ChemicalBook Product Catalog Chemical Reagents Organic reagents Amide N,N-Dimethylformamide dimethyl acetal

N,N-Dimethylformamide dimethyl acetal

Product NameN,N-Dimethylformamide dimethyl acetal
CAS4637-24-5
MFC5H13NO2
MW119.16
EINECS225-063-3
MOL File4637-24-5.mol

Chemical Properties

Melting point	-85°C
Boiling point	102-103 °C/720 mmHg (lit.)
Density	0.897 g/mL at 25 °C (lit.)
vapor pressure	34.5hPa at 20℃
refractive index	n20/D 1.396(lit.)
Flash point	45 °F
storage temp.	Store below +30°C.
solubility	Miscible with most organic solvents.
form	Solid
pka	5.00±0.50(Predicted)
color	White to off-white
PH	7 (H2O)
explosive limit	1.3-17.7%(V)
Water Solubility	hydrolysis
Sensitive	Moisture Sensitive
BRN	506020
Exposure limits	ACGIH: TWA 200 ppm; STEL 250 ppm (Skin) OSHA: TWA 200 ppm(260 mg/m3) NIOSH: IDLH 6000 ppm; TWA 200 ppm(260 mg/m3); STEL 250 ppm(325 mg/m3)
InChI	1S/C5H13NO2/c1-6(2)5(7-3)8-4/h5H,1-4H3
InChIKey	ZSXGLVDWWRXATF-UHFFFAOYSA-N
SMILES	COC(OC)N(C)C
LogP	0.750 (est)
CAS DataBase Reference	4637-24-5(CAS DataBase Reference)
NIST Chemistry Reference	Methanamine, 1,1-dimethoxy-N,N-dimethyl-(4637-24-5)
EPA Substance Registry System	Methanamine, 1,1-dimethoxy-N,N-dimethyl- (4637-24-5)

Safety Information

Hazard Codes	F,Xn,Xi
Risk Statements	11-22-36/37/38-36/38-20-20/21/22-10-52
Safety Statements	16-26-36/37-36/37/39-33-29-7/9
RIDADR	UN 3271 3/PG 2
WGK Germany	1
F	21
Autoignition Temperature	155 °C
TSCA	TSCA listed
HazardClass	3
PackingGroup	II
HS Code	29225000
Storage Class	3 - Flammable liquids
Hazard Classifications	Acute Tox. 4 Inhalation Eye Dam. 1 Flam. Liq. 2 Skin Sens. 1
Toxicity	LD50 orally in Rabbit: > 5000 mg/kg

MSDS

Provider	Language
N-Dimethoxymethyl-N,N-dimethylamine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

clear colourless liquid

Uses

Used to catalyze the coupling of epoxides with carbon dioxide under solvent free conditions leading to cyclic carbonates.

Uses

N,N-Dimethylformamide dimethyl acetal is used as an intermediate in the formation of pyridine derivatives, which exhibits inhibition against PI3 kinase p110alfa enzymes. It is utilized for the derivatization of primary sulfonamides and trifluoroacetic acid. It is also used in the preparation of formamidine derivatives. It is used as a reagent for n-dimethylaminomethylene and methyl esters. Further, it is used to catalyze the coupling of epoxides with carbon dioxide to prepare cyclic carbonates.

Uses

1,1-Dimethoxy-N,N-dimethylmethanamine is used as a reagent in the formation of pyridine derivatives that exhibit inhibition against PI3 kinase p110α enzymes.

Definition

ChEBI: An acetal obtained by formal condensation of N,N-dimethylformamide with methanol. N,N-dimethylformamide dimethyl acetal is a derivatisation agent used in gas-chromatography applica ions

General Description

Esterate M (N,N-Dimethylformamide dimethyl acetal, DMFDMA) is an methylating reagent. It has been used in methyl esterification of carboxylic acid and also in one-step derivatization of amino acids into N,N-Dimethylaminomethylene methyl esters.

Flammability and Explosibility

Highly flammable

reaction suitability

reagent type: derivatization reagent
reaction type: Acylations
reagent type: derivatization reagent
reaction type: Esterifications

Synthesis

124-41-4

68-12-2

4637-24-5

A method for synthesizing N,N-dimethylformamide dimethyl acetal, comprising the steps of (1) heating N,N-dimethylformamide to 70°C, mixing with dimethyl sulfate in a molar ratio of 1:1 and reacting for 4 hours after the end of dropwise addition to obtain the imine complex, and then cooling to room temperature; (2) adding solid sodium methanol to 200 solvent oil, dispersing it by ultrasonication, adjusting the temperature to 25 ℃ and maintained, dropwise addition of the imine complex, the reaction for 2 hours and then filtered, the filtrate often pressure fractionation, collection of 105-108 ℃ fraction, to obtain N,N-dimethylformamide dimethyl acetal, the yield was 75.3%, purity of 97%; wherein the molar ratio of sodium methanol to the imine complex is 1:1. The synthesis of the N,N-dimethylformamide dimethyl acetal of Example 6 is the same as that of Example 2, the The difference is that the organic solvent of this embodiment is a mixed solvent oil: D40 solvent oil, D60 solvent oil and 260 solvent oil, with a volume ratio of 2:1:1, to obtain N,N-dimethylformamide dimethyl acetal with a yield of 85.4% and a purity of 97%.

References

[1] Patent: CN106083611, 2016, A. Location in patent: Paragraph 0034-0037; 0048-0049

N,N-Dimethylformamide dimethyl acetal

Chemical Properties

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