425834

N-Boc-pyrrol

98%

• Synonym(e): tert-Butyl 1-pyrrolcarboxylat
• Empirische Formel (Hill-System): C₉H₁₃NO₂
• CAS-Nummer: 5176-27-2
• Molekulargewicht: 167.21
• MDL-Nummer: MFCD00209559
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24866669
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 100
• Assay: 98%
• Form: liquid
• Brechungsindex: n20/D 1.4685 (lit.)
• bp: 91-92 °C/20 mmHg (lit.)
• Dichte: 1 g/mL at 25 °C (lit.)
• SMILES String: CC(C)(C)OC(=O)n1cccc1
• InChI: 1S/C9H13NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H,1-3H3
• InChIKey: IZPYBIJFRFWRPR-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

N-Boc-pyrrole is an N-protected pyrrole. It undergoes Diels–Alder reaction with enantiomerically pure allene-1,3-dicarboxylates to form endo-adducts with retention in configurations at two newly generated stereogenic centers.[1] It also undergoes cyclopropanation with methyl phenyldiazoacetate to form both monocyclopropane and dicyclopropane.[2] Its Ir-catalyzed C-H borylation followed by cross coupling with 3-chlorothiophene to form biheterocycle has been reported.[3]

Anwendung

N-Boc-pyrrole was used in the synthesis of 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid by treating with n-BuLi and subsequent reaction with trimethyl borate.[4]
It may be used as starting material in the synthesis of the following:

• tropane drivatives[5][6]
• N-boc-2-(4-methoxyphenyl)pyrrole[7]
• N-boc-pyrrol-2-ylboronic acid[8]

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 10 - Combustible liquids
• WGK: WGK 3
• Flammpunkt (°F): 167.0 °F - closed cup
• Flammpunkt (°C): 75 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type ABEK (EN14387) respirator filter