Diethylformamide

Diethylformamide
Names
	Preferred IUPAC name N,N-Diethylformamide
	Other names Diethylformamide, DEF
Identifiers
CAS Number	617-84-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	11554 ;
ECHA InfoCard	100.009.577
EC Number	210-533-2;
PubChem CID	12051;
UNII	D4BLP8BN9H ;
CompTox Dashboard (EPA)	DTXSID3020463 ;
	InChI InChI=InChI=1S/C5H11NO/c1-3-6(4-2)5-7/h5H,3-4H2,1-2H3 Key: SUAKHGWARZSWIH-UHFFFAOYSA-N ;
	SMILES CCN(CC)C=O;
Properties
Chemical formula	C5H11NO
Molar mass	101.149 g·mol−1
Appearance	colorless liquid
Boiling point	176–177 °C (349–351 °F; 449–450 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diethylformamide is an organic compound with the formula C₅H₁₁NO.^[3] As its name indicates, it is structurally related to formamide, having two ethyl groups in place of the two hydrogens. It is used in place of the related dimethylformamide for niche applications.

Preparation

Diethylformamide may be prepared industrially by combining diethylamine and methyl formate at atmospheric pressure.^[4]

Applications

Diethylformamide is used as a solvent in the production of metal–organic frameworks to be used for gas storage.^[5]

References

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 841, 844. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The traditional name 'formamide' is retained for HCO-NH₂ and is the preferred IUPAC name. Substitution is permitted on the –NH₂ group.
^ "N,N-Diethylformamide". Sigma Aldrich. Retrieved May 7, 2023.
^ PubChem. "N,N-Diethylformamide". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-05-07.
^ CN application 103012183A, 王传良, "Preparation method of N,-N-diethyl-formamide", published 2013-04-03
^ Dincă, Mircea; Long, Jeffrey R. (2008). "Hydrogen Storage in Microporous Metal–Organic Frameworks with Exposed Metal Sites". Angewandte Chemie International Edition. 47 (36): 6766–6779. doi:10.1002/anie.200801163. PMID 18688902.

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 841, 844. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The traditional name 'formamide' is retained for HCO-NH₂ and is the preferred IUPAC name. Substitution is permitted on the –NH₂ group.

[2] "N,N-Diethylformamide". Sigma Aldrich. Retrieved May 7, 2023.

[3] PubChem. "N,N-Diethylformamide". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-05-07.

[4] CN application 103012183A, 王传良, "Preparation method of N,-N-diethyl-formamide", published 2013-04-03

[5] Dincă, Mircea; Long, Jeffrey R. (2008). "Hydrogen Storage in Microporous Metal–Organic Frameworks with Exposed Metal Sites". Angewandte Chemie International Edition. 47 (36): 6766–6779. doi:10.1002/anie.200801163. PMID 18688902.

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