Girard's Reagent T
[CAS# 123-46-6]

Identification

• Classification: Catalysts and additives
• Name: Girard's Reagent T
• Synonyms: (Carboxymethyl)trimethylammonium chloride hydrazide; 2-Hydrazino-N,N,N-trimethyl-2-oxo-ethanaminium chloride
• Molecular Formula: C₅H₁₄N₃O^.Cl
• Molecular Weight: 167.64
• CAS Registry Number: 123-46-6
• EC Number: 204-629-3
• SMILES: C[N+](C)(C)CC(=O)NN.[Cl-]

Properties

• Melting point: 188-192 ºC
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Girard's Reagent T, chemically known as 2,4-dinitrophenylhydrazine hydrochloride, is a specialized reagent used primarily for the detection and identification of carbonyl compounds, such as aldehydes and ketones. The discovery of Girard's Reagent T dates back to the mid-20th century when it was developed by the chemist Henri Girard. Girard's innovative approach aimed to create a selective reagent that could facilitate the analysis of carbonyl functionalities in organic compounds, thus enhancing the efficiency of chemical analysis in laboratories.

The structure of Girard's Reagent T features a hydrazine moiety that is particularly reactive toward carbonyl groups. When a carbonyl compound reacts with Girard's Reagent T, it forms a stable hydrazone derivative. This reaction not only helps in the identification of the carbonyl compound but also enhances its stability for subsequent analysis. The formation of these derivatives allows for easier purification and characterization of the target compounds through various techniques such as chromatography and spectrometry.

Girard's Reagent T is widely utilized in organic synthesis and analytical chemistry. One of its primary applications is in the qualitative and quantitative analysis of aldehydes and ketones in complex mixtures. For instance, in environmental chemistry, it is often employed to detect carbonyl pollutants in air and water samples. The reagent’s ability to form colored derivatives with carbonyls allows for straightforward visual or spectrophotometric determination of these compounds, making it a valuable tool in environmental monitoring.

Moreover, Girard's Reagent T plays a significant role in the pharmaceutical industry, where it is used in the synthesis and characterization of various drug intermediates. The formation of hydrazone derivatives can aid in purifying active pharmaceutical ingredients (APIs) by facilitating their separation from reaction mixtures. Additionally, the stability of these derivatives enhances the handling and storage of reactive carbonyl-containing compounds, which are otherwise prone to decomposition.

In recent years, the applications of Girard's Reagent T have expanded into proteomics and biomolecular research. It has been utilized for the labeling of carbonyl groups in proteins, which can help in studying post-translational modifications and protein interactions. This capability is particularly useful in understanding the biochemical pathways involved in various diseases, as it allows researchers to track changes in protein structure and function.

Furthermore, ongoing research continues to explore the potential of Girard's Reagent T in new areas, such as drug discovery and nanotechnology. Its unique reactivity toward carbonyl compounds positions it as a potential candidate for developing targeted delivery systems or novel therapeutic agents.

In conclusion, Girard's Reagent T is a crucial chemical reagent with extensive applications in analytical chemistry, organic synthesis, and biochemistry. Its ability to selectively react with carbonyl compounds has made it an invaluable tool in various scientific fields, from environmental analysis to pharmaceutical development. The continued exploration of its properties and applications is likely to yield new insights and innovations in chemical research.

References

2017. Liquid Chromatographic Analysis of α-Dicarbonyls Using Girard-T Reagent Derivatives. Journal of Chromatographic Science.
DOI: 10.1093/chromsci/bmx073

2019. Sensitive and robust MALDI-TOF-MS glycomics analysis enabled by Girard's reagent T on-target derivatization (GTOD) of reducing glycans. Analytica Chimica Acta.
DOI: 10.1016/j.aca.2018.10.015

2023. Facile one-precursor and one-pot synthesis of Girard�s reagent T-based carbon dots for bacteria-resistant and anti-biofilm applications. Biomedical Materials (Bristol, England).
DOI: 10.1088/1748-605x/acddc3