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
• UNSPSC Code: 12352302
• 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.
• sustainability: Greener Alternative Product
• 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

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.[1] It promotes the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild conditions.[2]

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Application

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

• as catalyst for carboxylic acid esterification with dimethyl carbonate[3]
• in the synthesis of duocarmycin and CC-1065 analogs[1]
• as catalyst in aza-Michael addition[4] and Knovenegal condensation reaction[5]
• 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)[6]
• in a new synthesis of the ABCD ring system of Camptothecin[7]

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.[8][9]

Used in a new synthesis of the ABCD ring system of Camptothecin.[7]

Features and Benefits

Strong hindered amine base.

Citation

An application review.[10]

Safety Information

• Pictograms: GHS06,GHS05
• 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