Formaldoxime

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]m

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

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

Synonyms

Source:^[3]

• Formoxime
• Nitrone
• Formaldehyde oxime
• formaldoxim
• methylenenitrone