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Technology Process of 2,2'-Dibromo-6,6'-dinitrobiphenyl-4,4'-dicarboxylic acid

2,2'-Dibromo-6,6'-dinitrobiphenyl-4,4'-dicarboxylic acid

Base Information
  • Chemical Name:2,2'-Dibromo-6,6'-dinitrobiphenyl-4,4'-dicarboxylic acid
  • CAS No.:5167-62-4
  • Molecular Formula:C5H5N
  • Molecular Weight:79.1014
  • Hs Code.:
  • NSC Number:169213,159254
  • DSSTox Substance ID:DTXSID90303597
  • Nikkaji Number:J3.201.470D
  • Wikidata:Q82048959
2,2'-Dibromo-6,6'-dinitrobiphenyl-4,4'-dicarboxylic acid

Synonyms:2,2'-dibromo-6,6'-dinitrobiphenyl-4,4'-dicarboxylic acid;5167-62-4;NSC169213;DTXSID90303597;NSC159254;NSC-159254;NSC-169213

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Chemical Property of 2,2'-Dibromo-6,6'-dinitrobiphenyl-4,4'-dicarboxylic acid
Chemical Property:
  • Boiling Point:584.1°Cat760mmHg 
  • Flash Point:307.1°C 
  • PSA：166.24000 
  • Density:2.077g/cm3 
  • LogP:5.13780 
  • XLogP3:3.6
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:8
  • Rotatable Bond Count:3
  • Exact Mass:489.84704
  • Heavy Atom Count:26
  • Complexity:555
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MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:C1=C(C=C(C(=C1[N+](=O)[O-])C2=C(C=C(C=C2Br)C(=O)O)[N+](=O)[O-])Br)C(=O)O
  • General Description 3-Butenenitrile,2-methylene- (also known as 2-cyano-1,3-butadiene or 2-cyanobutadiene) is a valuable reagent in organic synthesis, particularly for [4+2] cycloaddition reactions. It can be efficiently synthesized via Horner-Emmons olefination of 2-cyano-2-alkenyl- or 2-cyano-3-phenyl-2-propenylphosphonates with carbonyl compounds, yielding stereoselective products with high E-configuration for the newly formed double bond, though mixtures of E,E and Z,E isomers may arise for the other double bond. This method provides a straightforward and general approach to access substituted derivatives of 3-Butenenitrile,2-methylene-.
Refernces

A convenient synthesis of substituted 2-cyano-1,3-butadienes

10.1055/s-1991-26407

The research aimed to develop a convenient synthesis method for substituted 2-cyano-1,3-butadienes, which are valuable reagents in organic synthesis, particularly for [4+2] cyclo additions. The study focused on the Horner-Emmons olefination of 2-cyano-2-alkenyl- or 2-cyano-3-phenyl-2-propenylphosphonates 1 with selected carbonyl compounds to yield various alkyl or phenyl substituted 2-cyano-1,3-butadienes 2 with high stereoselectivity and satisfactory yield. The process involved the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF) as a reagent, followed by the reaction with the resultant lithium derivatives and carbonyl compounds. The newly formed double bond consistently had the E configuration, while the formation of the other double bond was not stereoselective, resulting in mixtures of E,E and Z,E isomers. The chemicals used in the process included 2-cyano-2-alkenylphosphonates 1, BuLi (1.6 M solution in hexanes), disopropylamine, and silica gel (70-230 mesh), among others. The conclusion of the research was that an efficient, simple, and general method for the preparation of substituted 2-cyano-1,3-butadienes 2 from readily accessible 2-cyano-2-alkenylphosphonates 1 had been successfully developed.

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