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33481

Sigma-Aldrich

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

purum, ≥98.0% (GC)

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:
229-713-7
MDL number:
MFCD00006930
UNSPSC Code:
12352005
PubChem Substance ID:
329754557

grade

purum

assay

≥98.0% (GC)

refractive index

n20/D 1.523

bp

115 °C/11 mmHg (lit.)

density

1.019 g/mL at 20 °C (lit.)

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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pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

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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Gui-Ling Zhao et al.
Organic letters, 7(20), 4527-4530 (2005-09-24)
[reaction: see text] DBU-catalyzed reactions of salicylic aldehydes with 3-methylpenta-3,4-dien-2-one, 3-benzylpenta-3,4-dien-2-one, or ethyl 2-methylbuta-2,3-dienoate gave the corresponding functionalized 2H-1-chromenes in good to excellent yields and good diastereoselectivities in some cases in DMSO, respectively.
Ning Zhu et al.
Journal of combinatorial chemistry, 12(4), 531-540 (2010-06-01)
The thiol-disulfide dynamic interchange reaction mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was extensively studied. By this synthetic method sulfides can be prepared successfully within seconds in high yields at room temperature from stable and readily available disulfides and an alkylating agent. The
Naoto Utsumi et al.
Organic letters, 10(16), 3405-3408 (2008-07-18)
Direct organocatalytic Mannich-type reactions of thioesters provide for the expedient and diastereoselective synthesis of protected beta-amino acids. A variety of thioesters were found to be reactive with different imines under mild conditions to provide beta-amino acids in good yields. This
Matthew O'Reilly et al.
Dalton transactions (Cambridge, England : 2003), (31)(31), 6092-6095 (2010-05-08)
With the new chiral phosphine ligand DBUP, obtained from DBU and Ph(2)PCl, a remarkable anion effect was observed on the diastereoselective formation of the bischelated complexes [Ni(DBUP)(2)](X)(n) (X = Cl, Br, n = 2; X = NiCl(4), n = 1)
Wanli Chen et al.
The Journal of organic chemistry, 77(3), 1585-1591 (2012-01-19)
DBU-promoted cyclization of ortho-(3-hydroxy-1-alkynyl)benzamide is presented, providing an efficient method for the synthesis of trans-3,4-dihydroisoquinolin-1(2H)-ones and (E)-4-(1-alkenyl)isoquinolin-1(2H)-ones under mild conditions.
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