542-85-8

Basic information

• Product Name: Ethyl isothiocyanate
• Synonyms: Ethyl senfoel;Ethyl isothiocyanate,96%;Ethyl isothiocyanate,99+%;Ethyl isothiocyanate, 96% 25GR;Ethyl isothiocyanate, 96% 5GR;Ethyl isothiocyanate 97%;Ethyl Isothiocyanate, 95.0%(GC);ethyleisothiocyanate
• CAS NO: 542-85-8
• Molecular Formula: C₃H₅NS
• Molecular Weight: 87.14
• EINECS: 208-831-2
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates;Armoracia rusticana (Horseradish);Building Blocks;Chemical Synthesis;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Sulfur Compounds
• Mol File: 542-85-8.mol
• Article Data: 26

Chemical Properties

• Melting Point: -6 °C
• Boiling Point: 130-132 °C(lit.)
• Flash Point: 90 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.995 g/mL at 25 °C(lit.)
• Vapor Pressure: 11.4mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Reacts with water. Soluble in chlorinated and aromatic hydrocarbons. Miscible in ethanol and ether.
• Sensitive: Moisture Sensitive
• Merck: 14,3815
• BRN: 1737705
• CAS DataBase Reference: Ethyl isothiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl isothiocyanate(542-85-8)
• EPA Substance Registry System: Ethyl isothiocyanate(542-85-8)

Safety Data

• Hazard Codes: T,N,F
• Statements: 10-23/24/25-34-42/43-50-36/37
• Safety Statements: 23-26-36/37/39-45-61-16-7/9
• RIDADR: UN 3286 3/PG 2
• WGK Germany: 3
• RTECS: NX8590000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 542-85-8(Hazardous Substances Data)

Usage

Description

Ethyl isothiocyanate, also known as mustard oil, is an isothiocyanate derivative with an ethyl group attached to the nitrogen. It is a colorless liquid with a sharp, mustard-like aroma and is characterized by its chemical properties as a clear colorless to slightly yellow liquid.

Uses

Used in Pharmaceutical Industry:
Ethyl isothiocyanate is used as a pharmaceutical intermediate for the synthesis of various drugs and medicinal compounds. Its unique chemical structure allows it to be a versatile building block in the development of new pharmaceuticals.
Used in Military Applications:
Ethyl isothiocyanate has been utilized as a military poison gas due to its toxic properties. When released, it can cause severe irritation to the eyes, skin, and respiratory system, making it a potent agent in warfare situations. However, it is important to note that the use of chemical weapons is highly regulated and condemned under international law.

InChI:InChI=1/C3H5NS/c1-2-4-3-5/h2H2,1H3

Synthetic route

Natrium-N-ethyl-dithiocarbamat (13036-87-8) + N-phenyl-benzimidoyl chloride (4903-36-0) → Ethyl isothiocyanate (542-85-8) + N-Phenylbenzothioamide (636-04-4)

Conditions	Yield
In diethyl ether 0 deg C to r.t.;	A 66% B 99%

diethyldithiocarbamic acid (29677-64-3) → Ethyl isothiocyanate (542-85-8) + ethanethiol (75-08-1)

Conditions	Yield
at 250 - 260℃;	A 87% B 93%

butyl ethyldithiocarbamate (83962-20-3) → 1-butanethiol (109-79-5) + Ethyl isothiocyanate (542-85-8)

Conditions	Yield
at 250 - 260℃;	A 92% B 87%

ethyldithiocarbamic acid (18879-98-6) → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With bis(trichloromethyl) carbonate In Petroleum ether at 20℃; for 2h; Temperature;	92%

Ethyl-dithiocarbamic acid isobutyl ester (83962-21-4) → 2-methylpropanethiol-1 (513-44-0) + Ethyl isothiocyanate (542-85-8)

Conditions	Yield
at 250 - 260℃;	A 89% B 87%

Ethyl-dithiocarbamic acid dodecyl ester (83962-22-5) → Ethyl isothiocyanate (542-85-8) + 1-dodecylthiol (112-55-0)

Conditions	Yield
at 250 - 260℃;	A 87% B 87%

thiophosgene (463-71-8) + N-Ethyl-O-methyl Acetimidate (31001-90-8) → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With calcium carbonate In dichloromethane for 1h; Ambient temperature;	40%

ethylamine (75-04-7) → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
Stage #1: ethylamine With carbon disulfide; triethylamine at 0℃; for 2h; Stage #2: With lead(II) nitrate; sulfuric acid In water Further stages.;	26%

3'-(N,N-dimethylaminomethylene)daunorubicin hydrochloride → Ethyl isothiocyanate (542-85-8) + 3'-N-formyldaunorubicin

Conditions	Yield
With pyridine; Ethyl isothiocyanate; water at 20℃; for 336h;	A 15% B 25%

ethyl-(3-ethyl-tetrahydro-[1,3]thiazin-2-yliden)-amine (78556-10-2) + CS2 → 3-ethyl-[1,3]thiazinane-2-thione (64067-72-7) + Ethyl isothiocyanate (542-85-8)

Conditions	Yield
at 150 - 200℃; for 5h;	A 10% B n/a

ethyl-carboximidoyl bromide (115197-42-7) → Ethyl isothiocyanate (542-85-8) + ethyl-carboximidoyl bromide; hydrobromide

Conditions	Yield
With carbon disulfide; hydrogen sulfide

N-ethyl-N'-cyano-thiourea (89125-07-5) → CYANAMID (420-04-2) + Ethyl isothiocyanate (542-85-8)

Conditions	Yield
in Gegenwart freier Saeure;

ethyl isocyanide (624-79-3) → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With carbon disulfide; sulfur at 110 - 120℃;

ethyl isocyanate (109-90-0) → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With tetraphosphorus decasulfide

2-Ethoxy-2,2-diisothiocyanato-1,3-dioxa-2λ5-phospha-indan (65007-84-3) → ethyl isothiocyanate (542-90-5) + Ethyl isothiocyanate (542-85-8) + (Brenzcatechyl-phophoryl)-isothiocyanat (17798-94-6)

C6H14N4S → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With sodium hydrogencarbonate

N1,N3-diethyl-N1-nitrosothiourea (79645-03-7) → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With potassium phosphate buffer at 37℃; for 12h;	34 % Chromat.

potassium ethylglucosinolate (89777-25-3) → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
at 0℃; for 1h; white mustard seed flour, pH = 6.7;	5 mg

ethyl isocyanate (109-90-0) + P2S5 → Ethyl isothiocyanate (542-85-8)

N,N'-diethylthiourea (105-55-5) + phosphorus pentoxide → Ethyl isothiocyanate (542-85-8) + ethylamine (75-04-7)

ethyl-2-thiourea (625-53-6) + cis-nitrous acid (7782-77-6) → Ethyl isothiocyanate (542-85-8)

N-ethylthiosemicarbazide (13431-34-0) + iron(III) chloride (7705-08-0) + acetic acid (64-19-7) → Ethyl isothiocyanate (542-85-8)

ethyl-carboximidoyl bromide (115197-42-7) + Ag2S → Ethyl isothiocyanate (542-85-8)

ethylamine (75-04-7) + CS2 → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
und Einw.von AgNO3 oder HgCl2 auf eine Loesung von N-aethyl-dithiocarbamidsaurem Aethylamin;

ethylamine (75-04-7) + CSCl2 → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With water

ethyl-carboximidoyl bromide (115197-42-7) + CuS → Ethyl isothiocyanate (542-85-8)

mercury salt of/the/ N-ethyl-dithiocarbamic acid → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
at 150 - 160℃;

N.N-diethyl-thiourea → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With phosphoric acid beim Destillieren;

N-ethyl-dithiocarbamidacidic ethylamine → Ethyl isothiocyanate (542-85-8)

Conditions	Yield
With ethanol; iodine man verwandelt des erhaltenen Diaethylthiuramdisulfids durch Zusatz von Natriumaethylat und oxydiert nochmals mit Jod;

oxalyl dichloride (79-37-8) + Ethyl isothiocyanate (542-85-8) → 2,2-Dichloro-3-ethyl-thiazolidine-4,5-dione (91466-84-1)

Conditions	Yield
Ambient temperature;	100%

(1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid (869304-06-3) + Ethyl isothiocyanate (542-85-8) → (3aS,10R)-2-Ethyl-10-(3-hydroxy-phenyl)-1-thioxo-1,2,3a,4,9,10-hexahydro-2,9,10a-triaza-cyclopenta[b]fluoren-3-one

Conditions	Yield
In dimethyl sulfoxide; acetone Heating;	100%

Ethyl isothiocyanate (542-85-8) + rac-(2R,4aR,6R,7S,8R,8aR)-7-amino-2-phenylhexahydro-4H-benzo[d][1,3]dioxine-6,8-diol → 1-((2R,4aR,6R,7S,8R,8aR)-6,8-dihydroxy-2-phenylhexahydro-4H-benzo[d][1,3]dioxin-7-yl)-3-ethylthiourea

Conditions	Yield
In acetonitrile at 60℃; for 20h;	100%

Ethyl isothiocyanate (542-85-8) + (1S,2S,3R,4R,5S)-2-amino-3,4-bis(benzyloxy)-5-(fluoromethyl)cyclohexanol (1417339-13-9) → (3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-N-ethyl-6-(fluoromethyl)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazol-2-amine (1417339-15-1)

Conditions	Yield
Stage #1: Ethyl isothiocyanate; (1S,2S,3R,4R,5S)-2-amino-3,4-bis(benzyloxy)-5-(fluoromethyl)cyclohexanol In tetrahydrofuran at 20℃; for 18h; Stage #2: In acetone	100%

Ethyl isothiocyanate (542-85-8) + 3-amino-7-methoxy-1H-pyrazolo[3,4-b]quinoline (129797-61-1) → N-ethyl-N'-(7-methoxy-1H-pyrazolo[3,4-b]quinolin-3-yl)thiourea

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 1h; regioselective reaction;	100%

Ethyl isothiocyanate (542-85-8) + 3-(5-methoxy-1H-indol-3-yl)propanehydrazide → 1-(3-(5-methoxy-1H-indol-3-yl)propanoyl)-4-ethylthiosemicarbazide

Conditions	Yield
In ethanol at 20℃; for 18h;	100%

Ethyl isothiocyanate (542-85-8) + 1-ethyl-6-fluoro-7-(4-{2-fluoro-4-[(2-hydrazino-2-oxoethyl)amino]phenyl}piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-ethyl-7-(4-{4-[(2-{2-[(ethylamino)carbonothioyl]hydrazino}-2-oxoethyl)amino]-2-fluorophenyl}piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.116667h; Temperature; Microwave irradiation; Sealed tube;	100%

7-[4-(2-hydrazino-2-oxoethyl)piperazin-1-yl]-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid + Ethyl isothiocyanate (542-85-8) → 1-ethyl-7-{4-{2-{2-[(ethylamino)carbonothioyl]hydrazino}-2-oxoethyl}piperazin-1-yl}-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
In N,N-dimethyl-formamide for 0.0833333h; Time; Microwave irradiation;	100%

Ethyl isothiocyanate (542-85-8) + methyl iodide (74-88-4) + vinyl ethylsulfide (627-50-9) → N-ethyl-2-ethylsulfanyl-1-methylsulfanyl-2-propen-1-imine

Conditions	Yield
Stage #1: vinyl ethylsulfide With n-butyllithium; potassium tert-butylate In tetrahydrofuran; hexane at -100 - -60℃; Stage #2: Ethyl isothiocyanate In tetrahydrofuran; diethyl ether; hexane at -100 - -35℃; Stage #3: methyl iodide In tetrahydrofuran; hexane at 20℃; for 0.166667h;	99.5%

Ethyl isothiocyanate (542-85-8) → ethyl-2-thiourea (625-53-6)

Conditions	Yield
With ammonia In 1,2-dimethoxyethane	99%
With ammonia In methanol; ethanol at 60℃; for 2.5h;	98%
With ammonia

Ethyl isothiocyanate (542-85-8) → N,N'-diethylthiourea (105-55-5)

Conditions	Yield
With water; triethylamine In 1,4-dioxane at 20℃; for 0.166667h;	99%
In pyridine; water at 60℃; for 48h; Condensation;	74%
With hydrogen sulfide

Ethyl isothiocyanate (542-85-8) + 2-{2-[4-(3-Fluoro-phenyl)-piperazin-1-yl]-ethoxy}-benzaldehyde (103076-71-7) + Cysteamine (60-23-1) → 2-(2-{2-[4-(3-Fluoro-phenyl)-piperazin-1-yl]-ethoxy}-phenyl)-thiazolidine-3-carbothioic acid ethylamide (103074-89-1)

Conditions	Yield
	99%

Ethyl isothiocyanate (542-85-8) + 1-methyl-4-hydroxy-4-(2'-phenyl-2'-aminoethyl)-piperidine (160193-19-1) → 1-Ethyl-3-[2-(4-hydroxy-1-methyl-piperidin-4-yl)-1-phenyl-ethyl]-thiourea (160193-30-6)

Conditions	Yield
In diethyl ether for 12h; Ambient temperature;	99%

Ethyl isothiocyanate (542-85-8) + N-benzylaminomethyl-dimethylphosphine oxide (97578-20-6) → 1-ethyl-3-benzyl-3-(dimethylphosphinylmethyl)thiourea

Conditions	Yield
In dichloromethane	99%

Ethyl isothiocyanate (542-85-8) + ethyl 3-amino-4,4,4-trifluorocrotonate (141860-78-8) → 3-ethyl-2-mercapto-6-trifluoromethyl-4-(3H)-pyrimidinone (216016-27-2)

Conditions	Yield
With hydrogenchloride In water; N,N-dimethyl-formamide	99%

4-morpholinomethyl aniline (51013-67-3) + Ethyl isothiocyanate (542-85-8) → N-ethyl-N'-[4-(4-morpholinylmethyl)phenyl]thiourea (1146977-57-2)

Conditions	Yield
With triethylamine In ethanol at 90℃; for 5h;	99%

Ethyl isothiocyanate (542-85-8) + tert-butyl 1,4-diazepine-1-carboxylate (112275-50-0) → tert-butyl 4-(ethylcarbamothioyl)-1,4-diazepane-1-carboxylate

Conditions	Yield
With triethylamine In diethyl ether at 20℃;	99%

Ethyl isothiocyanate (542-85-8) + 8-(1-hydrazonoethyl)-7-butoxy-4-methylcoumarin → C19H25N3O3S

Conditions	Yield
In ethanol; N,N-dimethyl-formamide for 8h; Reflux;	99%

Ethyl isothiocyanate (542-85-8) + 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide (69435-07-0) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-[(E)-ethylimino]-4-phenyl-[1,3,4]thiadiazolidin-(2E)-ylideneamino]-tetrahydro-pyran-3-yl ester

Conditions	Yield
In benzene for 4h; Heating;	98.5%

Ethyl isothiocyanate (542-85-8) + N-phenyl-4,5,6,7-tetrahydro-7,8,8-trimethyl-4,7-methano-2H-indazol-3-amine (66885-19-6, 85145-75-1) → 7,8,8-Trimethyl-3-phenylamino-4,5,6,7-tetrahydro-4,7-methano-indazole-2-carbothioic acid ethylamide

Conditions	Yield
In toluene	98%

Ethyl isothiocyanate (542-85-8) + 4-chlorobenzoic acid hydrazide (536-40-3) → 1-(4-chloro-benzoyl)-4-ethyl-thiosemicarbazide (26131-22-6)

Conditions	Yield
In ethanol for 4h; Heating;	98%
In ethanol

Ethyl isothiocyanate (542-85-8) + Diethyl-carbamic acid (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (187929-94-8) → Diethyl-carbamic acid (3aR,5R,6S,6aR)-5-((R)-2-ethylthiocarbamoyloxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Conditions	Yield
In pyridine for 96h;	98%

Ethyl isothiocyanate (542-85-8) + (6-phenylimidazo[2,1-b]thiazol-3-yl)acetic acid hydrazide (85731-93-7) → 4-ethyl-1-((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetyl)-3-thiosemicarbazide

Conditions	Yield
In ethanol for 3h; Addition; Heating;	98%

Ethyl isothiocyanate (542-85-8) + 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2, 10034-19-2, 10034-20-5, 34948-62-4, 110253-00-4) → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-ethylthioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate (1009816-89-0)

Conditions	Yield
With triethylamine In acetonitrile for 3h; Heating / reflux;	98%

1-methyl-piperazine (109-01-3) + Ethyl isothiocyanate (542-85-8) → N-ethyl-4-methylpiperazine-1-carbothioamide

Conditions	Yield
With triethylamine In diethyl ether at 20℃;	98%

1-Methylhomopiperazine (4318-37-0) + Ethyl isothiocyanate (542-85-8) → N-ethyl-4-methyl-1,4-diazepane-1-carbothioamide

Conditions	Yield
With triethylamine In diethyl ether at 20℃;	98%

Ethyl isothiocyanate (542-85-8) + 1-cyclopropyl-6-fluoro-7-{4-[(hydrazinecarbonyl)methyl]piperazin-1-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-cyclopropyl-7-[4-(2-{2-[(ethylamino)carbonothioil]hydrazino}-2-oxoethyl) piperazin-1-yl]-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions	Yield
for 0.833333h; Sealed tube; Microwave irradiation;	98%

Ethyl isothiocyanate (542-85-8) + 2-(5,6-dichloro-2-methyl-1H-benzimidazol-1-yl)acetohydrazide → 2-(2-(5,6-dichloro-2-methyl-1H-benzimidazol-1-yl)acetyl)-N-ethylhydrazine-1-carbothioamide

Conditions	Yield
In ethanol for 2h; Reflux;	98%

isoniazid (54-85-3) + Ethyl isothiocyanate (542-85-8) → 4-ethyl-1-(4-pyridylcarbonyl)thiosemicarbazide (26036-34-0)

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	97%
In ethanol for 0.5h; Heating;	96%
In ethanol at 50℃; for 1h;	88%

Upstream product

• 115197-42-7 ethyl-carboximidoyl bromide 
• 89125-07-5 N-ethyl-N'-cyano-thiourea 
• 29677-64-3 diethyldithiocarbamic acid 
• 79645-03-7 N₁,N₃-diethyl-N₁-nitrosothiourea 
• 78556-10-2 ethyl-(3-ethyl-tetrahydro-[1,3]thiazin-2-yliden)-amine 
• 109-90-0 ethyl isocyanate 
• 105-55-5 N,N'-diethylthiourea 
• 625-53-6 ethyl-2-thiourea 
• 7782-77-6 cis-nitrous acid 
• 13431-34-0 N-ethylthiosemicarbazide 
• 7705-08-0 iron(III) chloride 
• 64-19-7 acetic acid 
• 75-04-7 ethylamine 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 860746-63-0 triphenyl-thioacetic acid ethylamide 
• 64895-98-3 3-ethyl-1-methyl-2-thioxo-imidazolidin-4-one 
• 108015-70-9 N-ethyl-N'-(4-nitro-phenyl)-thiourea 
• 15361-86-1 N'-ethyl-N,N-dimethyl-thiourea 
• 29306-06-7 1,3,3-triethyl-thiourea 
• 102-06-7 diphenylguanidine 
• 2741-06-2 1-ethyl-3-phenylthiourea 
• 27421-82-5 1-phenyl-4-ethyl-3-thiosemicarbazide 
• 32900-09-7 N-allyl-N'-ethylthiourea 
• 624-79-3 ethyl isocyanide 
• 32093-89-3 1-ethyl-3-oxazol-2-yl-thiourea 
• 16578-52-2 1-Ethyl-3-{3-[(3-ethyl-thioureido)-methyl]-benzyl}-thiourea 
• 6171-12-6 N-Phenylsulfonyl-N'-aethylthioharnstoff 
• 6117-42-6 1-(4,5-diphenyl-oxazol-2-yl)-4-ethyl-thiosemicarbazide 

Relevant articles and documents

Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors

The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 μM range (except 1e, 2e, and 3d), and 1c is the most potent inhibitor (IC50 = 0.038 μM). The structure-activity relationship of synthetic thiosemicarbazones revealed that the diaryl-substitutes, specifically 2-pyridine and 2-hydroxylbenzene improved inhibitory activities of the inhibitors. The thiosemicarbazones exhibited synergistic antimycobacterial actions against E. coli-NDM-1, resulted a 2–512-fold reduction in MIC of meropenem, while 1c restored 16–256-, 16-, and 2-fold activity of the antibiotic on clinical isolates ECs, K. pneumonia and P. aeruginosa harboring NDM-1, respectively. Also, mice experiments showed that 1c had a synergistic antibacterial ability with meropenem, reduced the bacterial load clinical isolate EC08 in the spleen and liver. This work provided a highly promising scaffold for the development of NDM-1 inhibitors.

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