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D7148

Sigma-Aldrich

3,4-Diaminopyridine

≥98%

Synonym(s):

3,4-DAP, 4,5-Diaminopyridine, Amifampridine, DAP, Pyridine-4,5-diamine

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About This Item

Empirical Formula (Hill Notation):
C5H7N3
CAS Number:
Molecular Weight:
109.13
Beilstein/REAXYS Number:
110232
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Application

3,4-Diaminopyridine can be used as a heterocyclic building block to prepare:      
  • Imidazo[4,5-c]pyridine, an important scaffold used for the preparation of CP-885316.     
  • 9-Azajulolidine derivatives, which are used as efficient organocatalysts for acylation and aza-Morita-Baylis-Hillman reaction.      
  • 2-Phenylpyrido[3,4-b]pyrazine by condensation reaction with α-methylsulfinylacetophenone in benzene/acetic acid as a solvent.

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Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Eye Irrit. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Raman Tandon et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(20), 6435-6442 (2013-03-19)
New heterocyclic derivatives of 9-azajulolidine have been synthesized and characterized with respect to their nucleophilicity and Lewis basicity. The Lewis basicity of these bases as quantified through their theoretically calculated methyl-cation affinities correlate well with the experimentally measured reaction rates
Monika Cecilija Žužek et al.
Toxicology letters, 281, 95-101 (2017-09-25)
The effects of natural polymeric alkylpyridinium salt (nPoly-3-APS), a potent acetylcholinesterase inhibitor isolated from the marine sponge Reniera sarai, were studied on isolated mouse phrenic nerve-hemidiaphragm muscle preparations using electrophysiological approaches. nPoly-3-APS inhibited nerve-evoked isometric muscle twitch and tetanic contraction
Regioselective Synthesis of an Imidazo [4, 5-c] pyridine through Selective Acylation of 3, 4-Diaminopyridine: Synthesis of CP-885,316
Caron S, et al.
Organic Process Research & Development, 10(2), 257-261 (2006)
Synthesis of 2-Arylpyrido [3, 4-b] pyrazine Derivatives through Condensation of 3, 4-Diaminopyridine with ?-Keto Sulfoxides
Kano S and Yuasa Y
Journal of Heterocyclic Chemistry, 20(3), 769-770 (1983)
A G Smith et al.
Neurology, 46(4), 1143-1145 (1996-04-01)
Respiratory failure is a common manifestation of myasthenia gravis but is infrequent in Lambert-Eaton myasthenic syndrome (LEMS), where it is often related to the use of paralytic agents or intercurrent pulmonary pathology. Therapies that are effective acutely in myasthenia gravis

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