3 C₁₆H₁₄ClNO₄ 
• 1415246-99-9 C₁₇H₁₁ClN₂O₃ 
• 1415246-98-8 C₁₂H₁₁ClN₂O₃ 

Relevant articles and documents

METHOD FOR MAKING BIARYL COMPOUNDS, COMPOUNDS MADE BY THE METHOD, AND METHOD FOR THEIR USE

Certain disclosed embodiments of the present invention concern a method for making biaryl compounds by combining a diene with a dienophile under reaction conditions that facilitate a Diels-Alder reaction. Certain embodiments are particularly directed to making a tetra-ortho-substituted biaryl compounds. The disclosed method may involve using novel dienes, dienophiles, or both. Similarly, certain of the biaryl compounds are novel compounds too. Additional disclosed embodiments concern a method for making useful compounds by first making a Diels-Alder adduct. The Diels-Alder adduct is then further modified or coupled to other compounds. The method can be used to make carbazoles, such as Siamenol. Disclosed biaryl compounds are useful for a number of applications, such as pharmacophores and organocatalysts.

Diels - Alder approach for the construction of halogenated, o-nitro biaryl templates and application to the total synthesis of the anti-HIV agent siamenol

(Chemical Equation Presented) A rapid Diels - Alder approach to halogenated biaryl templates is described. These biaryl templates are available in two steps from the corresponding aromatic aldehydes. The scope of subsequent Suzuki couplings on the biaryl chlorides is explored. Good tolerance for both electron-donating and electron-withdrawing groups in the coupling process can be achieved. Further functionalization of the biaryl templates is described. Hydrogenation of the nitro moiety with concomitant removal of the benzyl ether yields the o-anilino, o-phenolic polyaryls. Selective reduction of the nitro group can be accomplished. Alternatively, the benzyl ether can be selectively removed under Lewis acidic conditions. The utilization of the Diels - Alder adducts for the synthesis of a series of chlorinated carbazoles via the Cadogan cyclization is also demonstrated. Finally, application of this technology to the total synthesis of siamenol, an anti-HIV agent, is reported.