Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

690481

Sigma-Aldrich

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(8a,9S)-6′-methoxy-9-cinchonanyl]thiourea

90%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C29H28F6N4OS
CAS Number:
852913-16-7
Molecular Weight:
594.61
MDL number:
MFCD16875670
UNSPSC Code:
12352005
PubChem Substance ID:
329761344
NACRES:
NA.22

Quality Level

100

Assay

≥89.0%
90%

form

lumps

functional group

amine
fluoro
thiourea

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-FRSFCCSCSA-N

Related Categories

Application

N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(8a,9S)-6′-methoxy-9-cinchonanyl]thiourea is a bifunctional cinchona organocatalyst, which can be used to synthesize:
  • Stereoselective diaryl(nitro)butanone via enantioselective Michael addition of nitromethane to chalcones.
  • Enantioselective β-amino acids via asymmetric Mannich reaction of malonates with aryl and alkyl imines.
  • The synthesis of 3-indolylmethanamines by the reaction of indoles with imines via asymmetric Friedel-Crafts reaction.
  • The enantioselective conjugate addition of active methylene compounds to enones to obtain the corresponding addition products.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

690481-BULK:
690481-250MG:
690481-VAR:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCG1174
BCBX7552
BCBP4868V
BCBN9831V
BCBM2210V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

(+)-Cinchonine 85%

Sigma-Aldrich

857270

(+)-Cinchonine

Quinine 90%

Sigma-Aldrich

145904

Quinine

(DHQD)2PHAL ≥95%

Sigma-Aldrich

392731

(DHQD)2PHAL

The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: enantioselective synthesis of ?-amino acids
Song J, et al.
Journal of the American Chemical Society, 128(18), 6048-6049 (2006)
Asymmetric Friedel- Crafts reaction of indoles with imines by an organic catalyst
Wang Y-Q, et al.
Journal of the American Chemical Society, 128(25), 8156-8157 (2006)
Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: inversion of configuration at C9 dramatically improves catalyst performance.
Séamus H McCooey et al.
Angewandte Chemie (International ed. in English), 44(39), 6367-6370 (2005-09-02)
Benedek Vakulya et al.
Organic letters, 7(10), 1967-1969 (2005-05-07)
Cinchona alkaloid-derived chiral bifunctional thiourea organocatalysts were synthesized and applied in the Michael addition between nitromethane and chalcones with high ee and chemical yields.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service