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36805-97-7 - N,N-Dimethylformamide di-tert-butyl acetal, tech. 90% - L00431 - Alfa Aesar

L00431 N,N-Dimethylformamide di-tert-butyl acetal, tech. 90%

CAS Number
36805-97-7
Synonyms

Size Price ($) Quantity Availability
5g 73.23
25g 311.06
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N,N-Dimethylformamide di-tert-butyl acetal, tech. 90%

MDL
MFCD00015002
EINECS
253-222-7

Chemical Properties

Formula
C11H25NO2
Formula Weight
203.33
Boiling Point
75-77°/12mm
Flash Point
33°(91°F)
Density
0.850
Refractive Index
1.4120
Sensitivity
Moisture Sensitive
Solubility
Miscible with toluene and benzene.

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.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents and acids.

Literature References

The conversion of carboxylic acids to their esters using DMF acetals (see for example, N,N-Dimethyl­formamide 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).

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.

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
969629
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2922.50
TSCA
No

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