di-tert-butylazodicarboxylat

Di-tert-butyl diazene-1,2-dicarboxylate

HCID 6034084CAS 870-50-8

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Grundinformationen

Standard-SMILES: CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C
InChIKey: QKSQWQOAUQFORH-VAWYXSNFSA-N
Summenformel: C10H18N2O4
Durchschnittliche Molmasse: 230,26 g/mol

Namen und Bezeichner

Bevorzugter Name: Di-tert-butyl diazene-1,2-dicarboxylate
IUPAC: tert-butyl (NE)-N-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate
Lokaler Name: di-tert-butylazodicarboxylat
Englischer Name: Di-tert-Butyl azodicarboxylate
Summenformel: C10H18N2O4
Molmasse: 230.26

Namen und Synonyme

Di-tert-butyl diazene-1,2-dicarboxylateDi-tert-butylazodicarboxylate(E)-N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide862421-89-4tert-butyl (NE)-N-[(2-methylpropan-2-yl)oxycarbonylimino]carbamateMFCD00015001N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamideEINECS 212-796-9NSC109889Di-tert-butyl azodiformatetert-butyl {[(tert-butyl)oxycarbonyl]diazenyl}formateDi-tert-butyl azodicarboxylate, 98%

Weitere Namen anzeigen

di-tert-butyl (E)-diazene-1,2-dicarboxylateDI-T-BUTYL AZODICARBOXYLATEDi-tert-Butyl azodicSKL270DI-TERT-BUTYL AZODICARBOXYALTEDI-TERT-BUTYL AZODICARBOXYLATEBis(tert-butoxycarbonyl)diazene

SBB056423AKOS015838065Bis(1,1-dimethylethyl)azodicarboxylateCS-W010378GS-3460NSC 109889NSC-109889BP-11490

Datenbank-Bezeichner

CAS: 870-50-8
PubChem CID: 6034084
Nikkaji: J195.144K、J2.463.995I

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,9
Polarare Oberfläche (TPSA): 77,3 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 4
Schwere Atome: 16
Formalladung: 0
Komplexität: 267

Physikochemische Eigenschaften

Schmelzpunkt: 89 · 89-92 °C(lit.)
Siedepunkt: 287.1 · 287.1±9.0 °C(Predicted)
Dichte: 1.06 · 1.06±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
Löslichkeit: Chloroform (Sparingly), Methanol (Slightly)
Aggregatzustand: Crystals or Crystalline Powder
Farbe: Yellow
Wasserlöslichkeit: Insoluble
BRN: 1911434 · 1911434
InChI: InChI=1S/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3
InChIKey: QKSQWQOAUQFORH-VAWYXSNFSA-N
SMILES: N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O
CAS Datenbank: 870 · 870-50-8(CAS DataBase Reference)

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk: 3
ridadr: 1325
hs_code: 29270000
risk_code: 36/37/38-11
hazard_code: Xi,F
hazard_note: Irritant
safety_code: 26-36-37/39-16
hazard_class: 3
packing_group: II
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenDi-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions.