Substance
ID:715629
Names and Identifiers
IUPAC name
2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine
IUPAC Traditional name
1,8-diazabicycloundec-7-ene
Synonyms
DBU1,8-Diazabicyclo[5.4.0]undec-7-ene1,8-二氮双环[5.4.0]十一-7-烯
Registration numbers
MDL Number
CAS Number
Beilstein Number
EC Number
Properties
Physical Property
Melting Point
-70°C
Refractive Index
1.5220
Boiling Point
261°C
Density
1.020
Flash Point
116°C(240°F)
Safety Information
Hazard Class
8
European Hazard Symbols
Corrosive (C)
Harmful (X)Packing Group
II
Safety Statements
26-36/37/39-45-60-61
TSCA Listed
是
Risk Statements
22-34-52/53
Storage Warning
Air Sensitive
GHS Precautionary statements
P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
UN Number
UN3267
GHS Pictograms
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
Acute toxicity (oral, dermal, inhalation), categories 1,2,3
GHS Hazard statements
H301-H314-H318-H402-H412
Product Information
Purity
99%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• Widely used as a base in elimination reactions, cf 1,5-Diazabicyclo[4.3.0]non-5-ene, A13437. For use in dehydrohalogenation, see, e.g. Org. Synth. Coll., 9, 247, 663 (1998).
• For use in the enantioselective conversion of benzylic alcohols to azides, see Diphenylphosphonic azide, A12124.
• Promotes the epoxidation of ɑ?-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995).
• In combination with NBS in MeOH, promotes the Hofmann rearrangement of amides to give methyl carbamates under mild conditions: J. Org. Chem., 62, 7495 (1997).
• DBU forms hydrogen-bonded complexes with carboxylic acids, which can be alkylated in good yield by alkyl bromides or iodides, in a simple esterification procedure: Bull. Chem. Soc. Jpn., 51, 2401 (1978).
• Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).
• For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).
• Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966).