N-Sulfinylaniline

N-Sulfinylaniline
Names
	Preferred IUPAC name (Phenylimino)-λ4-sulfanone
	Other names N-thionylaniline, phenyliminooxosulfurane, N-sulfinylbenzenamine
Identifiers
CAS Number	222851-56-1 ; 1122-83-4 (non-specific) ;
3D model (JSmol)	Interactive image;
ChemSpider	63904;
ECHA InfoCard	100.013.058
EC Number	214-362-4;
PubChem CID	70739;
UNII	SV7R5HC44R ;
CompTox Dashboard (EPA)	DTXSID0061533 ;
	InChI InChI=1S/C6H5NOS/c8-9-7-6-4-2-1-3-5-6/h1-5H Key: FIOJWGRGPONADF-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)N=S=O;
Properties
Chemical formula	C6H5NSO
Molar mass	139.18
Appearance	yellowish oil
Density	1.236 g/mL
Boiling point	88–95 °C (17–20 mm.)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H315, H319, H334, H335
Precautionary statements	P261, P264, P271, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P332+P313, P337+P313, P342+P311, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

N-Sulfinylaniline is the organosulfur compound with the formula C₆H₅NSO. It is a straw-colored liquid. N-Sulfinylaniline is an example of a sulfinylamine. It is a dienophile^[2] and a ligand in organometallic chemistry.^[3]

Synthesis and structure

It is prepared by treating aniline with thionyl chloride:^[4]

3 PhNH₂ + SOCl₂ → PhNSO + 2 [PhNH₃]Cl

X-ray crystallographic analysis confirms that N-sulfinylaniline is structurally related to sulfur dioxide as well as sulfur diimide. The C–S=N=O dihedral angle is –1.60°.^[5]

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1032. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ Kresze, G.; Wucherpfennig, W. (1967). "New Methods of Preparative Organic Chemistry V: Organic Syntheses with Imides of Sulfur Dioxide". Angewandte Chemie International Edition in English. 6 (2): 149–167. doi:10.1002/anie.196701491. PMID 4962859.
^ Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227
^ Rajagopalan, S.; Advani, B. G.; Talaty, C. N. (1969). "Diphenylcarbodiimide". Organic Syntheses. 49: 70. doi:10.15227/orgsyn.049.0070..
^ Romano, R.M; Della Védova, C.O; Boese, R. (1999). "A Solid State Study of the Configuration and Conformation of O=S=N–R (R=C₆H₅ and C₆H₃(CH₃–CH₂)₂-2,6)". Journal of Molecular Structure. 475 (1): 1–4. Bibcode:1999JMoSt.475....1R. doi:10.1016/S0022-2860(98)00439-6.