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684341

(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
NACRES:
NA.22
PubChem Substance ID:
329760905
UNSPSC Code:
12352005
MDL number:
MFCD10000886
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Quality Segment

assay

96%

form

solid

optical activity

[α]20/D -9.0°, c = 1 in methanol

reaction suitability

reagent type: chrial catalyst

manufacturer/tradename

ECACC

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

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
(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.

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This Item
901719658405PHR3701
(S)-(–)-5-(2-Pyrrolidinyl)-1H-tetrazole 96%

Sigma-Aldrich

684341

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

Benzyl (S)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate

Sigma-Aldrich

901719

Benzyl (S)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate

(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone 97%

Sigma-Aldrich

658405

(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone

(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone certified reference material, pharmaceutical secondary standard

Supelco

PHR3701

(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone

description

96%

description

-

description

97%

description

certified reference material, pharmaceutical secondary standard

reaction suitability

reagent type: organic catalyst

reaction suitability

-

reaction suitability

-

reaction suitability

-

assay

96%

assay

-

assay

97%

assay

-

form

solid

form

powder or crystals

form

solid

form

-

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

300

mp

253-258 °C

mp

191 °C

mp

107-111 °C

mp

107-111 °C

optical activity

[α]20/D -9.0°, c = 1 in methanol

optical activity

-

optical activity

-

optical activity

-

Pictograms

Skull and crossbones
GHS06

Signal Word

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

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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