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Merck

139009

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

greener alternative

98%

동의어(들):

2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU

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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):
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
Assay:
98%
Concentration:
≥98%
Form:
liquid

주요 문서

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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

Greener Alternative Product

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

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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관련 카테고리

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
GHS06,GHS05

signalword

Danger

저장 등급

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

flash_point_f

240.8 °F

flash_point_c

116 °C

ppe

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

hcodes

H301,H314

Hazard Classifications

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

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시험 성적서(COA)

Lot/Batch Number

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이 제품을 이미 가지고 계십니까?

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문서 라이브러리 방문

DBU (1, 8-diazabicyclo [5.4. 0] undec-7-ene)-A Nucleophillic Base.
Ghosh N
Synlett, 2004(03), 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
Synthesis of cellulose acetate propionate and cellulose acetate butyrate in a CO2/DBU/DMSO system.
Xu Q, et al.
Cellulose, 25(1), 205-216 (2018)
Tetrahedron, 60, 4821-4827 (2004)
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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