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331910 Sigma-Aldrich

2-Azabicyclo[2.2.1]hept-5-en-3-one

98%

Synonym: (±)-2-Azabicyclo[2.2.1]hept-5-en-3-one, 4-Amino-2-cyclopentene-1-carboxylic acid lactam

  • CAS Number 49805-30-3

  • Empirical Formula (Hill Notation) C6H7NO

  • Molecular Weight 109.13

  •  Beilstein/REAXYS Number 508342

  •  MDL number MFCD00213364

  •  PubChem Substance ID 24860009

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Carbonyl Compounds, Chemical Synthesis, Lactams, Organic Building Blocks More...
Quality Level   100
assay   98%
bp   102-106 °C/0.25 mmHg (lit.)
mp   54-58 °C (lit.)
SMILES string   O=C1N[C@H]2C[C@@H]1C=C2
InChI   1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1
InChI key   DDUFYKNOXPZZIW-CRCLSJGQSA-N

Description

General description

2-Azabicyclo[2.2.1]hept-5-en-3-one is also referred as vince lactam. It is a versatile intermediate in the synthesis of carbocyclic nucleosides. 2-Azabicyclo[2.2.1]hept-5-en-3-one and its monohydrated complex was investigated in a supersonic jet by Fourier transform microwave spectroscopy.

Application

2-Azabicyclo[2.2.1]hept-5-en-3-one was used in:
• preparation of (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine, a precursor of analog of bredinin
• synthesis of therapeutic drugs
• chemoenzymatic synthesis of (−)-carbovir

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
Flash Point(F) 
230.0 °F - closed cup
Flash Point(C) 
110 °C - closed cup

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Protocols & Articles
Peer-Reviewed Papers
15

References

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