Azidomethyl phenyl sulfide

Bezeichnung:Azidomethyl phenyl sulfide

CAS-Nr77422-70-9

Englisch Name:Azidomethyl phenyl sulfide

CBNumberCB9399545

SummenformelC7H7N3S

Molgewicht165.22

MOL-Datei77422-70-9.mol

Azidomethyl phenyl sulfide physikalisch-chemischer Eigenschaften

Siedepunkt	104-105 °C/5 mmHg (lit.)
Dichte	1.168 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.5904(lit.)
Flammpunkt	226 °F
storage temp.	2-8°C
Aggregatzustand	liquid
Farbe	colorless to light-gold
InChI	1S/C7H7N3S/c8-10-9-6-11-7-4-2-1-3-5-7/h1-5H,6H2
InChIKey	KIQGRMGPIMCXSC-UHFFFAOYSA-N
SMILES	[N-]=[N+]=NCSc1ccccc1

Sicherheit

R-Sätze:	44
S-Sätze:	36
WGK Germany	3
Speicherklasse	10 - Combustible liquids

Azidomethyl phenyl sulfide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R44:Explosionsgefahr bei Erhitzen unter Einschluss.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Verwenden
Azidomethyl Phenyl Sulfide is a reagent for amination of organomagnesium compounds; allows amination and oxidation of α,α- disubstituted ester enolates via 1,2,3-triazol-5-ones; a synthetic equivalent of methyl azide for the synthesis of methylaziridines; substituted α-azido sulfides undergo Beckmann-type rearrangements to provide lactams and imino thioethers.
synthetische
Preparative Method of Azidomethyl Phenyl Sulfide: chlorination of Thioanisole with Sulfuryl Chloride followed by treatment of the resultant α-chloro sulfide with Sodium Azide in acetonitrile^[1].
reaction suitability
reaction type: click chemistry
Lager
Azidomethyl Phenyl Sulfide is the same as with all azides of low or moderate molecular weight, heat or shock can cause vigorous, possibly explosive, nitrogen evolution. Distillation should be performed behind a blast shield at reduced pressure and temperatures less than 110 °C. Similar compounds have been shown to decompose with nitrogen evolution at ~120 °C. Striking neat azidomethyl phenyl sulfide with a hammer fails to cause detonation. Storage under nitrogen in an amber bottle in a refrigerator is recommended. It is incompatible with strong acids, bases, and oxidizing agents. When the reagent is used for the amination of organomagnesium reagents, an intermediate triazene is formed. Certain triazenes are known to be carcinogenic, thus caution in handling these intermediates should be exercised. Rinsing glassware with bleach will dispel the disagreeable odor associated with azidomethyl phenyl sulfide, phenylthiomethyltriazenes, and other sulfur-containing byproducts encountered in the use of this reagent. Handle in a fumehood.
Einzelnachweise
1. Trost, B. M.; Pearson, W. H. JACS 1981, 103, 2483.

Azidomethyl phenyl sulfide Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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