Imidazole-2-thiol supplier

Name
2-MERCAPTOIMIDAZOLE
EINECS
CAS No. 872-35-5
Article Data19
CAS DataBase
Density 1.36g/cm³
Solubility
Melting Point 228-231 °C(lit.)
Formula C3H4 N2 S
Boiling Point 152.4°C at 760 mmHg
Molecular Weight 100.144
Flash Point 46°C
Transport Information
Appearance
Safety Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NO_x and SO_x. See also MERCAPTANS.
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms 2-Imidazolemercaptan(3CI); 4-Imidazoline-2-thione (7CI); Imidazole-2-thiol (6CI,8CI);1,3-Dihydro-2H-imidazole-2-thione; 1,3-Dihydroimidazole-2-thione;1,3-Vinylenethiourea; 1H-Imidazole-2-thiol; 2-Mercapto-1H-imidazole;2-Mercaptoimidazole; 2-Thioimidazole; 2-Thioxo-2,3-dihydroimidazole; NSC 112715
PSA 67.48000
LogP 0.69840

Synthetic route

: 1147550-11-5
ammonium thiocyanate

: 141-46-8
Glycolaldehyde

: 872-35-5
1,3-dihydro-imidazole-2-thione

Conditions

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

: 22483-09-6
2,2-dimethoxyethylamine

: 872-35-5
1,3-dihydro-imidazole-2-thione

Conditions

Conditions	Yield
With hydrogenchloride

: 2,2'-dithiodi(imidazole) bis(perchloric acid) salt

A: 288-32-4
1H-imidazole

B: 872-35-5
1,3-dihydro-imidazole-2-thione

Conditions

Conditions	Yield
With Carbonate buffer at 25℃; Kinetics;

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 79-11-8
chloroacetic acid

: 14395-78-9
(1H-imidazol-2-ylsulfanyl)-acetic acid

Conditions

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%

: 58-27-5
menadione

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 1449761-93-6
2-(1H-imidazole-2-ylthio)-3-methylnaphthalene-1,4-dione

Conditions

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

: 99-40-1
2-chloro-3',4'-dihydroxyacetophenone

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 1-(3,4-dihydroxy-phenyl)-2-(1H-imidazol-2-ylsulfanyl)-ethanone; hydrochloride

Conditions

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

: (S)-benzyl 2-(bromomethyl)pyrrolidine-1-carboxylate

: 872-35-5
1,3-dihydro-imidazole-2-thione

: C16H19N3O2S

Conditions

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

: 3209-22-1
1,2-Dichloro-3-nitrobenzene

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 683276-68-8
2-(2-chloro-6-nitrophenylthio)imidazole

Conditions

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

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 2-(isobutylamino)benzyl chloride hydrochloride

: 128936-04-9
N-isobutyl-2-<(2-imidazolylthio)methyl>aniline

Conditions

Conditions	Yield
In ethanol; chloroform; water	94%

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 111-36-4
n-butyl isocyanide

: 2-mercaptoimidazole-carboxylic acid butylamide

Conditions

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

: 1585-17-7
2,4-bis(chloromethyl)mesitylene

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 1258931-95-1
1,3-bis(1-imidazolyl-2-thione)-2,4,6-trimethylbenzene

Conditions

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

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 89418-44-0
2,2'-dithiodi(1H-imidazole)

Conditions

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%

: 928793-94-6
3-tert-butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 928794-65-4
3-tert-butoxycarbonyl-7-chloro-6-(1H-imidazol-2-ylthiomethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Conditions

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

: 1027781-75-4
benzyl 3-bromo-5-[(methylsulfonyloxy)methyl]isoxazole-4-carboxylate

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 1027781-80-1
benzyl 3-bromo-5-[(1H-imidazol-2-ylthio)methyl]isoxazole-4-carboxylate

Conditions

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

: 19614-12-1
2-bromo-5-methoxybenzyl bromide

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 1353998-99-8
7-methoxy-5H-benzo[d]imidazo[2,1-b][1,3]thiazine

Conditions

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%

: 1062602-29-2
1-(p-methoxyphenyl)-3-(phenylsulfanyl)propargyl alcohol

: 872-35-5
1,3-dihydro-imidazole-2-thione

: C19H16N2OS2

Conditions

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

: 1062602-39-4
1-(4-methoxyphenyl)-3-(phenylselanyl)prop-2-yn-1-ol

: 872-35-5
1,3-dihydro-imidazole-2-thione

: C19H16N2OSSe

Conditions

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

: 872-35-5
1,3-dihydro-imidazole-2-thione

: C43H46N4O8S

Conditions

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

: 3-((3,4-dimethoxyphenethyl)imino)-2-phenylacrylic acid methyl ester

: 872-35-5
1,3-dihydro-imidazole-2-thione

: C43H46N4O8S

Conditions

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

: 111559-54-7
(3-Propionyl-oxiranylmethyl)-phosphonic acid diethyl ester

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 113250-36-5
<<2,3-Dihydro-2-(1-oxopropyl)imidazo<2,1-b>thiazol-3-yl>methyl>phosphonsaeure-diethylester

Conditions

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

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 121-17-5
2-chloro-3-nitro-5-trifluoromethylbenzene

: 88251-66-5
2-(2-nitro-4-trifluoromethylphenylthio)imidazole

Conditions

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

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 141956-48-1
-<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

: 141956-54-9
-<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

Conditions

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

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 2216-94-6
phenylpropynoic acid ethyl ester

: (Z)-2-benzylidene-imidazo[2,1-b]thiazol-3-one

Conditions

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

: 52548-14-8
2-iodoyl-5-methylbenzoic acid

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 7-methyl-5H-imidazo[2,1-b][1,3]benzothiazin-5-one

Conditions

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

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 2-(vinylthio)imidazole

Conditions

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

: 27656-88-8
n-propylmercaptoisothiourea hydrochloride

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 141400-55-7
2-Propyldisulfanyl-1H-imidazole

Conditions

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

: 141738-34-3
[RuCl2(PPh3)([9]aneS3)]

: 872-35-5
1,3-dihydro-imidazole-2-thione

: RuCl(P(C6H5)3)(C3H4N2S)(C6H12S3)(1+)*Cl(1-)*0.5CHCl3 = [RuCl(P(C6H5)3)(C3H4N2S)(C6H12S3)]Cl*0.5CHCl3

Conditions

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

: 32993-05-8
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II)

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 1663-45-2
1,2-bis-(diphenylphosphino)ethane

: 1257344-51-6
CpRu(bis(diphenylphosphino)ethane)S(2-imidazolyl)

Conditions

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%

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%

...Expand

: 658040-87-0
7-methoxy-2-methylsulfonyl-3-phenyl-4H-1-benzopyran-4-one

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 2-(1H-imidazol-2-ylsulfanyl)-7-methoxy-3-phenyl-chromen-4-one

Conditions

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

: 61150-57-0
2-bromo-4-fluorobenzyl bromide

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 1353999-05-9
8-fluoro-5H-benzo[d]imidazo[2,1-b][1,3]thiazine

Conditions

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%

: 637-87-6
1-Chloro-4-iodobenzene

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 2-((4-chlorophenyl)thio)-1H-imidazole

Conditions

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

: 99-40-1
2-chloro-3',4'-dihydroxyacetophenone

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 2-((1H-imidazol-2-yl)thio)-1-(3,4-dihydroxyphenyl)ethan-1-one hydrochloride

Conditions

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%

: 872-35-5
1,3-dihydro-imidazole-2-thione

: 109-77-3
malononitrile

: 1761-61-1
5-bromosalicyclaldehyde

: 5-(1H-imidazol-2-ylsulfanyl)-2,4-diamino-7-bromo-5H-chromeno[2,3-b]pyridine-3-carbonitrile

Conditions

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%

...Expand

Imidazole-2-thiol Chemical Properties

IUPAC: 1,3-Dihydroimidazole-2-thione
Imidazole-2-thiol with CAS NO.of 872-35-5 is also called for 2-Mercaptoimidazole ; 2-Imidazolethiol ; 1H-Imidazole-2-thiol ; Mercaptoimidazole ; 1,3-Vinylenethiourea ; 1H-Imidazolethiol ; Imidazole, 2-mercapto- ; 4-Imidazoline-2-thione ; USAF EL-57 and so on.
CAS: 872-35-5
Molecular Formula: C₃H₄N₂S
Molecular Weight: 100.14
EINECS: 212-823-4
ACD/LogP: 0.21
ACD/LogD (pH 5.5): 0.21
ACD/LogD (pH 7.4): 0.21
ACD/BCF (pH 5.5): 1
ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 31.14
ACD/KOC (pH 7.4): 31.14
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 0
Heavy Atom Count: 6
Formal Charge: 0
Complexity: 87
Isotope Atom Count: 0
Defined Atom StereoCenter Count: 0
Undefined Atom StereoCenter Count: 0
Defined Bond StereoCenter Count: 0
Undefined Bond StereoCenter Count: 0
Covalently-Bonded Unit Count: 1
Index of Refraction: 1.696
Molar Refractivity: 28.21 cm³
Molar Volume: 73.3 cm³
Surface Tension: 68.9 dyne/cm
Density: 1.36 g/cm³
Flash Point: 46°C
Enthalpy of Vaporization: 38.92 kJ/mol
Boiling Point: 152.4°C at 760 mmHg
Vapour Pressure: 3.5 mmHg at 25°C
The molecular structure of Imidazole-2-thiol with CAS NO.of 872-35-5:

Imidazole-2-thiol Toxicity Data With Reference

ipr-mus LD50:200 mg/kg

NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .

Imidazole-2-thiol Consensus Reports

Reported in EPA TSCA Inventory.

Imidazole-2-thiol Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NO_x and SO_x. See also MERCAPTANS.
Hazard Codes: Xi Irritant
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: NI8515000
F: 10

Imidazole-2-thiol Specification

Removal in wastewater treatment of Imidazole-2-thiol (CAS NO.872-35-5):
Total removal:1.90 percent
Total biodegradation:0.09 percent
Total sludge adsorption:1.75 percent
Total to air:0.05 percent
(using 10000 hr Bio P,A,S)

Product Name

2-MERCAPTOIMIDAZOLE

Synthetic route

Imidazole-2-thiol Chemical Properties

Imidazole-2-thiol Toxicity Data With Reference

Imidazole-2-thiol Consensus Reports

Imidazole-2-thiol Safety Profile

Imidazole-2-thiol Specification

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