53114-57-1

Usage

Uses

Used in Pharmaceutical Applications:
2-Methylisothiouronium chloride is used as a pharmaceutical compound for its potential therapeutic applications. Its chemical properties make it a valuable component in the development of new drugs and treatments.
Used in Research Applications:
In research, 2-Methylisothiouronium chloride is used as a source of thiol in synthesis reactions. Its role in these processes is crucial for the production of various chemical compounds and materials.
Used in Chemical Synthesis:
2-Methylisothiouronium chloride is used as a reagent in chemical synthesis, contributing to the formation of new compounds with potential applications in various industries.
Safety Precautions:
Due to its potentially harmful nature, 2-Methylisothiouronium chloride should be handled with care. It is essential to store it in a cool, dry, and well-ventilated location to prevent degradation or hazardous reactions. Additionally, it is crucial to avoid skin and eye contact, as well as inhalation or ingestion, to minimize health risks.

InChI:InChI=1/C2H6N2S.ClH/c1-5-2(3)4;/h1H3,(H3,3,4);1H

Synthetic route

S-methyl-isothiouronium picrate (2780-75-8) → S-methylisothiourea hydrochloride (53114-57-1)

Conditions	Yield
With hydrogenchloride for 18h; Ambient temperature;	70%

methanol (67-56-1) + thiourea (17356-08-0) → S-methylisothiourea hydrochloride (53114-57-1)

Conditions	Yield
With hydrogenchloride for 24h; Reflux;	70%
With hydrogenchloride In water for 12h; Reflux;	65%

thiourea (17356-08-0) + methyl chloroformate (79-22-1) → S-methylisothiourea hydrochloride (53114-57-1)

S-methylisothiourea hydrochloride (53114-57-1) + (S)-2-tert-butoxycarbonylamino-5-oxodeca-6-ynoic acid tert-butyl ester (197159-31-2) → (S)-α-tert-butoxycarbonylamino-γ-(2-methylthio-6-propylpyrimidin-4-yl)butyric acid α-tert-butyl ester (197159-49-2)

Conditions	Yield
With sodium carbonate In acetonitrile Heating;	95%

S-methylisothiourea hydrochloride (53114-57-1) + benzaldehyde (100-52-7) + Wang's resin-bound -OCOCH2CO2CH2CF3 → 2-methylsulfanyl-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carboxylic acid

Conditions	Yield
Multistep reaction;	94%

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl isothiocyanate (58214-53-2) + S-methylisothiourea hydrochloride (53114-57-1) → 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-S-methylisothiobiuret (77049-63-9)

Conditions	Yield
With triethylamine In acetonitrile for 3h; Ambient temperature;	92%

4,4-dimethoxy-3-oxo-butyric acid methyl ester (60705-25-1) + S-methylisothiourea hydrochloride (53114-57-1) → 6-(dimethoxymethyl)-2-(methylthio)pyrimidin-4-ol (21326-25-0)

Conditions	Yield
With potassium carbonate In water at 20℃;	92%

S-methylisothiourea hydrochloride (53114-57-1) + (S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester (197159-33-4) → (S)-α-tert-butoxycarbonylamino-β-(2-methylthio-6-phenylpyrimidin-4-yl)propanoic acid α-tert-butyl ester (197159-55-0)

Conditions	Yield
With sodium carbonate In acetonitrile at 40℃;	91%

S-methylisothiourea hydrochloride (53114-57-1) + 4-oxo-nona-2,5-diynoic acid ethyl ester (311348-66-0) → 2-methylthio-6-pent-1-ynyl-pyrimidine-4-carboxylic acid ethyl ester

Conditions	Yield
With potassium carbonate In water; acetonitrile at 20℃; for 0.5h;	90%

C14H11ClO4 + S-methylisothiourea hydrochloride (53114-57-1) → ethyl 2-[9-chloro-2-(methylthio)-5H-chromeno[4,3-d]pyrimidin-5-yl]acetate

Conditions	Yield
Stage #1: S-methylisothiourea hydrochloride With base In ethanol for 0.166667h; Stage #2: C14H11ClO4 In ethanol at 20℃; for 5h;	89%

S-methylisothiourea hydrochloride (53114-57-1) + 1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-phenyl-propynone (263006-28-6) → 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-6-phenyl-pyrimidine (263006-34-4)

Conditions	Yield
With sodium carbonate In water; acetonitrile at 80℃; for 24h; Condensation; cyclization;	88%

S-methylisothiourea hydrochloride (53114-57-1) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (14152-97-7) → 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-methylisothiobiuret (69435-12-7)

Conditions	Yield
With triethylamine In acetonitrile for 3h; Ambient temperature;	87%

S-methylisothiourea hydrochloride (53114-57-1) + (S)-2-tert-butoxycarbonylamino-4-oxohex-5-ynoic acid tert-butyl ester (197159-35-6) → (S)-α-tert-butoxycarbonylamino-β-(2-methylthiopyrimidin-4-yl)propanoic acid α-tert-butyl ester (197159-61-8)

Conditions	Yield
With sodium carbonate In acetonitrile at 40℃;	87%

S-methylisothiourea hydrochloride (53114-57-1) + 2-chloro-3-pyridinesulfonyl chloride (6684-06-6) → N3-[1-amino-1-methylsulfanylmethylidene]-2-chloro-3-pyridinesulfonamide

Conditions	Yield
With potassium hydroxide In dichloromethane; water at 0 - 20℃; for 8h;	87%

S-methylisothiourea hydrochloride (53114-57-1) + 4-oxo-6-phenyl-hexa-2,5-diynoic acid ethyl ester (311348-65-9) → 2-methylthio-6-phenylethynyl pyrimidine-4-carboxylic acid ethyl ester

Conditions	Yield
With potassium carbonate In water; acetonitrile at 20℃; for 0.5h;	85%

S-methylisothiourea hydrochloride (53114-57-1) + 4-oxo-deca-2,5-diynoic acid ethyl ester (311348-67-1) → 6-hex-1-ynyl-2-methylthio-pyrimidine-4-carboxylic acid ethyl ester

Conditions	Yield
With potassium carbonate In water; acetonitrile at 20℃; for 0.5h;	85%

S-methylisothiourea hydrochloride (53114-57-1) + benzyl chloroformate (501-53-1) → N-benzyloxycarbonyl-S-methyl-isothiourea (25508-19-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	84%

S-methylisothiourea hydrochloride (53114-57-1) + (S)-2-tert-butoxyxarbonylamino-5-oxohept-6-ynoic acid tert-butyl ester (197159-29-8) → (S)-α-tert-butoxycarbonylamino-γ-(2-methylthiopyrimidin-4-yl)butyric acid α-tert-butyl ester (197159-45-8)

Conditions	Yield
With sodium carbonate In acetonitrile Heating;	82%

N-(10-aminodecyl)-aminomethanephosphonic acid monohydrate + guanidine-N-phosphoric acid (3019-36-1) + S-methylisothiourea hydrochloride (53114-57-1) → N-(10-guanidinodecyl)-aminomethanephosphonic acid monohydrate

Conditions	Yield
With sodium hydroxide; methyloxirane In methanol; water	81%

3-aminopropanephosphonic acid (13138-33-5) + S-methylisothiourea hydrochloride (53114-57-1) → 3-guanidinopropanephosphonic acid

Conditions	Yield
With potassium hydroxide at 60℃; for 4h;	80.3%

S-methylisothiourea hydrochloride (53114-57-1) + 4-oxo-hepta-2,5-diynedioic acid diethyl ester (311348-69-3) → 6-ethoxycarbonylethynyl-2-methylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester

Conditions	Yield
With potassium carbonate In water; acetonitrile at 20℃; for 0.5h;	80%

S-methylisothiourea hydrochloride (53114-57-1) + (S)-2-tert-butoxycarbonylamino-5-oxo-7-phenylhept-6-ynoic acid tert-butyl ester (197159-27-6) → (S)-α-tert-butoxycarbonylamino-γ-(2-methylthio-6-phenylpyrimidin-4-yl)butyric acid α-tert-butyl ester (197159-43-6)

Conditions	Yield
With sodium carbonate In acetonitrile Heating;	79%

β-pinene oxide (56246-58-3) + S-methylisothiourea hydrochloride (53114-57-1) → 7,7-dimethyl-2-[(methylthio)methyl]bicyclo[3.1.1]heptan-2-ol (436799-38-1)

Conditions	Yield
With sodium ethanolate In ethanol at 90℃; for 5h;	78%

ethyl-3-(dimethylamino)-2-(phenylcarbonyl)prop-2-enoate (66129-60-0) + S-methylisothiourea hydrochloride (53114-57-1) → 5-ethoxycarbonyl-6-(4'-fluorophenyl)-2-(methylamino)pyrimidine (77995-06-3)

Conditions	Yield
With sodium ethanolate In ethanol Heating; reflux overnight;	77%

S-methylisothiourea hydrochloride (53114-57-1) + 2-oxo-4-piperidin-1-yl-6-p-tolyl-2H-pyran-3-carbonitrile (757235-51-1) → 2'-amino-6'-(p-tolyl)-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-carbonitrile

Conditions	Yield
potassium hydroxide In N,N-dimethyl-formamide for 1.5h;	76%

S-methylisothiourea hydrochloride (53114-57-1) + 6-(4-bromophenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (94835-43-5) → 2'-amino-6'-(4-bromophenyl)-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-carbonitrile

Conditions	Yield
potassium hydroxide In N,N-dimethyl-formamide for 1.33333h;	76%

S-methylisothiourea hydrochloride (53114-57-1) + 8-aminooctanephosphonic acid (35622-29-8) → 8-guanidinooctanephosphonic acid

Conditions	Yield
With potassium hydroxide at 60℃; for 4h;	75%

S-methylisothiourea hydrochloride (53114-57-1) + 4-piperidino-3-cyano-2H-pyran-2-one (94835-37-7) → 2'-amino-6'-phenyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-carbonitrile

Conditions	Yield
potassium hydroxide In N,N-dimethyl-formamide for 1.25h;	75%

4-ethoxy-2-oxobut-3-enoic acid ethyl ester (76240-19-2) + S-methylisothiourea hydrochloride (53114-57-1) → ethyl-2-methylsulfanylpyrimidine-4-carboxylate

Conditions	Yield
With triethylamine In 1,4-dioxane at 100℃; for 48h;	75%

C9H14O4 + S-methylisothiourea hydrochloride (53114-57-1) → ethyl 2-(methylthio)-5-methylpyrimidine-4-carboxylate

Conditions	Yield
With triethylamine In 1,4-dioxane at 100℃; for 48h;	75%

methyl 2-chloro-2-cyclopropylideneacetate (82979-45-1) + S-methylisothiourea hydrochloride (53114-57-1) → 3-methylthio-2,4-diazabicylo[4.2.0]octa-1(6),2-dien-5-one (908009-76-7)

Conditions	Yield
With triethylamine In 1,4-dioxane at 50℃; for 48h;	74%

S-methylisothiourea hydrochloride (53114-57-1) + 1-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-undec-2-yn-1-one (263006-27-5) → 4-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-6-octyl-pyrimidine (263006-32-2)

Conditions	Yield
With sodium carbonate In water; acetonitrile at 80℃; for 24h; Condensation; cyclization;	73%

S-methylisothiourea hydrochloride (53114-57-1) + 2-oxo-4-(piperidin-1-yl)-6-(thiophen-2-yl)-2H-pyran-3-carbonitrile (757235-61-3) → 2'-amino-6'-thiophen-2-yl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-carbonitrile

Conditions	Yield
potassium hydroxide In N,N-dimethyl-formamide for 1.16667h;	73%

Upstream product

• 17356-08-0 thiourea 
• 79-22-1 methyl chloroformate 
• 2780-75-8 S-methyl-isothiouronium picrate 
• 67-56-1 methanol 

Downstream Products

• 19010-47-0 bisguanidinohexane 
• 67337-40-0 N-carbamimidoyl-alanine 
• 13551-09-2 N,N'-diguanyl-L-cystine 
• 107776-32-9 (2-phenoxy-benzyl)-guanidine 
• 107774-30-1 (4-phenoxy-benzyl)-guanidine 
• 25508-17-2 S-methyl-N-benzoylisothiourea 
• 62476-84-0 1,1'-(propane-1,3-diyl)diguanidine 
• 352-97-6 guanidineacetic acid 
• 471-29-4 1-methylguanidine 
• 53554-29-3 ethyl 3,4-dihydro-2-methylthio-4-oxopyrimidine-5-carboxylate 
• 55215-15-1 2-Guanidinoethanphosphorsaeure 
• 77049-63-9 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-S-methylisothiobiuret 
• 55215-14-0 guanidinomethanephosphonic acid 
• 13429-32-8 N-(2-hydroxy-ethyl)-N-methyl-guanidine 

Relevant academic research and scientific papers

One-Dimensional Organic–Inorganic Hybrid Materials Based on Antimony

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