tert-Butyl 2-methylcarbazate
[CAS# 21075-83-2]

Identification

• Classification: Organic raw materials >> Organic derivative of hydrazine or hydrazine
• Name: tert-Butyl 2-methylcarbazate
• Synonyms: 1,1-Dimethylethyl 1-methylhydrazinecarboxylate; 1-Carbo-tert-butoxy-1-methylhydrazine; N-(tert-Butoxycarbonyl)-N-methylhydrazine; N-Boc-N-methylhydrazine; N-Methylhydrazinecarboxylic acid tert-butyl ester; tert-Butyl 1-methylhydrazinecarboxylate
• Molecular Formula: C₆H₁₄N₂O₂
• Molecular Weight: 146.19
• CAS Registry Number: 21075-83-2
• EC Number: 629-342-4
• SMILES: CC(C)(C)OC(=O)N(C)N

Properties

• Density: 1.029
• Boiling point: 186 °C
• Flash point: 66 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H227
• Safety Statements: P501-P210-P280-P370+P378-P403+P235

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	4	H227
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Tert-butyl 2-methylcarbazine (Boc-methylhydrazine) is an organic compound with the molecular formula C6H14N2O2. The chemical is primarily used as a protecting group for amines in organic synthesis, particularly in the development of pharmaceuticals and fine chemicals. The discovery and application of tert-butyl 2-methylcarbazine provided a reliable method for protecting and deprotecting functional groups during complex synthetic processes, greatly advancing the field of organic chemistry.

The development of tert-butyl 2-methylcarbazine can be linked to the broader exploration of carbazine compounds that began in the mid-20th century when chemists sought to create new reagents for use in synthetic chemistry. The introduction of the tert-butyl group as a protecting group for hydrazines and amines was a particularly useful innovation that allowed for greater control and selectivity in chemical reactions. The tert-butyl group was favored for its stability under a wide range of conditions, which allowed it to protect sensitive functional groups from undesirable side reactions.

One of the most important applications of tert-butyl 2-methylcarbazine is in the field of medicinal chemistry. In drug development, it is critical to synthesize complex molecules that often contain multiple functional groups, each of which must be manipulated selectively. tert-Butyl 2-methylcarbazate serves as a protecting group for hydrazine and amine functional groups, allowing chemists to temporarily deactivate these groups while modifying other parts of the molecule. Once the desired transformation is complete, the tert-butyl group can be removed under mild acidic conditions, exposing the free amine or hydrazine for further use or for use in the final product.

In addition to its use in drug synthesis, tert-Butyl 2-methylcarbazate is also used to prepare peptide-based therapeutics. Protecting groups are essential in peptide synthesis to prevent unwanted reactions between amino acids. The tert-butyl group helps ensure that the peptide is assembled in the correct order and has the desired structural integrity. This is particularly important for the development of new peptide-based therapeutics that can target specific biological pathways with high precision.

tert-Butyl 2-methylcarbazate can also be used in the synthesis of fine chemicals and specialty materials. Its role as a protecting group helps to build complex molecular structures for advanced materials and chemical intermediates. The stability and ease of removal of the tert-butyl group make it an attractive choice for synthetic chemists working in multi-step processes where intermediate compounds must be carefully controlled and manipulated.

The versatility of tert-butyl 2-methylcarbazate also extends to academic research. In a laboratory setting, this compound is used to study reaction mechanisms and develop new synthetic methods. Its ability to selectively protect and deprotect functional groups provides a powerful tool for exploring new chemical transformations and optimizing existing processes.

Safety and handling are important considerations when working with tert-butyl 2-methylcarbazate. While it is generally stable and non-reactive under normal conditions, appropriate precautions must be taken to avoid exposure and manage any potential risks associated with its use. Proper laboratory protocols and protective equipment are essential to ensure safe handling of this and other chemical reagents.

References

2013. Stereodynamics of Nitrogen Chiral Centers in aza-β3-Cyclodipeptides. *Chirality*, 25(9).
DOI: 10.1002/chir.22160

2009. Alkylation of Hydrazides. *Science of Synthesis*.
URL: SD-040-00831