2114-02-5

Basic information

• Product Name: Amidinothiourea
• Synonyms: GUANYLTHIOUREA;2-IMINO-4-THIOBIURET;[(AMINOCARBOTHIOYL)AMINO]METHANIMIDAMIDE;AMINOIMINOETHYL THIOUREA;AMIDINOTHIOUREA;ZERENEX ZX006496;1-amidino-2-thiourea;Guanphenisin BP
• CAS NO: 2114-02-5
• Molecular Formula: C₂H₆N₄S
• Molecular Weight: 118.16
• EINECS: 218-308-0
• Product Categories: Pharmaceutical Intermediates;Famotidine
• Mol File: 2114-02-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 171-173 °C(lit.)
• Boiling Point: 310.5 °C at 760 mmHg
• Flash Point: 141.6 °C
• Appearance: White to off-white/Crystalline Powder or Crystals
• Density: 1.301 (estimate)
• Vapor Pressure: 0.000599mmHg at 25°C
• Refractive Index: 1.5605 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.89±0.70(Predicted)
• Water Solubility: 7 g/100 mL (20 ºC)
• BRN: 1756620
• CAS DataBase Reference: Amidinothiourea(CAS DataBase Reference)
• NIST Chemistry Reference: Amidinothiourea(2114-02-5)
• EPA Substance Registry System: Amidinothiourea(2114-02-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-24/25-23
• RIDADR: 2811
• WGK Germany: 3
• RTECS: YR8250000
• PackingGroup: III
• Hazardous Substances Data: 2114-02-5(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystals or crystalline powder

Uses

2-Imino-4-thiobiuret is used in the design and synthesis of guanylthiourea derivatives which are potential inhibitors of plasmodium falciparum dihydrofolate reductase enzyme. 2-Imino-4-thiobiuret is also used as a reagent in recyclization reactions of N-arylmaleimides with polynucleophilic compounds.

InChI:InChI=1/C2H6N4S/c3-1(4)6-2(5)7/h(H6,3,4,5,6,7)/p+1

Synthetic route

N-Cyanoguanidine (127099-85-8, 780722-26-1) → amidinothiocarbamide (2114-02-5)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; hydrogen sulfide at 70 - 80℃; Substitution;	93%
With ammonium sulfide; sulfuric acid In water at 60 - 65℃; for 17h; pH=9.6; Addition;	50.5%
With hydrogen sulfide; water at 60 - 70℃;

cyanocarboxamidine (37507-70-3) → amidinothiocarbamide (2114-02-5)

Conditions	Yield
Stage #1: cyanocarboxamidine With hydrogenchloride In water at 20℃; Stage #2: With ammonium hydroxide; Sodium thiosulfate pentahydrate In water at 0℃; for 1h;	80%

thiophosgene (463-71-8) + thiourea (17356-08-0) → amidinothiocarbamide (2114-02-5)

Conditions	Yield
at 100 - 110℃;

thiourea (17356-08-0) → amidinothiocarbamide (2114-02-5)

Conditions	Yield
With thiophosgene at 100 - 110℃;
With phosphorus pentachloride at 100℃;

thiourea (17356-08-0) → amidinothiocarbamide (2114-02-5) + BIGUANIDE (56-03-1)

Conditions	Yield
With phosphorus pentachloride
With thiophosgene

N-Cyanoguanidine (127099-85-8, 780722-26-1) → amidinothiocarbamide (2114-02-5) + 2,4-Dithiobiuret (541-53-7)

Conditions	Yield
With water at 75℃; dann auf 65-70grad unter Durchleiten eines schwachen H2S-Stroms;

copper(II) dicyanamide (14890-16-5, 18447-47-7, 21962-69-6) → amidinothiocarbamide (2114-02-5)

Conditions	Yield
With ammonium hydroxide; hydrogen sulfide

C2H5ClN4*ClH → amidinothiocarbamide (2114-02-5)

Conditions	Yield
With sodium thiosulfate at 0 - 20℃; Yield given;

phosphorus pentachloride (10026-13-8, 874483-75-7) + thiourea (17356-08-0) → amidinothiocarbamide (2114-02-5)

Conditions	Yield
at 100℃;

N-Cyanoguanidine (127099-85-8, 780722-26-1) + ammonium sulfide → amidinothiocarbamide (2114-02-5) + ammonium thiocyanate (1147550-11-5) + thiourea (17356-08-0)

water (7732-18-5) + thiourea (17356-08-0) → dicyandiamide (504-66-5) + CYANAMID (420-04-2) + amidinothiocarbamide (2114-02-5) + guanidine sulfate(?)

Conditions	Yield
Einwirkung von γ-Strahlen.Irradiation;

4.6-diimino-2-thione-tetrahydro-1.3.5-thiodiazine → amidinothiocarbamide (2114-02-5)

Conditions	Yield
With mineral acids die Salze enstehen;
With organic acids die Salze enstehen;
With mineral acids die Salze enstehen;
With organic acids die Salze enstehen;

cyanogendiamidine salt → amidinothiocarbamide (2114-02-5)

Conditions	Yield
With hydrogen sulfide; water

dicyandiamide (127099-85-8, 780722-26-1) → amidinothiocarbamide (2114-02-5)

Conditions	Yield
With hydrogen sulfide In water 70-80°C;

dicyandiamide (127099-85-8, 780722-26-1) → amidinothiocarbamide (2114-02-5) + 2,4-Dithiobiuret (541-53-7)

Conditions	Yield
With ammonium hydroxide; hydrogen sulfide In water at 80℃; for 80h;

amidinothiocarbamide (2114-02-5) + acetone (67-64-1) → 2-guanidino-4-chloromethyl-thiazole (81152-53-6)

Conditions	Yield
With Oxone; lithium chloride In methanol at 60℃; for 1h; Reagent/catalyst;	98%

amidinothiocarbamide (2114-02-5) + acetone (67-64-1) → 2-guanidino-4-bromomethylthiazole

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	97%

amidinothiocarbamide (2114-02-5) + dimethyl sulfate (77-78-1) → C3H8N4S (40294-42-6)

Conditions	Yield
at 30 - 40℃; Methylation;	95%

ruthenium trichloride hydrate + amidinothiocarbamide (2114-02-5) + nitrogen(II) oxide (10102-43-9) → [Ru(SC(NH2)NC(NH2)NH)(NO)Cl2(H2O)]*2H2O

Conditions	Yield
In methanol NO and N2 passed through methanolic soln. of RuCl3*99H2O for 1 h, organic compound in methanol added; filtered, washed with methanol, dried in vacuum, elem. anal.;	95%

amidinothiocarbamide (2114-02-5) + nitrogen(II) oxide (10102-43-9) + cobalt(II) chloride (7646-79-9) → [Co(NHC(S)NHCNH(NH2))2(NO)(H2O)]

Conditions	Yield
With NH3 In water N2 and NO passed through CoCl2 soln. at 0°C for 30 min, aq. soln. of organic compound added at 0°C, passage of N2 and NO continued for 30 min, NH3 added, passage of N2 and NO for 8-12 h; soln. flushed with N2, filtered, washed with cold water and methanol, dried over fused CaCl2 under N2, elem. anal.;	95%

amidinothiocarbamide (2114-02-5) → 3,5-diamino-1,2,4-thiadiazole hydrochloride

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide In water at 18 - 20℃; for 1h; Cyclization;	93%

amidinothiocarbamide (2114-02-5) + ethyl acetoacetate (141-97-9) → ethyl 2-(carbamimidoylamino)-4-methyl-1,3-thiazole-5-carboxylate (7185-65-1)

Conditions	Yield
With Oxone; potassium bromide In ethanol at 80℃; for 2h;	93%

amidinothiocarbamide (2114-02-5) + acetoacetic acid methyl ester (105-45-3) → methyl 2-guanidino-4-methylthiazole-5-carboxylate

Conditions	Yield
With Oxone; sodium chloride In ethanol at 80℃; for 1h;	93%

amidinothiocarbamide (2114-02-5) + para-bromoacetophenone (99-90-1) → N-(4-(4-bromophenyl)-1,3-thiazol-2-yl)guanidine (7120-03-8)

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	93%

amidinothiocarbamide (2114-02-5) + 3-Methylacetophenone (585-74-0) → N-(4-(3-methylphenyl)-1,3-thiazol-2-yl)guanidine

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	93%

amidinothiocarbamide (2114-02-5) + 3'-Chloroacetophenone (99-02-5) → N-(4-(3-chlorophenyl)-1,3-thiazol-2-yl)guanidine

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	92%

amidinothiocarbamide (2114-02-5) + methyl 2-naphthyl ketone (93-08-3) → N-(4-(2-naphthyl)-1,3-thiazol-2-yl)guanidine

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	92%

amidinothiocarbamide (2114-02-5) + 1,3-diphenyl-2-propynone (7338-94-5) → (4,6-diphenyl-2H-1,3-thiazin-2-ylidene)guanidine hydrobromide

Conditions	Yield
With hydrogen bromide In acetic acid at 20℃; for 1h;	91%

amidinothiocarbamide (2114-02-5) + 1-(4-fluorophenyl)ethanone (403-42-9) → N-(4-(4-fluorophenyl)-1,3-thiazol-2-yl)guanidine

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	91%

amidinothiocarbamide (2114-02-5) + Methyl 4-chloroacetoacetate (32807-28-6) → methyl 2-(2-guanidinothiazol-4-yl)acetate hydrochloride (1395069-10-9)

Conditions	Yield
In methanol for 4h; Reflux;	90%

amidinothiocarbamide (2114-02-5) + 1,3-bis-(bromomethyl)benzene (626-15-3) → 1,3-bis(amidinothioureamethyl)benzene

Conditions	Yield
In acetonitrile Reflux;	90%

amidinothiocarbamide (2114-02-5) + 3-iodobenzylalcohol (57455-06-8) → (3-iodo)benzyl amidinoisothiourea

Conditions	Yield
With hydrogen bromide In water at 100℃;	90%

amidinothiocarbamide (2114-02-5) + 5-bromo-3-(2-chloroacetyl)-1-methoxyindole → 2-diaminomethyleneamino-4-(5-bromo-1-methoxyindol-3-yl)thiazole

Conditions	Yield
In methanol for 3h; Reflux;	90%

amidinothiocarbamide (2114-02-5) + acetone (67-64-1) → 2-guanidino-4-methylthiazole (7120-01-6)

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 3h;	90%

amidinothiocarbamide (2114-02-5) + 1-(3-Bromophenyl)ethanone (2142-63-4) → N-(4-(3-bromophenyl)-1,3-thiazol-2-yl)guanidine

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	90%

amidinothiocarbamide (2114-02-5) + 2-bromo-1-[4-(1-tricyclo[3.3.1.13,7]decyl)phenyl]ethanone → 1-{2-[4-(1-tricyclo[3.3.1.13,7]decyl)phenyl]thiazol-4-yl}guanidine hydrobromide

Conditions	Yield
In ethanol for 18h; Hantzsch Thiazole Synthesis; Reflux;	89%

amidinothiocarbamide (2114-02-5) + α-bromoacetophenone (70-11-1) → N-(4-phenyl-1,3-thiazol-2-yl)guanidine (2507-81-5)

Conditions	Yield
In 1,4-dioxane for 7h; Reflux;	88%
In acetone for 4h; Heating / reflux;	87%
In ethanol at 80℃; for 4h;	87%
In methanol Heating;

amidinothiocarbamide (2114-02-5) + 1-(3-fluorophenyl)ethanone (455-36-7) → N-(4-(3-fluorophenyl)-1,3-thiazol-2-yl)guanidine

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 1h;	88%

amidinothiocarbamide (2114-02-5) + C23H26O4 (1169703-80-3) → 1-{4-(2-hydroxy-4-methoxyphenyl)-5-[4-methoxy-3,5-bis(1-methylethyl)phenyl]pyrimidin-2-yl}thiourea (1233943-93-5)

Conditions	Yield
With sodium methylate In methanol for 3.5h; Reflux;	87%

amidinothiocarbamide (2114-02-5) + 2-bromo-1-(2-(4-butylphenyl)-4-methylthiazol-5-yl)ethan-1-one → 1-(2'-(4-butylphenyl)-4'-methyl-[5,5'-bithiazol]-2-yl)guanidine

Conditions	Yield
With potassium carbonate In ethanol Reflux;	87%

amidinothiocarbamide (2114-02-5) + para-chloroacetophenone (99-91-2) → N-(4-(4-chlorophenyl)-1,3-thiazol-2-yl)guanidine (7120-02-7)

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	87%

amidinothiocarbamide (2114-02-5) + 1-(4-methoxyphenyl)ethanone (100-06-1) → N-(4-(4-methoxyphenyl)-1,3-thiazol-2-yl)guanidine (91089-11-1)

Conditions	Yield
With Oxone; sodium bromide In methanol at 60℃; for 2h;	87%

amidinothiocarbamide (2114-02-5) → 1,2,4-thiadiazole-3,5-diamine (34283-30-2)

Conditions	Yield
With dihydrogen peroxide In methanol Heating;	86%
With pyridine; 4-bromo-3-methyl-<1H>-pyrazolin-5-one In ethanol for 3h; Heating;	52%
With hydrogenchloride; dihydrogen peroxide

amidinothiocarbamide (2114-02-5) + 2-hydroxy-5-nitrobenzyl chloride (2973-19-5) → (2-hydroxy-5-nitrophenyl)methyl amidinoisothiourea hydrochloride

Conditions	Yield
In acetonitrile at 85 - 100℃; for 0.0833333h; microwave irradiation;	86%

Upstream product

• 7732-18-5 water 
• 17356-08-0 thiourea 
• 37507-70-3 cyanocarboxamidine 
• 127099-85-8 N-Cyanoguanidine 
• 10026-13-8 phosphorus pentachloride 
• 14890-16-5 copper(II) dicyanamide 
• 463-71-8 thiophosgene 
• 127099-85-8 dicyandiamide 

Downstream Products

• 92132-60-0 <4-(3-cyanophenyl)-2-thiazolyl>guanidine hydrobromide 
• 92132-72-4 3-<2-<(aminoiminomethyl)amino>-4-thiazolyl>benzenecarboximidamide dihydrobromide hemiethanolate 
• 112598-39-7 2-guanidino-4-<3-(dimethylamino)phenyl>thiazole hydrobromide 
• 92132-60-0 [4-(3-Cyanophenyl)-2-Thiazolyl]Guanidine, Hydrobromide 
• 92132-55-3 [4-(4-Cyanophenyl)-2-Thiazolyl]Guanidine, Hydrobromide 
• 179419-39-7 2-Amidino-4-(3-trifluoromethylphenyl)thiazole Hydrobromide 
• 473551-95-0 N-{4-[3-(7-Chloro-8-dimethylamino-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-phenyl]-thiazol-2-yl}-guanidine 
• 289468-42-4 2-guanidino-4-methyl-5-(3-methoxypyridin-2-yl)thiazole 
• 69014-12-6 2-guanidino-4-chloromethyl-thiazol hydrochloride 
• 474969-90-9 N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]-[4-(2-guanidinothiazol-4-yl)thiazol-2-ylthio]acetamide 
• 232596-12-2 methyl 2-guanidino-5-phenyl-thiazol-4-carboxylate 

Relevant articles and documents

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ANTIBACTERIAL THERAPEUTICS AND PROPHYLACTICS

The present disclosure relates generally to novel molecules, compositions, and formulations for treatment of bacterial infections in general and more specifically to bacterial infections with antibiotic resistant pathogens.

New fluoro intermediates for herbicidal sulfonylureas

New pyrimidine and triazine intermediates for herbicidal sulfonylureas are prepared as follows: 2,4-dichloro-6-methylpyrimidine is converted via a halogenation, halogen exchange and substitution sequence to 2-amino-4-trifluoromethyl-6-trifluoromethoxypyrimidine. New fluoromethyl-triazines are available starting from guanidine, trichloroacetonitrile and difluoroacetic anhydride, or alternatively from thiocarbamoyl guanidine and chlorodifluoroacetic ester ring closure. To obtain new o-fluoroalkyl-benzenesulfonamide precursors, o-chlorobenzaldehyde was fluorinated with sulfur tetrafluoride, or a bromobenzene derivative was subjected to a substitution reaction with sodium pentafluoropropionate. Sulfonylureas derived from trifluoromethylpyrimidines with an m-methylthio substituent are selective post-emergence herbicides in cotton, presumably due to sulfone metabolization. Selectivity in wheat is obtained by combining 4-methoxy-6-trifluoromethyl-pyrimidine with a lipophilic difluoromethylbenzenesulfonamide moiety. Also in the difluoromethyl-triazine series, the combination with the difluoromethyl-benzenesulfonamide moiety is a good choice for wheat selectivity. Chlorodifluoromethyl- and trifluoromethyltriazines, however, combine better with an aromatic ester for best activity and selectivity in wheat. Selected compounds are undergoing broad field tests in wheat.