N,N-Dimethylformamide di-tert-butyl acetal Chemical Properties

Boiling point:

56-57 °C8 mm Hg(lit.)

Density 

0.848 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.413(lit.)

Flash point:

93 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Miscible with toluene and benzene.

form 

clear liquid

pka

5.34±0.50(Predicted)

color 

Colorless to Almost colorless

Specific Gravity

0.848

Sensitive 

Moisture Sensitive

BRN 

969629

InChI

InChI=1S/C11H25NO2/c1-10(2,3)13-9(12(7)8)14-11(4,5)6/h9H,1-8H3

InChIKey

DBNQIOANXZVWIP-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(OC(C)(C)C)N(C)C

CAS DataBase Reference

36805-97-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

26-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

10-21

HazardClass 

3

PackingGroup 

III

HS Code 

29221990

MSDS

• Language:English Provider:1,1-Di-tert-butoxy-N,N-dimethylmethylamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N,N-Dimethylformamide di-tert-butyl acetal Usage And Synthesis

Uses

Reagent used for the preparation of indolizines via intermolecular cyclization of picolinium salts.

Uses

N,N-Dimethylformamide di-tert-butyl acetal may be used in the synthesis of following:

• (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

Synthesis Reference(s)

Synthetic Communications, 15, p. 723, 1985 DOI: 10.1080/00397918508063864

General Description

N,N-Dimethylformamide di-tert-butyl acetal is an derivatizing reagent.

reaction suitability

reagent type: derivatization reagent
reaction type: Acylations

Synthesis

A mixture of 59.5 g (0.5 mol) of N, N-dimethylformamide dimethyl acetal and 147 mL (1.5 mol) of dry tert-butanol in a three-necked flask (250 mL) fitted with a thermometer magnetic stirrer, nitrogen inlet and a 33 x 1.9 cm silvered vacuum jacketed Goodloe column which was equipped with a reflux controlled take-off distilling head was heated at reflux for 1 hr, then 300 mg of 2,4,6-tri-tert-butylphenol was added. The reaction mixture was heated at 100-115°C for 48 hrs, during which time, at the rate of two drops/min, 56 mL of distillate was collected. Another 50 mL (0.52 mol) of tert-butanol was added to the reaction mixture, and the removal of methanol was continued for an additional 42 hrs to afford 64 mL of distillate. Distillation of the crude product with a similar but smaller column (20 x 1.4 cm) gave 53.2 g (52%) of N, N-Dimethylformamide di-tert-butyl acetal[1].

References

[1] Mohacsi, E. “A New Synthetic Method for the Preparation of N,N-Dimethylformamide DI-Tert-Butyl Acetal.” Synthetic Communications 15 1 (1985): 723–725.

N,N-Dimethylformamide di-tert-butyl acetal(36805-97-7)Related Product Information

• Butyl acetate
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• N,N-Dimethylformamide dimethyl acetal
• N,N-Dimethylformamide
• Buprofezin
• 2-Butoxyethanol
• Polyoxymethylene
• Acetal
• DI-TERT-BUTYL ETHER
• N,N-Dimethyformamide diethy acetal
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• PHENYLETHYL ACETAL
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