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Description
TCI D4811 4,5-Dimethoxy-2-nitrobenzyl Alcohol is a non-heterocyclic synthetic building block whose principal role in the laboratory is to serve as a precursor to photolabile protecting groups. Its molecular structure consists of a benzene ring bearing a hydroxymethyl group, two methoxy groups, and a single nitro group positioned ortho to the benzyl alcohol function. It is precisely this nitrobenzyl arrangement combined with an electron-rich aromatic ring that allows the compound's bond to be cleaved by light. In practical use, researchers employ this material to prepare "caged" compounds, photolabile tags, and photocleavable linkers for solid-phase synthesis.
The properties that make this compound a preferred choice centre on its photochemical profile. The two methoxy substituents shift light absorption to longer wavelengths than those of a simple nitrobenzyl system, which means cleavage can be triggered with near-ultraviolet light that is considerably gentler on biological systems. The primary hydroxyl group is readily converted into esters, carbonates, carbamates, ethers, or halide derivatives as well as the activated bromide, so attachment to a target molecule proceeds through straightforward chemistry with good yields. Release then occurs cleanly, without requiring any additional chemical reagent — only irradiation.
In Indonesian laboratories, this building block is typically handled in university research groups, institutional chemistry laboratories, and industrial R&D units working on protecting-group strategy, photoactivatable probes, and solid-phase methods. It is normally purchased in small research quantities and used on a milligram to gram scale for exploratory synthesis rather than bulk production. Because the material is light-sensitive by design, laboratories generally keep it in its original container and weigh it out under reduced ambient lighting.
Laboratory Applications
- Photolabile protecting group synthesis — the compound is converted into carbonates or carbamates that mask alcohols and amines, then removed later by irradiation instead of acid or base treatment.
- Caged compound preparation — the benzyl alcohol is attached to an active molecule so that its function stays masked until near-ultraviolet light restores biological or chemical activity on demand.
- Photocleavable linkers for solid-phase synthesis — assembled products can be released from resin supports by light alone, avoiding the harsh cleavage cocktails that would damage sensitive target structures.
- Photolabile tagging and labelling studies — the nitrobenzyl unit is installed as a light-removable marker, allowing researchers to trigger release at a chosen time point without adding reagents.
- General non-heterocyclic building block chemistry — the primary hydroxyl is derivatised to esters, ethers, halides, or the activated bromide, giving convenient entry points for further multi-step synthesis.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- CAS number: 1016-58-6
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Product code: D4811
- Pack sizes: available in standard TCI research pack sizes; please confirm the currently offered packaging when ordering
- Storage note: light-sensitive material — store protected from light in a cool, dry place in the original container
Handling and Storage
Store 4,5-Dimethoxy-2-nitrobenzyl Alcohol in a cool, dry, well-ventilated area, protected from light and away from heat sources, ignition sources, and incompatible chemicals such as strong oxidising agents. Keep the material in its original tightly closed container, or transfer it to amber glass or a light-opaque vessel with a chemically resistant closure. Because the compound is deliberately photolabile, minimise exposure to direct sunlight and laboratory UV sources during weighing and transfer. Handle it in a fume hood using safety glasses, chemically resistant gloves, and a laboratory coat, and avoid generating or inhaling dust. Consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials as chemical waste according to institutional procedures.
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