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366188

Sigma-Aldrich

N-Benzylcinchoninium chloride

98%

Synonym(s):
9-Hydroxy-1-(phenylmethyl)cinchonanium chloride, BCNC
Empirical Formula (Hill Notation):
C26H29ClN2O
CAS Number:
Molecular Weight:
420.97
Beilstein:
5232950
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

optical activity

[α]20/D +169°, c = 0.4 in H2O

mp

256 °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-YGNISETGSA-M

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Application

Phase-transfer catalyst involved in:
  • Enantioselective alkylation of malonic diester with alkyl halides
  • Hydrolysis of enol esters
  • Asymmetric 6π electrocyclization for synthesis of functionalized indolines
  • Asymmetric Michael addition
  • Alkylation of monosubstituted indolinones with alkylhalides
  • Asymmetric destruction and kinetic resolution of 1-benzylated Reissert compounds

Packaging

10 g in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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