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N,N-Dimethylformamide di-tert-butyl Acetal, tech. 90%
N,N-Dimethylformamide di-tert-butyl Acetal, tech. 90%
N,N-Dimethylformamide di-tert-butyl Acetal, tech. 90%
Thermo Scientific Chemicals

N,N-Dimethylformamide di-tert-butyl Acetal, tech. 90%

CAS: 36805-97-7 | C11H25NO2 | 203.326 g/mol
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25 g
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Catalog number L00431.14
also known as L00431-14
Price (JPY)
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Quantity:
25 g
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Chemical Identifiers
CAS36805-97-7
IUPAC Name[bis(tert-butoxy)methyl]dimethylazanium
Molecular FormulaC11H26NO2
InChI KeyDBNQIOANXZVWIP-UHFFFAOYSA-O
SMILESC[NH+](C)C(OC(C)(C)C)OC(C)(C)C
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SpecificationsSpecification SheetSpecification Sheet
FormLiquid
Identification (FTIR)Conforms
Appearance (Color)Clear colorless to pale yellow
Assay (GC)≥88.0%
Refractive Index1.4060-1.4150 @ 20?C
N,N-Dimethylformamide di-tert-butyl acetal is used as a reagent in the synthesis of (S)-2-(1-tert-butoxycarbonyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}ethylamino)benzoic acid methyl ester, 3-O-tert-butylmorphine, tert-butylesters of pyrrole and indolecarboxylic acids. Further, it is used in the preparation of indolizines by intermolecular cyclization of picolinium salts.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
N,N-Dimethylformamide di-tert-butyl acetal is used as a reagent in the synthesis of (S)-2-(1-tert-butoxycarbonyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}ethylamino)benzoic acid methyl ester, 3-O-tert-butylmorphine, tert-butylesters of pyrrole and indolecarboxylic acids. Further, it is used in the preparation of indolizines by intermolecular cyclization of picolinium salts.

Solubility
Miscible with toluene and benzene.

Notes
Moisture sensitive. Incompatible with strong oxidizing agents and acids.
RUO – Research Use Only

General References:

  1. The conversion of carboxylic acids to their esters using DMF acetals (see for example, N,N-Dimethyl formamide dimethyl acetal, A15350 ) can be extended to the preparation of t-butyl esters by using excess reagent in benzene or toluene as solvent: Synthesis, 135 (1983).
  2. Gatineau, D.; Nguyen, D. H.; Hérault, D.; Vanthuyne, N.; Leclaire, J.; Giordano, L.; Buono, G. H-adamantylphosphinates as universal precursors of P-stereogenic compounds. J. Org. Chem. 2015, 80 (8), 4132-4141.
  3. Hoecker, J.; Liffert, R.; Burch, P.; Wehlauch, R.; Gademann, K. Caged retinoids as photoinducible activators: Implications for cell differentiation and neurite outgrowth. Org. Biomol. Chem. 2013, 11 (20), 3314-3321.