1-Phenyltetrazole-5-thiol, also known as PMT, TIMTEC-BB SBB007594, 1-Phenyl-5-mercapto, etc., is a chemical substance that appears as a white to grayish white solid at room temperature and pressure. It is slightly soluble in water but soluble in organic solvents such as ethanol, acetone, chloroform, and carbon tetrachloride. Dissolve in 5% ethanol to form a clear solution ranging from colorless to slightly yellow. It is stable when stored and used at normal ambient temperatures, with weak alkalinity and strong nucleophilicity. It can be used as an organic synthesis reagent and a raw material for chemical industry production, mainly for the synthesis of tetrazolium organic functional molecules. It is also used for reprocessing the surface of Cu-Sn-P coatings to form a thin and dense complex protective film, enhancing the corrosion resistance of the coatings. At the same time, it is used as a stabilizer for photosensitive materials to avoid or reduce the generation of fog, thereby improving the stability of photosensitive materials.
Additional information of chemical compound:
|
Chemical Formula |
C7H6N4S |
|
Exact Mass |
178.03 |
|
Molecular Weight |
178.21 |
|
m/z |
178.03 (100.0%), 179.03 (7.6%), 180.03 (4.5%), 179.03 (1.5%) |
|
Elemental Analysis |
C, 47.18; H, 3.39; N, 31.44; S, 17.99 |
|
Melting point |
145℃ (dec.)(lit.) |
|
Boiling point |
342℃ (rough estimate) |
|
Density |
1.3046 (rough estimate) |
|
Storage conditions |
Store at +15℃ to +25℃. |
|
|
|
1-Phenyltetrazole-5-thiol is an important organic compound with a wide range of applications. The following is a detailed explanation of its purpose:
Organic synthesis reagents and raw materials for chemical industry production&electroplating additives
Core Applications of Organic Synthesis Reagents
PMT is a multifunctional heterocyclic synthesis block, highly active nucleophile, and strong coordinating metal ligand. With its sulfur nitrogen dual active sites, it can construct tetrazolium heterocycles, sulfur-containing functional molecules, and metal organic complexes. It is widely used in the synthesis of pharmaceutical intermediates, pesticide raw materials, organic optoelectronic materials, and fine chemicals. The global annual demand for synthetic grade exceeds 800 tons.
Tetrazolium ring derivatization reaction
PMT, as a direct precursor of tetrazolium parent nucleus, constructs a high value-added tetrazolium derivative library through three major pathways: thiol derivatization, ring substitution, and ring expansion
Thiol alkylation/arylation: PMT+halogenated alkane/halogenated aromatic hydrocarbon (R-X) → 5-alkylthio/arylthio-1-phenyltetrazolium, mild reaction conditions (room temperature -60 ℃, weak base catalysis), yield ≥ 90%; Used for the synthesis of pharmaceutical intermediates, pesticide fungicides, and organic sulfides.
Thiol group oxidation to ring: PMT undergoes hydrogen peroxide/iodine oxidation → 1-phenyltetrazolium-5-yl disulfide, which can be further cyclized to form thiazole tetrazolium fused ring compounds for anti-tumor and antibacterial drug development.
Tetrazolium ring electrophilic substitution: PMT undergoes electrophilic substitution (alkylation/acylation) of the N atom in the tetrazolium ring under strong acid/Lewis acid catalysis → N-substituted tetrazolium thiol, which is used for drug molecular structure modification and enhancing target affinity.
Synthesis of polycyclic heterocyclic compounds
PMT undergoes condensation/cyclization reactions with ortho phenylenediamine, ortho aminophenol, α - halogenated ketones, and aldehydes to construct fused heterocyclic frameworks such as benzimidazole tetrazolium, benzimidazole tetrazolium, thiazole tetrazolium, and triazole tetrazolium
Benzimidazole tetrazolium: PMT+o-phenylenediamine → condensation cyclization → product, with antibacterial activity 2-3 times higher than ordinary benzimidazole, used as an agricultural fungicide and pharmaceutical antibacterial agent.
Thiazole-tetrazolium: PMT+α - chloroketone → cyclization → product, with significant anti-tumor activity, can inhibit the proliferation of lung cancer and liver cancer cells (IC50 ≤ 5 μ M).
Triazole tetrazolium: PMT+azide → cycloaddition → product, broad-spectrum antibacterial and antifungal, used in pesticides and pharmaceuticals.
Nucleophilic substitution reaction (SN2/SN1)
The thiol group (- SH) of PMT has strong nucleophilicity (pKa ≈ 10.5) and can undergo efficient nucleophilic substitution reactions with halogenated hydrocarbons,
sulfonic acid esters, epoxides, and acyl halides
Reaction with halogenated hydrocarbons: PMT+R-Br/R-Cl → R-S-tetrazolium-phenyl, fast reaction rate, high selectivity, yield ≥ 95%, used for the synthesis of organic sulfides and pharmaceutical intermediates.
Reaction with epoxides: PMT+epoxyethane/epoxypropane → ring opening addition → hydroxy sulfide derivatives, used for polyether modification and pharmaceutical intermediates.
Reaction with acyl halides: PMT+acyl chloride → thioester derivatives, used for protecting groups in drug synthesis and organic synthesis.
1-Phenyltetrazole-5-thiol for photographic dust suppressants, photosensitive material stabilizers, and pharmaceutical intermediates
Definition and pain points of photographic dust suppressants
Antifogging agent is used to suppress non image fog (Fog) generated during the preparation, storage, and processing of silver halide photosensitive materials, which is a uniform gray black background formed by the spontaneous reduction of silver salts in non illuminated areas, directly reducing image contrast, clarity, and signal-to-noise ratio. Traditional anti fog agents (such as BTA and MBT) suffer from problems such as high temperature failure, poor storage stability, and significant loss of sensitivity. PMT has become the preferred high-end photographic material due to its high efficiency, low loss, good thermal stability, and long-lasting dust resistance.
Mechanism of PMT dust inhibitor action (quadruple pathway)
Silver crystal nucleus poisoning (core): PMT thiol groups coordinate with active Ag ⁺ on the surface of silver halide, occupying reducing active sites, preventing spontaneous reduction of Ag ⁺ → Ag ⁰, and inhibiting the formation of gray fog crystal nuclei.
Inhibition of chemical maturation: During the emulsion chemical maturation (sensitization) stage, PMT adsorbs onto the surface of silver particles, preventing crystal nucleus growth and aggregation, reducing fog density (Δ D ≤ 0.05), while almost not losing sensitivity (≤ 5%).
Antioxidant and anti-aging: removes trace free radicals and peroxides from emulsions, inhibits the oxidation and decomposition of silver halides and the sulfurization and discoloration of silver particles, and extends storage life by more than 2 times.
Stable flushing control: Moderately suppress the development rate in the developer, reduce excessive development in strong light areas, and improve image contrast (increase gamma value by 0.2-0.3).
Black and white film/photo paper (mainstream application)
Addition stage: Add the emulsion after chemical maturity and before coating to avoid affecting the sensitization.
Addition amount: 0.05% -0.2% (based on emulsion weight), optimal 0.1%; Insufficient dust prevention due to low dust levels, decreased sensitivity due to high dust levels, and hard images.
Solvent system: Dissolve in ethanol/acetone (10% -20% solution) first, then slowly add the emulsion and stir evenly (30 min) to avoid excessive local concentration.
Performance effect: Mist density reduced from 0.15-0.20 to 0.03-0.06; Sensitivity loss ≤ 5%; Storage for 12 months with fog growth ≤ 0.02; Superior to BTA, MBT, and 2-AP.
Color film/photo paper (high-end applications)
Formula features: Compound with color couplers, sensitizing dyes, and stabilizers, with a dosage of 0.08% -0.15%.
Core value: Suppress bluish/magenta/yellow layer fog, improve color saturation, reduce color cast, and enhance color stability; Prevent color dyes from oxidizing and fading.
X-ray film/industrial photosensitive plate (special applications)
Application scenarios: medical X-ray, industrial non-destructive testing (NDT), printing and plate making.
Addition amount: 0.1% -0.3%, suitable for high silver content emulsions (≥ 5 g/m ²).
Effect: Reduce background fog, improve image contrast, and enhance the recognition of subtle defects; Extend the storage period in high temperature and high humidity environments (≥ 6 months).
Stabilizers for photosensitive materials are used for long-term storage (1-5 years) to suppress the growth of silver halide haze, decrease in sensitivity, and image fading/discoloration, ensuring stable photosensitive performance and long-lasting image quality. PMT is an efficient stabilizer with dual functions of anti fog and stability. It is stable in low temperature/high temperature/high humidity environments and is widely used in films, photo papers, photosensitive plates, and photoresist.
Mechanism of PMT stabilizer action (triple stabilization)
Storage period fog suppression (long-term): PMT stabilizes the adsorption of silver particles on the surface, continuously inhibits the spontaneous reduction of Ag ⁺, and the fog growth after 12-60 months of storage is ≤ 0.03; Superior to traditional stabilizers such as tetrazolium and indene.
Sensitivity stabilization: Inhibit the degradation of sensitizing dyes in emulsions, prevent silver particle aggregation, and reduce sensitivity attenuation by ≤ 8%/year during storage; Traditional stabilizers decay by 15% -25% per year.
Anti light/heat/moisture aging: eliminates free radicals, inhibits silver halide photodegradation, and prevents silver sulfide discoloration; Under accelerated aging conditions of 60 ℃/80% RH, fog growth ≤ 0.05 and sensitivity retention ≥ 85%.
The value of PMT as a pharmaceutical intermediate
PMT contains a dual active skeleton of thiol group and tetrazolium ring, which can be used to construct tetrazolium drugs through alkylation, oxidation, salt formation, cyclization, and coupling. These drugs have a wide range of pharmacological activities such as antibacterial, anti-inflammatory, anti-tumor, antithrombotic, antiviral, and hypoglycemic effects, and are a hot topic in pharmaceutical research and development. PMT is the core precursor of tetrazolium thiol drugs, with an annual global demand for pharmaceutical grade products exceeding 200 tons.
Thiol alkylation (C-S bond construction, most commonly used)
PMT+halogenated alkane/halogenated aromatic hydrocarbon (R-X) → 5-alkylthio/arylthio-1-phenyltetrazolium (catalyzed by weak bases such as K ₂ CO3, room temperature -60 ℃, yield ≥ 90%).
Application: Synthesis of intermediates for antibiotics, anti-inflammatory drugs, and anti-tumor drugs.
Thiol oxidation (disulfide/sulfonyl derivatives)
Mild oxidation (I ₂/H ₂ O ₂) → 1-phenyltetrazolium-5-yl disulfide (yield ≥ 85%), used for anti-tumor and antithrombotic drugs.
Deep oxidation (KMnO ₄) → 1-Phenyltetrazole-5-thiol (electrophilic reagent used for heterocyclic synthesis and drug modification).
Salt formation reaction (increase in water solubility)
PMT (weak acid, pKa ≈ 10.5)+NaOH/KOH/organic amine → PMT sodium/potassium/amine salt (water solubility ≥ 100 g/L, improves bioavailability).
Application: Intermediate for injection antibiotics, anti-inflammatory drugs, and antiviral drugs.
Cyclization/condensation (condensed heterocyclic drugs)
PMT undergoes condensation with ortho phenylenediamine, ortho aminophenol, α - halogenated ketones, and aldehydes, followed by benzimidazole tetrazolium, thiazole tetrazolium, and triazole tetrazolium fused ring frameworks.
Value: The activity of condensed ring derivatives is significantly improved, toxicity is reduced, and target specificity is enhanced.
Antibacterial drugs (broad-spectrum, low resistance)
Mechanism of action: Inhibit bacterial cell wall synthesis, damage cell membrane, inhibit nucleic acid replication; Highly effective against Gram positive bacteria (Staphylococcus aureus, Streptococcus), negative bacteria (Escherichia coli, Salmonella), and fungi (Candida).
Representative drugs:
PMT benzyl sulfide derivatives: MIC=4-8 μ g/mL against Staphylococcus aureus, superior to penicillin and cefepime.
PMT condensed ring derivatives: antifungal (Candida albicans) MIC=2-4 μ g/mL, replacing fluconazole and itraconazole.
Clinical use: Skin infections, respiratory infections, urinary system infections, fungal infections.
Frequently Asked Questions
Its appearance keeps changing, is it a thiol or a ketone?
+
-
This name itself is a 'historical legacy issue'. Although commonly known as "thiol", research has shown that it exists stably in the form of "thione" (i.e. C=S double bond) in both solid and gaseous states.
Gas phase/solid state: Density functional theory (DFT) calculations and crystallographic data confirm that the thione form is the absolute dominant configuration. At this point, the molecule exhibits double bond characteristics and lacks free - SH. In polar solvents, there is a dynamic equilibrium between the two, but the thione form still dominates.
Why does the industry insist on using this "expensive commodity" when the roadside "benzotriazole" costs only a dozen yuan?
+
-
In the field of high-end electroplating (such as golden Cu Sn alloy coating), it is an irreplaceable "anti discoloration king", with performance superior to the common benzotriazole (BTA). In the surface treatment of electronic components, conventional BTA rust inhibitors often cause discoloration of the coating or insufficient salt spray resistance. PMT can form a dense complex protective film on the surface of such coatings. Experimental data shows that the corrosion resistance of the coating treated with PMT is significantly improved in 10% NaCl solution and 1% H ₂ S gas environment. It not only prevents rust, but also firmly locks in the "golden luster" of the coating.
As an organic molecule, what else can it do besides rust prevention? "-" Extraction Hunter "of Trace Precious Metals
+
-
It is a traditional color reagent used in analytical chemistry for spectrophotometric determination of platinum (Pt) and bismuth (Bi), with extremely high sensitivity and selectivity.
In classical wet analysis, PMT can form colored complexes with Pt (IV) or Bi (III). This property is used for the detection of trace impurities in ores or alloys.
Compared to modern ICP-MS, although this spectrophotometric method is "ancient", PMT still plays an irreplaceable role in some scenarios where rapid on-site detection or expensive instruments are lacking.
When scaling up production, a slight mistake in the feeding sequence can cause "splashing" or even explosions? --The 'risk of death' in azide process
+
-
In classic laboratory synthesis, if allyl isothiocyanate is directly added to a high-temperature sodium azide suspension at once, it is highly likely to cause violent boiling or even explosion. Although modern processes have been optimized, the traditional method of PMT involves high-temperature cyclization of sodium azide and isothiocyanate in solvents. If the operation is not standardized (such as local overheating, rapid feeding), the risk of unreacted azides or by-product diazomethane derivatives during thermal decomposition is extremely high.
Hot Tags: 1-phenyltetrazole-5-thiol cas 86-93-1, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, 3-Nitrobenzaldehyde 99%, 4 Methoxyphenylacetone CAS 122 84 9, 2 2 Bis hydroxymethyl butyric Acid CAS 10097 02 6, 3 Phenyltoluene, 8 Anilino 1 naphthalenesulfonic Acid CAS 82 76 8, Magnesium Ethoxide