di-tert-butylazodicarboxylat

Di-tert-butyl azodicarboxylate

HCID 97268CAS 870-50-8

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Grundinformationen

Standard-SMILES: CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C
InChIKey: QKSQWQOAUQFORH-UHFFFAOYSA-N
Summenformel: C10H18N2O4
Durchschnittliche Molmasse: 230,26 g/mol
Monoisotopische Masse: 230,12665706

Namen und Bezeichner

Bevorzugter Name: Di-tert-butyl azodicarboxylate
IUPAC: tert-butyl 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 azodicarboxylate870-50-8DTXSID201306310RefChem:586103DTXCID201736276212-796-9Di-tert-butyl diazene-1,2-dicarboxylateAzodicarboxylic Acid Di-tert-butyl EsterDi-tert-butylazodicarboxylateMFCD00015001di-t-butyl azodicarboxylate(E)-di-tert-butyl diazene-1,2-dicarboxylate

Weitere Namen anzeigen

di-tert-butyl (E)-diazene-1,2-dicarboxylateDi-tert-Butyl azodicDi-tert-butyl azodiformateSKL270NSC 109889DI-TERT-BUTYL AZODICARBOXYALTEBis(tert-butoxycarbonyl)diazene

Di-(tert-butyl) diazene-1,2-dicarboxylate1,2-Diazenedicarboxylic acid, 1,2-bis(1,1-dimethylethyl) esterDTADdi-tert-butylazocarboxylatetert-butyl {[(tert-butyl)oxycarbonyl]diazenyl}formatetert-butyl N-tert-butoxycarbonyliminocarbamatedi t-butyl azodicarboxylateDitertbutyl azodicarboxylate

Datenbank-Bezeichner

CAS: 870-50-8
PubChem CID: 97268
DTXSID: DTXSID201306310
EC Number: 212-796-9

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

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 10.7% (6 of 56) of reports.

Warning

H315 (89.3%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (89.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (87.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 56 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 6 of 56 reports by companies.；There are 7 notifications provided by 50 of 56 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (89.3%)；Eye Irrit. 2 (89.3%)；STOT SE 3 (87.5%)

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.