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  • 139009 - 1,8-Diazabicyclo[5.4.0]undec-7-ene

139009 Sigma-Aldrich


Green Alternative


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



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
InChI   1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2


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.


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.


2.5 kg in glass bottle

25, 100, 500 g in glass bottle

Features and Benefits

Strong hindered amine base.


An application review.

Safety & Documentation

Safety Information

Signal word 
Hazard statements 
UN 3267 8 / PGII
WGK Germany 
Flash Point(F) 
240.8 °F
Flash Point(C) 
116 °C


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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