331910

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

98%

• Synonym(s): (±)-2-Azabicyclo[2.2.1]hept-5-en-3-one, 4-Amino-2-cyclopentene-1-carboxylic acid lactam
• Empirical Formula (Hill Notation): C₆H₇NO
• CAS Number: 49805-30-3
• Molecular Weight: 109.13
• Beilstein: 508342
• MDL number: MFCD00213364
• UNSPSC Code: 12352100
• PubChem Substance ID: 24860009
• NACRES: NA.22

Properties

• 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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H317
• Precautionary Statements: P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352
• Hazard Classifications: Acute Tox. 4 Oral - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): 230.0 °F - closed cup
• Flash Point(C): 110 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves