10445

Anisaldehyde dimethyl acetal

≥98.5% (GC)

• Synonym(s): 4-Methoxybenzaldehyde dimethyl acetal, α,α,4-Trimethoxytoluene
• Empirical Formula (Hill Notation): C₁₀H₁₄O₃
• CAS Number: 2186-92-7
• Molecular Weight: 182.22
• UNSPSC Code: 12352100
• NACRES: NA.22
• PubChem Substance ID: 57646803
• EC Number: 218-577-4
• Beilstein/REAXYS Number: 2048930
• MDL number: MFCD00036507
• Assay: ≥98.5% (GC)

Properties

• Quality Segment: 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.)
• functional group: acetal, ether
• 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

Description

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

Safety Information

• 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