33482

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

puriss., ≥99.0% (GC)

• Synonym(s): 2,3,4,6,7,8,9,10-Octahydropyrimidol[1,2-a]azepine, DBU
• Empirical Formula (Hill Notation): C₉H₁₆N₂
• Molecular Weight: 152.24
• Beilstein: 508906
• EC Number: 229-713-7
• MDL number: MFCD00006930
• PubChem Substance ID: 329754558
• NACRES: NA.22

Properties

• grade: puriss.
• Quality Level: 200
• assay: ≥99.0% (GC)
• form: liquid
• 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

Description

Application

1,8-Diazabicyclo[5.4.0]undec-7-ene can be used:

• To mediate the aza-Michael addition of nitrogen nucleophiles to α,β-unsaturated carbonyl compounds.[1]
• As a nucleophilic catalyst for the esterification of carboxylic acid with dimethyl carbonate.[2]
• As a bidentate ligand in copper (I) bromide mediated atom transfer radical polymerization of methyl methacrylate.[3]
• As an efficient catalyst for the transesterification of dimethyl carbonate with glycerol.[4]

Other Notes

Amidine base used for dehydrohalogenation reactions to olefins[5]; Further important applications are e.g.: esterification of carboxylic acids with alkyl halides[6][7]; Alkylation and acylation of active methylene compounds[8]

Safety Information

• Pictograms: GHS05,GHS06
• Signal Word: Danger
• Hazard Statements: H290 - H301 - H314 - H412
• Precautionary Statements: P234 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B
• Storage Class Code: 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves