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Sigma-Aldrich

Anisaldehyde dimethyl acetal

≥98.5% (GC)

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Synonym(s):
4-Methoxybenzaldehyde dimethyl acetal, α,α,4-Trimethoxytoluene
Empirical Formula (Hill Notation):
C10H14O3
CAS Number:
2186-92-7
Molecular Weight:
182.22
Beilstein:
2048930
EC Number:
218-577-4
MDL number:
MFCD00036507
PubChem Substance ID:
57646803
NACRES:
NA.22

Quality Level

100

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.)

storage temp.

2-8°C

SMILES string

COC(OC)c1ccc(OC)cc1

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

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 Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

237.2 °F - closed cup

Flash Point(C)

114.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel-Crafts reaction of arylidenecyclopropanes with acetals.
Nakamura I, et al.
Tetrahedron Letters, 45(14), 2903-2906 (2004)
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
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)
R. Johansson et al.
Journal of the Chemical Society. Perkin Transactions 1, 2371-2371 (1984)
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