3001-72-7 Usage
Description
1,5-Diazabicyclo [4.3.0]non-5-ene is a amidine base used in organic synthesis. It is employed for dehydrohalogenation reactions as well as base-catalyzed rearrangements. It can also be used as the nucleophilic catalyst for the Friedel-Crafts acylation of pyrroles and indoles2. Further, it is used as a resin curing agent and polyurethane catalyst.
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.
Chemical Properties
clear colorless to yellowish liquid
Uses
Different sources of media describe the Uses of 3001-72-7 differently. You can refer to the following data:
1. 1,5-Diazabicyclo[4.3.0]non-5-ene is employed for dehydrohalogenation reactions and base-catalyzed rearrangements in organic synthesis. It is an amidine base used in organic synthesis. Further, it is used as a resin curing agent and polyurethane catalyst.
2. 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is an amidine base commonly used in the base-mediated eliminations, condensations, esterifications, isomerizations, carboxylations and carbonylations.It is used in the preparation of supertetrahedral chalcogenide clusters and single crystals of polymer-chalcogenide composites.It also acts as a catalyst for the regioselective Friedel-Crafts C-acylation of pyrroles.
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.