139009

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

98%

• Synonym(s): 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU
• Empirical Formula (Hill Notation): C₉H₁₆N₂
• Molecular Weight: 152.24
• Beilstein: 508906
• EC Number: 229-713-7
• MDL number: MFCD00006930
• PubChem Substance ID: 24848373
• NACRES: NA.22

Properties

• vapor pressure: 5.3 mmHg ( 37.7 °C)
• Quality Level: 200
• assay: 98%
• form: liquid
• 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

Description

General description

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.

Application

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 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.

Packaging

25, 100, 500 g in glass bottle

2.5 kg in glass bottle

Features and Benefits

Strong hindered amine base.

Citation

An application review.

Safety Information

• 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
• Hazard Classifications: Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B
• Storage Class Code: 6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 2
• Flash Point(F): 240.8 °F
• Flash Point(C): 116 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves