35600-34-1

Basic information

• Product Name: S-METHYL ISOTHIOSEMICARBAZIDE HYDROIODIDE
• Synonyms: AKOS 90781;HYDRAZINECARBOXIMIDOTHIOIC ACID METHYL ESTER HYDROIODIDE;S-METHYL ISOTHIOSEMICARBAZIDE HYDROIODIDE;S-Methyl isothiosemicarbazide hydroiodide, min. 95 %;METHYL HYDRAZINECARBIMIDOTHIOATE HYDROIODIDE;Methyl hydrazinecarbiMidothioate;(E)-amino-(amino-methylsulfanylmethylidene)azanium iodide;(Z)-amino-(amino-methylsulfanyl-methylene)ammonium i
• CAS NO: 35600-34-1
• Molecular Formula: C₂H₈N₃S*I
• Molecular Weight: 233.07
• Mol File: 35600-34-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 137-139 °C(Solv: ethanol (64-17-5))
• Boiling Point: 238.4 °C at 760 mmHg
• Flash Point: 98 °C
• Appearance: /
• Density: 1.38 g/cm³
• Vapor Pressure: 0.0424mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Very Slightly)
• CAS DataBase Reference: S-METHYL ISOTHIOSEMICARBAZIDE HYDROIODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: S-METHYL ISOTHIOSEMICARBAZIDE HYDROIODIDE(35600-34-1)
• EPA Substance Registry System: S-METHYL ISOTHIOSEMICARBAZIDE HYDROIODIDE(35600-34-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 35600-34-1(Hazardous Substances Data)

Usage

General Description

S-Methyl isothiosemicarbazide hydroiodide is a chemical compound used in the synthesis of organic compounds and pharmaceuticals. It is a white crystalline solid that is soluble in water and ethanol. S-Methyl isothiosemicarbazide hydroiodide is a potent inhibitor of xanthine oxidase, which is an enzyme involved in purine metabolism. S-METHYL ISOTHIOSEMICARBAZIDE HYDROIODIDE is also used as a reagent in the synthesis of thiosemicarbazide derivatives, which have various biological activities. Additionally, it has been studied for its potential use in the treatment of gout, a condition caused by the buildup of uric acid crystals in the joints.

InChI:InChI=1/C2H7N3S/c1-6-2(3)5-4/h4H2,1H3,(H2,3,5)

Synthetic route

thiosemicarbazide (79-19-6) + methyl iodide (74-88-4) → S-methyl isothiosemicarbazide hydroiodide (35600-34-1)

Conditions	Yield
In ethanol at 60℃; for 0.5h;	98%
In ethanol at 60℃; for 0.5h; Inert atmosphere;	91%
In ethanol for 2h; Heating;	80%

5-methoxyindole-3-carboxaldehyde (10601-19-1) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 1-((5-methoxy-1H-indol-3-yl)methylene)-S-methyl-isothiosemicarbazide

Conditions	Yield
With triethylamine In methanol at 25 - 30℃; for 2h;	100%

morpholine (110-91-8) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → C5H12N4O (31106-56-6)

Conditions	Yield
In ethanol for 4h; Reflux;	98.95%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + dimethylglyoxal (431-03-8) → 3-methylthio-5,6-dimethyl-1,2,4-triazine (7275-70-9)

Conditions	Yield
With sodium hydrogencarbonate In water at 20℃; for 16h;	95%
With sodium hydrogencarbonate In water at 20℃; for 16h; Inert atmosphere;	95%
	86%

C14H10O5 + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → methyl 3-(5-(3-(methylthio)-1,2,4-triazin-5-yl)furan-2-yl)benzoate (1529785-27-0)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 2h; Reflux; regioselective reaction;	95%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + 4-chlorophenylglyoxal (4998-15-6) → 5-(4-chlorophenyl)-3-(methylthio)-1,2,4-triazine (67642-94-8)

Conditions	Yield
	93%

C13H7F3O3 + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 3-(methylthio)-5-(5-(2-(trifluoromethyl)phenyl)furan-2-yl)-1,2,4-triazine (1529785-26-9)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 2h; Reflux; regioselective reaction;	91.5%

Glyoxal (131543-46-9) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 3-methylthio-1,2,4-triazine (28735-21-9)

Conditions	Yield
With sodium hydrogencarbonate In water for 0.166667h; Cooling with ice;	90%
	89%
With sodium hydrogencarbonate In water at 0℃; for 5h;	88%

5-methoxyindole-3-carboxaldehyde (10601-19-1) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 1-[(5-methoxy-1H-indole-3yl)methyleneamino]isothiourea hydroiodide (1285666-41-2)

Conditions	Yield
With hydrogenchloride In water; ethyl acetate pH=1 - 2;	90%

C14H9NO4 + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 3-(methylthio)-5-(3'-nitrobiphenyl-4-yl)-1,2,4-triazine (1529785-34-9)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 2h; Reflux; regioselective reaction;	87.3%

1-Adamantanamine (768-94-5) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 1-(3-aminoguanidino)adamantane hydroiodide (72685-51-9)

Conditions	Yield
In ethanol for 4h; Reflux;	85%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + 2a,10b-Dihydro-cyclobuta[l]phenanthrene-1,2-dione → 11-Methylsulfanyl-8b,12b-dihydro-9,10,12-triaza-benzo[3,4]cyclobuta[1,2-l]phenanthrene (105783-76-4)

Conditions	Yield
	84%

phenylglyoxal hydrate (1074-12-0) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 3-methylthio-5-phenyl-1,2,4-triazine (28735-27-5)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 2h; Reflux; regioselective reaction;	82.6%
	81%

2-(2-methylpyridin-4-yl)-2-oxoacetaldehyde + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 5-(2-methylpyridin-4-yl)-3-(methylthio)-1,2,4-triazine

Conditions	Yield
With sodium hydrogencarbonate In ethanol at 80℃; for 1h;	80.9%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + 4-(4-Nitro-phenyl)-2,4-dioxo-butyric acid methyl ester (39757-36-3) → 3-methylsulfanyl-6-[2-(4-nitro-phenyl)-2-oxo-ethyl]-2H-[1,2,4]triazin-5-one

Conditions	Yield
In ethanol Condensation; Cyclization; Heating;	80%

1,3-diaminoadamantane (10303-95-4) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 1,3-bis-(3-aminoguanidino)adamantane dihydroiodide

Conditions	Yield
In ethanol for 4h; Reflux;	80%

dimethyl 2,2′-((3-formyl-2-hydroxy-5-methylbenzyl)azanediyl)diacetate + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → C17H24N4O5S

Conditions	Yield
In methanol; water for 1h; Reflux;	76%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + 4-(4-iodo-phenyl)-2,4-dioxo-butyric acid → 6-[2-(4-iodo-phenyl)-2-oxo-ethyl]-3-methylsulfanyl-2H-[1,2,4]triazin-5-one

Conditions	Yield
In ethanol for 2h; Condensation; Cyclization; Heating;	75%

N-(2-adamantyl)amine (13074-39-0) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 2-(3-aminoguanidino)adamantane hydroiodide (1619986-41-2)

Conditions	Yield
In ethanol for 4h; Reflux;	75%

C12H7NO5 + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 3-(methylthio)-5-(5-(3-nitrophenyl)furan-2-yl)-1,2,4-triazine (1529785-25-8)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 2h; Reflux; regioselective reaction;	74.3%

4-Phenyl-cyclopenten-(3)-dion-(1,2) (91136-42-4) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 3-methylsulfanyl-5-(2-oxo-2-phenyl-ethylidene)-2,5-dihydro-1H-[1,2,4]triazin-6-one

Conditions	Yield
In 1,4-dioxane for 2h; Condensation; Cyclization; Heating;	74%

2-acetylpyridine (1122-62-9) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 2-acetylpyridine S-methylisothiosemicarbazone (220065-93-0)

Conditions	Yield
With sodium carbonate decahydrate In ethanol for 3h; Reflux;	74%

Z-2-amino-5-hydroxyadamantane + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → Z-2-(3-aminoguanidino)-5-hydroxyadamantane hydroiodide

Conditions	Yield
In ethanol for 4h; Reflux;	74%

ethyl 3-(6-chlorochromon-2-yl)-2-hydroxyacrylate + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 6-[(6-chloro-4-oxo-4H-chromen-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione

Conditions	Yield
In ethanol for 4h; Reflux;	74%

4-(4-chlorophenyl)-2,4-dioxobutanoic acid (38053-20-2) + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → 6-[2-(4-chloro-phenyl)-2-oxo-ethyl]-2H-[1,2,4]triazine-3,5-dione

Conditions	Yield
In ethanol for 10h; Condensation; Cyclization; Heating;	72%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + 4-(4-iodo-phenyl)-2,4-dioxo-butyric acid → 6-[2-(4-iodo-phenyl)-2-oxo-ethyl]-2H-[1,2,4]triazine-3,5-dione

Conditions	Yield
In ethanol for 10h; Condensation; Cyclization; Heating;	72%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + 4-(4-bromo-phenyl)-2,4-dioxo-butyric acid (58303-63-2) → 6-[2-(4-bromo-phenyl)-2-oxo-ethyl]-3-methylsulfanyl-2H-[1,2,4]triazin-5-one

Conditions	Yield
In ethanol for 2h; Condensation; Cyclization; Heating;	72%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + 4-p-tolyl-cyclopent-3-ene-1,2-dione → 3-methylsulfanyl-5-(2-oxo-2-p-tolyl-ethylidene)-2,5-dihydro-1H-[1,2,4]triazin-6-one

Conditions	Yield
In 1,4-dioxane for 2h; Condensation; Cyclization; Heating;	70%

S-methyl isothiosemicarbazide hydroiodide (35600-34-1) + copper(II) acetate monohydrate (6046-93-1) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → Cu[(CH3OC6H3OCHN)2NCSCH3]*H2O

Conditions	Yield
With AgNO3 In methanol; water byproducts: AgI; ligand in methanol added dropwise to semicarbazide in CH3OH, stirred at 50°C for 2 h, refluxed for 20 min, cooled, treated with Ag salt in CH3OH/H2O 1:2, filtered, treated with Cu salt in CH3OH; crystd.(overnight), filtered, washed (cold methanol), elem. anal.;	70%

E-2-amino-5-hydroxyadamantane + S-methyl isothiosemicarbazide hydroiodide (35600-34-1) → E-2-(3-aminoguanidino)-5-hydroxyadamantane hydroiodide

Conditions	Yield
In ethanol for 4h; Reflux;	70%

Upstream product

• 79-19-6 thiosemicarbazide 
• 74-88-4 methyl iodide 

Downstream Products

• 59394-85-3 4-chloro-benzaldehyde-(S-methyl-iso thiosemicarbazone) 
• 7410-58-4 benzaldehyde-(S-methyl-iso thiosemicarbazone) 
• 69466-52-0 3-methylsulfanyl-5-(thiophen-2-yl)-1,2,4-triazine 
• 125730-08-7 1-amino-3-(4-methoxybenzyl)guanidine 
• 31143-85-8 ethoxycarbonyl-6 hydroxy-5 methylmercapto-3 triazine-1,2,4 
• 69466-57-5 3-methylsulphanyl-5,6-di-pyridin-2-yl-[1,2,4]triazine 
• 71064-21-6 1-amino-3-furfurylguanidine hydriodide 
• 100524-19-4 3-Methylthio-5-oxo-dihydro-1,2,4-triazin-6-yl-propionsaeure 
• 1566-32-1 3-(methylthio)-6-methyl-1,2,4-triazin-5(2H)-one 
• 67642-94-8 5-(4-chlorophenyl)-3-(methylthio)-1,2,4-triazine 
• 33398-79-7 N-methylhydrazinecarboximidamide hydroiodide 
• 33398-79-7 C₂H₈N₄*HI 
• 3458-34-2 C₈H₁₂N₄*HI 
• 19380-83-7 N¹-(o-Chlorbenzyl)-N³-aminoguanidin 

Relevant articles and documents

Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate

A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH 3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.

Selenium-containing heterocycles from isoselenocyanates: Synthesis of 5-amino-2,4-dihydro-3H-1,2,4-triazole-3-selones

The reaction of S-methylisothiosemicarbazide hydroiodide (=S-methyl hydrazinecarboximido-thioate hydroiodide; 1), prepared from thiosemicarbazide by treatment with MeI in EtOH, and aryl isoselenocyanates 5 in CH 2Cl2 affords 3H-1,2,4-triazole-3-selone derivatives 7 in good yield (Scheme 2, Table 10). During attempted crystallization, these products undergo an oxidative dimerization to give the corresponding bis(4H-1,2,4-triazol-3-yl) diselenides 11 (Scheme 3). The structure of 11a was established by X-ray crystallography.

Synthesis and antioxidant activities of new nickel(II) complexes derived from 4-benzy-loxysalicylidene-S-methyl/propyl thiosemicarbazones

Six nickel(II) complexes of the N2O2chelating thiosemicarbazones were synthesized using N1-4-benzyloxysalicylidene-S-methyl/propyl thiosemicarbazone and methoxy-substitute-salicylaldehydes in the presence of Ni(II) ion by template reaction. The structures of thiosemicarbazones and nickel(II) complexes were characterized by elemental analysis, UV-Vis, IR, and 1H-NMR spectroscopies. The structure of the N1-4-benzyloxysalicylidene-S-propyl thiosemicarbazone (2) was determined by X-ray single-crystal diffraction method. The total antioxidant capacities of synthesized compounds were evaluated by using cupric reducing antioxidant capacity (CUPRAC) method. The thiosemicarbazones exhibited more potent antioxidant capacity than Ni(II) complexes. Trolox equivalent antioxidant capacity (TEAC) of 1c was found highest in tested nickel(II) complexes. In addition, antioxidant activities of tested compounds were evaluated by using the hydroxyl radical, DPPH radical, and ABTS radical scavenging abilities of these compounds.

New M(II) (M=Mn, Co, Ni, Cu, Zn, Pd) coordinative compounds with 2-formylpyridine S-methyl-isothiosemicarbazide

The synthesis and structure of the new organic proligand 2-formylpyridine S-methyl-isothiosemicarbazone in a bi-protonated form (HL.2HCl) and its coordination compounds with Mn(II) - [Mn(HL)·Cl2], Co(III) - [CoL2]·ClO4, Ni(II) - [Ni(HL)2]·2ClO4, Cu(II) - [Cu(HL)Cl2]·(H2O), Zn(II) - [Zn(HL)2]·2(ClO4)·(H2O) and Pd(II) - [Pd(HL)·Cl]·Cl are reported. According to the X-ray investigation, the ligand has the molecular form of HL in the case of Mn(II), Cu(II), Zn(II) and Pd(II) compounds, and the deprotonated form L? in case of the Co(III) complex. The ligand coordinates to the metal ions via a N,N,N set of donors atoms in case of Zn(II), Cu(II) and Co(III). For Mn(II), the ligand coordinates via N,N donor atoms, whereas in the case of Pd(II) metal ions, the coordination sphere is N,N,S. This latter coordination mode (via S(CH3)) has been previously reported in case of salicylaldehyde S-alkyl-isothiosemicarbazones.