53114-57-1

Basic information

• Product Name: 2-methylisothiouronium chloride
• Synonyms: 2-methylisothiouronium chloride;(Methylthio)formamidine·hydrochloride;Einecs 258-372-7;S-Methylisothioureahydrochloride;Carbamimidothioic acid methyl ester monohydrochloride;2-methylisothiouronium chloride ###2-METHYL-2-THIOPSEUDOUREA SULFATE
• CAS NO: 53114-57-1
• Molecular Formula: C₂H₆N₂S*ClH
• Molecular Weight: 126.60838
• EINECS: 258-372-7
• Mol File: 53114-57-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 138.8 °C at 760 mmHg
• Flash Point: 37.7 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 6.62mmHg at 25°C
• CAS DataBase Reference: 2-methylisothiouronium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylisothiouronium chloride(53114-57-1)
• EPA Substance Registry System: 2-methylisothiouronium chloride(53114-57-1)

Safety Data

• Hazardous Substances Data: 53114-57-1(Hazardous Substances Data)

Usage

General Description

2-Methylisothiouronium chloride is a chemical compound often used in pharmaceutical and research applications. It is categorized as an organic compound with the formula CH4ClNS, containing elements including carbon, hydrogen, chlorine, nitrogen, and sulfur. It is often used in research as it acts as a source of thiol in several synthesis reactions. The compound appears as white colored crystals and its physical state is solid at room temperature. In terms of handling, it needs to be stored in a cool, dry, and well-ventilated location. Due to its potentially harmful nature, precautions should be taken to avoid skin and eye contact, along with inhalation or ingestion.

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

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

Downstream Products

• 503-69-5 ethyl guanidine 
• 55215-15-1 2-Guanidinoethanphosphorsaeure 
• 55215-14-0 guanidinomethanephosphonic acid 
• 77995-06-3 5-ethoxycarbonyl-6-(4'-fluorophenyl)-2-(methylamino)pyrimidine 
• 90905-31-0 2-(methylsulfanyl)pyrimidine-5-carbaldehyde 
• 197159-55-0 (S)-α-tert-butoxycarbonylamino-β-(2-methylthio-6-phenylpyrimidin-4-yl)propanoic acid α-tert-butyl ester 
• 197159-43-6 (S)-α-tert-butoxycarbonylamino-γ-(2-methylthio-6-phenylpyrimidin-4-yl)butyric acid α-tert-butyl ester 
• 13845-72-2 (2-Diethyl-amino-ethyl)-guanidin 
• 556-64-9 methyl thiocyanate 
• 206436-62-6 2-methylthio-5-(2-chloroethyl)-4-(4-fluorophenyl)imidazole 
• 206436-62-6 2-methylthio-4-(2-chloroethyl)-5-(4-fluorophenyl)imidazole 
• 352-97-6 guanidineacetic acid 
• 62476-84-0 1,1'-(propane-1,3-diyl)diguanidine 
• 74-93-1 methylthiol 

Relevant articles and documents

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