684341
(S)-(–)-5-(2-Pyrrolidinyl)-1H-tetrazole
96%
Synonym(s):
(S)-(–)-2-Tetrazol-5-ylpyrrolidine, Proline Tetrazole Catalyst
Sign In to View Organizational & Contract Pricing.
Select a Size
Change View
About This Item
Empirical Formula (Hill Notation):
C5H9N5
CAS Number:
Molecular Weight:
139.16
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Quality Level
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
signalword
Danger
hcodes
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Related Content
The Yamamoto group has employed several applications in catalysis.
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 684341-100MG | 04061833550267 |
| 684341-500MG | 04061833540909 |