6590-94-9

Basic information

• Product Name: 3,4-DICHLOROPHENYL ISOTHIOCYANATE
• Synonyms: AKOS 90254;3,4-DICHLOROPHENYL ISOTHIOCYANATE;1,2-Dichloro-4-isothiocyanatobenzene;Benzene, 1,2-dichloro-4-isothiocyanato-;Isothiocyanic acid, 3,4-dichlorophenyl ester;isothiocyanicacid,3,4-dichlorophenylester;3,4-Dichlorophenyl isothiocyate, 99%
• CAS NO: 6590-94-9
• Molecular Formula: C₇H₃Cl₂NS
• Molecular Weight: 204.08
• EINECS: 229-526-0
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates
• Mol File: 6590-94-9.mol
• Article Data: 20

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 134-136 °C7 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.422 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00234mmHg at 25°C
• Refractive Index: n20/D 1.68(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 511101
• CAS DataBase Reference: 3,4-DICHLOROPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DICHLOROPHENYL ISOTHIOCYANATE(6590-94-9)
• EPA Substance Registry System: 3,4-DICHLOROPHENYL ISOTHIOCYANATE(6590-94-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 23-26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• RTECS: NX8490000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6590-94-9(Hazardous Substances Data)

Usage

General Description

3,4-Dichlorophenyl isothiocyanate is a chemical compound with the molecular formula C8H4Cl2NS. It is a colorless to pale yellow liquid with a pungent odor, and is commonly used in the synthesis of pharmaceuticals and agrochemicals. 3,4-Dichlorophenyl isothiocyanate is a potent inhibitor of the enzyme glyoxalase I, which plays a role in detoxifying methylglyoxal, a potentially toxic endogenous compound. 3,4-DICHLOROPHENYL ISOTHIOCYANATE has also been studied for its potential use in the treatment of cancer, as it has been found to induce apoptosis in cancer cells. However, it is important to handle this chemical with caution, as it can be harmful if it comes into contact with the skin, eyes, or respiratory system.

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

Synthetic route

thiophosgene (463-71-8) + 3,4-dichloroaniline hydrochloride (33240-95-8) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
In toluene Heating;	78%

carbon disulfide (75-15-0) + m,p-dichloroaniline (95-76-1) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
Stage #1: carbon disulfide; m,p-dichloroaniline With 3-azapentane-1,5-diamine at 20℃; for 8h; Stage #2: With bis(trichloromethyl) carbonate	75%
With potassium hydroxide at 20℃; for 1.5h; Milling; Green chemistry;	52%
Stage #1: carbon disulfide; m,p-dichloroaniline In water; ethyl acetate at 30℃; for 1h; Stage #2: With copper(ll) sulfate pentahydrate In water; ethyl acetate at 30℃; for 1h;	45%

[3,4-dichlorophenyl]dithioic acid (21878-59-1) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
With bis(trichloromethyl) carbonate In dichloromethane at 20℃; for 2h;	20%
With bis(trichloromethyl) carbonate In dichloromethane
With bis(trichloromethyl) carbonate In dichloromethane at 20℃; for 2h; Cooling with ice;

thiophosgene (463-71-8) + m,p-dichloroaniline (95-76-1) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
With triethylamine In benzene at 10 - 20℃;	19%
With chloroform Verruehren einer waessr. Suspension;
With calcium carbonate In dichloromethane; water at 25 - 40℃;
In ethyl acetate at 75℃; for 1.5h;
With sodium hydrogencarbonate In dichloromethane; water

-<(3,4-dichlorphenyl)-thiocarbaminsaeure>-thioanhydrid (5909-73-9) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
at 125 - 130℃;

m,p-dichloroaniline (95-76-1) + CS2 → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
With ammonium hydroxide; ethanol und Behandeln des Reaktionsprodukts mit wss.Pb(NO3)2;

m,p-dichloroaniline (95-76-1) + CSCl2 → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
With hydrogenchloride; toluene

3,4-dichlorophenylisocyanate (102-36-3) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 20 - 25 °C 2: 125 - 130 °C View Scheme

bis(trichloromethyl) carbonate (32315-10-9) + m,p-dichloroaniline (95-76-1) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
Stage #1: m,p-dichloroaniline With 1,4-diaza-bicyclo[2.2.2]octane; carbon disulfide at 20℃; for 12h; Stage #2: bis(trichloromethyl) carbonate Reflux;

C7H5Cl2NS2*C6H12N2 → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
With bis(trichloromethyl) carbonate In chloroform for 1h;

m,p-dichloroaniline (95-76-1) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetone / 0.17 h / 20 °C 1.2: 20 °C 2.1: bis(trichloromethyl) carbonate / chloroform / 1 h View Scheme
Multi-step reaction with 2 steps 1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 8 h / 20 °C 2: bis(trichloromethyl) carbonate / dichloromethane / 2 h / 20 °C 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: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 8 h / 20 °C 2: bis(trichloromethyl) carbonate / dichloromethane / 2 h / 20 °C / Cooling with ice View Scheme

1,1'-Thiocarbonyldiimidazole (6160-65-2) + m,p-dichloroaniline (95-76-1) → 3,4-dichlorophenyl isothiocyanate (6590-94-9)

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 2h;	224 mg
In tetrahydrofuran at 45℃;

piperidine (110-89-4) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → piperidine-1-carbothioic acid (3,4-dichlorophenyl)amide (404849-41-8)

Conditions	Yield
In dichloromethane at 25℃; for 2h; Inert atmosphere;	98%

2-(2,5-dimethyl-1H-pyrrol-1-yl)benzenamine (2405-01-8) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 1-(2-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl)-3-(3,4-dichlorophenyl)thiourea

Conditions	Yield
In chloroform Reflux;	98%

naphthalen-1-yl-acetic acid hydrazide (34800-90-3) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → C19H15Cl2N3OS (77052-80-3)

Conditions	Yield
In ethanol for 1h; Heating;	97%

3,4-dichlorophenyl isothiocyanate (6590-94-9) + isopropylamine (75-31-0) → 1-(3,4-dichlorophenyl)-3-isopropyl thiourea (74188-45-7)

Conditions	Yield
In dichloromethane at 20℃; for 18h; Inert atmosphere;	97%
In dichloromethane at 25℃; Inert atmosphere;	86%
In dichloromethane at 20℃; for 18h; Inert atmosphere;	86%

methyl (R)-2-(4-methoxyphenyl)-2-methylaminopropionate (959694-62-3) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → (R)-1-(3,4-dichlorophenyl)-3,4-dimethyl-4-(4-methoxyphenyl)-2-thioxoimidazolidin-5-one (959691-72-6)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h;	95%
With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	95%

2,2-dimethylpropylamine (5813-64-9) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 1-(3,4-dichlorophenyl)-3-(2,2-dimethyl-propyl)thiourea (1332704-14-9)

Conditions	Yield
In dichloromethane at 20℃; for 18h; Inert atmosphere;	93%

3,4-dichlorophenyl isothiocyanate (6590-94-9) + 1-cyanothioformanilide (4955-82-2) → 3-(3,4-dichlorophenyl)-4-imino-5-(phenylimino)-2-thiazolidinethione (116708-95-3)

Conditions	Yield
With triethylamine In ethanol at 0℃; for 2.33333h;	87%

3,4-dichlorophenyl isothiocyanate (6590-94-9) + 2-hydroxy-5-chloro-aniline (95-85-2) → N-(2-hydroxy-5-chlorophenyl)-N'-(3,4-dichlorophenyl)thiourea

Conditions	Yield
In methanol at 20℃; for 24h;	87%

1-Adamantanamine (768-94-5) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 1-(adamantan-1-yl)-3-(3,4-dichlorophenyl)thiourea (16192-98-6)

Conditions	Yield
In dichloromethane at 25℃; Inert atmosphere;	87%

ethylamine (75-04-7) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 1-(3,4-dichlorophenyl)-3-ethylthiourea (27020-72-0)

Conditions	Yield
In dichloromethane at 25℃; Inert atmosphere;	87%

N-(3-morpholinopropyl) 2-aminoacetamide (1093220-27-9) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → N-(3-morpholinopropyl) 2-(3-(3,4-dichlorophenyl)thioureido)acetamide

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 6h;	87%

2-{2-[2-(4-fluorophenyl)-4-methylthiazol-5-yl]-1H-benzo[d]imidazol-1-yl}acetohydrazide + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 4-(3,4-dichlorophenyl)-1-(2-{2-[2-(4-fluorophenyl)-4-methylthiazol-5-yl]-1H-benzo[d]imidazol-1-yl}acetyl)thiosemicarbazide

Conditions	Yield
In ethanol for 0.158333h; Microwave irradiation;	87%

4-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)benzohydrazide + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 2-(4-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)benzoyl)-N-(3,4-dichlorophenyl)hydrazine carbothioamide

Conditions	Yield
With triethylamine In ethanol Reflux;	86%

N-benzyloxy-α-bromopropionamide (1303507-83-6) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → (Z)-3-(benzyloxy)-2-((3,4-dichlorophenyl)imino)-5-methylthiazolidin-4-one

Conditions	Yield
With sodium carbonate In acetonitrile at 20℃; for 4h; Inert atmosphere; regioselective reaction;	86%

3,3'-(p-tolylmethylene)bis(1H-indole-5-carbohydrazide) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 2,2'-(3,3'-(p-tolylmethylene)bis(1H-indole-3,5-diyl-5-carbonyl))bis(N-(3,4-dichlorophenyl)hydrazine-1-carbothioamide)

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h;	86%

2-(4-chloro-3-methylphenoxy)acetohydrazide (72293-68-6) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → C16H14Cl3N3O2S (84396-80-5)

Conditions	Yield
	85%

3,4-dichlorophenyl isothiocyanate (6590-94-9) + 3-hydroxybenzoic hydrazide (5818-06-4) → 4-(3,4-dichlorophenyl)-1-(3-hydroxybenzoyl)-3-thiosemicarbazide

Conditions	Yield
In ethanol for 0.25h; Reflux;	85%
In methanol at 20℃; under 760.051 Torr; for 24h;	47%

4-Chloro-3-nitroaniline (635-22-3) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 1-(4-chloro-3-nitrophenyl)-3-(3,4-dichlorophenyl)thiourea

Conditions	Yield
In acetonitrile at 20℃; for 12h;	85%

4-(di(1H-indol-3-yl)methyl)benzohydrazide + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 2-(4-(di(1H-indol-3-yl)methyl)benzoyl)-N-(3,4-dichlorophenyl)hydrazinecarbothioamide

Conditions	Yield
With triethylamine In ethanol for 6h; Reflux;	85%

pyridin-2-yl-acetic acid hydrazide (673-05-2) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → N-(3,4-dichlorophenyl)-2-(pyridin-2-ylacetyl)hydrazinecarbothioamide

Conditions	Yield
In acetonitrile for 6h; Reflux;	85%

isoniazid (54-85-3) + 3,4-dichlorophenyl isothiocyanate (6590-94-9) → 4-(3,4-dichlorophenyl)-1-(pyridin-4-yl)carbonylthiosemicarbazide (13921-60-3)

Conditions	Yield
In methanol Reflux;	85%

Upstream product

• 463-71-8 thiophosgene 
• 95-76-1 m,p-dichloroaniline 
• 21878-59-1 [3,4-dichlorophenyl]dithioic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 58655-32-6 triethylammonium (3,4-dichlorophenyl)carbamodithioate 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 75-15-0 carbon disulfide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 102-36-3 3,4-dichlorophenylisocyanate 
• 33240-95-8 3,4-dichloroaniline hydrochloride 
• 5909-73-9 -<(3,4-dichlorphenyl)-thiocarbaminsaeure>-thioanhydrid 

Downstream Products

• 115049-58-6 2-thioxo-pyrrolidine-1-carbothioic acid-(3,4-dichloro-anilide) 
• 100123-93-1 N-(3,4-dichloro-phenyl)-N'-[2]thienylmethyl-thiourea 
• 25020-41-1 1-(3,4-dichloro-phenyl)-3-[4-(4-methyl-thiazol-2-yl)-phenyl]-thiourea 
• 25020-69-3 1-(3,4-dichloro-phenyl)-3-[4-(4-methyl-thiazol-5-yl)-phenyl]-thiourea 
• 25179-41-3 1-(3,4-dichloro-phenyl)-3-[4-(2,4-dimethyl-thiazol-5-yl)-phenyl]-thiourea 
• 90842-25-4 N-<2-Cyan-aethyl>-N'-<3,4-dichlor-phenyl>-thioharnstoff 
• 61343-68-8 (3,4-dichloro-phenyl)-(1,1-dioxo-1,5-dihydro-1λ⁶-[1,4,2]dithiazol-3-yl)-amine 
• 16240-24-7 1-n-Butylamino-2-(3,4-dichlor-phenyl-thiocarbamoyl)-cyclohexen-⁽¹⁾ 
• 16240-22-5 1-<1-Cyclohexenyl-(1)>-1-butyl-3-(3,4-dichlor-phenyl)-2-thioharnstoff 
• 20183-89-5 (3aR)-3-(3,4-dichloro-phenyl)-5t-((R)-1,2-dihydroxy-ethyl)-6t-hydroxy-(3ar,6ac)-hexahydro-furo[2,3-d]imidazole-2-thione 
• 20204-96-0 (3aS)-1-(3,4-dichloro-benzyl)-3-(3,4-dichloro-phenyl)-5c-((R)-1,2-dihydroxy-ethyl)-6c-hydroxy-(3ar,6ac)-hexahydro-furo[2,3-d]imidazole-2-thione 
• 21026-61-9 3-(3,4-Dichlor-anilino)-2-cyano-3-mercapto-acrylsaeureaethylester 
• 65172-53-4 7-[(3,4-dichloro-phenyl)-thiocarbamoyl]-6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazolium betaine 
• 38901-32-5 N-(3,4-dichlorophenyl)hydrazinecarbothioamide 

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