860687-65-6

Basic information

• Product Name: 4-CHLORO-2-ETHYNYL-1-NITRO-BENZENE
• Synonyms: 4-CHLORO-2-ETHYNYL-1-NITRO-BENZENE
• CAS NO: 860687-65-6
• Molecular Formula: C₈H₄ClNO₂
• Molecular Weight: 181.57586
• Mol File: 860687-65-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-CHLORO-2-ETHYNYL-1-NITRO-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-ETHYNYL-1-NITRO-BENZENE(860687-65-6)
• EPA Substance Registry System: 4-CHLORO-2-ETHYNYL-1-NITRO-BENZENE(860687-65-6)

Safety Data

• Hazardous Substances Data: 860687-65-6(Hazardous Substances Data)

Upstream product

• 20567-51-5 (5-chloro-2-nitro-phenyl)-propiolic acid 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 20357-28-2 5-chloro-2-nitro-trans-cinnamic acid 
• 20567-41-3 (2RS:3SR)-2,3-dibromo-3-(5-chloro-2-nitro-phenyl)-propionic acid 
• 63860-31-1 2-bromo-4-chloro-1-nitrobenzene 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 51282-49-6 methyl 5-chloro-2-nitrobenzoate 

Downstream Products

• 412947-46-7 4-chloro-2-ethynylaniline 

Relevant articles and documents

Gold-catalyzed stereoselective synthesis of azacyclic compounds through a redox/[2 + 2 + 1] cycloaddition cascade of nitroalkyne substrates

We report a new redox/cycloaddition cascade on readily available 1-alkynyl-2-nitrobenzenes that produces complex azacyclic compounds stereoselectively. The core structures of the resulting products are constructed through a formal [2 + 2 + 1] cycloaddition among α-carbonyl carbenoids, nitroso species, and external alkenes.

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.