425834

N-Boc-pyrrole

98%

• Synonym(s): tert-Butyl 1-pyrrolecarboxylate
• Empirical Formula (Hill Notation): C₉H₁₃NO₂
• CAS Number: 5176-27-2
• Molecular Weight: 167.21
• MDL number: MFCD00209559
• UNSPSC Code: 12352100
• PubChem Substance ID: 24866669
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 98%
• form: liquid
• refractive index: n20/D 1.4685 (lit.)
• bp: 91-92 °C/20 mmHg (lit.)
• density: 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
• InChI key: IZPYBIJFRFWRPR-UHFFFAOYSA-N

Description

General description

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. It also undergoes cyclopropanation with methyl phenyldiazoacetate to form both monocyclopropane and dicyclopropane. Its Ir-catalyzed C-H borylation followed by cross coupling with 3-chlorothiophene to form biheterocycle has been reported.

Application

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.
It may be used as starting material in the synthesis of the following:

• tropane drivatives
• N-boc-2-(4-methoxyphenyl)pyrrole
• N-boc-pyrrol-2-ylboronic acid

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 167.0 °F - closed cup
• flash_point_c: 75 °C - closed cup
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter