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| Product Name: | 1,5-Diazabicyclo[4.3.0]non-5-ene | | Synonyms: | 1,5-Diazabicyclo[4.3.0]non-5-ene,DBN;1,5-DIAZABICYCLO[4.3.0]NON-5-ENE FOR SYN;1,5-Diazabicyclo[4.3.0]non-5-ene purum, >=98.0% (GC);DBN 1,5-Diazabicyclo[4.3.0]non-5-ene;2H,3H,4H,6H,7H,8H-Pyrrolo[1,2-a]pyrimidine;1,5-Diazabicyclo[4.3.0]non-5-ene≥ 99%(GC);Diazabicyclononene (DBN);1,5-DiazabicycL | | CAS: | 3001-72-7 | | MF: | C7H12N2 | | MW: | 124.18 | | EINECS: | 221-087-3 | | Product Categories: | | | Mol File: | 3001-72-7.mol | ![1,5-Diazabicyclo[4.3.0]non-5-ene Structure](CAS/GIF/3001-72-7.gif) |
| | 1,5-Diazabicyclo[4.3.0]non-5-ene Chemical Properties |
| Boiling point | 95-98 °C7.5 mm Hg(lit.) | | density | 1.005 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.519(lit.) | | Fp | 202 °F | | storage temp. | Store below +30°C. | | solubility | soluble in Chloroform, Methanol | | form | Liquid | | pka | 13.42±0.20(Predicted) | | color | Clear colorless to yellow | | Water Solubility | soluble | | Sensitive | Air Sensitive | | BRN | 2417 | | InChIKey | SGUVLZREKBPKCE-UHFFFAOYSA-N | | CAS DataBase Reference | 3001-72-7(CAS DataBase Reference) | | NIST Chemistry Reference | 1,5-diazabicyclo[4.3.0]non-5-ene(3001-72-7) |
| Hazard Codes | C | | Risk Statements | 34 | | Safety Statements | 26-36/37/39-45 | | RIDADR | UN 3267 8/PG 2 | | WGK Germany | 3 | | F | 1-3-8-10 | | Hazard Note | Corrosive/Air Sensitive | | HazardClass | 8 | | PackingGroup | II | | HS Code | 29335995 |
| | 1,5-Diazabicyclo[4.3.0]non-5-ene Usage And Synthesis |
| 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 | 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. | | Uses | - 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.
| | Definition | ChEBI: 1,5-diazabicyclo[4.3.0]-non-5-ene is a pyrrolopyrimidine. | | 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.] |
| | 1,5-Diazabicyclo[4.3.0]non-5-ene Preparation Products And Raw materials |
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