Ethyl cyanoglyoxylate-2-oxime
[CAS# 3849-21-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Oxime
• Name: Ethyl cyanoglyoxylate-2-oxime
• Synonyms: Ethyl cyano(hydroxyimino)acetate; Ethyl oximinocyanoacetate
• Molecular Formula: C₅H₆N₂O₃
• Molecular Weight: 142.11
• CAS Registry Number: 3849-21-6
• EC Number: 223-351-3
• SMILES: CCOC(=O)/C(=N/O)/C#N

Properties

• Solubility: 10% (acetonitrile)
• Melting point: 127-132 ºC
• Boiling point: 373.8764-377.3746 ºC (760 mmHg)

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS07 Danger
• Hazard Statements: H228-H301-H317-H319
• Precautionary Statements: P210-P240-P264-P270-P280-P301+P310-P330-P370+P378-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H311
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Ethyl cyanuric acid-2-oxime is a special organic compound with important applications in chemical synthesis and analytical chemistry. Its unique structure and reactivity make it a valuable reagent in various chemical processes.

Ethyl cyanuric acid-2-oxime, also known as ethyl 2-oximino-2-cyanoacetate, was first synthesized in the mid-20th century when chemists were seeking new methods for organic synthesis and compound characterization. The compound has a cyanuric acid moiety and an oxime group, which give it unique reactivity in chemical reactions.

The chemical formula of ethyl cyanuric acid-2-oxime is C₈H₇N₃O₃, and it is characterized by a pale yellow crystalline appearance. It is soluble in organic solvents such as ethanol and acetone, but not easily soluble in water. The presence of both cyano and oxime groups in its structure makes it remarkably reactive, especially in condensation reactions.

Ethyl cyanoglyoxylate-2-oxime is used to synthesize a variety of heterocyclic compounds. Its ability to react with different nucleophiles and electrophiles makes it a useful building block for the formation of complex ring structures, which are important in pharmaceuticals and natural products.

This compound is used to generate α-keto acids via condensation reactions. These α-keto acids serve as intermediates in the synthesis of more complex molecules and can be further transformed into various functionalized compounds.

Ethyl cyanoglyoxylate-2-oxime is used in analytical chemistry due to its ability to form complexes with metal ions. This property can be used to detect and quantify metal ions in various samples, including environmental and biological samples.

In synthetic organic chemistry, ethyl cyanoglyoxylate-2-oxime can react with aldehydes and ketones to form oxime ethers. These reactions are very useful for modifying and functionalizing organic molecules in complex synthetic pathways.

Ethyl cyanoglyoxylate-2-oxime is chemically reactive and should be handled with care. It is irritating to the skin, eyes, and respiratory system. Appropriate safety measures include wearing protective clothing, gloves, and goggles, and working in a well-ventilated area. The compound should be stored in a cool, dry place away from incompatible materials and sources of ignition.