684341

(S)-(–)-5-(2-Pyrrolidinyl)-1H-tetrazole

96%

• Synonym(s): (S)-(–)-2-Tetrazol-5-ylpyrrolidine, Proline Tetrazole Catalyst
• Empirical Formula (Hill Notation): C₅H₉N₅
• CAS Number: 33878-70-5
• Molecular Weight: 139.16
• MDL number: MFCD10000886
• UNSPSC Code: 12352005
• PubChem Substance ID: 329760905
• NACRES: NA.22

Properties

• assay: 96%
• form: solid
• optical activity: [α]20/D -9.0°, c = 1 in methanol
• mp: 253-258 °C
• SMILES string: C1CN[C@@H](C1)c2nnn[nH]2
• InChI: 1S/C5H9N5/c1-2-4(6-3-1)5-7-9-10-8-5/h4,6H,1-3H2,(H,7,8,9,10)/t4-/m0/s1
• InChI key: XUHYQIQIENDJER-BYPYZUCNSA-N

Description

Application

(S)-(−)-5-(2-Pyrrolidinyl)-1H-tetrazole can be used as an organocatalyst:

• To prepare enantioselective chiral 1,2-oxazines from achiral ketones via an intramolecular Wittig reaction.
• To synthesize diastereoselective Michael addition products by addition of aliphatic aldehydes to β-nitrostyrene.
• In the direct asymmetric α-fluorination of linear and branched aldehydes using N-fluorobenzenesulfonamide as the fluorinating agent.

Organocatalyst used for:

• Direct asymmetric aldol reactions between acetone and aldehydes yielding β -hydroxy ketone and for synthesizing 1,1,1-trichloro-2-alkanols
• Mannich reactions for synthesis fo α -amino acids and generation of 1,4-diamines
• Conjugate additions of malonates to enones

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301,H315,H319,H335
• pcodes: P301 + P310 + P330 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges