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10445

Sigma-Aldrich

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:
2186-92-7
Molecular Weight:
182.22
Beilstein/REAXYS Number:
2048930
EC Number:
218-577-4
MDL number:
MFCD00036507
UNSPSC Code:
12352100
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

wgk_germany

WGK 1

flash_point_f

237.2 °F

flash_point_c

114.0 °C

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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