267-99-2

Basic information

• Product Name: Benzo[1,2-d:4,5-d']bisthiazole
• Synonyms: Benzo[1,2-d:4,5-d']bisthiazole
• CAS NO: 267-99-2
• Molecular Formula: C₈H₄N₂S₂
• Molecular Weight: 192.26076
• Mol File: 267-99-2.mol

Chemical Properties

• Boiling Point: 361.9±15.0 °C(Predicted)
• Appearance: /
• Density: 1.562±0.06 g/cm3(Predicted)
• PKA: -1.30±0.40(Predicted)
• CAS DataBase Reference: Benzo[1,2-d:4,5-d']bisthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[1,2-d:4,5-d']bisthiazole(267-99-2)
• EPA Substance Registry System: Benzo[1,2-d:4,5-d']bisthiazole(267-99-2)

Safety Data

• Hazardous Substances Data: 267-99-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzo[1,2-d:4,5-d']bisthiazole is utilized as a key building block in the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of molecules with diverse properties, making it an essential component in the development of new chemical entities.
Used in Material Science:
In the field of material science, Benzo[1,2-d:4,5-d']bisthiazole is employed for its potential to contribute to the development of advanced materials with specific properties. Its incorporation into material compositions can lead to enhanced performance characteristics, such as improved stability or reactivity.
Used in Optoelectronic Devices:
Benzo[1,2-d:4,5-d']bisthiazole is used as a component in the design and fabrication of optoelectronic devices. Its electronic properties make it suitable for applications in areas such as photovoltaics, light-emitting diodes (LEDs), and other devices that rely on the interaction of light with electronic materials.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Benzo[1,2-d:4,5-d']bisthiazole is explored for its potential as a starting material or intermediate in the synthesis of new drug candidates. Its unique structure may contribute to the development of novel therapeutic agents with specific pharmacological properties.
Overall, Benzo[1,2-d:4,5-d']bisthiazole's diverse applications across various industries highlight its importance and potential in the realm of chemical research and innovation.

Synthetic route

2,5-diaminobenzene-1,4-dithiol bis(hydrochloride) + trimethyl orthoformate (149-73-5) → benzo[1,2-d:4,5-d']bisthiazole (267-99-2)

Conditions	Yield
With pyridine; yttrium(III) trifluoromethanesulfonate In N,N-dimethyl acetamide at 50℃; for 2h;	85%
With sulfuric acid at 75℃; for 8h;	10 g

orthoformic acid triethyl ester (122-51-0) + 2,5-diaminobenzene-1,4-dithiol bis(hydrochloride) → benzo[1,2-d:4,5-d']bisthiazole (267-99-2)

Conditions	Yield
With pyridine; yttrium(III) trifluoromethanesulfonate In N,N-dimethyl acetamide at 55℃; for 1h;	68%

formic acid (64-18-6) + 2,5-bis-sulfosulfanyl-benzene-1,4-diamine (43036-83-5) → benzo[1,2-d:4,5-d']bisthiazole (267-99-2)

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C8H2Br2N2S2

Conditions	Yield
With bromine In N,N-dimethyl-formamide at 100℃; for 0.166667h; Inert atmosphere;	90%
With bromine In N,N-dimethyl-formamide at 75℃; for 2h;	11 g

meta-bromotoluene (591-17-3) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C22H16N2S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	81%

p-trifluoromethylphenyl bromide (402-43-7) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C22H10F6N2S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	77%

3,6-bis(trifluoromethyl)bromobenzene (328-70-1) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C24H8F12N2S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	72%

bromobenzene (108-86-1) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → 2,6-diphenyl[1,3]thiazolo[5,4-f][1,3]benzothiazole (13399-13-8)

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere;	71%

2-bromo-pyridine (109-04-6) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C13H7N3S2 + 2,6-di-[2]pyridyl-benzo[1,2-d;4,5-d']bis-thiazole (109591-64-2)

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	A 7% B 66%

3-Bromopyridine (626-55-1) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C18H10N4S2 + C13H7N3S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	A 58% B 23%

1-bromo-2-isopropylbenzene (7073-94-1) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C26H24N2S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	54%

Ethyl 4-bromobenzoate (5798-75-4) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C26H20N2O4S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	52%

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) + para-nitrophenyl bromide (586-78-7) → C14H7N3O2S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	51%

2-bromothiophene (1003-09-4) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C16H8N2S4

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	49%

3,6-bis(3,5-di-tert-butylphenyl)-1-bromocarbazole + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C48H51N3S2 + C88H98N4S2

Conditions	Yield
With palladium diacetate; caesium carbonate; copper(ll) bromide; tri tert-butylphosphoniumtetrafluoroborate In 1,3,5-trimethyl-benzene at 160℃; for 16h; Inert atmosphere;	A 41% B 49%

3-hexyl-2-bromothiophene (69249-61-2) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → 2,6-bis(3-hexylthiophen-2-yl)benzobisthiazole

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	43%

1-bromo-4-methoxy-benzene (104-92-7) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → 2,6-Bis-(4-methoxy-phenyl)-benzo[1,2-d;4,5-d']bisthiazole

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	38%

2-bromobenzoic acid ethyl ester (6091-64-1) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C26H20N2O4S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	37%

1-bromo-3,6-di(2,4,6-trimethylphenyl)carbazole + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C38H31N3S2 + C68H58N4S2

Conditions	Yield
With palladium diacetate; caesium carbonate; copper(ll) bromide; tri tert-butylphosphoniumtetrafluoroborate In 1,3,5-trimethyl-benzene at 160℃; for 16h; Inert atmosphere;	A 33% B 23%

1-bromo-3,6-di-butyl-tert-9H-carbazole (1357359-52-4) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C48H50N4S2 + C28H27N3S2

Conditions	Yield
With palladium diacetate; caesium carbonate; copper(ll) bromide; tri tert-butylphosphoniumtetrafluoroborate In 1,3,5-trimethyl-benzene at 160℃; for 16h; Inert atmosphere;	A 18% B 29%

tributyltin chloride (1461-22-9) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → 4,8-bis-tributylstannanylbenzo[1,2-d;4,5-d']bisthiazole

Conditions	Yield
Stage #1: benzo[1,2-d:4,5-d']bisthiazole With lithium diisopropyl amide In tetrahydrofuran at -40 - 20℃; for 1.5h; Stage #2: tributyltin chloride In tetrahydrofuran at -40 - 20℃; for 2h;	20%

2-bromo-N,N-diethylbenzamide (76041-86-6) + benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C30H30N4O2S2

Conditions	Yield
With copper diacetate; palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 135℃; for 18h; Inert atmosphere;	15%

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C28H28N2S2

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / N,N-dimethyl-formamide / 0.17 h / 100 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: bromine / N,N-dimethyl-formamide / 2 h / 75 °C 2: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium phosphate / tetrahydrofuran / 6 h / 70 °C View Scheme

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C42H34F6N2S2

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine / N,N-dimethyl-formamide / 0.17 h / 100 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: palladium diacetate; copper diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 18 h / 115 - 135 °C / Inert atmosphere View Scheme

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → 4,8-diiodo-2,6-bis-(5-triisopropylsilanylthiophen-2-yl)-benzo[1,2-d;4,5-d']bisthiazole

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -40 - 20 °C 1.2: 2 h / -40 - 20 °C 2.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / toluene / 7 h / Reflux 3.1: iodine; lithium diisopropyl amide / tetrahydrofuran / 2 h / -80 - 20 °C View Scheme

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → 4,8-bis-(thiophen-2-yl)-2,6-bis-(5-triisopropylsilanylthiophen-2-yl)-benzo[1,2-d;4,5-d']bisthiazole

Conditions

Yield

Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -40 - 20 °C 1.2: 2 h / -40 - 20 °C 2.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / toluene / 7 h / Reflux 3.1: iodine; lithium diisopropyl amide / tetrahydrofuran / 2 h / -80 - 20 °C 4.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; trifuran-2-yl-phosphane / tetrahydrofuran / 21 h / Reflux View Scheme

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → 2,6-bis-(5-triisopropylsilanylthiophen-2-yl)-benzo[1,2-d;4,5-d']bisthiazole

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -40 - 20 °C 1.2: 2 h / -40 - 20 °C 2.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / toluene / 7 h / Reflux View Scheme

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C28H26BF2N3S2

Conditions	Yield
Multi-step reaction with 2 steps 1: tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate; caesium carbonate; copper(ll) bromide / 1,3,5-trimethyl-benzene / 16 h / 160 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / Inert atmosphere View Scheme

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C48H48B2F4N4S2

Conditions	Yield
Multi-step reaction with 2 steps 1: tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate; caesium carbonate; copper(ll) bromide / 1,3,5-trimethyl-benzene / 16 h / 160 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / toluene / 2 h / 80 °C / Inert atmosphere View Scheme

benzo[1,2-d:4,5-d']bisthiazole (267-99-2) → C58H52B2F4N4S2

Conditions

Yield

Multi-step reaction with 3 steps 1: tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate; caesium carbonate; copper(ll) bromide / 1,3,5-trimethyl-benzene / 16 h / 160 °C / Inert atmosphere 2: tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate; caesium carbonate; copper(ll) bromide / 1,3,5-trimethyl-benzene / 48 h / 160 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / toluene / 3 h / 80 °C / Inert atmosphere View Scheme

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 75464-52-7 2,5-diaminobenzene-1,4-dithiol bis(hydrochloride) 
• 149-73-5 trimethyl orthoformate 
• 64-18-6 formic acid 
• 43036-83-5 2,5-bis-sulfosulfanyl-benzene-1,4-diamine 

Downstream Products

• 13399-13-8 2,6-diphenyl[1,3]thiazolo[5,4-f][1,3]benzothiazole 

Relevant articles and documents

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