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479969

Sigma-Aldrich

4-Amino-5-pyrimidinecarbonitrile

96%

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About This Item

Empirical Formula (Hill Notation):
C5H4N4
CAS Number:
16357-69-0
Molecular Weight:
120.11
MDL number:
MFCD00054552
UNSPSC Code:
12352100
PubChem Substance ID:
24871666
NACRES:
NA.22

Assay

96%

form

solid

mp

251-255 °C (lit.)

functional group

nitrile

SMILES string

Nc1ncncc1C#N

InChI

1S/C5H4N4/c6-1-4-2-8-3-9-5(4)7/h2-3H,(H2,7,8,9)

InChI key

JAIYUIOGVNRXEW-UHFFFAOYSA-N

General description

4-Amino-5-pyrimidinecarbonitrile (APC) is a pyrimidine derivative that has been synthesized via three-component reaction between benzaldehyde, benzamidine hydrochloride and malononitrile.[1] The infrared, 1H NMR, 13C NMR and mass spectra of APC have been recorded.[2]

Application

4-Amino-5-pyrimidinecarbonitrile may be used as a monodentate ligand to prepare metal complexes of Co(II), Ni(II), Cu(II) and Pd(II) ions.[3] It may be used as a reactant to prepare 1H-pyrimido[4,5-d]pyrimidine-2,4-dione.[4]

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
11011HJ
03126HH
07621JE
12430DB

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Synthesis, antimicrobial activity, structural and spectral characterization and DFT calculations of Co (II), Ni (II), Cu (II) and Pd (II) complexes of 4-amino-5-pyrimidinecarbonitrile.
Mohamed TA, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 135, 417-427 (2015)
Infrared and NMR spectra, tautomerism, vibrational assignment, normal coordinate analysis, and quantum mechanical calculations of 4-amino-5-pyrimidinecarbonitrile.
Afifi MS, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 111, 277-289 (2013)
Synthesis of quinazoline-2,4(1H,3H)-diones from carbon dioxide and 2-aminobenzonitriles using [Bmim]OH as a homogeneous recyclable catalyst.
Patil YP, et al.
Catalysis Today, 148(3), 355-360 (2009)
Three-component process for the synthesis of 4-amino-5-pyrimidinecarbonitriles under thermal aqueous conditions or microwave irradiation.
Sheibani H, et al.
ARKIVOC (Gainesville, FL, United States), 2, 115-123 (2008)

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