Iron(II) phthalocyanine

Base Information

• Chemical Name: Iron(II) phthalocyanine
• CAS No.: 132-16-1
• Molecular Formula: C32H16FeN8
• Molecular Weight: 568.38
• Hs Code.: 29319090
• European Community (EC) Number: 205-047-2
• Mol file: 132-16-1.mol

Synonyms:ferrous phthalocyanine;iron(II) phthalocyanine

Chemical Property of Iron(II) phthalocyanine

Chemical Property:

• Appearance/Colour: Dark purple, green or black powder
• Melting Point: >300 °C
• PSA: 84.02000
• Density: 0.326[at 20℃]
• LogP: 1.46190
• Water Solubility.: It is insoluble in water. It is soluble in conc. sulfuric acid.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 568.084728
• Heavy Atom Count: 41
• Complexity: 1080

Purity/Quality:

99% ^*data from raw suppliers

Iron(II) phthalocyanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Phthalocyanine Dyes
• Canonical SMILES: C1=CC=C2C(=C1)C3=NC4=NC(=NC5=C6C=CC=CC6=C([N-]5)N=C7C8=CC=CC=C8C(=N7)N=C2[N-]3)C9=CC=CC=C94.[Fe+2]
• General Description: Iron phthalocyanine (FePc) serves as an effective catalyst in biomimetic oxidative coupling cyclization reactions, facilitating the rapid construction of isochromanoindolenines from tetrahydrocarbolines. It plays a key role in generating reactive radicals by activating tert-butyl hydroperoxide (TBHP), which subsequently drives the oxidative coupling and cyclization process. The catalyst's efficiency is enhanced by acidic conditions, enabling broad substrate compatibility and moderate to excellent yields in the synthesis of complex heterocyclic scaffolds.

Technology Process of Iron(II) phthalocyanine

There total 51 articles about Iron(II) phthalocyanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

iron(II) chloride tetrahydrate + urea (57-13-6) + phthalonitrile (91-15-6) → iron(II) phthalocyanine (132-16-1)

Guidance literature:

With ammonium molybdate; at 110 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1142/S1088424612501106

Reference yield: 89.0%

phthalic anhydride (85-44-9) + iron(II) chloride tetrahydrate + urea (57-13-6) → iron(II) phthalocyanine (132-16-1)

Guidance literature:

With ammonium molybdate; at 130 ℃; for 0.0833333h; Microwave irradiation;

DOI:10.1142/S1088424612501106

Reference yield: 88.0%

phthalimide (136918-14-4,85-41-6) + iron(II) chloride tetrahydrate + urea (57-13-6) → iron(II) phthalocyanine (132-16-1)

Guidance literature:

With ammonium molybdate; at 120 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1142/S1088424612501106

upstream raw materials:

bis(pyridine)phthalocyanatoiron(II)

phthalic anhydride

urea

ferrocene

Downstream raw materials:

pyrographite

iron

bis(benzenemethanamine)[29H,31H-phthalocyaninato(2-)-κN(29),κN(30),κN(31),κN(32)]iron

C₄₆H₃₀FeN₁₀

Refernces

Biomimetic Oxidative Coupling Cyclization Enabling Rapid Construction of Isochromanoindolenines

10.1021/acs.orglett.8b02377

The study presents a biomimetic oxidative coupling cyclization strategy for the functionalization of tetrahydrocarbolines (THCs) to rapidly construct complex isochromanoindolenine scaffolds. The reaction involves using iron(II) phthalocyanine (FePc) as a catalyst and 2,3-bishydroxybenzoic acid as a coupling partner, with tert-butyl hydroperoxide (TBHP) as the oxidant. Acetic acid and methanesulfonic acid (MsOH) are also used to enhance the reaction efficiency. The FePc catalyst is crucial for the conversion, facilitating the formation of a tert-butyloxy radical from TBHP, which abstracts a hydrogen atom from the THC substrate. The resulting radical species then reacts with an unstable ortho-quinone intermediate formed from the oxidation of 2,3-bishydroxybenzoic acid, ultimately yielding the desired isochromanoindolenine product through acid-mediated transformation. This method is scalable, operationally simple, and compatible with a wide range of functional groups, including electron-donating and electron-withdrawing groups, and can be applied to various THCs, such as tetrahydro-β-carbolines (THβCs) and tetrahydro-γ-carbolines (THγCs), to produce the corresponding products in moderate to excellent yields.