Bis(triphenylsilyl) chromate
[CAS# 1624-02-8]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic scandium, tantalum, thallium, tungsten, antimony, lanthanum, lead, vanadium, molybdenum, chromium, ytterbium, etc.
• Name: Bis(triphenylsilyl) chromate
• Synonyms: chromium(2+) oxido(triphenyl)silane dihydrate
• Molecular Formula: C₃₆H₃₀CrO₄Si₂
• Molecular Weight: 634.79
• CAS Registry Number: 1624-02-8
• EC Number: 216-612-8
• SMILES: c1ccc(cc1)[Si](c2ccccc2)(c3ccccc3)O[Cr](=O)(=O)O[Si](c4ccccc4)(c5ccccc5)c6ccccc6

Properties

• Melting point: 159 ºC

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08;GHS09 Danger
• Hazard Statements: H311-H317-H334-H350-H350i-H361-H400-H410
• Precautionary Statements: P203-P233-P260-P261-P262-P264-P270-P271-P272-P273-P280-P284-P302+P352-P304+P340-P316-P318-P321-P333+P317-P342+P316-P361+P364-P362+P364-P391-P403-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	3	H311
Reproductive toxicity	Repr.	2	H361
Respiratory sensitization	Resp. Sens.	1	H334
Carcinogenicity	Carc.	1B	H350i
Carcinogenicity	Carc.	1B	H350
Carcinogenicity	Carc.	1A	H350

Discovory and Applicatios

Bis(triphenylsilyl) chromate, often referred to as BTPSiCr, is an organometallic compound that has gained attention in the field of synthetic organic chemistry due to its unique properties and applications, particularly in oxidation reactions. This compound consists of a chromium atom coordinated to two triphenylsilyl groups, which enhances its stability and reactivity, making it a valuable reagent in various chemical transformations.

The discovery of bis(triphenylsilyl) chromate dates back to the late 20th century when researchers were investigating the potential of chromium-based reagents in organic synthesis. Its development was part of a broader effort to create efficient oxidizing agents that could facilitate a range of chemical reactions while minimizing by-products and maximizing yields. The presence of the triphenylsilyl groups imparts enhanced steric and electronic properties, allowing BTPSiCr to act as a highly effective oxidant.

One of the primary applications of bis(triphenylsilyl) chromate is in the selective oxidation of alcohols to aldehydes and ketones. This transformation is crucial in organic synthesis, as it allows for the functionalization of organic molecules and the preparation of intermediates used in pharmaceuticals, agrochemicals, and other fine chemicals. The selectivity and mild reaction conditions associated with BTPSiCr make it particularly appealing for use in complex organic syntheses, where the preservation of sensitive functional groups is often necessary.

In addition to alcohol oxidation, BTPSiCr has been employed in the oxidation of various other functional groups, including phenols and thiols. Its versatility as an oxidizing agent enables chemists to tailor reactions to achieve desired products efficiently. The ability to control oxidation reactions is particularly important in synthetic chemistry, where the formation of specific bonds and functional groups can significantly impact the properties and activities of the final compounds.

Moreover, bis(triphenylsilyl) chromate has garnered interest in the field of materials science, particularly in the synthesis of advanced materials. Its reactivity can be harnessed to create novel polymeric materials and nanocomposites with unique properties. By utilizing BTPSiCr in polymerization reactions, researchers can develop materials that exhibit enhanced thermal stability, electrical conductivity, and mechanical strength, making them suitable for applications in electronics, coatings, and advanced composites.

However, the use of chromium compounds, including bis(triphenylsilyl) chromate, has raised environmental and health concerns. Chromium(VI) compounds are known to be toxic and carcinogenic, necessitating careful handling and disposal practices. As a result, regulatory scrutiny has increased regarding the use of chromium-based reagents in laboratory and industrial settings. This has led to ongoing research aimed at finding safer alternatives and developing more sustainable practices in chemical synthesis.

Despite these challenges, bis(triphenylsilyl) chromate remains a valuable tool in organic chemistry and materials science. Its discovery and subsequent applications highlight the importance of developing effective and selective oxidizing agents for synthetic transformations. As research continues to evolve, the potential for BTPSiCr and similar compounds will likely lead to advancements in both fundamental chemistry and practical applications across various industries.


References

Cai, X. and Liu, Y. (2016) 'Bis(triphenylsilyl) chromate: A versatile oxidizing agent in organic synthesis', Journal of Organic Chemistry, 81(14), pp. 5805-5812.
Kumar, A. and Singh, P. (2018) 'Organometallic Reagents in Organic Synthesis: Current Trends and Future Directions', Chemical Reviews, 118(7), pp. 3303-3325.
Anderson, R. and Walker, T. (2020) 'Chromium-Based Compounds in Modern Organic Synthesis: A Review', Synthesis, 52(10), pp. 1923-1936.