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Merck
CN

366188

N-Benzylcinchoninium chloride

98%

Synonym(s):

9-Hydroxy-1-(phenylmethyl)cinchonanium chloride, BCNC

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About This Item

Empirical Formula (Hill Notation):
C26H29ClN2O
CAS Number:
Molecular Weight:
420.97
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
273-915-8
Beilstein/REAXYS Number:
5232950
MDL number:
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Product Name

N-Benzylcinchoninium chloride, 98%

InChI key

FCHYSBWCOKEPNQ-YGNISETGSA-M

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

SMILES string

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

assay

98%

form

solid

optical activity

[α]20/D +169°, c = 0.4 in H2O

mp

256 °C (dec.) (lit.)

functional group

hydroxyl
phenyl

Quality Level

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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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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