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684341

Sigma-Aldrich

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

96%

Synonym(s):

(S)-(–)-2-Tetrazol-5-ylpyrrolidine, Proline Tetrazole Catalyst

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About This Item

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

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

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

pictograms

Skull and crossbones
GHS06

signalword

Danger

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

Certificates of Analysis (COA)

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Oelke, A. et al.
Synlett, 2548-2548 (2006)
Sirirat Kumarn et al.
Chemical communications (Cambridge, England), (30), 3211-3213 (2006-10-10)
A sequential, organocatalysed asymmetric reaction to access chiral 1,2-oxazines from achiral ketone starting materials is reported, which proceeds in moderate to good yields and excellent enantioselectivity.
Direct asymmetric α-fluorination of aldehydes
Steiner DD, et al.
Angewandte Chemie (International Edition in English), 117(24), 3772-3776 (2005)
A highly selective, organocatalytic route to chiral 1, 2-oxazines from ketones
Kumarn S, et al.
Chemical Communications (Cambridge, England), 3211-3213 (2006)
Asymmetric organocatalyzed Michael addition of aldehydes to β-nitrostyrene in ionic liquids
Mevciarova M, et al.
Tetrahedron Asymmetry, 20(20), 2403-2406 (2009)

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