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Merck

139009

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
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
24848373
EC Number:
229-713-7
Beilstein/REAXYS Number:
508906
MDL number:
MFCD00006930

Product Name

1,8-Diazabicyclo[5.4.0]undec-7-ene, 98%

InChI key

GQHTUMJGOHRCHB-UHFFFAOYSA-N

InChI

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

SMILES string

C1CCN2CCCN=C2CC1

vapor pressure

5.3 mmHg ( 37.7 °C)

assay

98%

form

liquid

greener alternative product characteristics

Catalysis
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sustainability

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Quality Level

200

concentration

≥98%

refractive index

n20/D 1.522-1.524 (lit.)

pH

12.8 (20 °C, 10 g/L)

bp

80-83 °C/0.6 mmHg (lit.)

mp

-70 °C

density

1.018 g/mL at 25 °C (lit.)

greener alternative category

, Aligned

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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.

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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pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

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Danger

Hazard Classifications

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

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 2

flash_point_f

240.8 °F

flash_point_c

116 °C

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6031
BCCN4385
BCCN0343
BCCL9833
BCCK6511

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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)
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
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
Synlett, 3, 574-575 (2004)
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