Formaldoxime

Formaldoxime
Names
	Preferred IUPAC name N-Hydroxymethanimine
Identifiers
CAS Number	75-17-2;
3D model (JSmol)	Interactive image;
ChemSpider	6110;
ECHA InfoCard	100.000.769
EC Number	200-845-7;
PubChem CID	6350;
UNII	420JFM0Z1Q;
CompTox Dashboard (EPA)	DTXSID9058785 ;
	InChI InChI=1S/CH3NO/c1-2-3/h3H,1H2 Key: SQDFHQJTAWCFIB-UHFFFAOYSA-N;
	SMILES C=NO;
Properties
Chemical formula	H2C=N−OH
Molar mass	45.041 g·mol−1
Appearance	colorless liquid
Melting point	2.5 °C (36.5 °F; 275.6 K)
Boiling point	84 °C (183 °F; 357 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Related compounds
Related compounds	Phosgene oxime; Formaldehyde; Oxime; Imine;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Formaldoxime is the organic compound with the formula H₂C=N−OH. It is the oxime of formaldehyde. A colorless liquid, the pure compound tends to polymerize into a cyclic trimer. Aqueous solutions are stable as is the formaldoxime hydrochloride ([H₂C=N(−H)(−OH)]⁺Cl⁻). It is a reagent in organic synthesis for the conversion of aryl diazonium salts to aryl aldehydes.^[1]

It is generated by combining hydroxylamine and formaldehyde.^[2]

^ De Kimpe, Norbert (2001). "Formaldoxime". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rf023. ISBN 0-471-93623-5.
^ S. D. Jolad, S. Rajagopalan (1966). "2-Bromo-4-methylbenzaldehyde". Org. Synth. 46: 13. doi:10.15227/orgsyn.046.0013.

[1] De Kimpe, Norbert (2001). "Formaldoxime". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rf023. ISBN 0-471-93623-5.

[2] S. D. Jolad, S. Rajagopalan (1966). "2-Bromo-4-methylbenzaldehyde". Org. Synth. 46: 13. doi:10.15227/orgsyn.046.0013.

[1]

[2]