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4909-78-8 - N,N-Dimethylformamide dineopentyl acetal, 98% - L02728 - Alfa Aesar

L02728 N,N-Dimethylformamide dineopentyl acetal, 98%

CAS Number
4909-78-8
Synonyms

Size Price ($) Quantity Availability
10g 44.40
50g 158.00
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N,N-Dimethylformamide dineopentyl acetal, 98%

MDL
MFCD00008851
EINECS
225-536-4

Chemical Properties

Formula
C13H29NO2
Formula Weight
231.38
Boiling Point
85-87°/10mm
Flash Point
63°(145°F)
Density
0.830
Refractive Index
1.4117
Sensitivity
Moisture Sensitive
Solubility
Hydrolyzes with water.

Applications

N,N-Dimethylformamide dineopentyl acetal helps in the lactonization of ω-hydroxyacids, giving lactones of up to 16-membered rings. It can be used to convert primary alcohols to alkylating agents for use in the alkylation of thiols. It is used in the esterification of Nα-9-fluorenylmethyloxycarbonylamino acids. It was used in the synthesis of 1,3-dialkyl, benzyl and cyclohexyl barbiturate derivatives. It was used as reagent during the synthesis of L-serine and L-cystine stereospecifically labeled with deuterium at the β-position.

Notes

Moisture Sensitive. Incompatible with water and oxidizing agents. Store under dry inert gas. Protect from humidity and water.

Literature References

F Albericio; G Barany. Improved approach for anchoring N alpha-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters in solid-phase peptide synthesis. International Journal of Peptide and Protein Reseach.1985, 26, (1), 92-97.

F Albericio; G Barany. Application of N,N-dimethylformamide dineopentyl acetal for efficient anchoring of N alpha-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters in solid-phase peptide synthesis. International Journal of Peptide and Protein Reseach.1985, 23, (4), 342-349.

This hindered acetal, in conjunction with an alcohol, converts carboxylic acids to esters of that alcohol: Angew. Chem. Int. Ed., 3, 62 (1964); Helv. Chim. Acta, 48, 1746 (1965). For application to the lactonization of ω-hydroxyacids, giving lactones of up to 16-membered rings, in modest yield, see: Angew. Chem. Int. Ed., 16, 876 (1977). Similarly, can be used to convert primary alcohols to alkylating agents for use in the alkylation of thiols (e.g. 2-Mercaptopyrimidine, A13382): Tetrahedron Lett., 585 (1972).

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
741992
Harmonized Tariff Code
2922.50
TSCA
No

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