76186-72-6

Basic information

• Product Name: 4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole
• Synonyms: 4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole;2,1,3-Benzothiadiazole, 4,7-dibroMo-5,6-dinitro-;4,7-Dibromo-5,6-dinitro-2,1,3-benzothiadiazole;4,7-Dibromo-5,6-dinitro-benzo[1,2,5]thiadiazole
• CAS NO: 76186-72-6
• Molecular Formula: C₆Br₂N₄O₄S
• Molecular Weight: 383.9616
• EINECS: -0
• Mol File: 76186-72-6.mol
• Article Data: 52

Chemical Properties

• Melting Point: 198 °C(Solv: ethanol (64-17-5))
• Boiling Point: 418.338 °C at 760 mmHg
• Flash Point: 206.804 °C
• Appearance: /
• Density: 2.469 g/cm³
• Storage Temp.: 2-8°C
• PKA: -8.74±0.50(Predicted)
• CAS DataBase Reference: 4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole(76186-72-6)
• EPA Substance Registry System: 4,7-dibroMo-5,6-dinitrobenzo[c][1,2,5]thiadiazole(76186-72-6)

Safety Data

• Hazardous Substances Data: 76186-72-6(Hazardous Substances Data)

Usage

Uses

4,7-Dibromo-5,6-dintiro-2,1,3-benzothiadiazole can be incorporated in light-emitting diodes producing near-IR sensitivity.

Synthetic route

4,7-dibromobenzo[c][1,2,5]thiadiazole (15155-41-6) → 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6)

Conditions	Yield
With sulfuric acid; nitric acid In toluene at 20℃; for 20h;	95%
With trifluorormethanesulfonic acid; nitric acid at 5 - 50℃;	94%
With trifluorormethanesulfonic acid; nitric acid	89%

benzo[1,2,5]thiadiazole (273-13-2, 22706-22-5) → 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HBr; Br2 / 130 °C 2: CF3CO2H; HNO3 / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: hydrogen bromide; bromine 2: trifluorormethanesulfonic acid; nitric acid View Scheme
Multi-step reaction with 2 steps 1: hydrogen bromide; bromine / water 2: nitric acid; sulfuric acid View Scheme

1,2-diamino-benzene (95-54-5) → 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride; triethylamine / dichloromethane 2: hydrogen bromide; bromine / water 3: sulfuric acid; nitric acid View Scheme
Multi-step reaction with 3 steps 1: triethylamine; thionyl chloride / dichloromethane / Reflux 2: bromine; hydrogen bromide / water / 6 h / 100 °C 3: nitric acid; sulfuric acid / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride; triethylamine / dichloromethane / 20 h / Reflux 2: hydrogen bromide; bromine / 6 h / Reflux 3: nitric acid; trifluorormethanesulfonic acid / 24 h / 0 °C / Heating View Scheme
Multi-step reaction with 3 steps 1: triethylamine; thionyl chloride / dichloromethane / 20 h / Reflux 2: hydrogen bromide; bromine / 6 h / Reflux 3: nitric acid; trifluorormethanesulfonic acid / 0 - 50 °C View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride; triethylamine / dichloromethane / 4 h / Reflux 2: bromine; hydrogen bromide / 6 h / Reflux 3: sulfuric acid; nitric acid / 8 h / 60 °C View Scheme

tributyl-(4-octyl-thiophen-2-yl)-stannane (504441-11-6) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 4,7-bis-(4-octylthiophen-2-yl)-5,6-dinitro-2,1,3-benzothiadiazole (1361452-97-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 20h; Stille coupling; Inert atmosphere; Reflux;	98%

tributyl(4-(tert-butyl)phenyl)stannane (115933-42-1) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → C26H26N4O4S (1394135-00-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 19h; Stille Cross Coupling; Inert atmosphere; Reflux;	98%

tributyl(thien-2-yl)stannane (54663-78-4) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 5,6-dinitro-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (165190-73-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In tetrahydrofuran Stille coupling;	96%
With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; sulfuric acid In tetrahydrofuran; water at 25℃; for 2h; Reflux; Inert atmosphere;	91%
With tris-(dibenzylideneacetone)dipalladium(0); sulfuric acid; tris-(o-tolyl)phosphine In tetrahydrofuran at 25℃; for 2h; Reflux; Inert atmosphere;	91%

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + phenylboronic acid (98-80-6) → 5,6-dinitro-4,7-diphenylbenzo[c][1,2,5]thiadiazole (165617-57-2)

Conditions	Yield
With caesium carbonate In toluene at 90℃;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 15h; Inert atmosphere; Reflux;	81%
With caesium carbonate In water; toluene at 90℃; Inert atmosphere;
With caesium carbonate In water; toluene at 90℃; Inert atmosphere;	6 g

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-stannane (175922-79-9) → 4,7-bis(2,3-dihydrothieno[3,4-b]dioxin-5-yl)-5,6-dinitrobenzo[c][1,2,5]thiadiazole (1003593-63-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In toluene for 12h; Inert atmosphere; Reflux;	96%
With bis-triphenylphosphine-palladium(II) chloride In toluene for 12h; Inert atmosphere; Reflux;

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + 1-trimethylstannyl-2-triisopropylsilylethyne (159641-97-1) → 5,6-dinitro-4,7-bis[2-[tris(1-methylethyl)silyl]ethynyl]-2,1,3-benzothiadiazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 16h; Stille Cross Coupling; Inert atmosphere;	93%
With bis-triphenylphosphine-palladium(II) chloride In toluene Stille Cross Coupling;	92%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 16h; Reflux;	92%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 16h; Inert atmosphere; Schlenk technique; Reflux;	76%

tributylphenylstannane (960-16-7) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 5,6-dinitro-4,7-diphenylbenzo[c][1,2,5]thiadiazole (165617-57-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Stille Cross Coupling; Reflux;	92%
With tetrakis(triphenylphosphine) palladium(0) In toluene Stille Cross Coupling; Reflux; Inert atmosphere;	70%

1,2-di(4-methylphenyl)-1,2-ethanedione (3457-48-5) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → C22H14Br2N4S

Conditions	Yield
Stage #1: 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole With iron; acetic acid Stage #2: 1,2-di(4-methylphenyl)-1,2-ethanedione	92%

tributyl(6-undecylthieno[3,2-b]thiophene-2-yl)stannane + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 5,6-dinitro-4,7-bis(6-undecylthieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 80℃; for 8h; Inert atmosphere;	91%
With bis-triphenylphosphine-palladium(II) chloride In toluene at 80℃; Inert atmosphere;	84.8%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 20h; Inert atmosphere;	10.54 g
With bis-triphenylphosphine-palladium(II) chloride In toluene

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + 2-(tributylstannyl)benzothiophene → C22H10N4O4S3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 19h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere; Reflux;	89%

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + (4-dodecylthiophen-2-yl)trimethylstannane → 4,7-bis(4-dodecylthiophen-2-yl)-5,6-dinitrobenzo[c][1,2,5]thiadiazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 16h; Stille Cross Coupling; Inert atmosphere;	88%
Stille Cross Coupling;

tri-n-butyl(thien-3-yl)tin (119405-65-1) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → C14H6N4O4S3 (1394134-99-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 13h; Stille Cross Coupling; Inert atmosphere; Reflux;	87%

(5-(2-ethylhexyl)thiophen-2-yl)trimethylstannane (1429306-71-7) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 4,7-bis(5-(2-ethylhexyl)thiophene-2-yl)-5,6-dinitrobenzo[c][1,2,5]thiadiazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 3h; Schlenk technique; Inert atmosphere;	86%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;	300mg

C25H37N3S2Sn + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → C50H56N10O4S5

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 24h;	86%

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 5,6-diamino-4,7-dibromobenzo[c][1,2,5]-thiadiazole (141215-32-9)

Conditions	Yield
With iron; acetic acid	85.1%
With iron; acetic acid at 100℃; for 1.5h;	70%
With iron; acetic acid at 0 - 20℃; for 12h;	65%

C30H34BNO6 + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → C30H22BrN5O8S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; triphenylphosphine In water; toluene for 24h; Inert atmosphere; Reflux;	85%

trimethyl(3-undecylselenopheno[3,2-b]thiophen-5-yl)stannane + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 5,6-dinitro-4,7-bis(3-undecylselenopheno[3,2-b]thiophen-5-yl)benzo[c][1,2,5]thiadiazole

Conditions	Yield
With Pd based catalyst In toluene for 12h; Stille Cross Coupling; Inert atmosphere;	82%

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + <(triisopropylsilyl)ethynyl>tributylstannane (141339-51-7) → 5,6-dinitro-4,7-bis[2-[tris(1-methylethyl)silyl]ethynyl]-2,1,3-benzothiadiazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20 - 80℃; Stille Cross Coupling; Schlenk technique; Inert atmosphere;	81%

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + 2-(tri-n-butylstannyl)benzofuran → C22H10N4O6S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 28h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere; Reflux;	81%

1-(N-naphthalen-1-yl-N-phenylamino)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (528610-01-7) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → N,N'-((5,6-dinitrobenzo[c][1,2,5]thiadiazole-4,7-diyl)bis(4,1-phenylene))bis(N-phenylnaphthalen-1-amine)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux; Darkness;	81%

(4-(2-decyltetradecyl)thiophen-2-yl)trimethylstannane + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 4,7-bis(4-(2-decyltetradecyl)thiophen-2-yl)-5,6-dinitrobenzo-[c][1,2,5]thiadiazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride Stille Cross Coupling;	80%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 16h; Stille Cross Coupling; Inert atmosphere;	71%

C24H31BN3O9PS + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → C30H29BrN7O11PS2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; triphenylphosphine In water; toluene for 48h; Inert atmosphere; Reflux;	80%

4,4,5,5–tetramethyl–2–(4–(1,2,2–triphenylvinyl)phenyl)–1,3,2–dioxaborolane (1260865-91-5) + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 5,6-dinitro-4,7-bis(4-(1,2,2-triphenylvinyl)phenyl)benzo[c][1,2,5]thiadiazole (1378502-40-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 24h; Inert atmosphere; Reflux; Darkness;	80%

(4,8-bis(octyloxy)-6-(trimethylstannyl)benzo[1,2-b:4,5-b’]dithiophen-2-yl)trimethylsilane + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → C64H90N4O8S5Si2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; Stille Cross Coupling; Inert atmosphere; Darkness;	80%

C37H39BBrNO5S + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → C37H27Br2N5O7S2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; triphenylphosphine In water; toluene for 6h; Reflux; Inert atmosphere;	79%

2-[4-[2,2-bis(4-methoxyphenyl)-1-phenylethenyl]phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane + 4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) → 4,7-bis(4-(2,2-bis(4-methoxyphenyl)-1-phenylvinyl)phenyl)-5,6-dinitrobenzo[c][1,2,5]thiadiazol (1378502-41-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux; Darkness;	79%

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + (benzo[b]thiophen-3-yl)tributylstannane (142913-28-8) → C22H10N4O4S3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 19h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere; Reflux;	78%

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + tributyl(4-hexyl-2-thienyl)stannane → 4,7-bis(4-hexylthiophen-2-yl)-5,6-dinitrobenzo[c][1,2,5]thiadiazole (1301247-04-0)

Conditions	Yield
With trans-bis(triphenylphosphine)palladium dichloride In tetrahydrofuran for 12h; Stille coupling; Reflux; Inert atmosphere;	77%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 12h; Inert atmosphere; Heating;	75%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 16h; Stille coupling; Inert atmosphere; Reflux;	68%
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; Stille Cross Coupling; Inert atmosphere;	4.4 g

4,7-dibromo-5,6-dinitrobenzo[2,1,3]thiadiazole (76186-72-6) + trimethyl(5-methylthiophen-2-yl)stannane (86134-27-2) → C16H10N4O4S3 (1355346-48-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;	77%

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 273-13-2 benzo[1,2,5]thiadiazole 
• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 

Downstream Products

• 141215-32-9 5,6-diamino-4,7-dibromobenzo[c][1,2,5]-thiadiazole 
• 165617-57-2 5,6-dinitro-4,7-diphenylbenzo[c][1,2,5]thiadiazole 
• 1292303-60-6 C₃₂H₁₄N₈O₄S₄ 
• 165617-60-7 4,8-diphenylbenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole) 
• 165617-58-3 4,7-diphenylbenzo[1,2,5]thiadiazolo-5,6-diamine 
• 165617-59-4 4,8-dibromo-1H,5H-benzo[1,2-c:4,5-c']bis([1,2,5] thiadiazole) 
• 1070910-90-5 4,4'-(5,6-dinitrobenzo[c][1,2,5]thiadiazole-4,7-diyl)bis(N,N-bis(4-(octyloxy)phenyl)aniline) 

Relevant articles and documents

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