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359580

Sigma-Aldrich

(8S,9R)-(−)-N-Benzylcinchonidinium chloride

98%

Synonym(s):

N-Benzylcinchonidinium chloride, BCDC

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About This Item

Empirical Formula (Hill Notation):
C26H29ClN2O
CAS Number:
Molecular Weight:
420.97
Beilstein:
5421832
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

powder

optical activity

[α]20/D −180°, c = 1.3 in H2O

mp

210 °C (dec.) (lit.)

SMILES string

[Cl-].O[C@@H]([C@@H]1C[C@@H]2CC[N+]1(C[C@@H]2C=C)Cc3ccccc3)c4ccnc5ccccc45

InChI

1S/C26H29N2O.ClH/c1-2-20-18-28(17-19-8-4-3-5-9-19)15-13-21(20)16-25(28)26(29)23-12-14-27-24-11-7-6-10-22(23)24;/h2-12,14,20-21,25-26,29H,1,13,15-18H2;1H/q+1;/p-1/t20-,21-,25-,26+,28?;/m0./s1

InChI key

FCHYSBWCOKEPNQ-IOPLZPHGSA-M

Other Notes

Chiral phase transfer catalyst;resolutions by crystallization of the inclusion complex

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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F Toda et al.
The Journal of Organic Chemistry, 59, 5748-5748 (1994)
S. Julia et al.
Journal of the Chemical Society. Perkin Transactions 1, 574-574 (1981)
C.M. Gasparski, M.J. Miller
Tetrahedron, 47, 5367-5367 (1991)
J.H. Zhang et al.
Tetrahedron Asymmetry, 13, 1363-1363 (2002)

Articles

Asymmetric phase-transfer catalysis (PTC) has been recognized as a “green” alternative to many homogeneous synthetic organic transformations, and has found widespread application. Synthetically modified cinchona alkaloids are typical chiral organocatalysts used in asymmetric PTC.

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