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Key Documents

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:
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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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)
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
Xuejing Song et al.
Materials (Basel, Switzerland), 11(10) (2018-10-27)
Pyrazine derivatives quinoxaline and pyridopyrazine were selected as the acceptors, and benzocarbazole was used as the donor to synthesize four different D⁻A⁻D compounds. The results showed that 2,3-bis(decyloxy)pyridine[3,4-b]pyrazine (DPP) exhibited stronger electron-withdrawing ability than that of 2,3-bis(decyloxy)quinoxaline (DPx), because DPP

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