1 8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE (C005B-226547)

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

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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
• 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.

Features and Benefits

Strong hindered amine base.

Citation

An application review.

Molecular Weight: 152.24. Empirical Formula: C₉H₁₆N₂. 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. 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: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter.

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UPC:

51113203

Condition:

New

Weight:

1.00 Ounces

HazmatClass:

Yes

Quantity:

4

Unit of Measurement:

GM

MPN:

139009-2X2G