1,8-Diazabicyclo[5.4.0]undec-7-ene
Empirical Formula (Hill Notation): | C9H16N2 |
Molecular Weight: | 152.24 |
Beilstein/REAXYS Number: | 508906 |
EC Number: | 229-713-7 |
MDL number: | MFCD00006930 |
PubChem Substance ID: | 24848373 |
NACRES: | NA.22 |
Кат. номер |
139009-2X2G |
139009-100G |
139009-2.5KG |
139009-500G |
139009-25G |
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.
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.
Used in a new synthesis of the ABCD ring system of Camptothecin.
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 Yamamotos 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.
25, 100, 500 g in glass bottle
2.5 kg in glass bottle
Strong hindered amine base.
An application review.
vapor pressure | 5.3 mmHg ( 37.7 °C) |
Quality Level | 200 |
assay | 98% |
greener alternative product characteristics | Catalysis Learn more about the Principles of Green Chemistry. |
refractive index | n20/D 1.522-1.524 (lit.) |
bp | 80-83 °C/0.6 mmHg (lit.) |
density | 1.018 g/mL at 25 °C (lit.) |
greener alternative category | Aligned |
SMILES string | C1CCN2CCCN=C2CC1 |
InChI | 1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 |
InChI key | GQHTUMJGOHRCHB-UHFFFAOYSA-N |
Pictograms | GHS05,GHS06 |
Signal Word | Danger |
Hazard Statements | H290 - H301 - H314 - H412 |
Precautionary Statements | P234 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 |
Personal Protective Equipment | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
RIDADR | UN 3267 8 / PGII |
WGK Germany | WGK 2 |
Flash Point(F) | 240.8 °F |
Flash Point(C) | 116 °C |