8.03068

N,N-Dimethylformamide dimethyl acetal

for synthesis

• Synonym(s): N,N-Dimethylformamide dimethyl acetal, N,N-Dimethyldimethoxymethylamine, DMF-DMA
• Linear Formula: (CH₃O)₂CHN(CH₃)₂
• CAS Number: 4637-24-5
• Molecular Weight: 119.16
• MDL number: MFCD00008482
• UNSPSC Code: 12352116
• EC Index Number: 225-063-3
• NACRES: NA.22

Properties

• Quality Level: 200
• form: liquid
• autoignition temp.: 155 °C
• potency: >5000 mg/kg LD₅₀, oral (Rat)
• expl. lim.: 1.3-17.7 % (v/v)
• pH: 7 ( in H₂O)
• mp: -85 °C
• transition temp: flash point 6 °C
• density: 0.895 g/cm³ at 20 °C
• storage temp.: 2-30°C
• SMILES string: [N+H](C(OC)OC)(C)C
• InChI: 1S/C5H13NO2/c1-6(2)5(7-3)8-4/h5H,1-4H3/p+1
• InChI key: ZSXGLVDWWRXATF-UHFFFAOYSA-O

Description

General description

N, N-Dimethylformamide dimethyl acetal (DMF-DMA) plays an important role in organic synthesis due to its higher reactivity.

• As a methylating agent, DMF-DMA has been used in the synthesis of methyl esters from acids, methyl ethers, and thioethers from phenols and aromatic thiols.
• DMF-DMA has been used as a formulating agent to synthesize enamines from active methylenes and active methyl groups, and amidines from amines and amides or thioamide.
• It is also possible to produce heterocyclic compounds using DMF-DMA by cyclizing two functional groups.[1]

Application

N,N-Dimethylformamide dimethyl acetal is used:

• In the synthesis of spirooxindole and pyrazole scaffolds via [3+2] cycloaddition reaction of electron-deficient olefins-based pyrazole motif.[2]
• As a reagent in the synthesis of3-acetyl-4-arylquinoline-based enaminones under microwave irradiation.[3]

Analysis Note

Assay (HClO₄): ≥ 96.0 %
Density (d 20 °C/ 4 °C): 0.893 - 0.897
Identity (IR): passes test

Safety Information

• Pictograms: GHS02,GHS05,GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H225 - H317 - H318 - H332 - H360D
• Precautionary Statements: P210 - P280 - P303 + P361 + P353 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Inhalation - Eye Dam. 1 - Flam. Liq. 2 - Repr. 1B - Skin Sens. 1
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 1
• Flash Point(F): 42.8 °F
• Flash Point(C): 6 °C