NorrChemica™
Salen (N,N'-Bis(salicylidene)ethylenediamine)
CAS 94-93-9
≥98%
Salen (N,N'-Bis(salicylidene)ethylenediamine) | CAS 94-93-9 | ≥98%
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Technical Specifications
| CAS Number | 94-93-9 |
| EC / EINECS Number | 202-376-3 |
| MDL Number | MFCD00002244 |
| RTECS Number | SL3780000 |
| SMILES | C1=CC=C(C(=C1)C=NCCN=CC2=CC=CC=C2O)O |
| InChI | InChI=1S/C16H16N2O2/c19-15-7-3-1-5-13(15)11-17-9-10-18-12-14-6-2-4-8-16(14)20/h1-8,11-12,19-20H,9-10H2 |
| InChIKey | VEUMANXWQDHAJV-UHFFFAOYSA-N |
| PubChem CID | 26518 |
| Molecular Formula | C₁₆H₁₆N₂O₂ |
| Molecular Weight | 268.31 g/mol |
| Melting Point | 127–128 °C |
| Solubility | Soluble in hot methanol and hot ethanol. Sparingly soluble in cold methanol and ethanol. Insoluble in water. |
| Purity | ≥98% |
| Physical Form | Yellow crystalline powder |
| HS Code | 2925.29 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Keep container tightly closed and dry. Store at room temperature; a cool, dark place is recommended. |
| SDS / CoA | Download PDF |
Product Description & Scientific Applications
Salen, N,N'-bis(salicylidene)ethylenediamine, is the unsubstituted tetradentate Schiff base formed from two salicylaldehyde units and ethylenediamine. It stabilises metal ions across a range of oxidation states.
It binds a single metal centre through two phenoxide oxygens and two imine nitrogens, filling the equatorial plane and leaving axial sites open for a co-ligand. Its two phenolic protons make it an O-H acidic ligand, and the ligand is sterically demanding with several distinct coordination sites.
Applications and Reactions
- Making the metal complex: Reaction with a metal acetate gives the metal salen complex directly, as when nickel(II) acetate tetrahydrate and the ligand give Ni(salen). It also forms complexes with second-row metals, reacting with [Ru(PPh3)3Cl2] in methanol to give the mononuclear Ru(III) complex [Ru(salen)(PPh3)Cl].
- Manganese catalysis: In ligand screening for manganese-catalysed acceptorless alcohol dehydrogenation it gave the most promising result of the ligands tested with a manganese carbonyl precursor.
- Artificial metalloenzymes: Its cobalt complex, CoSalen, serves as a first-row transition-metal water-oxidation catalyst hosted inside an electron-transfer protein.
- Sandwich complexes: In lanthanide and actinide chemistry it appears in bis-tetradentate arrangements, with a pair of ligands sandwiching the metal centre.
- Nanoparticle synthesis: Outside coordination chemistry it binds crystal surfaces during particle growth, inhibiting growth and giving smaller particles.
- Documented limits: In catalyst screening a four-hydroxyl analogue outperformed it, which places the parent as the baseline rather than the optimum. The ligand can be released intact from its metal complex under photochemical turnover, and is detected free in solution.
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Safety Information
| GHS Pictograms |
|
| Signal Word | Warning |
| Hazard Class | Not regulated for transport |
| Transport Category | Not classified as dangerous goods for transport (ADR/IATA/IMDG) |
| H-Statements | H315 - H319 |
| P-Statements | P261 - P264 - P271 - P280 - P302+P352 - P305+P351+P338 |
Documentation
| Safety Data Sheet | Download PDF |
