N-Sulfinylaniline

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N-Sulfinylaniline
Names
Preferred IUPAC name
(Phenylimino)-λ4-sulfanone[1]
Other names
N-thionylaniline, phenyliminooxosulfurane, N-sulfinylbenzenamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.058 Edit this at Wikidata
EC Number
  • 214-362-4
UNII
  • InChI=1S/C6H5NOS/c8-9-7-6-4-2-1-3-5-6/h1-5H
    Key: FIOJWGRGPONADF-UHFFFAOYSA-N
  • C1=CC=C(C=C1)N=S=O
Properties
C6H5NSO
Molar mass 139.18
Appearance yellowish oil
Density 1.236 g/mL
Boiling point 88–95 °C (17–20 mm.)
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Danger
H315, H319, H334, H335
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).

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]

References

  1. ^ 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.
  2. ^ 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.
  3. ^ Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227
  4. ^ Rajagopalan, S.; Advani, B. G.; Talaty, C. N. (1969). "Diphenylcarbodiimide". Organic Syntheses. 49: 70. doi:10.15227/orgsyn.049.0070..
  5. ^ 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.
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