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M72803

Sigma-Aldrich

2-Methylpiperidine

98%

Synonym(s):

α-Pipecoline, 2-Pipecoline, NSC 31047, NSC 462

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About This Item

Empirical Formula (Hill Notation):
C6H13N
CAS Number:
109-05-7
Molecular Weight:
99.17
Beilstein:
79804
EC Number:
203-642-1
MDL number:
MFCD00005982
UNSPSC Code:
12352100
PubChem Substance ID:
24897152
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.445 (lit.)

bp

118-119 °C/753 mmHg (lit.)

density

0.844 g/mL at 25 °C (lit.)

SMILES string

CC1CCCCN1

InChI

1S/C6H13N/c1-6-4-2-3-5-7-6/h6-7H,2-5H2,1H3

InChI key

NNWUEBIEOFQMSS-UHFFFAOYSA-N

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Application

Reactant for C-2 arylation of piperidines through directed transition metal-catalyzed sp3 C-H activation

Reactant for synthesis of:
  • Azepan-4-ones via two step [5+2] annulation
  • 2-Aminobenzoxazoles
  • Unsymmetrically substituted ureas
  • Corticotropin-releasing factor receptor type 1 antagonists
  • Gefitinib analogues with anti-tumor activity

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

50.0 °F - closed cup

Flash Point(C)

10 °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’.

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Dmitry Zuev et al.
Bioorganic & medicinal chemistry letters, 20(12), 3669-3674 (2010-05-18)
A novel series of [6-chloro-2-trifluoromethyl-7-aryl-7H-imidazo[1,2-a]imidazol-3-ylmethyl]-dialkylamines was discovered as potent CRF(1)R antagonists. The optimization of binding affinity in the series by the parallel reaction approach is discussed herein.
Christopher L Cioffi et al.
The Journal of organic chemistry, 75(22), 7942-7945 (2010-10-27)
The synthesis of 2-aminobenzoxazoles can be readily achieved by two versatile, one-pot procedures utilizing commercially available tetramethyl orthocarbonate or 1,1-dichlorodiphenoxymethane, an amine, and an optionally substituted 2-aminophenol. The reactions were conducted under mild conditions and provided 2-aminobenzoxazoles in modest to
Li Cui et al.
Chemical communications (Cambridge, England), 46(19), 3351-3353 (2010-05-06)
A surprisingly efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation is developed. This reaction involves a key gold catalysis and shows generally high regioselectivities and good to excellent diastereoselectivities.
Xiaoqing Wu et al.
Bioorganic & medicinal chemistry, 18(11), 3812-3822 (2010-05-15)
There is an urgent need to design and develop new and more potent EGFR inhibitors with improved anti-tumor activity. Here we describe the design and synthesis of two series of 4-benzothienyl amino quinazolines as new analogues of the EGFR inhibitor
C-2 arylation of piperidines through directed transition-metal-catalyzed sp3 C-H activation.
Hana Prokopcová et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(44), 13063-13067 (2010-10-29)
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