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

• Catalog No.: A12449
• CAS Number: 6674-22-2
• M. F.: C9H16N2
• M. W.: 152.23674
• Purity: 99%

SYNONYMS

• Title: 1,8-二氮双环[5.4.0]十一-7-烯
• IUPAC name: 2H,3H,4H,6H,7H,8H,9H,10H-pyrimido[1,2-a]azepine
• IUPAC Traditional name: 1,8-diazabicycloundec-7-ene
• Synonyms: DBU

DATABASE IDS

• CAS Number: 6674-22-2
• EC Number: 229-713-7
• Beilstein Number: 508906
• MDL Number: MFCD00006930

PROPERTIES

• Purity: 99%
• Boiling Point: 261°C
• Density: 1.020
• Flash Point: 116°C(240°F)
• Melting Point: -70°C
• Refractive Index: 1.5220
• GHS Hazard statements: H301-H314-H318-H402-H412
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 22-34-52/53
• Safety Statements: 26-36/37/39-45-60-61
• Storage Warning: Air Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3267
• Packing Group: II

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.
• 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).
• 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).
• For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).
• Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).
• Promotes the epoxidation of ɑ?-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995).
• Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966).