47714
4-Formyl-1-methylpyridinium benzenesulfonate
≥95.0%
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About This Item
Empirical Formula (Hill Notation):
C13H13NO4S
CAS Number:
Molecular Weight:
279.31
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
5695963
Assay:
≥95.0%
Form:
solid
Quality Level
assay
≥95.0%
form
solid
impurities
≤2.0% water
mp
~95 °C
functional group
aldehyde, sulfonic acid
SMILES string
[H]C(=O)c1cc[n+](C)cc1.[O-]S(=O)(=O)c2ccccc2
InChI
1S/C7H8NO.C6H6O3S/c1-8-4-2-7(6-9)3-5-8;7-10(8,9)6-4-2-1-3-5-6/h2-6H,1H3;1-5H,(H,7,8,9)/q+1;/p-1
InChI key
HSVLGIFAXFDLMU-UHFFFAOYSA-M
General description
4-Formyl-1-methylpyridinium benzenesulfonate is a pyridinium salt widely used for the conversion of primary amines to the carbonyl compounds like aldehydes and ketones. The reaction conditions are mild, suitable for compounds with sensitive functional groups thereby providing an efficient alternative for such transformations.
Application
4-Formyl-1-methylpyridinium benzenesulfonate may be used as a reagent in the synthesis of the following:
- tetrazolic analogs of chalcones
- (+)-ferruginol
- Ecteinascidin 743
- Galipea alkaloids
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Short syntheses of (+)-ferruginol from (+)-dehydroabietylamine.
Gonzalez MA and Perez-Guaita D.
Tetrahedron, 68(47), 9612-9615 (2012)
Jinchun Chen et al.
Journal of the American Chemical Society, 128(1), 87-89 (2006-01-05)
A convergent total synthesis of ecteinascidin 743 is realized from five building blocks of almost equal size. It takes 23 steps from l-3-hydroxy-4-methoxy-5-methyl phenylalanol (5) with an overall yield of 3%.
Zacharias Amara et al.
Natural product reports, 30(9), 1211-1225 (2013-07-31)
This review focuses on recent applications of the aza-Michael reaction in alkaloids total synthesis with a special emphasis on stereoselectivity. The report highlights achievements and challenges over the past five years and describes stereoselective intra- and inter-molecular conjugate addition of
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 47714-10G | 04061832545080 |