N-METHOXY-N-METHYLTRIFLUOROACETAMIDE Chemical Properties

Boiling point:

53 °C/30 mmHg (lit.)

Density 

1.299 g/mL at 25 °C (lit.)

refractive index 

1.3630 to 1.3670

Flash point:

118 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow

InChI

InChI=1S/C4H6F3NO2/c1-8(10-2)3(9)4(5,6)7/h1-2H3

InChIKey

JDBJZZTZYKUFFK-UHFFFAOYSA-N

SMILES

C(N(OC)C)(=O)C(F)(F)F

CAS DataBase Reference

104863-67-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

10-25-36

Safety Statements 

16-26-45

RIDADR 

UN 1992 3/PG 3

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2924190090

MSDS

• Language:English Provider:SigmaAldrich

N-METHOXY-N-METHYLTRIFLUOROACETAMIDE Usage And Synthesis

Chemical Properties

Clear colorless liquid

Synthesis

To a suspension of N,O-dimethylhydroxylamine hydrochloride (107.2 kg, 1.1 kmol) in dichloromethane (400 L) was sequentially added trifluoroacetic anhydride (210 kg, 1 kmol) and pyridine (174 kg, 2.2 kmol) at 0 °C. The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, the reaction solution was diluted with ice water (300 L) and washed with 2M hydrochloric acid (300 L). The aqueous phase was extracted twice with dichloromethane, the organic phases were combined and dried with anhydrous magnesium sulfate. After concentration of the organic phase, the crude N-methoxy-N-methyl-2,2,2-trifluoroacetamide (Weinreb amide) was obtained with 90% purity and 95% yield, which could be used in the subsequent reaction without further purification.

References

[1] Asian Journal of Chemistry, 2015, vol. 27, # 7, p. 2406 - 2408
[2] Journal of Organic Chemistry, 1991, vol. 56, # 13, p. 4260 - 4263
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 26, p. 7887 - 7896
[4] Patent: WO2003/101932, 2003, A2. Location in patent: Page 64
[5] Patent: WO2003/82787, 2003, A1. Location in patent: Page/Page column 108

N-METHOXY-N-METHYLTRIFLUOROACETAMIDE(104863-67-4)Related Product Information

• N-Methoxy-N-Methyltetrahydropyran-4-carboxaMide
• N-Methyl-2,2,2-trifluoroacetamide
• N-METHYL-N-METHOXYDIFLUOROACETAMIDE
• N-METHOXY-N-METHYLTRIFLUOROACETAMIDE