872-35-5

Basic information

• Product Name: 2-MERCAPTOIMIDAZOLE
• Synonyms: 1,3-dihydro-2h-imidazole-2-thion;1,3-Dihydro-2H-imidazole-2-thione;1,3-Dihydro-imidazole-2-thione;1,3-Vinylenethiourea;2H-Imidazole-2-thione,1,3-dihydro-;2-mercapto-imidazol;2-Thioxo-2,3-dihydroimidazole;Imidazole, 2-mercapto-
• CAS NO: 872-35-5
• Molecular Formula: C₃H₄N₂S
• Molecular Weight: 100.14
• EINECS: 212-823-4
• Product Categories: Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Heterocyclic Compounds
• Mol File: 872-35-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 228-231 °C(lit.)
• Boiling Point: 152.4°C at 760 mmHg
• Flash Point: 46°C
• Appearance: White to yellow to tan/Crystalline Powder or Crystals
• Density: 1.36g/cm³
• Vapor Pressure: 3.5mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble50mg/mL, clear to slightly hazy, colorless to y
• PKA: 11.40±0.30(Predicted)
• BRN: 105775
• CAS DataBase Reference: 2-MERCAPTOIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MERCAPTOIMIDAZOLE(872-35-5)
• EPA Substance Registry System: 2-MERCAPTOIMIDAZOLE(872-35-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: NI8515000
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 872-35-5(Hazardous Substances Data)

Usage

Chemical Properties

White to light brown solid

Uses

2-Mercaptoimidazole has been used in chemical modification of silica gel for selective separation of mercury(II) from an aqueous solution.

General Description

The kinetics of inhibition on mushroom tyrosinase by 2-mercaptoimidazole has been investigated. The pH dependent surface-enhanced Raman scattering (SERS) spectra of biologically and industrially significant, 2-mercaptoimidazole molecule at 1.0×10-10M concentration have been investigated.

Purification Methods

Crystallise 2-mercaptoimidazole from Me2CO or H2O. UV: at 208 and 252nm (H2O). max [Fox et al. J Am Chem Soc 67 496 1947, Beilstein 24 II 7, 24 III/IV 61.]

InChI:InChI=1/C3H4N2S/c6-3-4-1-2-5-3/h1-2H,(H2,4,5,6)

Synthetic route

ammonium thiocyanate (1147550-11-5) + Glycolaldehyde (141-46-8) → 1,3-dihydro-imidazole-2-thione (872-35-5)

Conditions	Yield
With ammonium dihydrogen phosphate; ammonium chloride at 60℃; pH=4; Reagent/catalyst;	7.8%

2,2-dimethoxyethylamine (22483-09-6) → 1,3-dihydro-imidazole-2-thione (872-35-5)

Conditions	Yield
With hydrogenchloride

2,2'-dithiodi(imidazole) bis(perchloric acid) salt → 1H-imidazole (288-32-4) + 1,3-dihydro-imidazole-2-thione (872-35-5)

Conditions	Yield
With Carbonate buffer at 25℃; Kinetics;

1,3-dihydro-imidazole-2-thione (872-35-5) + chloroacetic acid (79-11-8) → (1H-imidazol-2-ylsulfanyl)-acetic acid (14395-78-9)

Conditions	Yield
Stage #1: 1,3-dihydro-imidazole-2-thione With base catalyst In ethanol at 50℃; for 1h; Stage #2: chloroacetic acid In ethanol at 80℃; for 2h;	100%

menadione (58-27-5) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 2-(1H-imidazole-2-ylthio)-3-methylnaphthalene-1,4-dione (1449761-93-6)

Conditions	Yield
In methanol at 20℃; for 8h;	98%

2-chloro-3',4'-dihydroxyacetophenone (99-40-1) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 1-(3,4-dihydroxy-phenyl)-2-(1H-imidazol-2-ylsulfanyl)-ethanone; hydrochloride

Conditions	Yield
In acetonitrile for 16h; Heating;	95%

(S)-benzyl 2-(bromomethyl)pyrrolidine-1-carboxylate + 1,3-dihydro-imidazole-2-thione (872-35-5) → C16H19N3O2S

Conditions	Yield
With potassium carbonate In acetone Reflux; Inert atmosphere;	95%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 2-(2-chloro-6-nitrophenylthio)imidazole (683276-68-8)

Conditions	Yield
With potassium carbonate In acetonitrile for 6.5h; Heating / reflux;	94%

1,3-dihydro-imidazole-2-thione (872-35-5) + 2-(isobutylamino)benzyl chloride hydrochloride → N-isobutyl-2-<(2-imidazolylthio)methyl>aniline (128936-04-9)

Conditions	Yield
In ethanol; chloroform; water	94%

1,3-dihydro-imidazole-2-thione (872-35-5) + n-butyl isocyanide (111-36-4) → 2-mercaptoimidazole-carboxylic acid butylamide

Conditions	Yield
at 50℃; for 0.5h;	93%

2,4-bis(chloromethyl)mesitylene (1585-17-7) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 1,3-bis(1-imidazolyl-2-thione)-2,4,6-trimethylbenzene (1258931-95-1)

Conditions	Yield
In methanol for 24h; Reflux;	92.5%

1,3-dihydro-imidazole-2-thione (872-35-5) → 2,2'-dithiodi(1H-imidazole) (89418-44-0)

Conditions	Yield
With dihydrogen peroxide In water; ethyl acetate at 20℃; for 0.833333h; Green chemistry;	92%
With pyridine; benzenesulfonyl chloride In dichloromethane Ambient temperature;	65%

3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (928793-94-6) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 3-tert-butoxycarbonyl-7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (928794-65-4)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone at 20 - 50℃; for 16h;	92%

benzyl 3-bromo-5-[(methylsulfonyloxy)methyl]isoxazole-4-carboxylate (1027781-75-4) + 1,3-dihydro-imidazole-2-thione (872-35-5) → benzyl 3-bromo-5-[(1H-imidazol-2-ylthio)methyl]isoxazole-4-carboxylate (1027781-80-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 48h;	92%

2-bromo-5-methoxybenzyl bromide (19614-12-1) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 7-methoxy-5H-benzo[d]imidazo[2,1-b][1,3]thiazine (1353998-99-8)

Conditions	Yield
With copper(l) iodide; caesium carbonate; L-proline In N,N-dimethyl-formamide at 110℃; for 20h; Ullmann coupling cascade reaction; Inert atmosphere;	92%

1-(p-methoxyphenyl)-3-(phenylsulfanyl)propargyl alcohol (1062602-29-2) + 1,3-dihydro-imidazole-2-thione (872-35-5) → C19H16N2OS2

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; ytterbium(III) triflate In 1,2-dichloro-ethane at 85℃; for 0.166667h; regioselective reaction;	92%

1-(4-methoxyphenyl)-3-(phenylselanyl)prop-2-yn-1-ol (1062602-39-4) + 1,3-dihydro-imidazole-2-thione (872-35-5) → C19H16N2OSSe

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; ytterbium(III) triflate In 1,2-dichloro-ethane at 85℃; for 3h; regioselective reaction;	92%

3-((3,4-dimethoxyphenethyl)imino)-2-phenylacrylic acid methyl ester + 1,3-dihydro-imidazole-2-thione (872-35-5) → C43H46N4O8S

Conditions	Yield
With triethylamine In acetonitrile at 75℃; for 2h; Inert atmosphere;	92%

3-((3,4-dimethoxyphenethyl)imino)-2-phenylacrylic acid methyl ester + 1,3-dihydro-imidazole-2-thione (872-35-5) → C43H46N4O8S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 80℃; for 1.5h; Inert atmosphere; regioselective reaction;	92%

(3-Propionyl-oxiranylmethyl)-phosphonic acid diethyl ester (111559-54-7) + 1,3-dihydro-imidazole-2-thione (872-35-5) → <<2,3-Dihydro-2-(1-oxopropyl)imidazo<2,1-b>thiazol-3-yl>methyl>phosphonsaeure-diethylester (113250-36-5)

Conditions	Yield
In ethanol for 18h; Heating;	91%

1,3-dihydro-imidazole-2-thione (872-35-5) + 2-chloro-3-nitro-5-trifluoromethylbenzene (121-17-5) → 2-(2-nitro-4-trifluoromethylphenylthio)imidazole (88251-66-5)

Conditions	Yield
With sodium ethanolate In ethanol for 4h; Heating;	91%

1,3-dihydro-imidazole-2-thione (872-35-5) + -<2-<<2-<(2-bromoacetyl)amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>carbamic acid tricyclo<3.3.1.13,7>dec-2-yl ester (141956-48-1) → -<2-<<2-<<(1H-imidazol-2-ylthio)acetyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>carbamic acid tricyclo<3.3.1.13,7>dec-2-yl ester (141956-54-9)

Conditions	Yield
With triethylamine In tetrahydrofuran for 3h; Ambient temperature;	91%

1,3-dihydro-imidazole-2-thione (872-35-5) + phenylpropynoic acid ethyl ester (2216-94-6) → (Z)-2-benzylidene-imidazo[2,1-b]thiazol-3-one

Conditions	Yield
tributylphosphine In toluene at 70℃; for 8h;	91%

2-iodoyl-5-methylbenzoic acid (52548-14-8) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 7-methyl-5H-imidazo[2,1-b][1,3]benzothiazin-5-one

Conditions	Yield
Stage #1: 2-iodoyl-5-methylbenzoic acid; 1,3-dihydro-imidazole-2-thione With iron(III) chloride; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With acetic acid In N,N-dimethyl-formamide at 110℃; for 1h; Schlenk technique; Inert atmosphere;	91%

calcium carbide + 1,3-dihydro-imidazole-2-thione (872-35-5) → 2-(vinylthio)imidazole

Conditions	Yield
With water; potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Sealed tube;	91%

n-propylmercaptoisothiourea hydrochloride (27656-88-8) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 2-Propyldisulfanyl-1H-imidazole (141400-55-7)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 1h; Ambient temperature;	90%

[RuCl2(PPh3)([9]aneS3)] (141738-34-3) + 1,3-dihydro-imidazole-2-thione (872-35-5) → RuCl(P(C6H5)3)(C3H4N2S)(C6H12S3)(1+)*Cl(1-)*0.5CHCl3 = [RuCl(P(C6H5)3)(C3H4N2S)(C6H12S3)]Cl*0.5CHCl3

Conditions	Yield
In methanol reflux (2 h); solvent removal, addn. of CHCl3, filtration, crystn. on layering with hexane (-18°C); elem. anal.;	90%

chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) (32993-05-8) + 1,3-dihydro-imidazole-2-thione (872-35-5) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → CpRu(bis(diphenylphosphino)ethane)S(2-imidazolyl) (1257344-51-6)

Conditions

Yield

With methyllithium In tetrahydrofuran; diethyl ether byproducts: LiCl; N2; THF soln. of thiol (1 mmol) cooled to -78°C, Et2O soln. of MeLi (1.12 mmol) added dropwise, stirred for 10 min, stirred for 15 min atroom temp., Ru compd. (0.68 mmol) and dppe (0.68 mmol) added, mixt. ref luxed for 4 h; evapd., dissolved (toluene), filtered (LiCl), soln. concd., pptd. (cold hexane), filtered off, recrystd. (THF/hexane), elem. anal.;

90%

7-methoxy-2-methylsulfonyl-3-phenyl-4H-1-benzopyran-4-one (658040-87-0) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 2-(1H-imidazol-2-ylsulfanyl)-7-methoxy-3-phenyl-chromen-4-one

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;	89%

2-bromo-4-fluorobenzyl bromide (61150-57-0) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 8-fluoro-5H-benzo[d]imidazo[2,1-b][1,3]thiazine (1353999-05-9)

Conditions	Yield
With copper(l) iodide; caesium carbonate; L-proline In N,N-dimethyl-formamide at 110℃; for 20h; Ullmann coupling cascade reaction; Inert atmosphere;	89%

1-Chloro-4-iodobenzene (637-87-6) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 2-((4-chlorophenyl)thio)-1H-imidazole

Conditions	Yield
With potassium phosphate; copper In dimethyl sulfoxide at 100℃; for 24h;	89%

2-chloro-3',4'-dihydroxyacetophenone (99-40-1) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 2-((1H-imidazol-2-yl)thio)-1-(3,4-dihydroxyphenyl)ethan-1-one hydrochloride

Conditions	Yield
Stage #1: 2-chloro-3',4'-dihydroxyacetophenone; 1,3-dihydro-imidazole-2-thione With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 90℃; Microwave irradiation; Stage #2: With hydrogenchloride In acetonitrile	89%

1,3-dihydro-imidazole-2-thione (872-35-5) + malononitrile (109-77-3) + 5-bromosalicyclaldehyde (1761-61-1) → 5-(1H-imidazol-2-ylsulfanyl)-2,4-diamino-7-bromo-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions	Yield
With 1,4-bis(3-methylimidazolium-1-yl)butane hydroxide In ethanol; water; N,N-dimethyl-formamide at 87℃; for 2.3h;	89%
With (1E,1'E)-N,N'-(4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(1-(pyridin-2-yl)methanimine) In ethanol at 80℃;	86%

Upstream product

• 7666-04-8 2-methylsulfanyl-1H-imidazole 
• 333-20-0 potassium thioacyanate 
• 645-36-3 2,2-diethoxy-ethanamine 
• 1147550-11-5 ammonium thiocyanate 
• 141-46-8 Glycolaldehyde 
• 89418-44-0 2,2'-dithiodi(1H-imidazole) 
• 50-00-0 formaldehyd 
• 17356-08-0 thiourea 
• 623-33-6 glycine ethyl ester hydrochloride 
• 25271-85-6 2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylic acid 
• 22483-09-6 2,2-dimethoxyethylamine 

Downstream Products

• 159189-37-4 3-(Imidazol-2-ylthio)-5-(3-methoxyphenylthio)phthalodinitrile 
• 159189-27-2 3-(imidazol-2-ylthio)phthalodinitrile 
• 159189-33-0 3-(imidazol-2-ylthio)-5-nitrophthalodinitrile 
• 1020662-79-6 C₁₂H₅Cl₃N₂OS 
• 1020662-80-9 C₁₃H₈Cl₂N₂OS 
• 1020662-81-0 C₁₃H₉ClN₂O₂S 
• 1020662-82-1 C₁₃H₆ClN₃OS 
• 1020662-83-2 C₁₂H₄ClF₃N₂OS 
• 1020662-75-2 C₁₂H₆Cl₂N₂OS 
• 1020662-77-4 C₁₂H₆Cl₂N₂OS 
• 1020662-78-5 C₁₂H₅Cl₃N₂OS 
• 1020662-73-0 7-chloro-6-phenyl-imidazo[2,1-b][1,3]thiazin-5-ne 

Relevant articles and documents

Common and Potentially Prebiotic Origin for Precursors of Nucleotide Synthesis and Activation

We have recently shown that 2-aminoimidazole is a superior nucleotide activating group for nonenzymatic RNA copying. Here we describe a prebiotic synthesis of 2-aminoimidazole that shares a common mechanistic pathway with that of 2-aminooxazole, a previously described key intermediate in prebiotic nucleotide synthesis. In the presence of glycolaldehyde, cyanamide, phosphate and ammonium ion, both 2-aminoimidazole and 2-aminooxazole are produced, with higher concentrations of ammonium ion and acidic pH favoring the former. Given a 1:1 mixture of 2-aminoimidazole and 2-aminooxazole, glyceraldehyde preferentially reacts and cyclizes with the latter, forming a mixture of pentose aminooxazolines, and leaving free 2-aminoimidazole available for nucleotide activation. The common synthetic origin of 2-aminoimidazole and 2-aminooxazole and their distinct reactivities are suggestive of a reaction network that could lead to both the synthesis of RNA monomers and to their subsequent chemical activation.

Kinetics and mechanism of the formation and reactions of S-nitroso derivatives of some heterocyclic thiones

Rate and equilibrium measurements have been obtained for the nitrosation (using nitrous acid in dilute acid aqueous solution) of the following thione-thiol nitrogen heterocyclic species and for the decomposition reactions of the formed S-NO- io

Equilibrium Studies on the Cleavage of Disulfide Bond in 2,2'-Dithio-Diimidazoles with Iodide Ion in Aqueous Solutions

The equilibrium of the reaction between 2,2'-dithio-diimidazoles and iodide ion in acidic aqueous solutions was studied spectrophotometrically.Cleavage of -S-S- bond and formation of imidazole-2-thiones and iodine, as reaction products, was observed.Factor analysis and spectra's deconvolution were used for estimation of equilibrium system composition and for determination of equilibrium constants.Occurrence of an additional band (with maximum at 30.000 cm-1) in equilibrium spectra was ascribed to the formation of imidazolethione-I2-charge-transfer complex. Key words: charge transfer, complex compounds, equilibrium constants