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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

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About This Item

Empirical Formula (Hill Notation):
C9H16N2
Molecular Weight:
152.24
Beilstein/REAXYS Number:
508906
EC Number:
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22
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vapor pressure

5.3 mmHg ( 37.7 °C)

Quality Level

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.)

mp

-70 °C

density

1.018 g/mL at 25 °C (lit.)

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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.

pictograms

Skull and crossbonesCorrosion

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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_germany

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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