3001-72-7 Usage
Description
1,5-Diazabicyclo[4.3.0]non-5-ene, also known as DBN, is an amidine base used in organic synthesis. It is characterized by its clear colorless to yellowish liquid appearance and is known for its versatility in various chemical reactions.
Uses
1. Used in Organic Synthesis:
1,5-Diazabicyclo[4.3.0]non-5-ene is used as a base in organic synthesis for dehydrohalogenation reactions and base-catalyzed rearrangements. It is particularly effective in base-mediated eliminations, condensations, esterifications, isomerizations, carboxylations, and carbonylations.
2. Used in the Preparation of Supertetrahedral Chalcogenide Clusters and Single Crystals of Polymer-Chalcogenide Composites:
DBN is employed in the synthesis of supertetrahedral chalcogenide clusters and the formation of single crystals of polymer-chalcogenide composites, which have potential applications in various fields, including electronics and materials science.
3. Used as a Catalyst for the Regioselective Friedel-Crafts C-acylation of Pyrroles:
1,5-Diazabicyclo[4.3.0]non-5-ene acts as a nucleophilic catalyst for the regioselective Friedel-Crafts C-acylation of pyrroles and indoles, which is an important reaction in the synthesis of various organic compounds.
4. Used as a Resin Curing Agent and Polyurethane Catalyst:
DBN is also utilized as a curing agent for resins and as a catalyst in the production of polyurethane, a versatile polymer with a wide range of applications in the industry, including coatings, adhesives, and foams.
Reference
Taylor, James E., et al. "Friedel?Crafts Acylation of Pyrroles and Indoles using 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) as a Nucleophilic Catalyst." Cheminform 42.13(2015):5740.
Purification Methods
Distil DBN from BaO. It forms a hydroiodide on addition of 47% HI; dry it and dissolve it in MeCN, evaporate and repeat; recrystallise from EtOH, dry at 25o/1mm for 5hours, then at 80o/0.03mm for 12hours and store and dispense it in a dry box, m 154-156o [Jaeger et al. J Am Chem Soc 101 717 1979]. The methiodide is recrystallised from CHCl3/Et2O, m 248-250o, and hydrogen fumarate has m 159-160o and is crystallised from iso-PrOH [Rokach et al. J Med Chem 22 237 1979, Oediger et al. Chem Ber 99 2012 1966, Reppe et al. Justus Liebigs Ann Chem 596 210 1955]. [Beilstein 23/5 V 239.]
Check Digit Verification of cas no
The CAS Registry Mumber 3001-72-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,0,0 and 1 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 3001-72:
(6*3)+(5*0)+(4*0)+(3*1)+(2*7)+(1*2)=37
37 % 10 = 7
So 3001-72-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H12N2/c10-11-8-4-2-6-9(11)5-1-3-7(8)9/h1-6H2
3001-72-7Relevant articles and documents
Synthesis of squalamine utilizing a readily accessible spermidine equivalent
Zhang,Rao,Jones,Shao,Feibush,McGuigan,Tzodikov,Feibush,Sharkansky,Snyder,Mallis,Sarkahian,Wilder,Turse,Kinney,Kjeersgaard,Michalak
, p. 8599 - 8603 (1998)
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RESIST COMPOSITION CONTAINING NOVEL SULFONIUM COMPOUND, PATTERN-FORMING METHOD USING THE RESIST COMPOSITION, AND NOVEL SULFONIUM COMPOUND
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, (2009/03/07)
A resist composition includes (A) a compound represented by the following formula (I): wherein each of R1 to R13 independently represents a hydrogen atom or a substituent, provided that at least one of R1 to R13 is a substituent containing an alcoholic hydroxyl group; Z represents a single bond or a divalent linking group; and X? represents an anion containing a proton acceptor functional group.
An Efficient Synthesis of Bicyclic Amidines by Intramolecular Cyclization
Kumagai, Naoya,Matsunaga, Shigeki,Shibasaki, Masakatsu
, p. 478 - 482 (2007/10/03)
A real step-saver! In a one-step procedure for the synthesis of bicyclic amidines, the azido group is used directly as the nucleophile in the ring-forming reaction. Many functionalized and chiral bicyclic amidines were synthesized in good yield under mild reaction conditions.