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
• Article Data: 3

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

General Description

Benzo[1,2-d:4,5-d']bisthiazole is a chemical compound with a unique molecular structure consisting of two thiazole rings fused to a benzo ring. It is a heterocyclic compound that is widely used in organic synthesis and material science. It has been studied for its potential as a building block for various organic compounds, as well as for its potential applications in optoelectronic devices and pharmaceuticals. Benzo[1,2-d:4,5-d']bisthiazole has attracted interest due to its structural diversity and potential applications in various fields, making it a valuable chemical for research and development.

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

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

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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