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MilliporeSigma

A78403

4-Aminopyridine

98%

Synonym(s):

4-Pyridinamine, 4-Pyridylamine, 4AP, Fampridine

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25 G

$53.90

100 G

$153.00

$53.90


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About This Item

Empirical Formula (Hill Notation):
C5H6N2
CAS Number:
Molecular Weight:
94.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-987-9
Beilstein/REAXYS Number:
105782
MDL number:
Assay:
98%
Form:
crystals

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InChI key

NUKYPUAOHBNCPY-UHFFFAOYSA-N

InChI

1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)

SMILES string

Nc1ccncc1

assay

98%

form

crystals

bp

273 °C (lit.)

mp

155-158 °C (lit.)

solubility

H2O: 50 mg/mL, clear, colorless

Quality Level

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1 of 4

This Item
275875A77997736023
assay

98%

assay

≥99%

assay

99%

assay

97%

solubility

H2O: 50 mg/mL, clear, colorless

solubility

DMF: soluble(lit.), DMSO: soluble(lit.), THF: soluble(lit.), acetone: soluble(lit.), acetonitrile: soluble(lit.), ethanol: soluble(lit.), isopropanol: soluble(lit.), methanol: soluble(lit.), water: soluble(lit.)

solubility

-

solubility

-

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

mp

155-158 °C (lit.)

mp

155-158 °C (lit.)

mp

54-58 °C (lit.)

mp

65-70 °C

form

crystals

form

solid

form

crystals

form

solid

bp

273 °C (lit.)

bp

273 °C (lit.)

bp

204-210 °C (lit.)

bp

-

General description

4-aminopyridine is a ligand and an ion channel modulator used as an acetylcholine release enhancing agent. [1] [2]

Application

4-Aminopyridine (4-AP) can be used as a:
  • Catalyst in the regioselective acylation of N-tosylhydrazide.[3]
  • Starting material in the synthesis of 4-aminopyridine derivatives for neurological disorder studies.[4]
  • Precursor for the synthesis of enantiomerically pure 4-(pyrrolidino)pyridine (PPY) derivatives by cyclocondensation reaction.[5]

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Chronic 2 - Eye Dam. 1 - Skin Corr. 1B

Storage Class

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

wgk

WGK 3

flash_point_f

312.8 °F

flash_point_c

156 °C

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Development of novel 4-aminopyridine derivatives as potential treatments for neurological injury and disease
Smith DT, et al.
European Journal of Medicinal Chemistry, 40(9), 908-917 (2005)
Effect of protonated aminopyridines on the structural divergences of M (II)--malonate complexes (M= Cu, Ni, Co)
Amrita D et al.
Polyhedron, 29, 1317-1325 (2010)
Synthesis of C 2-symmetric analogues of 4-(pyrrolidino) pyridine: new chiral nucleophilic catalysts
Spivey AC, et al.
Journal of the Chemical Society, Part 1, 1(20), 3460-3468 (2000)
4-Aminopyridine catalyzed direct and regioselective acylation of N-tosylhydrazide
Namba K, et al.
Organic Letters, 11(21), 4970-4973 (2009)
4-Aminopyridine derivatives with antiamnesic activity
Aldo A et al.
European Journal of Medicinal Chemistry, 35, 77-82 (2000)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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