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

CAS Number
36805-97-7
Synonyms

Stock No. Size Price ($) Quantity Availability
L00431-06 5g 79.10
L00431-14 25g 329.00
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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
Storage & Sensitivity
Moisture Sensitive. Store under Nitrogen. Ambient temperatures.
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-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

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

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