10445
Anisaldehyde dimethyl acetal
≥98.5% (GC)
Synonym(s):
4-Methoxybenzaldehyde dimethyl acetal, α,α,4-Trimethoxytoluene
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About This Item
Empirical Formula (Hill Notation):
C10H14O3
CAS Number:
Molecular Weight:
182.22
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
218-577-4
Beilstein/REAXYS Number:
2048930
MDL number:
Assay:
≥98.5% (GC)
InChI
1S/C10H14O3/c1-11-9-6-4-8(5-7-9)10(12-2)13-3/h4-7,10H,1-3H3
InChI key
NNHYAHOTXLASEA-UHFFFAOYSA-N
SMILES string
COC(OC)c1ccc(OC)cc1
assay
≥98.5% (GC)
refractive index
n20/D 1.505
bp
85-87 °C/0.1 mmHg (lit.)
solubility
H2O: soluble, alcohol: soluble
density
1.07 g/mL at 20 °C (lit.)
functional group
acetal, ether
storage temp.
2-8°C
Quality Level
Related Categories
General description
Anisaldehyde dimethyl acetal is a clear, colorless to light yellow liquid. The flash point for anisaldehyde dimethyl acetal is 114.0°C. It undergoes allylation reactions with allyltrimethylsilane catalysed by Iron(III) chloride. Anisaldehyde dimethyl acetal undergoes ytterbium-catalyzed tandem carboalkoxylation/Friedel–Crafts reaction with 1-phenylbenzylidenecyclopropane to yield 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene.
Application
Anisaldehyde dimethyl acetal was used in the synthesis of lipid A mimic precursor. It was also used in the synthesis of 2,5-dioxopyrrolidin-1-yl-3-((4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane-4-carboxamido)propanoate.
Other Notes
Protecting group reagent for diols, used e.g. in carbohydrate chemistry; the acetal protection can be selectively cleaved under mild conditions
Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
237.2 °F - closed cup
flash_point_c
114.0 °C - closed cup
ppe
Eyeshields, Gloves
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Iron (III) chloride-catalyzed effective allylation reactions of aldehydes with allyltrimethylsilane.
Watahiki T and Oriyama T.
Tetrahedron Letters, 43(49), 8959-8962 (2002)
Synthesis of a Precursor of a Lipid A Mimic.
Barath M, et al.
Chemical Papers, 57(2), 125-130 (2003)
M. Kloosterman et al.
Rec. Trav. Chim., 103, 243-243 (1984)
R. Johansson et al.
Journal of the Chemical Society. Perkin Transactions 1, 2371-2371 (1984)
Yasumasa Hara et al.
Journal of natural medicines, 72(1), 280-289 (2017-12-07)
A new amide, named dehydropropylpantothenamide (1), was obtained by a co-culture of Nocardia tenerifensis IFM 10554
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