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142875

Sigma-Aldrich

2,6-Pyridinedicarbonyl dichloride

97%

Synonym(s):

2,6-Pyridinedicarbonyl chloride, Pyridine-2,6-dicarboxylic acid chloride

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About This Item

Empirical Formula (Hill Notation):
C7H3Cl2NO2
CAS Number:
3739-94-4
Molecular Weight:
204.01
Beilstein:
131556
EC Number:
223-125-4
MDL number:
MFCD00006289
UNSPSC Code:
12352100
PubChem Substance ID:
24848540
NACRES:
NA.22

Assay

97%

form

solid

bp

284 °C (lit.)

mp

56-58 °C (lit.)

SMILES string

ClC(=O)c1cccc(n1)C(Cl)=O

InChI

1S/C7H3Cl2NO2/c8-6(11)4-2-1-3-5(10-4)7(9)12/h1-3H

InChI key

GWHOGODUVLQCEB-UHFFFAOYSA-N

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Application

2,6-Pyridinedicarbonyl dichloride can be used as a starting material to synthesize:
  • Pyridine-based polyamido-polyester optically active macrocycles by reacting with chiral diamine dihydrobromides.
  • Pyridine-bridged 2,6-bis-carboxamide Schiff′s bases by treating with L-alanine or 2-methyl-alanine methyl esters.
  • N,N′-bis(1-pyrenylmethyl)pyridine-2,6-dicarboxamide by reacting with 1-pyrenemethylamine hydrochloride in the presence of a base.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H332,H317,H412

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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H Zhao et al.
The Journal of organic chemistry, 65(10), 2933-2938 (2000-05-18)
Five new chiral macrocycles, 3a-e, have been prepared by the acylation cyclization of chiral diamine dihydrobromide intermediates 2a-c with 2,6-pyridinedicarbonyl dichloride in highly diluted solution at room temperature. The chiral diesters 1a-c needed for the preparation of the macrocycles were
Mohamed A Al-Omar et al.
Molecules (Basel, Switzerland), 15(7), 4711-4721 (2010-07-27)
A series of pyridine-bridged 2,6-bis-carboxamide Schiff's bases has been prepared starting from 2,6-pyridinedicarbonyl dichloride (1) and L-alanine or 2-methyl-alanine methyl ester.The coupling of acid chloride 1 with L-alanine methyl ester hydrochloride -or 2-methylalanine methyl ester hydrochloride gave the corresponding 2,6-bis-carboxamide
Synthesis of some new pyridine-2, 6-carboxamide-derived Schiff bases as potential antimicrobial agents
Al-Omar MA and Amr Abd El-Galil E
Molecules (Basel), 15(7), 4711-4721 (2010)
Howard M Colquhoun et al.
Faraday discussions, 143, 205-220 (2009-01-01)
A novel type of tweezer molecule containing electron-rich 2-pyrenyloxy arms has been designed to exploit intramolecular hydrogen bonding in stabilising a preferred conformation for supramolecular complexation to complementary sequences in aromatic copolyimides. This tweezer-conformation is demonstrated by single-crystal X-ray analyses

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