137-97-3

Basic information

• Product Name: 1,3-DI(O-TOLYL)THIOUREA
• Synonyms: usafek-1651;N,N'-DI(O-TOLYL)-2-THIOUREA;N,N'-DI-O-TOLYLTHIOUREA;AKOS B029093;1,3-DI(O-TOLYL)THIOUREA;1,3-DI-O-TOLYL-2-THIOUREA;2,2'-DIMETHYLTHIOCARBANILIDE;AURORA KA-6697
• CAS NO: 137-97-3
• Molecular Formula: C₁₅H₁₆N₂S
• Molecular Weight: 256.37
• EINECS: 205-309-6
• Product Categories: Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;DIG-DY;Organic Building Blocks;Sulfur Compounds;Thioureas
• Mol File: 137-97-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 157-159 °C(lit.)
• Boiling Point: 367.5°Cat760mmHg
• Flash Point: 176°C
• Appearance: /
• Density: 1.1437 (rough estimate)
• Vapor Pressure: 1.36E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• PKA: 12.02±0.70(Predicted)
• BRN: 2125770
• CAS DataBase Reference: 1,3-DI(O-TOLYL)THIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DI(O-TOLYL)THIOUREA(137-97-3)
• EPA Substance Registry System: 1,3-DI(O-TOLYL)THIOUREA(137-97-3)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38-50/53
• Safety Statements: 22-24/25-61-60-45-26
• WGK Germany: 3
• RTECS: FE0700000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 137-97-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless, crystalline leaflets; pungent odor. Not hygroscopic; soluble in alcohol, ether, and benzene; insoluble in water.

Uses

Different sources of media describe the Uses of 137-97-3 differently. You can refer to the following data:
1. 1,3-Di-o-tolylthiourea is a inhibitor of secreted aspartic protease SAP2. Effective in the treatment of drug-resistant Candida albicans infections
2. Metal-pickling inhibitor.

Hazard

Toxic by ingestion.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and SOx

InChI:InChI=1/C15H16N2S/c1-11-7-3-5-9-13(11)16-15(18)17-14-10-6-4-8-12(14)2/h3-10H,1-2H3,(H2,16,17,18)

Synthetic route

carbon disulfide (75-15-0) + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With sodium carbonate; triethylamine In water at 20 - 90℃; for 19h;	99.3%
With triethanolamine; Lac sulfur; water for 1.5h; Heating;	85%
With potassium hydroxide at 20℃; for 0.75h; Milling; Green chemistry;	84%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With quinoclamine at 0℃;	95%

sodium trithiocarbonate (534-18-9) + o-toluidine (95-53-4) → 1-methyl-2-pyridinethione (2044-27-1) + N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide In dimethyl sulfoxide at 40℃; for 4h;	A n/a B 94%

zinc diethyldithiocarbamate + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With triethanolamine; triethylamine In N,N-dimethyl-formamide for 2h; Heating;	82%

Ziram + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With triethanolamine; triethylamine In N,N-dimethyl-formamide for 2h; Heating;	80%

thiourea (17356-08-0) + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With PEG-400 In water for 0.0333333h; microwave irradiation;	77%

carbon disulfide (75-15-0) + o-toluidine (95-53-4) + benzylamine (100-46-9) → N,N'-di(o-tolyl)thiourea (137-97-3) + N-benzyl-N'-(2-methylphenyl)thiourea (40288-37-7) + dibenzyl thiourea (1424-14-2)

Conditions	Yield
at 100℃; Ionic liquid; Green chemistry;	A 13% B 75% C 12%

2-tolyl isothiocyanate (614-69-7) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With copper(l) iodide; caesium carbonate; 2-bromo-4,5-dimethoxy-benzamide; N,N`-dimethylethylenediamine In toluene at 20 - 120℃; Inert atmosphere;	62%

tetrachloromethane (56-23-5) + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With sodium sulfide; N-benzyl-N,N,N-triethylammonium chloride In water for 8h; Ambient temperature;	36%

(5-amino-[1,2,4]dithiazol-3-ylidene)-phenyl-amine (40229-47-8) + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With ethanol

N,N-dimethyl-o-toluidine (609-72-3) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With sulfur

thiophosgene (463-71-8) + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With water

o-toluidine (95-53-4) + N-allyl isothiocyanate (57-06-7) → N,N'-di(o-tolyl)thiourea (137-97-3)

o-toluidine (95-53-4) + 2-tolyl isothiocyanate (614-69-7) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With ethanol

o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With sulfur dichloride
With water; sulfur at 60℃;

Thiram (137-26-8) + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
In N,N-dimethyl-formamide for 1.5h; Heating;

bis(dimethylthiocarbamoyl)sulfide (97-74-5) + o-toluidine (95-53-4) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Heating;

ammonium salt of/the/ o-tolyl-dithiocarbamic acid → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With water

N,N'-bis(2-methylphenyl)urea (617-07-2) + CS2 → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
at 200℃;

o-toluidine (95-53-4) + CS2 → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With ethanol
With dihydrogen peroxide

o-hydrazotoluene + CS2 → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
at 150℃;

o-toluidine (95-53-4) + zinc-trithiocarbonate → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
With water

N-(o-tolyl)dithiocarbamic acid (45892-06-6) + water (7732-18-5) → N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
das Ammonium-Salz reagiert;

N-(o-tolyl)dithiocarbamic acid (45892-06-6) + water (7732-18-5) + ammonium carbonate → o-tolylthiourea (614-78-8) + N,N'-di(o-tolyl)thiourea (137-97-3)

Conditions	Yield
das Ammonium-Salz reagiert;

N-(o-tolyl)dithiocarbamic acid (45892-06-6) + water (7732-18-5) → N,N'-di(o-tolyl)thiourea (137-97-3) + 2-tolyl isothiocyanate (614-69-7)

Conditions	Yield
das Kupfer(II)-Salz reagiert;

bis(trichloromethyl) carbonate (32315-10-9) + N,N'-di(o-tolyl)thiourea (137-97-3) → C16H14N2OS

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 0.25h;	100%

N,N'-di(o-tolyl)thiourea (137-97-3) + C8H12N2O4 → 5-(ethoxycarbonyl)-4-methyl-3-o-tolyl-2-(o-tolylimino)-2,3-dihydrothiazole

Conditions	Yield
Stage #1: N,N'-di(o-tolyl)thiourea; C8H12N2O4 In tetrahydrofuran at 25℃; for 0.5h; Cycloaddition; Stage #2: In tetrahydrofuran for 8.5h; Rearrangement; Elimination; Heating;	96%

N,N'-di(o-tolyl)thiourea (137-97-3) → N,N'-bis(o-methylphenyl)carbodiimide (1215-57-2)

Conditions	Yield
With dicarbonyl(cyclopentadienyl)methyliron(II); Triethoxysilane In tetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere;	95%
With dmap; di-tert-butyl dicarbonate In ethyl acetate at 20℃; for 0.5h;	75%
With diethoxydisulfane; 4 A molecular sieve In dichloromethane for 2h; Heating;	43%

N,N'-di(o-tolyl)thiourea (137-97-3) → N,N'-bis(2-methylphenyl)urea (617-07-2)

Conditions	Yield
With sodium chlorite for 0.5h; Heating; further reagents;	94%
With potassium superoxide In dimethyl sulfoxide for 24h; Ambient temperature;	72%
With potassium hydroxide; dihydrogen peroxide

N,N'-di(o-tolyl)thiourea (137-97-3) + 3-phenylcarbamoylazo-crotonic acid ethyl ester (94126-56-4, 146000-79-5) → 5-(ethoxycarbonyl)-4-methyl-3-o-tolyl-2-(o-tolylimino)-2,3-dihydrothiazole

Conditions	Yield
Stage #1: N,N'-di(o-tolyl)thiourea; 3-phenylcarbamoylazo-crotonic acid ethyl ester In tetrahydrofuran at 25℃; for 0.5h; Cycloaddition; Stage #2: In tetrahydrofuran for 8.5h; Rearrangement; Elimination; Heating;	94%

malonic acid (141-82-2) + N,N'-di(o-tolyl)thiourea (137-97-3) → 1,3-di(2-methylphenyl)-2-thiobarbituric acid (85788-84-7)

Conditions	Yield
With acetyl chloride for 0.0125h; Irradiation;	92%
With chloroform; acetyl chloride

N,N'-di(o-tolyl)thiourea (137-97-3) → 4-methyl-N-(o-tolyl)benzo[d]thiazol-2-amine (74821-71-9)

Conditions	Yield
With polymer-supported tribromide at 100℃; for 0.166667h; Solvent; Temperature; Microwave irradiation;	86%
With disulfur dichloride at 60℃;	77%

bis(bis(diphenylphosphino)methanido)platinum(II) + N,N'-di(o-tolyl)thiourea (137-97-3) → {(bis(diphenylphosphino)methane)PtN(o-tolyl)C(=N(o-tolyl))S} * CH2Cl2

Conditions	Yield
With CH2Cl2 In dichloromethane byproducts: (C6H5)2PCH2P(C6H5)2; stirring equimolar amts. in CH2Cl2 for several minutes at room temp.; addn. of pentane;; crystn. on standing at -5°C;;	85%

tungsten hexacarbonyl (14040-11-0) + N,N'-di(o-tolyl)thiourea (137-97-3) → pentacarbonyl(sym-di-o-tolylthiourea)tungsten(0) (796047-40-0)

Conditions	Yield
In toluene under Ar or vac., 1 equiv. of S-compd., reflux for 4.5 h; soln. was cooled and evapd. in vac., solid was washed with petroleum ether (40-60 °C), recrystn. from benzene, elem. anal.;	82.4%
In tetrahydrofuran Irradiation (UV/VIS); under Ar or vac., 1 equiv. of S-compd., irradn. for 25 h with UV light; soln. was cooled and evapd. in vac., solid was washed with petroleum ether (40-60 °C), recrystn. from benzene;

N,N'-di(o-tolyl)thiourea (137-97-3) → [3H]-1,3-di-(2-tolyl)guanidine (97-39-2)

Conditions	Yield
With benzyl(triethyl)ammoniumpermanganate; ammonia In tetrahydrofuran at 5 - 10℃; for 0.5h;	82%
With triethanolamine; lac sulfur on alumina; sodium amide In tetrahydrofuran for 1h; Heating;	68%

N,N'-di(o-tolyl)thiourea (137-97-3) + ethyl 2-cyanoacetate (105-56-6) → 6-amino-1,3-di(2-methylbenzene)-2-thiouracil (130749-40-5)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 0 - 5℃;	80%

morpholine (110-91-8) + N,N'-di(o-tolyl)thiourea (137-97-3) → N-o-tolyl-morpholine-4-carboximidic acid 2-methyl-anilide

Conditions	Yield
With triethanolamine; lac sulfur on alumina In tetrahydrofuran for 1.5h; Heating;	80%

N,N'-di(o-tolyl)thiourea (137-97-3) → N,N'-bis(2-methylphenyl)urea (617-07-2) + [3H]-1,3-di-(2-tolyl)guanidine (97-39-2)

Conditions	Yield
With sodium periodate; ammonia In water; N,N-dimethyl-formamide at 80 - 85℃; for 0.5h;	A n/a B 80%

tetracarbonyl(1,10-phenanthroline)tungsten(0) (14729-20-5) + N,N'-di(o-tolyl)thiourea (137-97-3) → (o-phenanthroline)tricarbonyl(sym-di-o-tolylthiourea)tungsten(0) (796047-60-4)

Conditions	Yield
In xylene under Ar or vac., 1 equiv. of S-compd., reflux for 4 h; soln. was cooled to room temp., filtered, solid was washed with petroleum ether (40-60 °C) and 2-3 times with benzene, elem. anal.;	78.3%

(2,2'-bipyridine)tetracarbonyltungsten(0) (15668-66-3) + N,N'-di(o-tolyl)thiourea (137-97-3) → (2,2'-bipyridine)tricarbonyl(sym-di-o-tolylthiourea)tungsten(0) (796047-55-7)

Conditions	Yield
In xylene under Ar or vac., 1 equiv. of S-compd., reflux for 4 h; soln. was cooled to room temp., filtered, solid was washed with petroleum ether (40-60 °C) and 2-3 times with benzene, elem. anal.;	76.4%

N,N'-di(o-tolyl)thiourea (137-97-3) + o-toluidine (95-53-4) → N,N',N''-tri(2-tolyl)guanidine (87927-72-8)

Conditions	Yield
With potassium hydroxide In water; nitrobenzene at 105℃; for 6h;	75%

pentacarbonyl(triphenylarsine)tungsten(0) (29743-02-0) + N,N'-di(o-tolyl)thiourea (137-97-3) → cis-tetracarbonyl(sym-di-o-tolylthiourea)(triphenylarsine)tungsten(0) (796047-50-2)

Conditions	Yield
In xylene under Ar or vac., 1 equiv. of S-compd., reflux for 5 h; soln. was cooled to room temp., solvent was removed in vac., residue waswashed 4-5 times with petroleum ether (40-60 °C), dried in vac., elem. anal.;	70.2%

triphenylphosphine tungsten pentacarbonyl (15444-65-2) + N,N'-di(o-tolyl)thiourea (137-97-3) → cis-tetracarbonyl(sym-di-o-tolylthiourea)(triphenylphosphine)tungsten(0) (796047-45-5)

Conditions	Yield
In xylene under Ar or vac., 1 equiv. of S-compd., reflux for 4 h; soln. was cooled to room temp., solvent was removed in vac., residue waswashed 4-5 times with petroleum ether (40-60 °C), dried in vac., elem. anal.;	68.4%

N,N'-di(o-tolyl)thiourea (137-97-3) + manganese triacetate (638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3) → 1-acetyl-1,3-di-o-tolyl-urea

Conditions	Yield
In acetonitrile for 3h; Heating;	63%

N,N'-di(o-tolyl)thiourea (137-97-3) → N,N'-bis(2-methylphenyl)urea (617-07-2) + N,N',N''-tri(2-tolyl)guanidine (87927-72-8)

Conditions	Yield
With KO2 In tetrahydrofuran at 20℃; for 35h;	A n/a B 60%

N,N'-di(o-tolyl)thiourea (137-97-3) + bromoacetic acid (79-08-3) → 2-(o-tolyl)imino-3-(o-tolyl)-thiazolidin-4-one (16240-00-9)

Conditions	Yield
With sodium acetate In ethanol for 6h; Heating;	55.4%

N,N'-di(o-tolyl)thiourea (137-97-3) → o-toluidine (95-53-4) + N,2-dimethylaniline (611-21-2)

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 1h;	A 44% B 48%

Upstream product

• 40229-47-8 (5-amino-[1,2,4]dithiazol-3-ylidene)-phenyl-amine 
• 95-53-4 o-toluidine 
• 17356-08-0 thiourea 
• 75-15-0 carbon disulfide 
• 57-06-7 N-allyl isothiocyanate 
• 614-69-7 2-tolyl isothiocyanate 
• 56-23-5 tetrachloromethane 
• 534-18-9 sodium trithiocarbonate 
• 45892-06-6 N-(o-tolyl)dithiocarbamic acid 
• 7732-18-5 water 
• 100-46-9 benzylamine 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 617-07-2 N,N'-bis(2-methylphenyl)urea 
• 97-74-5 bis(dimethylthiocarbamoyl)sulfide 

Downstream Products

• 85788-84-7 1,3-di(2-methylphenyl)-2-thiobarbituric acid 
• 1215-77-6 1-phenyl 3-o-tolylthiocarbamide 
• 617-07-2 N,N'-bis(2-methylphenyl)urea 
• 97-39-2 1,3-Di(2-tolyl)guanidine 
• 614-69-7 2-tolyl isothiocyanate 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 33913-15-4 N-o-tolylbutyramide 
• 10023-39-9 (4-oxo-3-o-tolyl-2-o-tolylimino-thiazolidin-5-yl)-acetic acid 
• 35252-24-5 (7-methyl-3-o-tolyl-3H-thiazolo[4,5-b]quinoxalin-3-ylidene)-o-tolyl-amine 
• 21352-63-6 3,8-di-o-tolyl-2,7-bis-o-tolylimino-1,6-dithia-3,8-diaza-spiro[4.4]nonane-4,9-dione 
• 63208-32-2 [3-(2-methyl-anilino)-4-o-tolyl-4H-[1,2,4]thiadiazol-5-ylidene]-o-tolyl-amine 
• 38716-59-5 C₁₅H₁₆N₂O₂S 
• 1215-57-2 N,N'-bis(o-methylphenyl)carbodiimide 
• 36220-73-2 [4-(4-chloro-phenyl)-3-o-tolyl-3H-thiazol-2-ylidene]-o-tolyl-amine 

Relevant articles and documents

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Synthesis method of thiourea

The invention relates to a synthesis method of thiourea. A method for generating thiourea from amine and carbon disulfide under the action of tertiary amine alkali is a common synthesis method adoptedin the prior art; and when the method is used for preparing the thiourea, a byproduct, namely hydrogen sulfide is generate, and the hydrogen sulfide needs to be fully absorbed by an alkali absorptionsystem and also reacts with the tertiary amine alkali to generate an amine salt, so a large amount of a tertiary amine alkali catalyst needs to be added in the reaction. In order to solve the above problem, the invention provides the synthesis method for thiourea; and according to the synthesis method, a proper amount of an inorganic base is added into a reaction system, so the inorganic base cantimely react with the byproduct hydrogen sulfide to form an inorganic salt without a subsequent alkali absorption system, the usage amount of the catalyst tertiary amine alkali can be greatly reduced, and the subsequent recovery work of a large amount of the tertiary amine alkali is also reduced.

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