4-nitro-2,7,12,17-tetraphenyl-21,23,24,25-tetraaza-22-cuprahexacyclo[9.9.3.13,6.113,16.08,23.018,21]pentacosa-1(20),4,8,10,14,18-hexaene

• ChemBase ID: 138082
• Molecular Formular: C44H37CuN5O2
• Molecular Mass: 731.34288
• Monoisotopic Mass: 730.22432295
• SMILES: c1ccc(cc1)C1c2ccc3n2[Cu]n2c(ccc2C(C2NC(C3c3ccccc3)C=C2[N+](=O)[O-])c2ccccc2)C(C2NC1C=C2)c1ccccc1
• Canonical SMILES: [O-][N+](=O)C1=CC2NC1C(c1ccccc1)c1ccc3n1[Cu]n1c(C2c2ccccc2)ccc1C(c1ccccc1)C1NC(C3c2ccccc2)C=C1
• InChI: InChI=1S/C44H37N5O2.Cu/c50-49(51)39-27-38-42(30-17-9-3-10-18-30)36-24-23-34(46-36)40(28-13-5-1-6-14-28)32-21-22-33(45-32)41(29-15-7-2-8-16-29)35-25-26-37(47-35)43(44(39)48-38)31-19-11-4-12-20-31;/h1-27,32-33,38,40-45,48H;/q-2;+2
• InChIKey: YXUQKIDKKPBZKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitro-2,7,12,17-tetraphenyl-21,23,24,25-tetraaza-22-cuprahexacyclo[9.9.3.1^3,^6.1^1^3,^1^6.0^8,^2^3.0^1^8,^2^1]pentacosa-1(20),4,8,10,14,18-hexaene
• IUPAC Traditional name: 4-nitro-2,7,12,17-tetraphenyl-21,23,24,25-tetraaza-22-cuprahexacyclo[9.9.3.1^3,^6.1^1^3,^1^6.0^8,^2^3.0^1^8,^2^1]pentacosa-1(20),4,8,10,14,18-hexaene
• Synonyms: 2-Nitro-5,10,15,20-tetraphenyl-21H,23H-porphine copper(II); 2-硝基-5,10,15,20-四苯基-21H,23H-卟吩铜(II)

Database IDs

• CAS Number: 71147-55-2
• MDL Number: MFCD06227749
• PubChem SID: 162232340; 24871664
• PubChem CID: 71310101

CALCULATED PROPERTIES

• Acid pKa: 18.625921
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.8978734
• LogD (pH = 7.4): 1.1070385
• Log P: 6.0801
• Molar Refractivity: 205.076 cm^3
• Polarizability: 80.23165 Å^3
• Polar Surface Area: 79.74 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.)
• Absorption Wavelength: λmax 420 nm

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Compostion: Dye content, 95%
• Empirical Formula (Hill Notation): C44H27CuN5O2

DETAILS

Sigma Aldrich - 479934

Application
Versatile starting material for the introduction of new functionality at the β-pyrrolic positions of the porphyrin ring, especially in the synthesis of 2-amino-3-nitroporphyrins,1 functionalized trans-chlorins,2 and 2-alkylporphyrins.3
Packaging
250 mg in glass bottle