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346802 Sigma-Aldrich

(S)-(−)-Indoline-2-carboxylic acid

99%

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Proline-Based Organocatalysts
assay   99%
optical activity   [α]20/D −114°, c = 1 in 1 M HCl
mp   177 °C (dec.) (lit.)
SMILES string   OC(=O)[C@@H]1Cc2ccccc2N1
InChI   1S/C9H9NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-4,8,10H,5H2,(H,11,12)/t8-/m0/s1
InChI key   QNRXNRGSOJZINA-QMMMGPOBSA-N

Description

Packaging

1, 5 g in glass bottle

Application

Catalyst for enantioselective cyclopropanations.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Aldrich ChemFiles 2007, 7.9, 3. | Proline Analogs

The first examples were reported in the mid-70s, when L-proline was applied to Robinson annulation reactions. However, the big potential of proline as an organocatalyst was discovered at the beginnin...
Aldrich ChemFiles 2007, 7.9, 3.
Keywords: Aldol condensation, Aldol reaction, Alkylations, Aminations, Annulations, Asymmetric synthesis, Building blocks, Catalysis, Chemfiles, Condensations, Cyclopropanations, Help, Mannich Reaction, Methods, Michael Addition, Organocatalysis, Robinson Annulation, transformation

Proline Analogs

Coined by Jacobsen1 as the “simplest enzyme,” L-proline is capable of effecting a variety of catalytic asymmetric transformations. The first examples were reported in the mid-70s, when L-proline was ...
Aldrich ChemFiles 2006, 6.4, 3.
Keywords: Aldol reaction, Alkylations, Aminations, Annulations, Asymmetric synthesis, Catalysis, Chemfiles, Cyclopropanations, Drug discovery, Epoxidations, Help, Mannich Reaction, Methods, Michael Addition, Robinson Annulation, Tools, transformation

Peer-Reviewed Papers
15

References

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