1. Product Overview
3-(tert-Butylthio)pyridin-2-amine (CAS 551950-47-1) is a pyridine-based organosulfur compound featuring a tert-butylthio (S-t-Bu) substituent at the 3-position and an amino group at the 2-position of the pyridine ring. The bulky tert-butyl group imparts enhanced lipophilicity (LogP ~1.94–3.14) and steric hindrance around the sulfur atom, making the thioether bond more resistant to oxidation compared to linear alkylthio analogs. This compound serves as a versatile intermediate in pharmaceutical synthesis, particularly in the preparation of sulfur-containing heterocycles, kinase inhibitor scaffolds, and agrochemical active ingredients.
2. Key Features and Benefits
• Sterically Hindered Thioether: The tert-butyl group protects the sulfur from easy oxidation to sulfoxide/sulfone, improving shelf stability compared to methylthio or ethylthio analogs.
• Orthogonal Reactivity: The 2-amino group (–NH₂) can be diazotized, acylated, or alkylated, while the pyridine nitrogen and thioether provide additional handles for metal-catalyzed cross-coupling (e.g., Buchwald-Hartwig amination after activation).
• Lipophilicity Enhancement: The tert-butylthio moiety significantly increases membrane permeability (LogP ~1.94–3.14), making it valuable in drug design for improving oral bioavailability.
• High Purity: Supplied at ≥95% or ≥98% (HPLC/GC), with full lot-specific CoA including ¹H NMR verification.
• Room Temperature Stable: Unlike many organosulfur compounds, this thioether is stable at room temperature under proper storage conditions.
3. Major Applications
• Pharmaceutical Intermediate: Key building block for synthesizing APIs targeting kinase inhibition, GPCR modulation, and anti-inflammatory pathways where pyridine-thioether scaffolds are therapeutically relevant.
• Agrochemical R&D: Used in the development of sulfur-containing pesticides, fungicides, and herbicides as a core heterocyclic intermediate.
• Heterocyclic Library Synthesis: Employed in Diversity-Oriented Synthesis (DOS) to generate pyridine-based compound libraries for high-throughput screening in drug discovery.
• Materials & Ligand Design: The pyridine-thioether framework can serve as a chelating ligand precursor for transition metal catalysis or as a building block for functional materials.
• Academic Research: Studied as a representative pyridine-2-amine derivative in heterocyclic chemistry, nucleophilic aromatic substitution, and C–H activation methodologies.
4. Technical Specifications
Item Description
Product Name 3-(tert-Butylthio)pyridin-2-amine
Synonyms 3-tert-Butylsulfanyl-pyridin-2-ylamine; 2-Amino-3-(tert-butylthio)pyridine; 3-[(1,1-Dimethylethyl)thio]-2-pyridinamine; 3-tert-Butylsulfanylpyridin-2-amine
CAS Number 551950-47-1
Molecular Formula C₉H₁₄N₂S
Molecular Weight 182.29 g/mol
MDL Number MFCD05663516
PubChem CID 17750171
Assay (Purity) ≥95% / ≥98% (HPLC / GC)
Appearance White to off-white crystalline solid or powder
Melting Point Not reported (typical for alkylthiopyridines: 50–120 °C)
Boiling Point ~284.7 °C at 760 mmHg (Predicted)
Density ~1.09 g/cm³ (Predicted)
Flash Point ~126 °C (Predicted)
pKa (Predicted) ~6.5–7.5 (Pyridine N protonation); ~3.5 (NH₃⁺)
Calculated LogP ~1.94–3.14
Polar Surface Area (PSA) ~64.21 Ų
Hydrogen Bond Donors 1 (NH₂)
Hydrogen Bond Acceptors 2 (Pyridine N + S)
Rotatable Bonds 2
Solubility Soluble: DMSO (>50 mg/mL), DMF, Methanol, Ethanol, DCM, Chloroform, THF, Acetone, Acetic acid.
Slightly Soluble:Water (very low aqueous solubility due to high LogP).
Insoluble:Hexane (very low).
Spectral Data (Predicted) ¹H NMR (CDCl₃, 400 MHz): δ 1.35 (s, 9H, C(CH₃)₃), 4.95 (br s, 2H, NH₂), 6.80 (dd, J≈7.5, 5.0 Hz, 1H, Py-H4), 7.15 (dd, J≈7.5, 1.5 Hz, 1H, Py-H5), 7.85 (dd, J≈5.0, 1.5 Hz, 1H, Py-H6).
¹³C NMR (CDCl₃):δ 30.0 (C(CH₃)₃), 44.5 (C(CH₃)₃), 115–150 (pyridine Cs), 155.0 (C-2, NH₂-bearing).
SMILES CC(C)(C)SC1=C(N)C=CC=N1
InChI Key JBLSSTPVTVGUEG-UHFFFAOYSA-N
Storage (Powder) Room Temperature or 2–8 °C, sealed, protected from light & moisture; stable ≥18–24 months
Sensitivity Light-sensitive (moderate); store protected from light
HS Code 2933.39.99 / 2933.99.90
5. Storage and Handling
• Storage: Store in a tightly sealed container at room temperature or 2–8 °C, protected from light and moisture. For long-term storage (>12 months), a desiccator is recommended. The thioether bond is stable under these conditions, but prolonged exposure to strong oxidizers, acids, or UV light should be avoided.
• Handling: Allow vial to reach room temperature before opening to prevent moisture condensation. Dissolve in anhydrous DMSO, DMF, MeOH, DCM, or THF as required. Minimize light exposure during handling.
• Thioether Stability: Unlike primary/secondary thiols, this tertiary thioether is resistant to aerial oxidation and does not form disulfides. However, strong oxidizers (H₂O₂, mCPBA) will convert it to the sulfoxide or sulfone—useful for intentional derivatization.
• Solution Stability: Prepare fresh for critical reactions. DMSO stocks may degrade slowly under light exposure; store aliquots in amber vials at -20 °C for up to 1–2 months.
6. Safety Summary (Full SDS Highlights)
• GHS Classification: GHS07 – Warning
• Signal Word: Warning
• Hazard Statements:
• H302: Harmful if swallowed.
• Precautionary Statements:
• P261: Avoid breathing dust/mist/vapors. Use only in a well-ventilated area or fume hood.
• P264: Wash hands, forearms, and face thoroughly after handling.
• P270: Do not eat, drink, or smoke in areas where this material is used.
• P271: Use only outdoors or in a well-ventilated area.
• P280: Wear protective gloves (nitrile), safety glasses with side shields, and lab coat.
• P301+P312: IF SWALLOWED: Call a POISON CENTER or physician if you feel unwell.
• P302+P352: IF ON SKIN: Wash with plenty of soap and water.
• P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
• P330: Rinse mouth if swallowed.
• P337+P313: If eye irritation persists: Get medical advice/attention.
• P403+P233: Store in a well-ventilated place. Keep container tightly closed.
• P501: Dispose of contents/container in accordance with local, regional, and national regulations.
• First Aid Measures:
• Inhalation: Remove to fresh air. If breathing difficult, administer oxygen and seek medical attention.
• Skin Contact: Immediately wash with plenty of soap and water. Remove contaminated clothing. Seek medical advice if irritation or rash develops.
• Eye Contact: Flush immediately with copious lukewarm water for at least 15 minutes. Remove contact lenses if possible. Seek medical attention.
• Ingestion: Rinse mouth. Do NOT induce vomiting. Give water to drink if conscious. Seek medical advice.
• Fire-Fighting Measures:
• Suitable Extinguishing Media: Water spray, alcohol-resistant foam, dry chemical, or CO₂.
• Special Hazards: Combustion may produce irritating/acrid smoke (SOₓ, NOₓ, CO). Sulfur oxides are toxic.
• Protective Equipment: Wear self-contained breathing apparatus (SCBA) and full protective clothing.
• Spill Response:
• Avoid dust generation. Sweep up and place in a suitable closed container for disposal. Do not allow entry to drains or waterways. Ventilate area after cleanup.
• Handling & Storage:
• Handle in fume hood. Keep container closed when not in use. Store at room temperature or 2–8 °C, protected from light and moisture. Keep away from strong oxidizers (peroxides, hypochlorites) and strong acids.
• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use.
