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2-mercaptopyridine
2-Mercaptopyridine is a heterocyclic organosulfur compound featuring a thiol group attached to a pyridine ring, known for its use in chemical research and specific odor attributes.
General Material Description
2-Mercaptopyridine is an organosulfur heterocyclic compound characterized by a five-membered pyridine ring with a thiol group at the second position. Its molecular formula is C5H5NS. Exhibiting a distinct burnt odor, it also appears in literature under numerous synonyms including pyridine-2-thiol and 2-pyridinethione, reflecting its tautomeric forms. The substance is typically a crystalline solid and is soluble in water and alcohol, with reversible tautomerism between thiol and thione forms. It is often sourced by synthetic organic chemistry methods rather than natural derivation. For detailed chemical data, it is indexed under CHEBI:45223.
Occurrence, Applicability & Potential Uses
2-Mercaptopyridine occurs primarily as a synthetic chemical used in specialized applications such as coordination chemistry and as a building block in pharmaceutical research. It is not commonly found in natural biological systems. Although known for its burnt flavor note, usage in fragrances or flavorings is not recommended or authorized according to relevant standards. Regulatory frameworks including REACH (European Union) classify it as an irritant requiring careful handling. Its role in material science and organic synthesis defines its principal applicability rather than direct consumer product use.
Physico-Chemical Properties Summary
2-Mercaptopyridine exhibits a melting point range between 128 and 130 °C and boils between 184 and 186 °C at standard atmospheric pressure (760 mm Hg). Its flash point is approximately 150 °F (roughly 66 °C), indicating moderate flammability. The compound shows slight hydrophilicity, dissolving well in water (around 139 mg/L at 25 °C) and alcohol solvents, enabling diverse formulation contexts. With a log P near -0.13, it demonstrates limited lipophilicity which affects its partitioning behavior. Shelf life extends beyond 12 months when refrigerated in sealed containers, reflecting its relative stability under controlled conditions.
FAQ
What is 2-mercaptopyridine and what are its key characteristics?
2-Mercaptopyridine is a sulfur-containing heterocyclic compound with a molecular formula C5H5NS. It contains a pyridine ring substituted with a thiol group at the 2-position. The compound displays tautomerism between thiol and thione forms, influencing its chemical behavior. It typically appears as a solid with a burnt odor note and is utilized mostly in research and synthetic chemistry contexts.
How is 2-mercaptopyridine typically used and where is it found?
This compound is predominantly synthesized for use in chemical research and as an intermediate in pharmaceutical syntheses. It is not naturally abundant and is not employed in fragrance or flavor applications. Its utility lies in organosulfur chemistry and as a ligand in coordination compounds. Its physical properties make it suitable for controlled laboratory handling rather than consumer products.
What safety considerations and regulations apply to 2-mercaptopyridine?
2-Mercaptopyridine is classified as an irritant to eyes, skin, and respiratory system under European regulations (REACH, EU). Handling requires protective clothing, gloves, and eye protection. It is not approved for flavor or fragrance use, with no established safe exposure levels for these industries. Safety data sheets advise storage in tightly sealed containers under refrigeration to maintain stability and minimize risk.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 1H-pyridine-2-thione | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 2723698 |
| Pubchem (sid): | 134982422 |
| Publications by US Patents | |
| 3,952,024 - Furfurylthioacetone | |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2902.19.0050 |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | 2-mercaptopyridine |
| Trivial Name | 2-Mercaptopyridine |
| Short Description | 2(1H)-pyridinethione |
| Formula | C5 H5 N S |
| CAS Number | 2637-34-5 |
| Deleted CAS Number | 1120-96-3 |
| ECHA Number | 220-131-9 |
| FDA UNII | EE982KT952 |
| Nikkaji Number | J51.344J |
| Beilstein Number | 0105787 |
| MDL | MFCD00006285 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| BOC Sciences | LBB Specialties |
| Santa Cruz Biotechnology | Sigma-Aldrich: Aldrich |
| TCI AMERICA | Tengzhou Jitian Aroma Chemiclal |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 111.166847229 |
| Melting Point | 128 to 130°C @ 760 mm Hg |
| Boiling Point | 184 to 186°C @ 760 mm Hg |
| Vapor Pressure | 0.631 mmHg @ 25 °C |
| Flash Point TCC Value | 65.56 °C TCC |
| logP (o/w) | -0.13 |
| Shelf life | 12 months (or longer if stored properly.) |
| Storage notes | Refrigerate in tightly sealed containers. |
| Solubility | |
| alcohol | Yes |
| water, 1.392e+005 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Flavor Type: Burnt | |
| burnt | |
| General comment | Burnt, enhances the burnt note |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| intraperitoneal-mouse LD50 250 mg/kg National Technical Information Service. Vol. AD691-490 intravenous-mouse LD50 250 mg/kg Archives Internationales de Pharmacodynamie et de Therapie. Vol. 93, Pg. 143, 1953. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| information only not used for fragrances or flavors | |||
| Recommendation for 2-mercaptopyridine usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for 2-mercaptopyridine flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):2637-34-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :2723698 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 1H-pyridine-2-thione |
| Chemidplus:0002637345 |
| RTECS:UT9600000 for cas# 2637-34-5 |