133546-47-1

Basic information

• Product Name: Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole
• Synonyms: Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole;Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole >98% (HPLC)
• CAS NO: 133546-47-1
• Molecular Formula: C₁₀H₄N₄S₂
• Molecular Weight: 244.29556
• Mol File: 133546-47-1.mol

Chemical Properties

• Melting Point: 203-208℃
• Boiling Point: 430.1±18.0 °C(Predicted)
• Appearance: /
• Density: 1.700
• PKA: -3.60±0.30(Predicted)
• CAS DataBase Reference: Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole(133546-47-1)
• EPA Substance Registry System: Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole(133546-47-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 133546-47-1(Hazardous Substances Data)

Usage

Uses

Used in Photovoltaic Applications:
Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole is used as a key component in the development of high-performance polymers for photovoltaic applications. Its presence in the polymer PBDT-DTNT has been shown to enhance the interchain packing and improve charge mobility, which in turn results in a lower band gap. This contributes to the polymer's considerably better photovoltaic performance, with a power conversion efficiency (PCE) of 6.00%.
Used in Polymer Synthesis for Solar Cells:
In the solar cell industry, Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole is used as a building block for synthesizing polymers with improved photovoltaic properties. The incorporation of NTz into the polymer backbone enhances the overall performance of the solar cells, making them more efficient in converting sunlight into electricity. This advancement is crucial for the development of more sustainable and efficient solar energy technologies.

Synthetic route

1,5-dibromo-2,6-dihydroxynaphthalene (132178-78-0) → naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1)

Conditions	Yield
With tetrasulphure tetranitride In toluene for 48h; Heating;	88%

1,2,5,6-naphthalenetetraamine tetrahydrochloride salt → naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1)

Conditions	Yield
With thionyl chloride In pyridine at 75℃; for 3h; Inert atmosphere;	86%

2,6-Dihydroxynaphthalene (581-43-1) → naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1)

Conditions	Yield
With tetrasulphure tetranitride In toluene for 48h; Heating;	43%

2,6-dibromo-1,5-naphthalenediol (84-59-3) → naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) + naphtho<1,2-c:3,4-c':5,6-c''>tris<1,2,5>thiadiazole (133546-48-2)

Conditions	Yield
With tetrasulphure tetranitride In toluene for 48h; Heating;	A 35% B 11%

1,6-dihydroxynaphthalene (575-44-0) → naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1)

Conditions	Yield
With tetrasulphure tetranitride In toluene for 48h; Heating;	5%

1,5-dihydroxynaphthalene (83-56-7) → naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) + naphtho<1,2-c:3,4-c':5,6-c''>tris<1,2,5>thiadiazole (133546-48-2)

Conditions	Yield
With tetrasulphure tetranitride In toluene for 48h; Heating;	A 5% B n/a

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) + bis(pinacol)diborane (73183-34-3) → 5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphtho[1,2-c:5,6-c']bis([1,2,5]thiadiazole)

Conditions	Yield
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In cyclohexane for 0.5h; Inert atmosphere; Reflux; Stage #2: naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole In cyclohexane for 12h; Reflux;	70%

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 1,2,5,6-naphthalenetetramine dihydrochloride (51772-73-7, 144284-50-4) + naphtho<1,2-c><1,2,5>thiadiazole-5,6-diamine hydrochloride (144284-51-5)

Conditions	Yield
With hydrogenchloride; tin In 1,4-dioxane for 48h; Heating;	A 36% B 0.4%
With hydrogenchloride; tin In 1,4-dioxane for 48h; Heating;	A 34% B 0.4%

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 7,8-diphenyl<1,2,5>thiadiazolo<33',4'-5,6>naphto<1,2-b>pyrazine (144153-02-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.4 percent / Sn, conc. HCl / dioxane / 48 h / Heating 2: 39 percent / CH3COOH / ethanol / 3 h / Heating View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 2,3,8,9-tetraphenyl<1,2-b;5,6-b'>dipyrazine (144153-01-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 34 percent / Sn, conc. HCl / dioxane / 48 h / Heating 2: 52 percent / CH3COOH / ethanol / 21 h / Heating View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 3,7-di(3-hexylthiophen-5-yl)-naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole (1308677-36-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; sulfuric acid / 26 h / 60 °C 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; sulfuric acid 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 5,10-bis(5-bromo-4-hexylthiophen-2-yl)naphtho[1,2-c:5,6-c]bis(1,2,5-thiadiazole) (1308677-37-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; sulfuric acid / 26 h / 60 °C 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere 3: N-Bromosuccinimide / tetrahydrofuran / 4 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; sulfuric acid 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide 3: N-Bromosuccinimide / tetrahydrofuran View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 4,9-dibromonaphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-50-6)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid at 60℃; for 26h;
With N-Bromosuccinimide; sulfuric acid
Multi-step reaction with 2 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / cyclohexane / 0.5 h / Inert atmosphere; Reflux 1.2: 12 h / Reflux 2.1: copper(ll) bromide / water; methanol; 1-methyl-pyrrolidin-2-one / Reflux View Scheme
With N-Bromosuccinimide; sulfuric acid

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → C50H58Br2N4S6 (1433218-19-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; sulfuric acid 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere 3: N-Bromosuccinimide / tetrahydrofuran / 24 h / Darkness View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → C34H40N4S4 (1433218-16-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; sulfuric acid 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → C50H60N4S6 (1433218-17-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; sulfuric acid 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → C34H38Br2N4S4 (1433218-18-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; sulfuric acid 2: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere 3: N-Bromosuccinimide / tetrahydrofuran / 24 h / Darkness View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → naphtho[1,2-c:5,6-c]bis(1H-[1,2,3]triazole)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; tin / 1,4-dioxane 2: sodium nitrite / water View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → naphtho[1,2-c:5,6-c]bis(2-octyl-[1,2,3]triazole)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride; tin / 1,4-dioxane 2: sodium nitrite / water 3: potassium tert-butylate / methanol / 24 h / 760.05 Torr / Inert atmosphere; Reflux View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 3,7-dibromo-naphtho[1,2-c:5,6-c]bis(2-octyl-[1,2,3]triazole)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride; tin / 1,4-dioxane 2: sodium nitrite / water 3: potassium tert-butylate / methanol / 24 h / 760.05 Torr / Inert atmosphere; Reflux 4: bromine / hydrogen bromide / Reflux; liquid HBr View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 3,7-di(thiophen-5-yl)-naphtho[1,2-c:5,6-c]bis(2-octyl-[1,2,3]triazole)

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogenchloride; tin / 1,4-dioxane 2: sodium nitrite / water 3: potassium tert-butylate / methanol / 24 h / 760.05 Torr / Inert atmosphere; Reflux 4: bromine / hydrogen bromide / Reflux; liquid HBr 5: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 6 h / 760.05 Torr / Inert atmosphere; Reflux View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 3,7-di(2-bromo-thiophen-5-yl)-naphtho[1,2-c:5,6-c]bis(2-octyl-[1,2,3]triazole)

Conditions

Yield

Multi-step reaction with 6 steps 1: hydrogenchloride; tin / 1,4-dioxane 2: sodium nitrite / water 3: potassium tert-butylate / methanol / 24 h / 760.05 Torr / Inert atmosphere; Reflux 4: bromine / hydrogen bromide / Reflux; liquid HBr 5: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 6 h / 760.05 Torr / Inert atmosphere; Reflux 6: N-Bromosuccinimide / tetrahydrofuran / 4 h / 20 °C View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 1,2,5,6-naphthalenetetramine dihydrochloride (51772-73-7, 144284-50-4)

Conditions	Yield
With hydrogenchloride; tin In 1,4-dioxane

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → 5-bromo-10-(4-methoxycarbonylphenyl)naphtho[1,2-c:5,6-c′]-bis[1,2,5]thiadiazole

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; sulfuric acid 2: cesium fluoride; palladium dichloride; tri tert-butylphosphoniumtetrafluoroborate; copper(l) iodide / N,N-dimethyl-formamide / 17 h / 45 °C View Scheme

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → C10H3BrN4S2 + 4,9-dibromonaphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-50-6)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid

naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole (133546-47-1) → C26H16N4O4S2 + C18H10N4O2S2

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; sulfuric acid 2: cesium fluoride; palladium dichloride; tri tert-butylphosphoniumtetrafluoroborate; copper(l) iodide / N,N-dimethyl-formamide / 120 °C View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; sulfuric acid 2: cesium fluoride; palladium dichloride; tri tert-butylphosphoniumtetrafluoroborate; copper(l) iodide / N,N-dimethyl-formamide / 120 °C View Scheme

Upstream product

• 575-44-0 1,6-dihydroxynaphthalene 
• 84-59-3 2,6-dibromo-1,5-naphthalenediol 
• 132178-78-0 1,5-dibromo-2,6-dihydroxynaphthalene 
• 83-56-7 1,5-dihydroxynaphthalene 
• 581-43-1 2.6-dihydroxynaphthalene 

Downstream Products

• 133546-50-6 4,9-dibromonaphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole 
• 1467776-41-5 5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphtho[1,2-c:5,6-c']bis([1,2,5]thiadiazole) 
• 144153-01-5 2,3,8,9-tetraphenyl<1,2-b;5,6-b'>dipyrazine 
• 144153-02-6 7,8-diphenyl<1,2,5>thiadiazolo<33',4'-5,6>naphto<1,2-b>pyrazine 

Relevant articles and documents

Molecular Organization of 2,1,3-Benzothiadiazoles in the Solid State

Derivatives of 2,1,3-benzothiadiazole (1) are widely used in many areas of science and are particularly valuable as components of active layers in various thin-film optoelectronic devices. Even more effective benzothiadiazoles are likely to result if a deeper understanding of their preferred patterns of molecular association can be acquired. To provide new insight, we have analyzed the structures of compounds in which multiple benzothiadiazole units are attached to well-defined planar and nonplanar molecular cores. Our results show that molecular organization can be controlled in complex structures by using directional S···N bonding of benzothiadiazole units and other characteristic interactions. Moreover, the observed structures are distinctly different from those of analogous arenes. Replacing benzene rings in arenes by thiadiazoles thereby provides a strategy for making new compounds with extended systems of π-conjugation and unique patterns of molecular organization, including the ability to co-crystallize with the fullerenes C60 and C70.

Sulfur Nitride in Organic Chemistry. Part 19. Selective Formation of Benzo- and Benzobisthiadiazole Skeleton in the Reaction of Tetrasulfur Tetranitride with Naphthalenols and Related Compounds

Tetrasulfur tetranitride (N4S4) reacted with 2-naphthols to afford naphthothiadiazoles (13) in high yields, while 1-naphthols gave naphtholbisthiadiazoles as a major product, together with a small amount of 13.In the reactions with naphthalenediols such as 1,5-, 2,6-, 2,7-, 1,6-, and 1,7-diol, naphtho- or naphthobisthiadiazoles were obtained in varying yields.In some cases, naphthotristhiadiazole was formed as a by-product.In reaction with 5-isoquinolinol, 8-quinolinoles,9H-carbazol-2-ol, and dibenzofuran-2-ol, one and/or two 1,2,5-thiadiazole-ringfused heteroaromatic compounds were obtained.