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Sigma-Aldrich

N-Boc-pyrrole

98%

Synonym(s):

tert-Butyl 1-pyrrolecarboxylate

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About This Item

Empirical Formula (Hill Notation):
C9H13NO2
CAS Number:
5176-27-2
Molecular Weight:
167.21
MDL number:
MFCD00209559
UNSPSC Code:
12352100
PubChem Substance ID:
24866669

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

Related Categories

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

pictograms

Exclamation mark
GHS07

signalword

Warning

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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