139009

Sigma-Aldrich

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

greener alternative

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/REAXYS Number:
508906
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

5.3 mmHg ( 37.7 °C)

Quality Level

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

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.
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

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

Packaging

25, 100, 500 g in glass bottle
2.5 kg in glass bottle

Features and Benefits

Strong hindered amine base.

Citation

An application review.

pictograms

CorrosionSkull and crossbones

signalword

Danger

hazcat

Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B

storage_class_code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK Germany

WGK 2

Flash Point F

240.8 °F

Flash Point C

116 °C

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

DBU (1, 8-diazabicyclo [5.4. 0] undec-7-ene)-A Nucleophillic Base.
Ghosh N
Synlett, 2004(03), 574-575 (2004)
Zhi-Hao Cui et al.
Journal of chemical theory and computation, 16(1), 119-129 (2019-12-10)
We describe an efficient quantum embedding framework for realistic ab initio density matrix embedding theory (DMET) calculations in solids. We discuss in detail the choice of orbitals and mapping to a lattice, treatment of the virtual space and bath truncation...
Synlett, 3, 574-575 (2004)
W C Shieh et al.
Organic letters, 3(26), 4279-4281 (2002-01-11)
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) is a novel and active catalyst in promoting the methylation reaction of phenols, indoles, and benzimidazoles with dimethyl carbonate under mild conditions. Additional rate enhancement is accomplished by applying microwave irradiation. By incorporating tetrabutylammonium iodide, the same microwave...
Weixiang Dai et al.
Organic letters, 8(20), 4665-4667 (2006-09-22)
A new synthetic pathway to the parent and substituted ABCD ring cores of the camptothecin family of alkaloids was developed. The N-alkylation of 1,6-dihydro-6-oxo-2-pyridinecarbonitrile (2) with 3-bromo-1-phenylpropyne provided 3a using Curran's protocol. Treatment of 3a with a catalytic amount of...
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