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139009 Aldrich

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

98%

Synonym: 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU

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Properties

Related Categories Acids & Bases, Bases, Chemical Reagents, Chemical Synthesis, Development Quantities for Research,
vapor pressure   5.3 mmHg ( 37.7 °C)
InChI Key   GQHTUMJGOHRCHB-UHFFFAOYSA-N
assay   98%
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.)

Description

Features and Benefits

Strong hindered amine base.

Packaging

2.5 kg in glass bottle

25, 100, 500 g in glass bottle

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

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.

Citation

An application review.

Price and Availability


Cross-Coupling Guide
Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3267 8 / PGII
WGK Germany 
2
Flash Point(F) 
240.8 °F
Flash Point(C) 
116 °C
Protocols & Articles

Articles

Deoxyfluorination with 2-Pyridinesulfonyl Fluoride (PyFluor)

The prevalence of organofluorine compounds in industry and drug design necessitates the ability to introduce C–F bonds to molecules. Deoxyfluorination of alcohols is a well-precedented technique for ...
Keywords: Eliminations, Fluorinations, Melting, Purification, Solvents

Knoevenagel Condensation Reaction

The Knoevenagel Condensation Reaction is a classic organic synthesis, described by Emil Knoevenagel in the 1890’s. The Knoevenagel reaction is a modified Aldol Condensation with a nucleophilic additi...
Keywords: Aldol condensation, C-C bond formation, Condensations, Dehydration reaction, Knoevenagel Condensation, Nucleophilic additions, Organic synthesis

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Peer-Reviewed Papers
15

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