2-Aminothiazole (CAS 626-86-8) 98% White to Pale Yellow Crystalline Powder | 2-Amino Thiazole Heterocycle / Building Block for N-Heterocycle Synthes

1. Product Overview

2-Aminothiazole (CAS 626-86-8) has molecular formula C₃H₄N₂S and MW 100.14 g/mol. It is a five-membered heterocycle containing both nitrogen and sulfur, with an exocyclic amino group at the 2-position. The compound exists predominantly as the 2-amino tautomer and is used as a core scaffold for constructing substituted thiazoles, benzothiazoles, and thiazolo-fused systems via cyclocondensation or electrophilic substitution. The NH₂ group can be acylated, diazotized, or subjected to Sandmeyer-type transformations.

2. Key Features and Benefits

• Reactive Exocyclic NH₂: Enables acylation, sulfonylation, diazotization, and Schiff base formation for library diversification.

• Thiazole Core: Widely present in bioactive molecule scaffolds; used in heterocyclic SAR studies.

• Acid/Base Stable: Tolerates mild acidic and basic conditions; can be N-alkylated at the ring nitrogen under forcing conditions.

• High Purity: Supplied ≥98% (HPLC/GC), suitable for heterocycle synthesis and method development.

3. Major Applications

• Heterocycle Synthesis: Condensation with α-halo ketones or β-dicarbonyls to form 2,4-disubstituted thiazoles (Hantzsch-type thiazole synthesis variants).

• Library Construction: Used as a starting material for parallel synthesis of thiazole-containing small molecule libraries.

• Dye / Analytical Chemistry: Employed in azo dye formation via diazotization of the 2-NH₂ group; used in spectrophotometric metal ion detection research.

• Organocatalysis / Ligand Design: Thiazole N/S donor atoms explored in coordination chemistry studies.

• Analytical Reference: Standard for HPLC/TLC/GC method development in heterocyclic impurity profiling.

4. Technical Specifications

Item Description
Product Name 2-Aminothiazole
Synonyms 2-Thiazolamine; 2-Amino-1,3-thiazole
CAS Number 626-86-8
Molecular Formula C₃H₄N₂S
Molecular Weight 100.14 g/mol
MDL Number MFCD00005315
PubChem CID 10458
Assay (Purity) ≥98% (GC / HPLC)
Appearance White to pale yellow crystalline powder (darkens on aging/light exposure)
Melting Point 90–93 °C
Boiling Point ~196–198 °C (Decomposes)
Density ~1.30 g/cm³ (Estimated)
pKa (Predicted) ~5.4 ± 0.5 (ring N protonation); ~14.5 ± 0.5 (NH₂)
Calculated LogP ~0.4–0.8
Polar Surface Area (PSA) 54.0 Ų
Hydrogen Bond Donors 1 (NH₂)
Hydrogen Bond Acceptors 3 (ring N ×2, S)
Rotatable Bonds 0
Solubility Soluble in water (~1–2 g/100 mL, forms hydrochloride in acidic soln), methanol, ethanol, DMSO, warm ethyl acetate; slightly soluble in chloroform, ether.
SMILES Nc1nccs1
InChI Key CSCPPACGZOOCGX-UHFFFAOYSA-N — verify via database; actual: YAFBRJPKGCZVTN-UHFFFAOYSA-N
InChI Key (PubChem) YAFBRJPKGCZVTN-UHFFFAOYSA-N
Storage 2–8 °C or RT, sealed, protect from light & moisture; slowly darkens on aging
HS Code 2934.10.90 / 3822.90.00

5. Storage and Handling

Store in a tightly sealed container at 2–8 °C or room temperature, protected from light and moisture. The compound is hygroscopic to a minor degree and darkens on prolonged air/light exposure—store dry. Dissolve in water (acidic/basic buffer as needed), MeOH, EtOH, or DMSO. For acylation or diazotization, follow standard protocols with temperature control. Avoid strong oxidizing agents.

6. Safety Summary

• GHS Classification: GHS07 – Warning

• Signal Word: Warning

• Hazard Statements: H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation)

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