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139009 Sigma-Aldrich

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

Green Alternative

98%

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

  • CAS Number 6674-22-2

  • 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

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Properties

Related Categories 12 Principles Aligned Products, Acids & Bases, Bases, Chemical Reagents, Chemical Synthesis,
Quality Level   200
vapor pressure   5.3 mmHg ( 37.7 °C)
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

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

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.

Packaging

2.5 kg in glass bottle

25, 100, 500 g in glass bottle

Features and Benefits

Strong hindered amine base.

Citation

An application review.

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

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

AISF: A Stable, Solid Alternative to Sulfuryl Fluoride Gas

Fluorosulfates and sulfamoyl fluorides have applications ranging from chemical biology to polymer chemistry in addition to being valuable synthetic precursors to diaryl sulfates, sulfamides and sulfa...
Keywords: Chemical biology, Chromatography, Flash chromatography, Polymer science

Carbohydrate-Catalyzed Enantioselective Alkene Diboration

Enantioselective diboration of olefins is a valuable strategy for transforming unsaturated hydrocarbons into useful chiral building blocks. Typically, the process is carried out via transition-metal ...
Keywords: Asymmetric synthesis, Building blocks, Solvents

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

References

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