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  • 690600 - N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxy-9-cinchonanyl]thiourea

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690600 Sigma-Aldrich

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxy-9-cinchonanyl]thiourea

≥90.0%

Synonym: 1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(R)(6-methoxy-4-quinolinyl)-[(2R,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl]methyl}thiourea, epi-N-Quinidyl-N′-bis(3,5-trifluoromethyl)phenylthiourea

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Cinchona Alkaloids, Privileged Ligands and Complexes More...
Quality Level   100
assay   ≥90.0% (HPLC)
  ≥90.0%
SMILES string   COc1ccc2nccc([C@@H](NC(=S)Nc3cc(cc(c3)C(F)(F)F)C(F)(F)F)C4CC5CCN4C[C@@H]5C=C)c2c1
InChI   1S/C29H28F6N4OS/c1-3-16-15-39-9-7-17(16)10-25(39)26(22-6-8-36-24-5-4-21(40-2)14-23(22)24)38-27(41)37-20-12-18(28(30,31)32)11-19(13-20)29(33,34)35/h3-6,8,11-14,16-17,25-26H,1,7,9-10,15H2,2H3,(H2,37,38,41)/t16-,17-,25+,26+/m0/s1
InChI key   IQMKPBFOEWWDIQ-ZRJNXXGPSA-N

Description

General description

The product is a cinchona-alkaloid-derived, bifunctional catalyst containing a thiourea group at position 9.

Application

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxy-9-cinchonanyl]thiourea may be used to catalyze the formation of optically active Mannich adducts from stable N-carbamate amido sulfones via enantioselective Mannich reaction.

Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts

Packaging

250 mg in glass bottle

Features and Benefits

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(9R)-6′-methoxy-9-cinchonanyl]thiourea as an organocatalyst has the following advantages over transition-metal catalysis:
• Lower toxicity
• Lower costs
• Air and moisture stability for simple reaction setup

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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