View source for Chemistry:N-Sulfinylaniline

{{DISPLAYTITLE:''N''-Sulfinylaniline}}
{{Chembox
| Name= ''N''-Sulfinylaniline
| ImageFile = PhNSO-2.svg
| ImageSize = 140 px
| ImageAlt = 
| PIN = (Phenylimino)-λ<sup>4</sup>-sulfanone<ref>{{cite book |author=[[Organization:International Union of Pure and Applied Chemistry|International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Organization:Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=1032 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames = ''N''-thionylaniline, phenyliminooxosulfurane, ''N''-sulfinylbenzenamine 
|Section1={{Chembox Identifiers
| CASNo_Ref = {{Cascite|correct|CAS}}
| CASNo = 222851-56-1
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 1122-83-4
| CASNo1_Comment = (non-specific) 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SV7R5HC44R
| ChemSpiderID = 63904
| EC_number = 214-362-4
| PubChem = 70739
| StdInChI=1S/C6H5NOS/c8-9-7-6-4-2-1-3-5-6/h1-5H
| StdInChIKey = FIOJWGRGPONADF-UHFFFAOYSA-N
| SMILES = C1=CC=C(C=C1)N=S=O
 }}
|Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>5</sub>NSO
| MolarMass =139.18
| Appearance = yellowish oil
| Density = 1.236 g/mL
| MeltingPt = 
| BoilingPt = 88–95 °C (17–20 mm.)
<!--| Refractive index = 1.6253-->
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|315|319|334|335}}
| PPhrases = {{P-phrases|261|264|271|280|285|302+352|304+340|304+341|305+351+338|312|321|332+313|337+313|342+311|362|403+233|405|501}}
| MainHazards = 
| FlashPt = 
| AutoignitionPt = }}
}}

'''''N''-Sulfinylaniline''' is the organosulfur compound with the formula C<sub>6</sub>H<sub>5</sub>NSO. It is a straw-colored liquid. ''N''-Sulfinylaniline is an example of a [[Chemistry:Sulfinylamine|sulfinylamine]]. It is a dienophile<ref name= Kresze>{{cite journal|doi=10.1002/anie.196701491|title=New Methods of Preparative Organic Chemistry V: Organic Syntheses with Imides of Sulfur Dioxide|year=1967|last1=Kresze|first1=G.|last2=Wucherpfennig|first2=W.|journal=Angewandte Chemie International Edition in English|volume=6|issue=2|pages=149–167|pmid=4962859}}</ref> and a [[Chemistry:Ligand|ligand]] in [[Chemistry:Organometallic chemistry|organometallic chemistry]].<ref>Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227</ref>

==Synthesis and structure==
It is prepared by treating [[Chemistry:Aniline|aniline]] with [[Chemistry:Thionyl chloride|thionyl chloride]]:<ref>{{cite journal|doi=10.15227/orgsyn.049.0070|title=Diphenylcarbodiimide|journal=Organic Syntheses|year=1969|volume=49|page=70|first1=S.|last1=Rajagopalan|first2=B. G.|last2=Advani|first3=C. N.|last3=Talaty}}.</ref>
:3 PhNH<sub>2</sub>  +  SOCl<sub>2</sub>   →   PhNSO  +  2 [PhNH<sub>3</sub>]Cl


[[Physics:X-ray crystallography|X-ray crystallographic analysis]] confirms that ''N''-sulfinylaniline is structurally related to sulfur dioxide as well as [[Chemistry:Sulfur diimide|sulfur diimide]]. The C–S=N=O [[Dihedral angle|dihedral angle]] is –1.60°,<ref>{{cite journal|doi=10.1016/S0022-2860(98)00439-6|title=A Solid State Study of the Configuration and Conformation of O=S=N–R (R=C<sub>6</sub>H<sub>5</sub> and C<sub>6</sub>H<sub>3</sub>(CH<sub>3</sub>–CH<sub>2</sub>)<sub>2</sub>-2,6)|year=1999|last1=Romano|first1=R.M|last2=Della Védova|first2=C.O|last3=Boese|first3=R.|journal=Journal of Molecular Structure|volume=475|issue=1|pages=1–4|bibcode=1999JMoSt.475....1R}}</ref> 

==References==
<references />

{{DEFAULTSORT:Sulfinylaniline, N-}}
[[Category:Phenyl compounds]]

{{Sourceattribution|N-Sulfinylaniline}}