2-Amino-1,3,4-thiadiazole Chemical Properties

Melting point:

188-191 °C (dec.) (lit.)

Boiling point:

238.9±23.0 °C(Predicted)

Density 

1.385 (estimate)

refractive index 

1.5800 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

water: soluble25mg/mL, clear, colorless

form 

Crystals or Crystalline Powder

pka

pKa 3.2 (Uncertain)

color 

White to light yellow

Water Solubility 

It is soluble in water, hot methanol- very faint turbidity.

BRN 

107135

InChIKey

QUKGLNCXGVWCJX-UHFFFAOYSA-N

CAS DataBase Reference

4005-51-0(CAS DataBase Reference)

NIST Chemistry Reference

2-Amino-1,3,4-thiadiazole(4005-51-0)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

68-63-36/37/38-20/21/22-22

Safety Statements 

36/37/39-26-36

RIDADR 

2811

WGK Germany 

3

RTECS 

XI3000000

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29349990

Toxicity

LD50 oral in rat: 253mg/kg

MSDS

• Language:English Provider:1,3,4-Thiadiazol-2-amine
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Amino-1,3,4-thiadiazole Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

A thiadiazole derivative with fungacidal properties. An antitumor agent.

Uses

2-Amino-1,3,4-thiadiazole, is used as an intermediate for ceftraoline.

General Description

2-Amino-1,3,4-thiadiazole (donor) form charge transfer complexes with 2,3-dichloro-5,6-dicyano-p-benzoquinone, p-chloranil, o-chloranil, p-bromanil and chloranilic acid (acceptors). Effects of 2-amino-1,3,4-thiadiazole [aminothiadiazole (NSC 4728)] on purine and pyrimidine ribonucleotide pools of L1210 ascites cells in vivo has been reported.

Safety Profile

Poison by subcutaneous andintraperitoneal routes. An experimental teratogen. Otherexperimental reproductive effects. When heated todecomposition it emits very toxic fumes of NOx and SOx.

Synthesis

General procedure for the synthesis of 2-amino-1,3,4-thiadiazole from formic acid and aminothiourea: 5.00 g of aminothiourea was accurately weighed and placed in a 50 mL three-necked flask fitted with a stirring magnet, and 5.00 mL of formic acid was added at once. The reaction was stirred under the condition of cooling in an ice bath, and after the formation of a slurry, 6.00 mL of concentrated hydrochloric acid was added slowly and dropwise. After the dropwise addition, the reaction mixture was transferred to an oil bath preheated to 107 °C with stirring turned on and the reaction was carried out for 4.5 to 5.0 h. During this time, the reaction progress was monitored by thin-layer chromatography (TLC), and the reaction was stopped when the raw material point disappeared. After the reaction solution was cooled to room temperature, the pH was adjusted with concentrated ammonia to 8-9. The mixture was placed in a refrigerator overnight, white crystals were precipitated, filtered, washed three times with ice water, and finally recrystallized with distilled water to give 4.96 g of white crystal product in about 90% yield. The melting point of the product was 198 to 201 °C. The resulting product was confirmed to be 2-amino-1,3,4-thiadiazole by infrared spectroscopy (IR), nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis.

References

[1] Nature Communications, 2017, vol. 8, # 1,
[2] Journal of Chemical Research, 2005, # 5, p. 341 - 343
[3] Journal of the Chemical Society of Pakistan, 2015, vol. 37, # 1, p. 115 - 121
[4] Patent: CN106117268, 2016, A. Location in patent: Paragraph 0030; 0031
[5] Patent: CN106167502, 2016, A. Location in patent: Paragraph 0032; 0033

2-Amino-1,3,4-thiadiazole(4005-51-0)Related Product Information

• 3-Aminophenol
• 6-Aminocaproic acid
• 2-Mercapto-5-methyl-1,3,4-thiadiazole
• 2,1,3-Benzothiadiazole
• Dibenzylamine
• Triethanolamine
• ALTRENOGEST
• Aminopyrine
• Bis(2-ethylhexyl)amine
• Acetaminophen
• Sulfamic acid
• Glucosamine
• EC 2.6.1.2
• Triallylamine
• Glycine
• Tris(hydroxymethyl)aminomethane
• 5-AMINO-2-DIISOPROPYLAMINO-1,3,4-THIADIAZOLE
• Acetazolamide