139009

1,8-Diazabicyclo[5.4.0]undec-7-ene

98%

• Synonim(y): 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU
• Wzór empiryczny (zapis Hilla): C₉H₁₆N₂
• Masa cząsteczkowa: 152.24
• Beilstein: 508906
• Numer WE: 229-713-7
• Numer MDL: MFCD00006930
• Kod UNSPSC: 12352302
• Identyfikator substancji w PubChem: 24848373
• NACRES: NA.22

Właściwości

• ciśnienie pary: 5.3 mmHg ( 37.7 °C)
• Poziom jakości: 200
• Próba: 98%
• Postać: liquid
• charakterystyka ekologicznej alternatywy: Catalysis; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• współczynnik refrakcji: n20/D 1.522-1.524 (lit.)
• tw: 80-83 °C/0.6 mmHg (lit.)
• gęstość: 1.018 g/mL at 25 °C (lit.)
• kategoria ekologicznej alternatywy: , Aligned
• ciąg SMILES: C1CCN2CCCN=C2CC1
• InChI: 1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2
• Klucz InChI: GQHTUMJGOHRCHB-UHFFFAOYSA-N

Opis

Opis ogólny

1,8-Diazabicyclo[5.4.0]undec-7-ene 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.

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Zastosowanie

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) may be used:

• as catalyst for carboxylic acid esterification with dimethyl carbonate
• in the synthesis of duocarmycin and CC-1065 analogs
• as catalyst in aza-Michael addition and Knovenegal condensation reaction
• as 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 Camptothecin

1,8-Diazabicyclo[5.4.0]undec-7-ene 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.

Cechy i korzyści

Strong hindered amine base.

Cytowanie

An application review.

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS06,GHS05
• Hasło ostrzegawcze: Danger
• Zwroty wskazujące rodzaj zagrożenia: H290,H301,H314,H412
• Zwroty wskazujące środki ostrożności: P234 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Klasyfikacja zagrożeń: Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B
• Kod klasy składowania: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Klasa zagrożenia wodnego (WGK): WGK 2
• Temperatura zapłonu (°F): 240.8 °F
• Temperatura zapłonu (°C): 116 °C
• Środki ochrony indywidualnej: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter