5-Amino-1,3,4-thiadiazole-2-thiol supplier

Name
5-Amino-1,3,4-thiadiazole-2-thiol
EINECS 219-078-4
CAS No. 2349-67-9
Article Data78
CAS DataBase
Density 2.04 g/cm³
Solubility Insoluble in water
Melting Point 231-236 °C
Formula C₂H₃N₃S₂
Boiling Point 242.3 °C at 760 mmHg
Molecular Weight 133.198
Flash Point 100.3 °C
Transport Information
Appearance white or pale yellow to cream powder
Safety 26-36-36/37
Risk Codes 36/37/38-22-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms 1,3,4-Thiadiazole-2-thiol,5-amino- (6CI,8CI);2-Amino-1,3,4-thiadiazole-5-mercaptan;2-Amino-5-mercapto-1,3,4-thiadiazole;2-Amino-5-mercaptothiadiazole;2-Mercapto-5-amino-1,3,4-thiadiazole;2-Thiol-5-amino-1,3,4-thiadiazole;5-Amino-1,3,4-thiadiazole-2-thiol;5-Amino-1,3,4-thiadiazoline-2-thione;5-Amino-1,3,4-thidiazole-2-thiol;5-Amino-3H-1,3,4-thiadiazole-2-thione;5-Thio-2-amino-[1,3,4]thiadiazole;ATT;NSC 209061;NSC 21402;WR 180;
PSA 118.84000
LogP 0.99020

Synthetic route

: 75-15-0
carbon disulfide

: 79-19-6
thiosemicarbazide

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

Conditions

Conditions	Yield
With choline chloride; urea at 80℃; for 2h;	96.9%
In N,N-dimethyl-formamide for 6h; Reflux;	89%
With sodium carbonate In ethanol for 5h; Reflux;	89%

: 68967-31-7
2-mercapto-7-methyl-5-oxo-5H-1,3,4-thiadiazolo[3,2-a]pyrimidine

A: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

B: 28004-46-8
3-amino-6-methyl-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With hydrogenchloride In water	A 24% B 64%

: 140-89-6
potassium ethyl xanthogenate

: 79-19-6
thiosemicarbazide

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

Conditions

Conditions	Yield
In water	64%

: 79-19-6
thiosemicarbazide

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

Conditions

Conditions	Yield
With carbon disulfide In N-methyl-acetamide; ethanol
With carbon disulfide In N-methyl-acetamide; ethanol; benzene
With carbon disulfide In N-methyl-acetamide; benzene	42 wt. %
With carbon disulfide In N-methyl-acetamide

: bis(2-mercapto-5-amino-1,3,4-thiadiazole)copper(II)

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

Conditions

Conditions	Yield
With sodiumsulfide nonahydrate

: 16672-04-1
5-thiocyanato-1,3,4-thiadiazol-2-amine

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 1h;

: 2530-83-8
3-glycidoxypropyltrimethoxysilane

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: C11H23N3O5S2Si

Conditions

Conditions	Yield
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole In methanol Stage #2: 3-glycidoxypropyltrimethoxysilane In methanol at 65℃; for 18h;	100%
In methanol at 65℃; for 18h;

: C20H36Au4N4O12S4

: 584-08-7
potassium carbonate

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: potassium hydroxide

: C7H9AuN4O3S3(1-)*K(1+)

Conditions

Conditions	Yield
In water at 60℃;	100%

...Expand

: copper(ll) sulfate pentahydrate

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: bis(2-mercapto-5-amino-1,3,4-thiadiazole)copper(II)

Conditions

Conditions	Yield
In ethyl acetate Milling; Green chemistry;	99.6%
With sodium hydroxide In water at 40℃; for 0.333333h; Temperature;	9.66 g

: aluminum(III) sulfate

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 3C2H2N3S2(1-)*Al(3+)

Conditions

Conditions	Yield
In dimethyl sulfoxide Milling; Green chemistry;	99.5%

: 638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3
manganese(II) acetate

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 2C2H2N3S2(1-)*Mn(2+)

Conditions

Conditions	Yield
In acetonitrile Milling; Green chemistry;	99.4%

: tin (II) sulfate

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 2C2H2N3S2(1-)*Sn(2+)

Conditions

Conditions	Yield
In butan-1-ol Milling; Green chemistry;	99.2%

: 5970-45-6
zinc(II) acetate dihydrate

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: bis(2-mercapto-5-amino-1,3,4-thiadiazole)zinc(II)

Conditions

Conditions	Yield
In water Milling; Green chemistry;	99.1%
In water High Pressure; hydrothermal synthesis;	76%

: ferrous phosphate octahydrate

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 2C2H2N3S2(1-)*Fe(2+)

Conditions

Conditions	Yield
In chloroform Milling; Green chemistry;	99.1%

: nickel(II) sulphate

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 2C2H2N3S2(1-)*Ni(2+)

Conditions

Conditions	Yield
In 2-methyl-propan-1-ol Milling; Green chemistry;	99.1%

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 14867-28-8
3-iodopropyltrimethoxysilane

: 2-amino-5-[3-(trimethoxysilyl)propylthio]-1,3,4-thiadiazole

Conditions

Conditions	Yield
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With sodium methylate In methanol at 20℃; for 0.5h; Stage #2: 3-iodopropyltrimethoxysilane In methanol at 37 - 40℃; for 5.5h;	98.7%

: 100-44-7
benzyl chloride

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 25660-71-3
2-amino-5-benzylthio-1,3,4-thiadiazole

Conditions

Conditions	Yield
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With potassium hydroxide In ethanol; water at 20 - 30℃; for 0.166667h; Stage #2: benzyl chloride In ethanol; water at 20 - 30℃;	98%
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With pyridine; triethylamine for 0.166667h; Stage #2: benzyl chloride at 20℃; for 3h;	93.4%
With sodium methylate In methanol at 20℃;	85%

: C26H36BClO7

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: C28H38BN3O7S2

Conditions

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	97.8%

: C27H38BClO8

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: C29H40BN3O8S2

Conditions

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;	97.7%

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 459-46-1
4-Fluorobenzyl bromide

: 299936-22-4
5-((4-fluorobenzyl)thio)-1,3,4-thiadiazol-2-amine

Conditions

Conditions	Yield
With sodium hydroxide In water at 22℃; for 15h;	97%
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With potassium hydroxide In ethanol for 0.166667h; Stage #2: 4-Fluorobenzyl bromide In ethanol for 2h;	88%
With sodium methylate In methanol at 20℃;	69%
With Amberlite(R) IRA-67 In acetonitrile at 20℃; for 24h;

: 100-39-0
benzyl bromide

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 25660-71-3
2-amino-5-benzylthio-1,3,4-thiadiazole

Conditions

Conditions	Yield
With sodium hydroxide In water at 22℃; for 15h;	96%
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With potassium hydroxide In ethanol for 0.166667h; Stage #2: benzyl bromide In ethanol for 2h;	90%
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With potassium tert-butylate In tetrahydrofuran Sonication; Stage #2: benzyl bromide In tetrahydrofuran at 20℃; for 0.333333h; Reagent/catalyst; Sonication;	85%

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 65060-93-7
N-methyl bromomaleimide

: N-methyl-3-(5-amino-1,3,4-thiadiazol-2-ylthio)-maleimide

Conditions

Conditions	Yield
With triethylamine In water at 20℃; for 6h;	96%

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 81516-46-3
2-chloromethyl-7-methyl-5-oxo-5H-1,3,4-thiadiazolo<3,2-a>pyrimidine

: 2-(5-Amino-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-7-methyl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 2h; Heating;	95.5%

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 18908-07-1
3-methoxyphenyl isocyanate

: C10H10N4O2S2

Conditions

Conditions	Yield
With triethylamine In acetonitrile Reflux;	95.1%
In acetonitrile Reflux;
In dichloromethane at 20℃; for 24h; Inert atmosphere;
In dichloromethane at 20℃; Inert atmosphere;

: 90-02-8
salicylaldehyde

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 2-salicylideneimino-5-mercapto-1,3,4-thiadiazole

Conditions

Conditions	Yield
In ethanol for 2h; Heating;	95%

: 31643-49-9
4-Nitrophthalonitrile

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 4-S-(5-amino-1,3,4-thiadiazole-2-mercapto)phthalonitrile

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 40℃; for 3.5h;	95%
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Reagent/catalyst; Solvent; Time; Temperature; Sealed tube; Molecular sieve;	81.4%

: 100-10-7
4-dimethylamino-benzaldehyde

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 2-mercapto-5-((4-(dimethylamino)benzylidene)amino)-1,3,4-thiadiazole

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride at 90℃; for 0.166667h; neat (no solvent);	95%
With acetic acid In methanol at 65℃;	85%
With acetic acid In ethanol for 4h; Reflux;	75%
With magnesium sulfate In dichloromethane at 20℃;	59%
In ethanol

: 137-43-9
Cyclopentyl bromide

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 40177-33-1
5-(cyclopentylthio)-1,3,4-thiadiazol-2-amine

Conditions

Conditions	Yield
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With potassium hydroxide In ethanol for 0.166667h; Stage #2: Cyclopentyl bromide In ethanol for 2h;	95%

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 1548-13-6
p-trifluoromethyl-phenylisocyanate

: 1370256-57-7
1-(5-mercapto-[1,3,4]thiadiazol-2-yl)-3-[4-(trifluoromethyl)phenyl]urea

Conditions

Conditions	Yield
With triethylamine In acetonitrile Reflux;	94.6%
In acetonitrile Reflux;

: 75-03-6
ethyl iodide

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 25660-70-2
2-amino-5-(ethylthio)-1,3,4-thiadiazole

Conditions

Conditions	Yield
With potassium hydroxide In water; isopropyl alcohol at 0 - 60℃; for 2h;	94.4%
With potassium hydroxide In water; isopropyl alcohol at 65℃; for 2.5h; Cooling with ice;	80%
With potassium hydroxide In ethanol at 10 - 20℃;	52.5%
With sodium carbonate In water

: 1271-55-2
acetylferrocene

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: C14H13FeN3S2

Conditions

Conditions	Yield
With methanesulfonic acid; choline chloride at 40℃;	94.1%

: 108-24-7
acetic anhydride

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 32873-56-6
2-acetylamino-5-mercapto-1,3,4-thiadiazole

Conditions

Conditions	Yield
Heating;	94%
In acetic acid Heating;	90%
With pyridine at 70℃; for 1h; Heating;	76.8%

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 135-19-3
β-naphthol

: 1416178-73-8
(E)-1-((1,3,4-thiadiazol-2-yl)diazenyl)naphthalen-2-ol

Conditions

Conditions	Yield
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With hydrogenchloride; sodium nitrite In water Stage #2: β-naphthol With sodium hydroxide In water at -5 - 0℃;	94%

: C18H17Cl2FN2O4

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 7-(3-(2-(5-amino-1,3,4-thiadiazol-2-ylsulfanyl)acetamido)-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Conditions

Conditions	Yield
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Stage #2: C18H17Cl2FN2O4 In N,N-dimethyl-formamide at 45℃; for 1.3h;	94%

: C19H18Cl2FN3O4

: 2349-67-9
2-Amino-5-mercapto-1,3,4-thiadiazole

: 7-(3-(2-(5-amino-1,3,4-thiadiazol-2-ylsulfanyl)acetamido)-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Conditions

Conditions	Yield
Stage #1: 2-Amino-5-mercapto-1,3,4-thiadiazole With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: C19H18Cl2FN3O4 In N,N-dimethyl-formamide at 45℃; for 1.3h;	94%

5-Amino-1,3,4-thiadiazole-2-thiol Consensus Reports

Reported in EPA TSCA Inventory.

5-Amino-1,3,4-thiadiazole-2-thiol Specification

The 2-Amino-5-mercapto-1,3,4-thiadiazole , with cas registry number of 2349-67-9, belongs to the categories of Xanthones; Amines; Cephalosporins. It also has other other registry numbers which are 17374-12-8, 36369-18-3. Its IUPAC name is 5-amino-3H-1,3,4-thiadiazole-2-thione . Its systematic name is called 5-amino-1,3,4-thiadiazole-2(3H)-thione .

Physical properties of 2-Amino-5-mercapto-1,3,4-thiadiazole are: (1) ACD/LogP: -0.77 ; (2) # of Rule of 5 Violations: 0 ; (3) ACD/LogD (pH 5.5): -2.69 ; (4) ACD/LogD (pH 7.4): -2.71 ; (5) ACD/BCF (pH 5.5): 1 ; (6) ACD/BCF (pH 7.4): 1 ; (7) ACD/KOC (pH 5.5): 1 ; (8) ACD/KOC (pH 7.4): 1 ; (9) #H bond acceptors: 3 ; (10) #H bond donors: 3 ; (11) #Freely Rotating Bonds: 0 ; (12) Index of Refraction: 1.99 ; (13) Molar Refractivity: 32.36 cm3 ; (14) Molar Volume: 65.1 cm3 ; (15) Surface Tension: 92 dyne/cm ; (16) Enthalpy of Vaporization: 47.93 kJ/mol ; (17) Vapour Pressure: 0.0342 mmHg at 25°C.

Uses of 2-Amino-5-mercapto-1,3,4-thiadiazole : (1) It is used as an intermediate of pesticide and pharmaceutical. (2) This compound can also be used to prepare many other chemicals. For example, 2-Amino-5-mercapto-1,3,4-thiadiazole could react with adamantan-1-ol to prepare 5-(adamantan-1-ylsulfanyl)-[1,3,4]thiadiazol-2-ylamine using the solvent of Trifluoroacetic acid for 20 min. During the process, Heating is also necessary. The yield is about 58%.

Preparation of 2-Amino-5-mercapto-1,3,4-thiadiazole : It is synthesized from ambazone by cyclization, which is formed from the hydrazine sulfate and ammonium thiocyanate by rearrangement-condensation.

When you are using this chemical, please be cautious about it as the following:
The 2-Amino-5-mercapto-1,3,4-thiadiazole is irritating to eyes, respiratory system and skin. And it harmful by inhalation, in contact with skin and if swallowed. So when use it, remember wear suitable protective clothing and gloves. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. It should be stored in a tightly closed container in a cool, dry, well-ventilated area away from incompatible substances. Keep container closed when not in use.

You can still convert the following datas into molecular structure:
(1) SMILES:S=C1S\C(=N/N1)N ;
(2) InChI:InChI=1/C2H3N3S2/c3-1-4-5-2(6)7-1/h(H2,3,4)(H,5,6) ;
(3) InChIKey:GDGIVSREGUOIJZ-UHFFFAOYAQ

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	250mg/kg (250mg/kg)		National Technical Information Service. Vol. AD691-490,

Product Name

5-Amino-1,3,4-thiadiazole-2-thiol

Synthetic route

5-Amino-1,3,4-thiadiazole-2-thiol Consensus Reports

5-Amino-1,3,4-thiadiazole-2-thiol Specification

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