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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

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About This Item

Empirical Formula (Hill Notation):
C9H16N2
Molecular Weight:
152.24
Beilstein:
508906
EC Number:
229-713-7
MDL number:
MFCD00006930
UNSPSC Code:
12352302
PubChem Substance ID:
24848373
NACRES:
NA.22

vapor pressure

5.3 mmHg ( 37.7 °C)

Quality Level

200

Assay

98%

form

liquid

greener alternative product characteristics

Catalysis
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sustainability

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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

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.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H290,H301,H314,H412

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

240.8 °F

Flash Point(C)

116 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sustainable succinylation of cellulose in a CO 2-based switchable solvent and subsequent Passerini 3-CR and Ugi 4-CR modification.
Soyler Z, et al.
Green Chemistry, 20(1), 214-224 (2018)
DBU (1, 8-diazabicyclo [5.4. 0] undec-7-ene)-A Nucleophillic Base.
Ghosh N
Synlett, 2004(03), 574-575 (2004)
Tetrahedron, 60, 4821-4827 (2004)
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
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