160199-05-3

Basic information

• Product Name: 2,4-dichloro-benzo[4,5]thieno[3,2-d]pyrimidine
• Synonyms: 2,4-dichloro-benzo[4,5]thieno[3,2-d]pyrimidine;2,4-dichlorobenzo[4,5]thieno[3,2-d]pyridine;2,4-Dichloro-[1]benzothieno[3,2-d]pyrimidine
• CAS NO: 160199-05-3
• Molecular Formula: C₁₀H₄Cl₂N₂S
• Molecular Weight: 255.12316
• Mol File: 160199-05-3.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Density: 1.619±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -0.76±0.40(Predicted)
• CAS DataBase Reference: 2,4-dichloro-benzo[4,5]thieno[3,2-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dichloro-benzo[4,5]thieno[3,2-d]pyrimidine(160199-05-3)
• EPA Substance Registry System: 2,4-dichloro-benzo[4,5]thieno[3,2-d]pyrimidine(160199-05-3)

Safety Data

• Hazardous Substances Data: 160199-05-3(Hazardous Substances Data)

Usage

General Description

2,4-dichloro-benzo[4,5]thieno[3,2-d]pyrimidine is a complex chemical compound with potentially significant applications in the field of pharmaceuticals and agrochemicals. It is a heterocyclic compound containing a benzene ring fused to a thieno[3,2-d]pyrimidine ring structure, with two chlorine atoms attached at the 2 and 4 positions. 2,4-dichloro-benzo[4,5]thieno[3,2-d]pyrimidine has been investigated for its potential as a therapeutic agent, with studies indicating that it may have anti-cancer, anti-inflammatory, and anti-microbial properties. Additionally, it has shown promise as a pesticide in agricultural settings due to its ability to control the growth of specific plant species. Further research is needed to fully understand and leverage the potential applications of 2,4-dichloro-benzo[4,5]thieno[3,2-d]pyrimidine in various industries.

Synthetic route

(benzo-1H-thieno[3,2-d]pyrimidine-2,4-dione) (1018670-15-9) → 2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3)

Conditions	Yield
With trichlorophosphate	85%
With trichlorophosphate for 6h; Reflux;	85%
With trichlorophosphate for 6h; Reflux;	85%

2-fluorobenzonitrile (394-47-8) → 2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium tert-butylate / N,N-dimethyl-formamide 2: 2 h / 200 °C 3: trichlorophosphate View Scheme

3-Amino-benzo[b]thiophene-2-carboxylic acid methyl ester (35212-85-2) → 2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / 200 °C 2: trichlorophosphate View Scheme
Multi-step reaction with 2 steps 1: 2 h / 200 °C 2: trichlorophosphate / 6 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: 2 h / 200 °C 2: trichlorophosphate / 8 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: 2 h / 200 °C 2: trichlorophosphate / 7.5 h / Reflux View Scheme

salicylonitrile (611-20-1) → 2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dimethyl sulfoxide / 3 h / 100 °C 2: 2 h / 200 °C 3: trichlorophosphate / 6 h / Reflux View Scheme

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene (1257220-47-5) → C31H20ClN3S

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux;	90%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 2-(4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl)-4,6-diphenylpyrimidine → C32H19ClN4S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 9h; Inert atmosphere; Heating;	85%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + phenylboronic acid (98-80-6) → 4-chloro-6-phenyl-8-thia-3,5-diazatricyclo[7.4.0.0,]trideca-1(13),2,4,6,9,11-hexaene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 7h; Inert atmosphere; Heating;	83%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 9h; Inert atmosphere; Heating;	83%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 7h; Heating;	83%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 2,4-diphenyl-6-(4-(4,4',5,5'-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine → C31H18ClN5S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 9h; Inert atmosphere; Heating;	81%

N-phenyl-9H-carbazol-3-boronic acid (854952-58-2) + 2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) → C28H16ClN3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 80℃;	80%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + (9‐phenyl‐9H‐carbazol‐2‐yl)boronic acid (1001911-63-2) → 2-chloro-4-(9-phenyl-9H-carbazol-2-yl)benzo[4,5]thieno[3,2-d]pyrimidine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In 1,4-dioxane; water at 80℃;	78%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → C34H20ClN3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 80℃;	75%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 9,9-dimethyl-9H-fluoren-2-yl-2-boronic acid (333432-28-3) → C25H17ClN2S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 3h; Suzuki Coupling; Reflux;	74%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + (1-boronic acid)-8-chlorodibenzofuran → C22H10Cl2N2OS

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Reflux;	71%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Reflux;	71%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole (1126522-69-7) → C28H16ClN3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 6h; Reflux; Inert atmosphere;	70%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 9‐{[1,1'‐biphenyl]‐4‐yl}carbazol‐3‐ylboronic acid (1028648-22-7) → C34H20ClN3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; Alkaline conditions;	70%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 3-Biphenylboronic acid (5122-95-2) → C22H13ClN2S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 55℃; for 12h; Inert atmosphere;	69%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 12h; Inert atmosphere;	69%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 2,2-dimethyl-5-phenyl-4H-benzo[d][1,3]dioxin-4-one → 2-chloro-4-(dibenzo[b,d]furan-3-yl)benzo[4,5]thieno[3,2-d]pyrimidine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 60℃; for 12h; Inert atmosphere;	67%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-chloro-4-(dibenzo[b,d]furan-1-yl)benzo[4,5]thieno[3,2-d]pyrimidine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; ethanol; water at 120℃; Alkaline conditions;	65%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 9H-carbazole (86-74-8) → 2,4-di(9H-carbazol-9-yl)benzo[4,5]thieno[3,2-d]pyrimidine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	60%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 4,4,5,5-tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane (256652-04-7) → 2-chloro-4-(naphthalen-2-yl)benzo[4,5]thieno[3,2-d]pyrimidine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 6h;	45%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 6h;	45%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80 - 90℃;	45%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80 - 90℃;	45%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 1-naphthylboronic acid pinacol ester (68716-52-9) → C20H11ClN2S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water	45%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 4-chloro-6-phenyl-8-thia-3,5-diazatricyclo[7.4.0.0,]trideca-1(13),2,4,6,9,11-hexaene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃;	44%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃;	44%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 4,4,5,5-tetramethyl-2-{8-oxatricyclo[7.4.02,7,]trideca-1(9),2,4,6,10,12-hexaen-4-yl}-1,3,2-dioxaborolane (947770-80-1) → C22H11ClN2OS

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃;	43%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃;	43%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃;	43%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + C10H5BCl2N2O2S → C20H6Cl4N4S2

Conditions	Yield
Suzuki Coupling;	35%

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + dimethyl amine (124-40-3) → 2-chloro-4-dimethylamino-benzo[4,5]thieno[3,2-d]pyrimidine (952443-74-2)

Conditions	Yield
In 1,4-dioxane; ethanol; water at 40℃; for 1h;

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + phenylboronic acid (98-80-6) → C34H19N3S2

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C / Alkaline conditions 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 100 °C View Scheme

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) → C46H28N4S

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C / Alkaline conditions 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 100 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 12 h / Reflux; Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene; 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux; Inert atmosphere View Scheme

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) → C52H32N4S

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C / Alkaline conditions 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 100 °C View Scheme

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) → C52H32N4S

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C / Alkaline conditions 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 100 °C View Scheme

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) → C40H23N3S2

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 80 - 90 °C / Alkaline conditions 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 100 °C View Scheme

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) + 4-biphenylboronic acid (5122-94-1) → C22H13ClN2S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran Reflux;

2,4-dichlorobenzo[4,5]thiophene[3,2-d]pyrimidine (160199-05-3) → C46H28N2OS

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 12 h / 55 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 12 h / Inert atmosphere; Reflux View Scheme

Upstream product

• 611-20-1 salicylonitrile 
• 35212-85-2 3-Amino-benzo[b]thiophene-2-carboxylic acid methyl ester 
• 1018670-15-9 (benzo-1H-thieno[3,2-d]pyrimidine-2,4-dione) 
• 394-47-8 2-fluorobenzonitrile 

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