6590-96-1

Basic information

• Product Name: 2,4-DICHLOROPHENYL ISOTHIOCYANATE
• Synonyms: 2,4-DICHLORO-1-ISOTHIOCYANATOBENZENE;2,4-DICHLOROPHENYL ISOTHIOCYANATE;Benzene, 2,4-dichloro-1-isothiocyanato-;2,4-Dichlorophenyl isothiocyanate,95%;2,4-Dichlorophenyl isothiocyanate 95%;2,4-Dichlorophenyl isothiocyate, 98%
• CAS NO: 6590-96-1
• Molecular Formula: C₇H₃Cl₂NS
• Molecular Weight: 204.08
• EINECS: 229-527-6
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates
• Mol File: 6590-96-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 36-40 °C(lit.)
• Boiling Point: 260 °C(lit.)
• Flash Point: >230 °F
• Appearance: White/Crystalline Solid
• Density: 1.41 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00396mmHg at 25°C
• Refractive Index: 1.6750 (estimate)
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• Sensitive: Moisture Sensitive
• BRN: 777072
• CAS DataBase Reference: 2,4-DICHLOROPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLOROPHENYL ISOTHIOCYANATE(6590-96-1)
• EPA Substance Registry System: 2,4-DICHLOROPHENYL ISOTHIOCYANATE(6590-96-1)

Safety Data

• Hazard Codes: C
• Statements: 34-42-20/21/22
• Safety Statements: 22-26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• F: 10-19-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6590-96-1(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline solid

InChI:InChI=1/C7H3Cl2NS/c8-5-1-2-7(10-4-11)6(9)3-5/h1-3H

Synthetic route

4-Chlorophenyl isothiocyanate (2131-55-7) → 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; copper dichloride In tetrahydrofuran at 20℃; for 6h;	75%

carbon disulfide (75-15-0) + 2,4-Dichloroaniline (554-00-7) → 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
Stage #1: carbon disulfide; 2,4-Dichloroaniline In acetone at 20℃; Stage #2: With iron(II) sulfate; triethylamine In acetone chemoselective reaction;	79%
Stage #1: carbon disulfide; 2,4-Dichloroaniline With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃; for 8h; Stage #2: With bis(trichloromethyl) carbonate In dichloromethane at -5℃; Reflux;	60%
Stage #1: carbon disulfide; 2,4-Dichloroaniline With 1,4-diaza-bicyclo[2.2.2]octane In toluene Stage #2: With benzene-1,3,5-tricarboxylic acid In chloroform

C7H5Cl2NS2 (56356-90-2) → 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
With benzene-1,3,5-tricarboxylic acid In dichloromethane
With bis(trichloromethyl) carbonate In dichloromethane
With bis(trichloromethyl) carbonate In dichloromethane at -5℃; for 8h; Reflux;
With bis(trichloromethyl) carbonate In dichloromethane
With bis(trichloromethyl) carbonate In dichloromethane at 20℃; for 2h; Cooling with ice;

thiophosgene (463-71-8) + 2,4-Dichloroaniline (554-00-7) → 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
Stage #1: 2,4-Dichloroaniline With sodium carbonate In chloroform Cooling with ice; Stage #2: thiophosgene In chloroform for 2h; Cooling with ice;	99%
With chloroform Verruehren einer waessr. Suspension;
In chloroform at 20℃; for 2h;

o-phenyl (2,4-dichlorophenyl)carbamothioate (1449510-30-8) → 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
With sodium hydroxide In dichloromethane at 20℃; for 1h;	99%

2,4-Dichloroaniline (554-00-7) → 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,4-diaza-bicyclo[2.2.2]octane / toluene 2: benzene-1,3,5-tricarboxylic acid / dichloromethane View Scheme
Multi-step reaction with 2 steps 1: 1,4-diaza-bicyclo[2.2.2]octane / toluene 2: bis(trichloromethyl) carbonate / dichloromethane View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / Reflux 2: sodium hydroxide / dichloromethane / 1 h / 20 °C View Scheme

2,4-Dichloroaniline (554-00-7) + phenylcarbonochloridothioate (1005-56-7) → 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
With sodium hydroxide In dichloromethane at 0 - 20℃; for 73h;	21%

N-phenyl-N'-<2.4-dichloro-phenyl>-thiourea → 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
With sulfuric acid Destillieren mit Wasserdampf;

sulfuric acid (7664-93-9) + N-(2,4-dichlorophenyl)-N'-phenylthiourea (13528-25-1) → phenyl isothiocyanate (103-72-0) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1)

Conditions	Yield
Destillieren des Gemisches mit Wasserdampf;

methyl 2-((1s,4s)-4-(5-(2-hydrazinyl-2-oxoacetamido)pyridin-2-yloxy)cyclohexyl)acetate + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → methyl 2-((1s,4s)-4-(5-(5-(2,4-dichlorophenylamino)-1,3,4-oxadiazole-2-carboxamido)pyridin-2-yloxy)cyclohexyl)acetate

Conditions	Yield
Stage #1: methyl 2-((1s,4s)-4-(5-(2-hydrazinyl-2-oxoacetamido)pyridin-2-yloxy)cyclohexyl)acetate; 2, 4-dichlorophenyl isothiocyanate In N,N-dimethyl-formamide at 45℃; for 1.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 85℃; for 0.75h;	100%

(1s,4s)-ethyl 4-(5-(2-hydrazinyl-2-oxoacetamido)pyridin-2-yloxy)methylcyclohexanecarboxylate + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → ethyl 4-(5-((5-((2,4-dichlorophenyl)amino)1,3,4-oxadiazole-2-carbonyl)amino)pyridin-2-yl)oxy-1-methylcyclohexane-1-carboxylate (1124175-21-8)

Conditions	Yield
Stage #1: (1s,4s)-ethyl 4-(5-(2-hydrazinyl-2-oxoacetamido)pyridin-2-yloxy)methylcyclohexanecarboxylate; 2, 4-dichlorophenyl isothiocyanate In N,N-dimethyl-formamide at 40℃; for 0.416667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 1.41667h;	100%

2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 2,4-dichlorophenylthiourea (6326-14-3)

Conditions	Yield
With ammonia In 1,2-dimethoxyethane	99%
With ethanol; ammonia
With ethanol; ammonia

2, 4-dichlorophenyl isothiocyanate (6590-96-1) + ethyl-2-aminocyano acetate (32683-02-6) → 5-amino-2-(2,4-dichloro-phenylamino)-thiazole-4-carboxylic acid ethyl ester

Conditions	Yield
In 1,4-dioxane	99%

4-amino-1-phenylpyrazole-3-carbonitrile (1426541-60-7) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 1-(3-cyano-1-phenyl-1H-pyrazol-4-yl)-3-(2,4-dichlorophenyl)thiourea

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	98%

potassium cyanide (151-50-8) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → N-(2,4-dichlorophenyl)cyanothioformamide (5595-58-4)

Conditions	Yield
Stage #1: potassium cyanide; 2, 4-dichlorophenyl isothiocyanate In water; acetonitrile at 0 - 20℃; for 4h; Stage #2: With hydrogenchloride; water In acetic acid at 0℃;	97%

3-chloropentane-2,4-dione (1694-29-7) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) + N,N,N',N'-tetramethylguanidine (80-70-6) → 1-[2-(2,4-dichlorophenylimino)-3-di(dimethylamino)methyl-4-methyl-2,3-dihydro-1,3-thiazol-5-yl]-1-ethanone chloride (1607015-04-2)

Conditions	Yield
Stage #1: 2, 4-dichlorophenyl isothiocyanate; N,N,N',N'-tetramethylguanidine In acetone at 20℃; for 0.5h; Stage #2: 3-chloropentane-2,4-dione In acetone at 20℃;	97%

aminoethylpiperazine (140-31-8) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 4-{2-[3-(2,4-Dichloro-phenyl)-thioureido]-ethyl}-piperazine-1-carbothioic acid (2,4-dichloro-phenyl)-amide (77995-01-8)

Conditions	Yield
In ethanol for 4h; Heating;	95%

cyclohexanecarbohydrazide (38941-47-8) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 1-cyclohexylcarbonyl-4-(2,4-dichlorophenyl)thiosemicarbazide

Conditions	Yield
70 In ethanol for 0.5h; Heating;	94%

adamantane-1-carbohydrazide (17846-15-0) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 4-(2,4-dichlorophenyl)-1-[(1-tricyclo[3.3.3.1.13,7]decane)carbonyl]thiosemicarbazide

Conditions	Yield
In ethanol for 0.5h; Heating;	94%

butyl (2E)-3-(2-amino-5-methylphenyl)acrylate (1449337-31-8) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → butyl 2-(3-(2,4-dichlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-yl)acetate

Conditions	Yield
In water at 80℃; for 16h; Inert atmosphere;	94%

ethyl 5-methyl-1-(6-(piperazin-1-yl)pyrimidin-4-yl)-1H-pyrazole-4-carboxylate + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → ethyl 1-(6-(4-((2,4-dichlorophenyl)carbamothioyl)piperazin-1-yl)pyrimidin-4-yl)-5-methyl-1H-pyrazole-4-carboxylate

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	94%

naphthalen-1-yl-acetic acid hydrazide (34800-90-3) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → C19H15Cl2N3OS (77052-79-0)

Conditions	Yield
In ethanol for 1h; Heating;	93%

2, 4-dichlorophenyl isothiocyanate (6590-96-1) + tert-butyl (E)-3-(2'-aminophenyl)propenoate → tert-butyl 2-(3-(2,4-dichlorophenyl)-2-thioxo-1,2,3,4-tetrahydroquinazolin-4-yl)acetate

Conditions	Yield
In water at 80℃; for 16h; Inert atmosphere;	93%

isatoic anhydride (118-48-9) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 3-(2,4-dichlorophenyl)-2,3-dihydro-2-thioxoquinazolin-4(1H)-one

Conditions	Yield
With iron(II,III) oxide; methylamine In water for 1h; Reflux;	92%

Nicotinic acid hydrazide (553-53-7) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 4-(2,4-dichlorophenyl)-1-(pyridin-3-yl)carbonyl thiosemicarbazide

Conditions	Yield
In methanol for 0.5h; Reflux;	92%
In methanol Reflux;	92%

2, 4-dichlorophenyl isothiocyanate (6590-96-1) + 2-[4-(4-nitrophenyl)piperazin-1-yl]acetohydrazide (24636-90-6) → 4-(2,4-dichlorophenyl)-1-[4-(4-nitrophenyl)piperazineacetyl]thiosemicarbazide (204973-89-7)

Conditions	Yield
In ethanol for 0.5h; Addition; Heating;	91%

cyclopentanecarboxylic acid hydrazide (3400-07-5) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 2-(cyclopentylcarbonyl)-N-(2,4-dichlorophenyl)hydrazinecarbothioamide

Conditions	Yield
at 90℃; for 12h;	91%

picolinic acid hydrazide (1452-63-7) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 4-(2,4-dichlorophenyl)-1-(pyridin-2-yl)carbonylthiosemicarbazide

Conditions	Yield
In methanol for 0.5h; Reflux;	91%
In methanol Reflux;	91%

1H-indol-3-acetohydrazide (5448-47-5) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 2-(2-(1H-indol-3-yl)acetyl)-N-(2,4-dichlorophenyl)hydrazincarbothioamide

Conditions	Yield
In ethanol at 80 - 85℃;	91%

2, 4-dichlorophenyl isothiocyanate (6590-96-1) + N-(4-methoxyphenyl)piperazineacetohydrazide (68104-78-9) → 4-(2,4-dichlorophenyl)-1-[4-(4-methoxyphenyl)piperazineacetyl]semicarbazide (204973-91-1)

Conditions	Yield
In ethanol for 0.5h; Addition; Heating;	90%

4-chlorobenzoic acid hydrazide (536-40-3) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 1-(4-chlorobenzoyl)-4-(2,4-dichlorophenyl)thiosemicarbazide (891643-33-7)

Conditions	Yield
In ethanol for 0.25h; Reflux;	90%
In ethanol for 0.0833333h; Reflux;	90%

pyrazine-2-carbohydrazide (768-05-8) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 4-(2,4-dichlorophenyl)-1-pyrazinecarbonylthiosemicarbazide

Conditions	Yield
70 In ethanol for 0.5h; Heating;	88%

4-(4,6-dimethoxypyrimidin-2-yloxy)benzenamine (1311199-93-5) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 1-(2,4-dichlorophenyl)-3-(4-(4,6-dimethoxypyrimidin-2-yloxy)phenyl)thiourea (1352544-45-6)

Conditions	Yield
In dichloromethane at 0℃;	88%

1-[(4-chlorophenyl)methyl]piperazine (23145-88-2) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → 4-(4-chlorobenzyl)-N-(2,4-dichlorophenyl)piperazine-1-carbothioamide

Conditions	Yield
In chloroform	88%

2, 4-dichlorophenyl isothiocyanate (6590-96-1) + [4-(2-methoxyphenyl)piperazin-1-yl]acetohydrazide (204973-87-5) → 4-(2,4-dichlorophenyl)-1-[4-(2-methoxyphenyl)piperazineacetyl]thiosemicarbazide (204973-93-3)

Conditions	Yield
In ethanol for 0.5h; Addition; Heating;	87%

2, 4-dichlorophenyl isothiocyanate (6590-96-1) + 1-phenyl-5-methyl-1,2,3-triazol-4-formyl hydrazide (91129-91-8) → C17H14Cl2N6OS

Conditions	Yield
In ethanol at 20℃; for 5h;	87%

2-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)morpholine (944937-08-0) + 2, 4-dichlorophenyl isothiocyanate (6590-96-1) → C17H21Cl2N3OS (1051375-23-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	87%

Upstream product

• 463-71-8 thiophosgene 
• 554-00-7 2,4-Dichloroaniline 
• 7664-93-9 sulfuric acid 
• 13528-25-1 N-(2,4-dichlorophenyl)-N'-phenylthiourea 
• 541-41-3 chloroformic acid ethyl ester 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 1449510-30-8 o-phenyl (2,4-dichlorophenyl)carbamothioate 
• 1005-56-7 phenylcarbonochloridothioate 
• 56356-90-2 C₇H₅Cl₂NS₂ 
• 75-15-0 carbon disulfide 

Downstream Products

• 77995-01-8 4-{2-[3-(2,4-Dichloro-phenyl)-thioureido]-ethyl}-piperazine-1-carbothioic acid (2,4-dichloro-phenyl)-amide 
• 73692-85-0 2-(N-2,4-Dichlorphenyl-thiocarbamoyl)-4,5-dihydro-2H-3-benzothiepin-1-on 
• 90272-25-6 3-(2,4-dichloro-phenyl)-2-thioxo-thiazolidin-4-one 
• 1033590-95-2 C₁₄H₁₂Cl₂N₂OS 
• 891578-16-8 4-(2,4-dichlorophenyl)-1-(4-hydroxybenzoyl)thiosemicarbazide 
• 1346176-75-7 4-(2,4-dichlorophenyl)-1-(4-methylthiadiazol-5-yl)carbonylthiosemicarbazide 
• 1412891-41-8 4-(3-(3-(2,4-dichlorophenyl)thioureido)phenoxy)-N-methylpicolinamide 
• 1423569-37-2 ethyl 3-(2,4-dichlorophenyl)-2-dicyanomethylene-4-cyclohexylamino-2,3-dihydrothiazole-5-carboxylate 
• 1423569-41-8 ethyl 4-(2,4,4-trimethylpentan-2-ylamino)-3-(2,4-dichlorophenyl)-2-dicyanomethylene-2,3-dihydrothiazole-5-carboxylate 
• 1472650-85-3 dimethyl 1-(2,4-dichlorophenyl)-10b-hydroxy-3-(4-methoxybenzyl)-2-thioxo-2,3,5,10b-tetrahydro-1H-furo[2’,3’:2,3]indeno[1,2-d]imidazole-5,6-dicarboxylate 
• 22014-73-9 1-Butyl-3-(2,4-dichlorphenyl)-thioharnstoff 

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