1,8-Diazabicyclo(5.4.0)undec-7-en
DBU · 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE · 2,3,4,6,7,8,9,10-OCTAHYDROPYRIMIDO[1,2-A]AZEPINE · Diazabicycloundecene · 1,5-DIAZABICYCLO(5,4,0)UNDEC-5-ENE · 1,8-DIAZABICYCLO[5,4,0]-7-UNDECENE · 1,8-Diazabicyclo[5.4.0]undecane-7-ene · 1,8-DiazabicycL
Identifikatoren & physikalische Daten
| CAS No. | 6674-22-2 |
|---|---|
| Summenformel | C9H16N2 |
| Durchschnittliche Molmasse | 152,24 g/mol |
| Monoisotopische Masse | 152,13134851 g/mol |
| SMILES | C1CCC2=NCCCN2CC1 |
| InChIKey | GQHTUMJGOHRCHB-UHFFFAOYSA-N |
| PubChem CID | 81184 |
| ChEMBL | CHEMBL1489129 |
| EC No. | 229-713-7 |
| DTXSID | DTXSID2049424 |
| Lokaler Name | 1,8-Diazabicyclo(5.4.0)undec-7-en |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 15,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 163 |
| Stoffklassen | Nitrogen Compounds -> Other Nitrogen Compounds |
| LogP (Verteilungskoeffizient) | 1.38 |
| Dichte | 1.018 @25 °C1.019 g/mL at 20 °C(lit.) |
| Dampfdruck | 0.05 [mmHg]5.3 [mm Hg] @37.700000000000003 °C5.3 mm Hg ( 37.7 °C) |
| Physical Description | LiquidDry PowderLight yellow liquid with unpleasant odor[MSDSonline] |
| Ionization Efficiency | Positive4.242.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Schmelzpunkt | -70 °C |
| Siedepunkt | 80-83 °C0.6 mm Hg(lit.) |
| Brechungsindex | n20/D 1.523 |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | soluble |
| pKa (Säurekonstante) | 13.28±0.20(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to light yellow |
| Geruch | Unpleasant |
| pH | 12.8 (10g/l, H2O, 20℃) |
| Explosionsgrenze | 1.1-6.5%(V) |
| BRN | 508906 |
| Stabilität | Stable. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides. |
| InChI | 1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 |
| InChIKey | GQHTUMJGOHRCHB-UHFFFAOYSA-N |
| SMILES | C1CCN2CCCN=C2CC1 |
| CAS Datenbank | 6674-22-2(CAS DataBase Reference) |
| NIST chemische Informationen | 1,8-diazabicyclo [5.4.0]undec-7-ene(6674-22-2) |
| EPA chemische Informationen | Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- (6674-22-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 6.2% (48 of 776) of reports.DangerH290 (18.3%): May be corrosive to metals [Warning Corrosive to Metals]P234, P260, P264, P264+P265, P270, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P390, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 776 reports by companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro-Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 19-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/102511,8-Diazabicyclo[5.4.0]undec-7-ene: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Harmful after ingestionCorrosive to skinCan cause chemical pneumonitis[MSDSonline] |
| Hazard Classes and Categories | Met. Corr. 1 (18.3%) |
| Protective Action Criteria (PAC) | 1.2 [mg/m3]13 [mg/m3]79 [mg/m3] |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| F | 34 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3267 8/PG 2 |
| Zollcode | 29339930 |
| R-Sätze (R) | 22-34-52/53-35-40-37-19-11-67 |
| Toxizität | LD50 orally in Rabbit: 215 - 681 mg/kg |
| Gefahrensymbole | C,F |
| Sicherheitshinweise (S) | 26-36/37/39-45-61-27-16 |
| Gefahrenklasse | 8Acute Tox. 3 OralAquatic Chronic 3Eye Dam. 1Met. Corr. 1Skin Corr. 1B |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Selbstentzündungstemperatur | 260 °C |
Anwendungen & Verwendung
Beschreibung
DBU is a bicyclic amidine base. It is non-nucleophilic, sterically hindered, tertiary amine base in organic chemistry. It is reported to be superior to amine catalyst in Baylis-Hillman reaction.It promotes the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild conditions.
Occurrence
Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis.The biosynthesis of DBU has been proposed to begin with 1,6-hexanedial and 1,3-diaminopropane.
Verwenden
DBU may be used:as catalyst for carboxylic acid esterification with dimethyl carbonatein the synthesis of duocarmycin and CC-1065 analogsas catalyst in aza-Michael addition and Knovenegal condensation reactionas base for dehalogenation of halogenated Diels-Alder adducts and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3)in a new synthesis of the ABCD ring system of CamptothecinDBU may be used as an catalyst for the dissolution and activation of cellulose by a reversible reaction of its hydroxyl groups with carbon dioxide. This dissolved cellulose system can be derivatized to form cellulose mixed esters.Used in a new synthesis of the ABCD ring system of Camptothecin.