Production Method 1

5182-67-2

82679-28-5

Reaction Conditions

1.1 Reagents: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Pyridine ,  Water ;  8 d, 40 °C

Reference

Facile Synthesis, Triplet-State Properties, and Electrochemistry of Hexaiodo-Subphthalocyanine

Obloza, Magdalena; et al, Chemistry - A European Journal, 2018, 24(64), 17080-17090

Production Method 2

82679-28-5

Reaction Conditions

1.1 Reagents: Iodine ,  Fuming sulfuric acid ;  40 h, 80 - 85 °C
1.2 Reagents: Potassium hydroxide Solvents: Water ;  12 h, reflux
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Design, Synthesis, and Properties of New Derivatives of Pentacene

Jiang, Jinyue; et al, Journal of Organic Chemistry, 2006, 71(5), 2155-2158

Production Method 3

82679-28-5

Reaction Conditions

1.1 Reagents: Iodine Catalysts: Sulfuric acid ;  24 h, rt → 80 °C
2.1 Reagents: Potassium hydroxide Solvents: Water ;  12 h, 115 °C; 115 °C → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 5

Reference

Distance Measurement of a Noncovalently Bound Y@C82 Pair with Double Electron Electron Resonance Spectroscopy

Gil-Ramirez, Guzman; et al, Journal of the American Chemical Society, 2018, 140(24), 7420-7424

Production Method 4

82679-28-5

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  pH 5

Reference

Distance Measurement of a Noncovalently Bound Y@C82 Pair with Double Electron Electron Resonance Spectroscopy

Gil-Ramirez, Guzman; et al, Journal of the American Chemical Society, 2018, 140(24), 7420-7424

Production Method 5

82679-28-5

Reaction Conditions

1.1 Reagents: Iodine chloride Solvents: Carbon tetrachloride
2.1 Reagents: Sodium iodide Catalysts: Chlorotrimethylsilane

Reference

A new organosilicon synthon, 2,3,5,6-tetrakis(trimethylsilyl)-1,3-cyclohexadiene. Versatile polyfunctionalization of o-dichlorobenzene

Dunogues, Jacques; et al, Organometallics, 1982, 1(11), 1525-8

Production Method 6

762-42-5

82679-28-5

Reaction Conditions

1.1 -
2.1 Reagents: Iodine chloride Solvents: Carbon tetrachloride
3.1 Reagents: Sodium iodide Catalysts: Chlorotrimethylsilane

Reference

A new organosilicon synthon, 2,3,5,6-tetrakis(trimethylsilyl)-1,3-cyclohexadiene. Versatile polyfunctionalization of o-dichlorobenzene

Dunogues, Jacques; et al, Organometallics, 1982, 1(11), 1525-8

Production Method 7

5182-67-2

82679-28-5

Reaction Conditions

1.1 Reagents: Pyridine ,  Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Water ;  48 h, reflux

Reference

Efficient Blue and Yellow Organic Light-Emitting Diodes Enabled by Aggregation-Induced Emission

Venkatramaiah, N.; et al, ACS Applied Materials & Interfaces, 2018, 10(4), 3838-3847

Production Method 8

5182-67-2

82679-28-5

Reaction Conditions

1.1 Reagents: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Pyridine ,  Water ;  48 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1 - 2, heated

Reference

Synthesis of Hexadehydrotribenzo[a,e,i][12]annulenes by Acetylene Insertion into an Open-Chain Precursor

Dudic, Miroslav; et al, Journal of Organic Chemistry, 2012, 77(1), 68-74

Production Method 9

82679-28-5

Reaction Conditions

1.1 Reagents: Iodine ,  Sulfuric acid
1.2 Reagents: Potassium hydroxide Solvents: Water

Reference

Conformational Polymorphism of Octadehydrodibenzo[12]annulene with Dimethyl Phthalate Moieties

Hisaki, Ichiro; et al, Crystal Growth & Design, 2009, 9(1), 414-420

Production Method 10

68218-30-4

82679-28-5

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Water ;  20 h, 100 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials

Yamamoto, Koji; et al, Tetrahedron, 2016, 72(32), 4918-4924

Production Method 11

68218-30-4

82679-28-5

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Water ;  12 h, 115 °C; 115 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 5

Reference

Distance Measurement of a Noncovalently Bound Y@C82 Pair with Double Electron Electron Resonance Spectroscopy

Gil-Ramirez, Guzman; et al, Journal of the American Chemical Society, 2018, 140(24), 7420-7424

Production Method 12

67193-32-2

82679-28-5

Reaction Conditions

1.1 Reagents: Sodium iodide Catalysts: Chlorotrimethylsilane

Reference

A new organosilicon synthon, 2,3,5,6-tetrakis(trimethylsilyl)-1,3-cyclohexadiene. Versatile polyfunctionalization of o-dichlorobenzene

Dunogues, Jacques; et al, Organometallics, 1982, 1(11), 1525-8

Production Method 13

82679-28-5

Reaction Conditions

1.1 Reagents: Iodine ,  Sulfuric acid ,  Periodic acid Solvents: Acetic acid ,  Water ;  overnight, 70 °C
2.1 Reagents: Pyridine ,  Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Water ;  48 h, reflux

Reference

Efficient Blue and Yellow Organic Light-Emitting Diodes Enabled by Aggregation-Induced Emission

Venkatramaiah, N.; et al, ACS Applied Materials & Interfaces, 2018, 10(4), 3838-3847

Production Method 14

82679-28-5

Reaction Conditions

1.1 Reagents: Iodine ,  Sulfuric acid ,  Periodic acid Solvents: Acetic acid ,  Water ;  24 h, 60 - 65 °C
1.2 Reagents: Sodium carbonate Solvents: Water ;  pH 7
2.1 Reagents: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Pyridine ,  Water ;  8 d, 40 °C

Reference

Facile Synthesis, Triplet-State Properties, and Electrochemistry of Hexaiodo-Subphthalocyanine

Obloza, Magdalena; et al, Chemistry - A European Journal, 2018, 24(64), 17080-17090

Production Method 15

82679-28-5

Reaction Conditions

1.1 Reagents: Acetic acid ,  Iodine ,  Sulfuric acid ,  Sodium periodate Solvents: Water ;  70 °C
2.1 Reagents: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Pyridine ,  Water ;  48 h, reflux
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1 - 2, heated

Reference

Synthesis of Hexadehydrotribenzo[a,e,i][12]annulenes by Acetylene Insertion into an Open-Chain Precursor

Dudic, Miroslav; et al, Journal of Organic Chemistry, 2012, 77(1), 68-74

Production Method 16

82679-28-5

68218-30-4

Reaction Conditions

1.1 Reagents: Iodine ,  Fuming sulfuric acid ;  40 h, 80 - 85 °C

Reference

Design, Synthesis, and Properties of New Derivatives of Pentacene

Jiang, Jinyue; et al, Journal of Organic Chemistry, 2006, 71(5), 2155-2158

4,5-diiodo-phthalic acid Raw materials

• 1,4-dimethyl but-2-ynedioate
• 1H-Isoindole-1,3(2H)-dione, 5,6-diiodo-
• Benzene,1,2-diiodo-4,5-dimethyl-
• 1,2-BENZENEDICARBOXYLIC ACID, 4,5-DIIODO-, DIMETHYL ESTER

4,5-diiodo-phthalic acid Preparation Products

• 1H-Isoindole-1,3(2H)-dione, 5,6-diiodo- (68218-30-4)
• 4,5-diiodo-phthalic acid (82679-28-5)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Halobenzoic acids and derivatives

• 133232-58-3(5-Iodotoluic Acid)
• 54811-38-0(5-Iodo-2-methylbenzoic acid)
• 35674-20-5(3,4-Diiodobenzoic acid)
• 6301-60-6(4-Iodophthalic acid)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)