Methyl N-(triethylammoniosulfonyl)carbamate

HCID 2724994

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Grundinformationen

CAS: 29684-56-8
Standard-SMILES: CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC
InChIKey: YSHOWEKUVWPFNR-UHFFFAOYSA-N
Summenformel: C8H18N2O4S
Durchschnittliche Molmasse: 238,31 g/mol

Überblick

See also: Methyl-N-(triethylammoniumsulfonyl)carbamate (preferred).

Namen und Bezeichner

Bevorzugter Name: Methyl N-(triethylammoniosulfonyl)carbamate
IUPAC: 1-methoxy-N-(triethylazaniumyl)sulfonylmethanimidate
Englischer Name: Burgess reagent
Summenformel: C8H18N2O4S
Molmasse: 238.3

Namen und Synonyme

Methyl N-(triethylammoniosulfonyl)carbamate(1E)-1-methoxy-N-(triethylazaniumyl)sulfonylmethanimidateSCHEMBL22689389MFCD00077815(methoxycarbonyl)[(triethylazaniumyl)sulfonyl]azanideAS-14675Burgess-reagent((Methoxycarbonyl)su(Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt, 97%SCHEMBL289869SCHEMBL616972SCHEMBL616973

Weitere Namen anzeigen

Burgess(METHOXYCARBONYLSULFAMOYL)TRIETHYLAMMONIUM HYDROXIDE(METHOXYCARBONYLSULFAMOYL)TRIETHYLAMMONIUM HYDROXIDE, INNER SALTTP05704urgess reagentBURGESS REAGENTBurgess's reagentBurgess reagent ,97%

SCHEMBL3027571YSHOWEKUVWPFNR-UHFFFAOYSA-NPB42486SY0185001-methoxy-N-triethylammoniosulfonylmethanimidate1-methoxy-N-triethylammoniosulfonyl-methanimidateF044565Q410969

Datenbank-Bezeichner

CAS: 29684-56-8
PubChem CID: 2724994

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2
Polarare Oberfläche (TPSA): 87,2 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 6
Schwere Atome: 15
Formalladung: 0
Komplexität: 306

Physikochemische Eigenschaften

Schmelzpunkt: 76 · 76-79 °C(lit.)
Dichte: 1.3023 · 1.3023 (rough estimate)
Brechungsindex: 1.63 · 1.6300 (estimate)
storage temp.: -20 °C · -20°C
Löslichkeit: Soluble in organic solvents.
Aggregatzustand: Crystalline Powder
Farbe: Slightly yellow
Merck: 14 · 14,1502
BRN: 1432131 · 1432131
InChI: InChI=1S/C8H18N2O4S/c1-5-10(6-2,7-3)15(12,13)9-8(11)14-4/h5-7H2,1-4H3
InChIKey: YSHOWEKUVWPFNR-UHFFFAOYSA-N
SMILES: [N+](CC)(CC)(CC)S(=O)(=O)[N-]C(=O)OC
CAS Datenbank: 29684 · 29684-56-8(CAS DataBase Reference)

Sicherheit und Regulatorisches

Sicherheitsdaten

F: 10-21
wgk: 3
tsca: No
hs_code: 29299090
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36-37/39
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenBurgess reagent is a selective dehydrating reagent used in organic synthesis. It is used to convert secondary and tertiary alcohol, with an adjacent proton, into alkenes. Burgess reagent is also utilized to promote great synthetic values in medicinal chemistry. It has been used in dehydration of primary amides, formamides and primary nitroalkanes to generate nitriles, isocyanides and nitrile oxides respectively. It forms urethanes when it reacts with primary alcohols.

Darstellung · 1 Eintrag

synthetischeMethoxycarbonylsulfamoyl]triethylammonium hydroxide, inner salt is easily prepared in two simple steps from chlorosulfonyl isocyanate as shown in the following scheme. The white crystalline solid Burgess reagent (m.p : 71-72°C from toluene) is air and moisture sensitive and, as such, needs to be stored in the cold and under an inert atmosphere.