2-Amino-2,3-dimethylbutyronitrile
[CAS# 13893-53-3]

Identification

• Classification: Chemical pesticide >> Herbicide >> Herbicide intermediate
• Name: 2-Amino-2,3-dimethylbutyronitrile
• Molecular Formula: C₆H₁₂N₂
• Molecular Weight: 112.17
• CAS Registry Number: 13893-53-3
• EC Number: 604-102-1
• SMILES: CC(C)C(C)(C#N)N

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.444, Calc.^*
• Boiling Point: 173.5±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 58.8±22.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS09 Danger
• Risk Statements: H301-H310-H330-H400-H410
• Safety Statements: P260-P262-P264-P270-P271-P273-P280-P284-P301+P316-P302+P352-P304+P340-P316-P320-P321-P330-P361+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	1	H310
Acute toxicity	Acute Tox.	1	H330
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Amino-2,3-dimethylbutyronitrile is an organic compound that belongs to the class of amino nitriles, characterized by the presence of both an amino group and a nitrile functional group within its molecular structure. The compound has garnered attention due to its potential applications in organic synthesis and medicinal chemistry. Its discovery can be traced back to research focusing on amino acids and their derivatives, which have been pivotal in the development of various pharmaceuticals and agrochemicals.

The synthesis of 2-amino-2,3-dimethylbutyronitrile typically involves multi-step organic reactions starting from readily available precursors. Common methods for its synthesis include the alkylation of cyanoacetate with isobutyl bromide, followed by hydrolysis and subsequent reactions to introduce the amino group. This synthetic route has been optimized over the years, allowing for the efficient production of the compound in laboratory and industrial settings.

One of the primary applications of 2-amino-2,3-dimethylbutyronitrile is in the synthesis of pharmaceutical intermediates. The compound serves as a building block for various biologically active molecules, particularly those exhibiting anti-inflammatory and analgesic properties. Its structural features contribute to the development of drugs targeting multiple therapeutic areas, including pain management and inflammation.

Additionally, 2-amino-2,3-dimethylbutyronitrile is explored for its potential use in the synthesis of chiral compounds, which are essential in the pharmaceutical industry due to their unique properties and interactions with biological systems. The presence of both the amino and nitrile groups in its structure allows for the possibility of further functionalization and modification, facilitating the creation of a diverse range of chiral intermediates.

The compound has also been studied for its utility in agricultural chemistry, particularly in the development of herbicides and pesticides. Its nitrile functionality can be a key feature in designing active ingredients that effectively control weed and pest populations while minimizing environmental impact.

Moreover, research has indicated that compounds related to 2-amino-2,3-dimethylbutyronitrile may exhibit antimicrobial properties, making them candidates for the development of novel antimicrobial agents. The increasing demand for effective antimicrobial agents in the face of rising antibiotic resistance has prompted exploration into the potential of such compounds in therapeutic applications.

In summary, 2-amino-2,3-dimethylbutyronitrile is an important organic compound with a range of applications in organic synthesis, pharmaceuticals, and agricultural chemistry. Its discovery and continued study highlight its relevance in developing new therapeutic agents and agrochemicals, contributing to advancements in multiple scientific fields.

References

2010. 2-Amino-2,3-dimethyl-butanamide. Acta crystallographica. Section E, Structure reports online.
DOI: 10.1107/s1600536810015679

2017. Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures. Nature Chemistry.
DOI: 10.1038/nchem.2703

2011. Biosynthesis of 2-amino-2,3-dimethylbutyramide by nitrile hydratase from a newly isolated cyanide-resistant strain of Rhodococcus qingshengii. Biotechnology Letters.
DOI: 10.1007/s10529-011-0623-7