4-amino-3-iodobenzonitrile

• ChemBase ID: 142784
• Molecular Formular: C7H5IN2
• Molecular Mass: 244.03247
• Monoisotopic Mass: 243.94974617
• SMILES: c1cc(c(cc1C#N)I)N
• Canonical SMILES: N#Cc1ccc(c(c1)I)N
• InChI: InChI=1S/C7H5IN2/c8-6-3-5(4-9)1-2-7(6)10/h1-3H,10H2
• InChIKey: UOWVTQFTEAYDLM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-3-iodobenzonitrile
• IUPAC Traditional name: 4-amino-3-iodobenzonitrile
• Synonyms: 1-Amino-2-iodo-4-cyanobenzene; 4-Cyano-2-iodoaniline; 4-Amino-3-iodobenzonitrile; 4-Amino-3-iodobenzonitrile; 4-氨基-3-碘苯甲腈; 4-氨基-3-碘苯腈

Database IDs

• CAS Number: 33348-34-4
• MDL Number: MFCD04039964
• PubChem SID: 162237010; 24884265
• PubChem CID: 4416395

CALCULATED PROPERTIES

• Acid pKa: 19.517103
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.9293555
• LogD (pH = 7.4): 1.9293605
• Log P: 1.9293605
• Molar Refractivity: 49.8425 cm^3
• Polarizability: 18.499607 Å^3
• Polar Surface Area: 49.81 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 112-115 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Linear Formula: IC6H3(NH2)CN

DETAILS

Sigma Aldrich - 657123

Application
Palladium-catalyzed carbonylation of iodoanilines provides ketoamides in the presence of primary and secondary amines.8
Reactant involved in:
• Hydroamination-double hydroarylation for synthesis of fuzed carbazoles1
• Cycloisomerizations of aromatic homo- and bis-homopropargylic amine / amide intermediates2
• Asymmetric organocatalytic condensation and cycloaddition3
• Regioselective aryl C-H bond functionalization4
• Synthesis of [(triisopropylsilyl)ethynyl]indole derivatives5
• Domino condensation / S-arylation / heterocyclization reactions6,7
Packaging
1, 5 g in glass bottle