4100-41-8

Basic information

• Product Name: 5-Amino-1,2,3-thiadiazole
• Synonyms: 5-AMINO-1,2,3-THIADIAZOLE;5-AMINO-1,2,3-ANILIDOTHIODIAZOLE;1,2,3-Thiadiazol-5-amine;5-AMINO-1,2,3-ANILIDOTHIOBIAZOLE;1,2,3-Thiadiazol-5-amine(9CI);thiadiazol-5-amine;thiadiazol-5-ylamine;5-AMINO-1,2,3-THIADIAZOLE (MFCD00082810)
• CAS NO: 4100-41-8
• Molecular Formula: C₂H₃N₃S
• Molecular Weight: 101.13
• EINECS: 223-868-4
• Product Categories: VARIOUSAMINE
• Mol File: 4100-41-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 224-235°C (dec.)
• Boiling Point: 239.8 °C at 760 mmHg
• Flash Point: 98.9 °C
• Appearance: white to light yellow crystal powder
• Density: 1.495 g/cm³
• Vapor Pressure: 0.0392mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 0.34±0.50(Predicted)
• CAS DataBase Reference: 5-Amino-1,2,3-thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-1,2,3-thiadiazole(4100-41-8)
• EPA Substance Registry System: 5-Amino-1,2,3-thiadiazole(4100-41-8)

Safety Data

• Hazardous Substances Data: 4100-41-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

5-Amino-1,2,3-thiadiazole, as a thiadiazole derivative, is a privileged structure in medicinal chemistry and has been investigated for anticonvulsant and antimicrobial activities.

InChI:InChI=1/C2H3N3S/c3-2-1-4-5-6-2/h1H,3H2

Synthetic route

methyl 2-chloroethylhydrazinoformate → 1,2,3-thiadiazol-5-ylamine (4100-41-8)

Conditions	Yield
Stage #1: methyl 2-chloroethylhydrazinoformate With thionyl chloride; sodium hydroxide In chloroform at 30℃; pH=10; Cooling with ice; Stage #2: With ammonia for 4h; Cooling with ice;	97.1%

diazoacetonitrile (13138-21-1) → 1,2,3-thiadiazol-5-ylamine (4100-41-8)

Conditions	Yield
With hydrogen sulfide; triethylamine In tetrachloromethane; dichloromethane at -10℃; for 0.75h;	73%
With triethylamine In hexane; dichloromethane
With triethylamine In hexane; dichloromethane
With sodium hydrogensulfide In ethanol
With sodium methylate In methanol

N-[1,2,3]thiadiazol-5-yl-phthalimide (4100-40-7) → 1,2,3-thiadiazol-5-ylamine (4100-41-8)

Conditions	Yield
With hydrazine hydrate In ethanol

(1,2,3-thiadiazole-5-yl)-carbamic acid phenylester (2039-13-6) → 1,2,3-thiadiazol-5-ylamine (4100-41-8)

Conditions	Yield
With magnesium oxide In water; acetone Heating;

diazoacetonitrile (13138-21-1) + Diethyl amine → 1,2,3-thiadiazol-5-ylamine (4100-41-8)

Conditions	Yield
In dichloromethane

diazoacetonitrile (13138-21-1) + sodium sulfide (Na2 S) → 1,2,3-thiadiazol-5-ylamine (4100-41-8)

Conditions	Yield
In dichloromethane

5-chloro-1,2,3-thiadiazole (4113-57-9) → 1,2,3-thiadiazol-5-ylamine (4100-41-8)

Conditions	Yield
With ammonia

1,2,3-thiadiazol-5-ylamine (4100-41-8) + trichloromethyl chloroformate (503-38-8) → 1,2,3-thiadiazol-5-ylisocyanate

Conditions	Yield
In tetrahydrofuran at -10 - 30℃; for 0.666667h;	95%

carbon monoxide (201230-82-2) + p-toluidine (106-49-0) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → 1-[1,2,3]thiadiazol-5-yl-3-p-tolyl-urea (51707-59-6)

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	74%

carbon monoxide (201230-82-2) + 4-methoxy-aniline (104-94-9) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → C10H10N4O2S

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	74%

carbon monoxide (201230-82-2) + aniline (62-53-3) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → thidiazuron (51707-55-2)

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	70%

6'-bromo-8'-chloro-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → 6'-((1,2,3-thiadiazol-5-yl)amino)-8'-chloro-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; XPhos In 1,4-dioxane at 100℃; for 4h; Inert atmosphere; Sealed tube;	66%

carbon monoxide (201230-82-2) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) + 1-amino-3-methylbenzene (108-44-1) → 1-[1,2,3]thiadiazol-5-yl-3-m-tolyl-urea (51707-60-9)

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	60%

carbon monoxide (201230-82-2) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) + benzylamine (100-46-9) → N-benzyl-N'-1,2,3-thiadiazol-5-yl urea

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	54%

carbon monoxide (201230-82-2) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) + o-toluidine (95-53-4) → 1-(2-methylphenyl)-3-(1,2,3-thiadiazole-5-yl)-urea (67021-62-9)

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	50%

carbon monoxide (201230-82-2) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) + 3-chloro-aniline (108-42-9) → 1-(3-chloro-phenyl)-3-[1,2,3]thiadiazol-5-yl-urea (51707-58-5)

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	49%

2-aminopyridine (504-29-0) + carbon monoxide (201230-82-2) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → N-2-pyridyl-N'-1,2,3-thiadiazol-5-yl urea (65408-00-6)

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	46%

propylamine (107-10-8) + carbon monoxide (201230-82-2) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → C6H10N4OS

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	42%

carbon monoxide (201230-82-2) + 4-chloro-aniline (106-47-8) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → 1-(4-chloro-phenyl)-3-[1,2,3]thiadiazol-5-yl-urea (51707-56-3)

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	41%

carbon monoxide (201230-82-2) + 1-amino-naphthalene (134-32-7) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → C13H10N4OS

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	40%

carbon monoxide (201230-82-2) + N-butylamine (109-73-9) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → C7H12N4OS

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	36%

carbon monoxide (201230-82-2) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) + 2-Chloroaniline (95-51-2) → 1-(2-Chloro-phenyl)-3-[1,2,3]thiadiazol-5-yl-urea

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	33%

carbon monoxide (201230-82-2) + isobutylamine (78-81-9) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → C7H12N4OS

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	32%

carbon monoxide (201230-82-2) + cyclohexylamine (108-91-8) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → 1-cyclohexyl-3-[1,2,3]thiadiazol-5-yl-urea (51707-57-4)

Conditions	Yield
With selenium; oxygen; triethylamine In N,N-dimethyl-formamide at 100℃; for 8h;	28%

chloroformic acid ethyl ester (541-41-3) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → μ-[1,2,3]thiadiazol-5-yl-μ-imido-dicarbonic acid diethyl ester (5027-28-1)

Conditions	Yield
With triethylamine In diethyl ether

acetic anhydride (108-24-7) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → N-[1,2,3]thiadiazol-5-yl-acetamide (4194-08-5)

2-Methylpropionic anhydride (97-72-3) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → N-[1,2,3]thiadiazol-5-yl-isobutyramide (4113-49-9)

4-methoxy-benzaldehyde (123-11-5) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → (4-methoxy-benzylidene)-[1,2,3]thiadiazol-5-yl-amine (4113-53-5)

Conditions	Yield
In ethanol

propionic acid anhydride (123-62-6) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → N-[1,2,3]thiadiazol-5-yl-propionamide (4113-48-8)

chloroacetyl chloride (79-04-9) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → 2-chloro-N-[1,2,3]thiadiazol-5-yl-acetamide (4113-50-2)

Conditions	Yield
In diethyl ether

phosgene (75-44-5) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → N,N'-di-1,2,3-thiadiazol-5-yl urea (4194-06-3)

Conditions	Yield
In ethyl acetate

dichloroacethyl chloride (79-36-7) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → 2,2-dichloro-N-[1,2,3]thiadiazol-5-yl-acetamide (6015-04-9)

Conditions	Yield
In diethyl ether

4-hydroxy-2-methoxybenzaldehyde (18278-34-7) + 1,2,3-thiadiazol-5-ylamine (4100-41-8) → 3-methoxy-4-([1,2,3]thiadiazol-5-yliminomethyl)-phenol

Conditions	Yield
In ethanol

1,2,3-thiadiazol-5-ylamine (4100-41-8) + β-naphthol (135-19-3) → 1-[1,2,3]thiadiazol-5-ylazo-naphthalen-2-ol (6440-16-0)

Conditions	Yield
(i) NaNO2, H3PO4, (ii) /BRN= 742134/, MeOH; Multistep reaction;

1,2,3-thiadiazol-5-ylamine (4100-41-8) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → 4-acetylamino-N-[1,2,3]thiadiazol-5-yl-benzenesulfonamide (4100-42-9)

Conditions	Yield
With pyridine

Upstream product

• 4100-40-7 N-[1,2,3]thiadiazol-5-yl-phthalimide 
• 2039-13-6 (1,2,3-thiadiazole-5-yl)-carbamic acid phenylester 
• 4113-57-9 5-chloro-1,2,3-thiadiazole 
• 13138-21-1 diazoacetonitrile 

Downstream Products

• 4100-42-9 4-acetylamino-N-[1,2,3]thiadiazol-5-yl-benzenesulfonamide 
• 4113-57-9 5-chloro-1,2,3-thiadiazole 
• 372089-60-6 tert-butyl N-(thiadiazol-5-yl)carbamate 
• 51707-55-2 thidiazuron 
• 51707-57-4 1-cyclohexyl-3-[1,2,3]thiadiazol-5-yl-urea 
• 51707-56-3 1-(4-chloro-phenyl)-3-[1,2,3]thiadiazol-5-yl-urea 
• 51707-58-5 1-(3-chloro-phenyl)-3-[1,2,3]thiadiazol-5-yl-urea 
• 51707-59-6 1-[1,2,3]thiadiazol-5-yl-3-p-tolyl-urea 
• 51707-60-9 1-[1,2,3]thiadiazol-5-yl-3-m-tolyl-urea 
• 67021-62-9 1-(2-methylphenyl)-3-(1,2,3-thiadiazole-5-yl)-urea 
• 1208552-76-4 C₁₃H₁₄ClN₃OS 
• 4194-08-5 N-[1,2,3]thiadiazol-5-yl-acetamide 

Relevant articles and documents

A secure and convenient synthesis of 5-amino-1, 2, 3-thiadiazole by diazoacetonitrile

A new synthesis of 5-amino-1,2,3-thiadiazole (3) by diazoacetonitrile (2) and H2S in the presence of a base is described. The compound (2) is undoubtedly explosive but with our method we found it could be used for industrial purposes.

Process for preparing 5-amino-1,2,3-thiadiazoles

There is provided a process for preparing a 5-amino-1,2,3-thiadiazole represented by the formula STR1 wherein R represents a hydrogen atom, a lower alkyl group or an aryl group, which comprises bringing a diazoacetonitrile represented by the formula STR2 wherein R has the same meaning as defined above, into contact with hydrogen sulfide in the presence of a base or with a salt of hydrogen sulfide, in a solvent.