1-Phenyltetrazole-5-thiol Chemical Properties

Melting point:

145 °C (dec.)(lit.)

Boiling point:

342°C (rough estimate)

Density 

1.3046 (rough estimate)

refractive index 

1.5500 (estimate)

Flash point:

138°C

storage temp. 

Store at +15°C to +25°C.

solubility 

ethanol: soluble5%, clear, colorless to faintly yellow

pka

-3.85±0.20(Predicted)

form 

Solid

color 

White to Off-White

PH

3-5 (H2O, 20℃)suspension

Water Solubility 

Soluble in 5% ethanol, water (partly), acetone, chloroform, and methanol.

Sensitive 

Air Sensitive

BRN 

139068

InChIKey

GGZHVNZHFYCSEV-UHFFFAOYSA-N

CAS DataBase Reference

86-93-1(CAS DataBase Reference)

NIST Chemistry Reference

1H-tetrazole-5-thiol, 1-phenyl-(86-93-1)

EPA Substance Registry System

5H-Tetrazole-5-thione, 1,2-dihydro-1-phenyl- (86-93-1)

Safety Information

Hazard Codes 

Xn,F

Risk Statements 

5-22-2017/5/22

Safety Statements 

22-24/25

RIDADR 

UN 1325 4.1/PG 2

WGK Germany 

1

RTECS 

XF7700000

F 

4.10

Hazard Note 

Flammable

TSCA 

Yes

HazardClass 

4.1

PackingGroup 

III

HS Code 

29339990

MSDS

• Language:English Provider:1-Phenyltetrazole-5-thiol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Phenyltetrazole-5-thiol Usage And Synthesis

Chemical Properties

white fluffy or crystalline powder or crystals

Uses

1-Phenyl-1H-tetrazole-5-thiol is used as a corrosion inhibitor and as a reagent in the synthesis of Microcarpalide, a microfilament disrupting agent that is weakly cytotoxic to mammalian cells.

Definition

ChEBI: 1-Phenyl-5-mercaptotetrazole is a member of tetrazoles.

Application

1-Phenyl-1H-tetrazole-5-thiol is an effective inhibitor of aluminum corrosion in 1M HCl solution. It was used in the synthesis of oxacyclic building blocks via highly stereoselective radical cyclization and olefin metathesis reactions. It was also used in the synthesis of metallated tetradecyl sulfone. It is also used in the spectrophotometric determination of Pt and Bi.

Synthesis Reference(s)

Canadian Journal of Chemistry, 44, p. 2315, 1966 DOI: 10.1139/v66-347

Synthesis

Sodium azide, 0.79 g (12.1 mmol), and 1.65 g (12.1 mmol) of ZnCl2 were added to 30 mL of MeCN. The mixture was heated with stirring until boiling (80 °C), and then 1 g (10.1 mmol) of allyl isothiocyanate was added. The reaction mixture was stirred for 1 h at 80 °C, and the solvent was then removed in a vacuum. The residue was treated with 5% aqueous NaOH (50 mL) with stirring for 20 min. The suspension was filtered, and the filtrate was treated with chloroform (2×10 mL) to remove impurities. The aqueous layer was acidified with conc. HCl to pH 1. The formed precipitate was filtered off, washed with water, and dried in air to afford 1-Phenyltetrazole-5-thiol. Yield 1.31 g(99%), colorless crystals.

Purification Methods

Purify the tetrazole by recrystallisation from EtOH or CHCl3 (m 152o) [Tautomerism: Kauer & Sheppard J Org Chem 32 3580 1967, UV: Leiber et al. Can J Chem 37 563 1959]. The ammonium salt crystallises from EtOH and decomposes at 176o. The sodium salt crystallises from EtOH/*C6H6, melts at 96o and decomposes at 145o [Stollé J Prakt Chem [2] 133 60 1932]. It is used for the determination of Bi and Pd. [Fresenius Z Anal Chem 261 151 1972, Beilstein 26 III/IV 2065.]

1-Phenyltetrazole-5-thiol(86-93-1)Related Product Information

• 5-Phenyltetrazole
• PHENYL VALERATE
• 3-Mercaptopropionic acid
• 6-Mercaptopurine
• Nitrotetrazolium blue chloride
• Sodium thioglycolate
• Tetrazole
• 2,3,5-Triphenyltetrazolium chloride
• 1H-Tetrazole-1-acetic acid
• 2-Ethylhexyl mercaptoacetate
• Mercaptoacetic acid
• Phenylhydrazine
• 1H-TETRAZOLE
• Malathion
• 2-Mercaptoethanol
• 1-Phenyltetrazole-5-thiol