Cyanoacetic acid
[CAS# 372-09-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Halogenation, sulfonation, nitration or nitrosation of carboxylic acids
• Name: Cyanoacetic acid
• Molecular Formula: C₃H₃NO₂
• Molecular Weight: 85.06
• CAS Registry Number: 372-09-8
• EC Number: 206-743-9
• SMILES: C(C#N)C(=O)O

Properties

• Melting point: 65-67 °C
• Boiling point: 108 °C (15 mmHg)
• Flash point: 107 °C
• Water solubility: 1000 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302+H332-H302-H314-H318-H332-H412
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	3	H331
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	4	H312
Skin corrosion	Skin Corr.	1C	H314
Skin corrosion	Skin Corr.	1	H314

• Transport Information: UN 3261

Discovery and Applications

Cyanoacetic acid, a compound with the formula NCCH2COOH, was first synthesized in the late 19th century as chemists explored derivatives of acetic acid. Cyanoacetic acid is characterized by the presence of both a cyano group (–CN) and a carboxyl group (–COOH), making it a versatile intermediate in various chemical reactions. Its unique structure allows it to act as a building block for more complex organic compounds.

In pharmaceuticals, cyanoacetic acid serves as a crucial intermediate in the synthesis of various drugs. It is involved in the production of barbiturates, which are used as sedatives and anesthetics. Cyanoacetic acid is also a key starting material in the synthesis of several other active pharmaceutical ingredients (APIs), such as non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive agents.

Cyanoacetic acid is used in the production of agrochemicals, including herbicides and fungicides. For example, cyanoacetic acid is a precursor to cyanoacetamide, which is used to synthesize various herbicidal compounds.

In organic synthesis, cyanoacetic acid is valued for its versatility as a building block. It is used to produce cyanoacrylates, which are the main component of fast-acting adhesives like super glue. Additionally, cyanoacetic acid is used in the synthesis of dyes, pigments, and various polymers. Its ability to participate in multiple types of chemical reactions, such as Knoevenagel condensations and Michael additions, makes it a valuable reagent in synthetic organic chemistry.

Cyanoacetic acid and its derivatives are also employed in the field of electronics and materials science. They are used in the production of photoactive compounds for photovoltaic cells. Additionally, cyanoacetic acid is used in the synthesis of fluorescent dyes and materials for optoelectronic devices.

In academic research, cyanoacetic acid is used as a model compound to study reaction mechanisms and develop new synthetic methodologies. Its reactivity and functional group versatility make it an excellent subject for exploring organic reaction pathways and designing novel compounds with potential applications in various industries.

References

2024. Self-Assembled Monolayers as Hole-Selective Contacts in Inverted Perovskite Solar Cells: A Review. Korean Journal of Chemical Engineering, 41(12).
DOI: 10.1007/s11814-024-00335-7

2024. Spectroscopic, thermal, electrical, and nonlinear optical investigation of benzimidazolium cyanoacetate single crystals for optoelectronics device applications. Journal of Materials Science: Materials in Electronics, 35(34).
DOI: 10.1007/s10854-023-11725-8

2024. Investigation of the Combination of Indoline and Naphthalimide in the Preparation of Photosensitizers for Photovoltaic Devices. Journal of Electronic Materials, 53(11).
DOI: 10.1007/s11664-024-11538-3