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Description
TCI D3417 Diisobutyl Phosphite, CAS number 1189-24-8, is an organophosphorus reagent belonging to the dialkyl hydrogen phosphonate family, and it serves an important role in the synthesis laboratory as a source of the phosphorus–hydrogen bond. Its molecule consists of a phosphorus atom bearing two isobutoxy groups together with one reactive hydrogen atom, which allows the compound to act as a phosphorus nucleophile in a range of carbon–phosphorus bond-forming reactions. Having it on the reagent shelf lets researchers introduce phosphonate groups directly into organic molecular frameworks, without first having to prepare intermediate phosphorus reagents whose handling is far more complicated and demands specialised equipment.
The characteristic that makes this reagent a preferred choice is the high yet still controllable reactivity of its P–H bond. It can take part in the Pudovik reaction with aldehydes, ketones, and imines to give α-hydroxy and α-amino phosphonates, and it can also undergo Michael-type addition to unsaturated acceptors. The two branched isobutyl groups provide good solubility in organic solvents and a steric profile that differs from the diethyl analogue, a factor that is frequently exploited to tune selectivity. Because the material is a liquid, it can be measured and transferred by syringe or pipette, which simplifies stoichiometric work on a small scale.
In Indonesian laboratories, this reagent is typically found in university and institutional research groups working on organic synthesis, phosphonate chemistry, and the preparation of building blocks for further study. It is generally ordered as part of a broader set of non-heterocyclic building blocks, and used at bench scale for exploratory reactions, method development, and the preparation of intermediates that are subsequently characterised in-house. Its role as a ready-to-use phosphorus source is particularly valued where facilities for preparing more demanding phosphorus reagents are limited.
Laboratory Applications
- Pudovik reaction with aldehydes and ketones: the reactive P–H bond adds directly across the carbonyl group, giving α-hydroxy phosphonates without the need for a separately prepared phosphorus nucleophile.
- Synthesis of α-amino phosphonates from imines: the same P–H addition chemistry applies to C=N acceptors, letting researchers build nitrogen-bearing phosphonate frameworks in a single, straightforward bench-scale operation.
- Michael-type addition to unsaturated acceptors: the phosphorus nucleophile adds to activated alkenes and related systems, providing a direct route to extended phosphonate chains for further functionalisation.
- Carbon–phosphorus bond formation in general synthesis: the reagent acts as a convenient nucleophilic phosphorus source, allowing phosphonate groups to be installed into existing organic molecular frameworks directly.
- Selectivity studies against diethyl analogues: the branched isobutyl substituents give a different steric environment and solubility behaviour, which researchers use deliberately to adjust the selectivity of a reaction.
Specifications
- Brand: TCI
- CAS number: 1189-24-8
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: supplied in the standard TCI catalogue pack sizes for this item; please refer to the product listing for the options currently offered
- Physical form: liquid
- Storage note: keep tightly closed in a cool, dry place, protected from moisture
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from moisture, heat, and sources of ignition, and separated from strong oxidising agents. Because the material is a liquid, keep it in its original tightly sealed bottle whenever possible; if transfer is required, use clean, dry, chemically compatible glassware and dispense with a syringe or pipette rather than pouring. Handle in a fume hood, wear safety glasses, gloves, and a laboratory coat, and avoid contact with skin, eyes, and clothing as well as inhalation of vapour. Label all secondary containers clearly, and always consult the manufacturer's safety data sheet before use and before deciding on a disposal route.
