Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

425834

Sigma-Aldrich

N-Boc-pyrrole

98%

Synonym(s):

tert-Butyl 1-pyrrolecarboxylate

Sign Into View Organizational & Contract Pricing
All Photos(1)

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
NACRES:
NA.22

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

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Pyrrole reagent grade, 98%

Sigma-Aldrich

131709

Pyrrole

Methyl 2-pyrrolecarboxylate 97%

Sigma-Aldrich

640425

Methyl 2-pyrrolecarboxylate

CuO/SiO2 as a simple, effective and recoverable catalyst for alkylation of indole derivatives with diazo compounds.
Fraile JM, et al.
Organic & Biomolecular Chemistry, 11(26), 4327-4332 (2013)
Venkata A Kallepalli et al.
The Journal of organic chemistry, 74(23), 9199-9201 (2009-11-10)
Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions beta to N. The Boc group can be removed on thermolysis or left intact during subsequent
Synthetic approaches to enantiomerically pure 8-azabicyclo [3.2. 1] octane derivatives.
Pollini GP, et al.
Chemical Reviews, 106(6), 2434-2454 (2006)
Huw M L Davies et al.
Chemical Society reviews, 38(11), 3061-3071 (2009-10-23)
The metal catalyzed reactions of diazo compounds have been broadly used in organic synthesis. The resulting metal-carbenoid intermediates are capable of undergoing a range of unconventional reactions, and due to their high energy, they are ideal for initiating cascade sequences
Recent progress in the synthesis of five-membered heterocycle boronic acids and esters.
Primas N, et al.
Tetrahedron, 66(41), 8121-8136 (2010)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service