5-[(2S)-pyrrolidin-2-yl]-1H-1,2,3,4-tetrazole

• ChemBase ID: 141248
• Molecular Formular: C5H9N5
• Molecular Mass: 139.15846
• Monoisotopic Mass: 139.08579531
• SMILES: C1C[C@H](NC1)c1[nH]nnn1
• Canonical SMILES: C1CN[C@@H](C1)c1nnn[nH]1
• InChI: 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
• InChIKey: XUHYQIQIENDJER-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2S)-pyrrolidin-2-yl]-1H-1,2,3,4-tetrazole
• IUPAC Traditional name: 5-[(2S)-pyrrolidin-2-yl]-1H-1,2,3,4-tetrazole
• Synonyms: (S)-(-)-2-Tetrazol-5-ylpyrrolidine; Proline Tetrazole Catalyst; (S)-(-)-5-(2-Pyrrolidinyl)-1H-tetrazole; (S)-(-)-2-四唑-5-基吡咯烷; 脯氨酸四唑催化剂; (S)-5-(吡咯烷-2-基)-1H-四唑

Database IDs

• CAS Number: 33878-70-5
• MDL Number: MFCD10000886
• PubChem SID: 162235483
• PubChem CID: 11275040

CALCULATED PROPERTIES

• Acid pKa: 2.9229047
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.2764807
• LogD (pH = 7.4): -2.2742264
• Log P: -2.2756891
• Molar Refractivity: 38.1799 cm^3
• Polarizability: 13.601287 Å^3
• Polar Surface Area: 66.49 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 253-258 °C
• Optical Rotation: [α]20/D -9.0°, c = 1 in methanol

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C5H9N5

DETAILS

Sigma Aldrich - 684341

Application
Organocatalyst used for asymmetric synthesis of dihydropyridazines and 1,2-oxazines.8,9
Organocatalyst used for:
• Direct asymmetric aldol reactions between acetone and aldehydes yielding β -hydroxy ketone1,2 and for synthesizing 1,1,1-trichloro-2-alkanols3
• Mannich reactions for synthesis fo α -amino acids4,5 and generation of 1,4-diamines6
• Conjugate additions of malonates to enones7
Packaging
100, 500 mg in glass bottle
Protocols & Applications
Organocatalytic Applciations with a L-Proline Isoster