Ethyl isocyanoacetate

Base Information

• Chemical Name: Ethyl isocyanoacetate
• CAS No.: 2999-46-4
• Molecular Formula: C5H7NO2
• Molecular Weight: 113.116
• Hs Code.: 29299090
• European Community (EC) Number: 221-077-9
• DSSTox Substance ID: DTXSID20184078
• Nikkaji Number: J150.099F
• Wikidata: Q72475591
• Mol file: 2999-46-4.mol

Synonyms:Ethyl isocyanoacetate;2999-46-4;ethyl 2-isocyanoacetate;Isocyanoacetic Acid Ethyl Ester;Acetic acid, isocyano-, ethyl ester;EINECS 221-077-9;ETHYLISOCYANOACETATE;MFCD00000007;Acetic acid, 2-isocyano-, ethyl ester;ethyl iso-cyanoacetate;ethyl isocyano-acetate;ethyl 2-isocyanoacetat;ethyl isocyano- acetate;ethyl-2-isocyanoacetate;SCHEMBL7225;Ethyl isocyanoacetate(EICA);isocyano-acetic acid ethylester;AMY403;isocyano-acetic acid ethyl ester;DTXSID20184078;BCP11231;STR02697;BBL021319;GEO-01356;STK894028;AKOS005144095;AB00104;SB40700;2-ISOCYANO-ACETIC ACID ETHYL ESTER;BB 0262985;FT-0627402;I0562;EN300-50660;J-017729;J-521262;F0001-2483

Chemical Property of Ethyl isocyanoacetate

Chemical Property:

• Appearance/Colour: Light yellow to brom liquid
• Vapor Pressure: 61.7Pa at 25℃
• Melting Point: 194-196 °C(lit.)
• Refractive Index: n20/D 1.418(lit.)
• Boiling Point: 194-196°C(lit.)
• Flash Point: 84 °C
• PSA: 26.30000
• Density: 1.03 g/cm³
• LogP: -0.30050
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Water Solubility.: Miscible with organic solvents. Slightly miscible with water.
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 113.047678466
• Heavy Atom Count: 8
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

Ethyl isocyanoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/22-20/21/22
• Safety Statements: 36/37/39-26-36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C[N+]#[C-]
• General Description: Ethyl isocyanoacetate is a versatile reagent used in the synthesis of biologically active compounds, particularly in the copper(I)-catalyzed formation of 3-aminocoumarin derivatives. It serves as a key building block in medicinal chemistry, enabling the construction of pharmacologically relevant scaffolds with potential applications as CNS depressants, antitumor agents, anti-inflammatory drugs, antimicrobials, and fluorescent markers. Its reactivity in multicomponent reactions highlights its utility in generating privileged structures for pharmaceutical and agrochemical development.

Technology Process of Ethyl isocyanoacetate

There total 8 articles about Ethyl isocyanoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl N-formylglycinate (3154-51-6) → Ethyl isocyanoacetate (2999-46-4)

Guidance literature:

With triethylamine; trichlorophosphate; In dichloromethane; at 5 - 20 ℃; Inert atmosphere; Cooling with ice;

DOI:10.1021/ja907428e

Reference yield: 90.0%

potassium 2-isocyanoacetate (58948-98-4) → Ethyl isocyanoacetate (2999-46-4)

Guidance literature:

In N,N-dimethyl-formamide; at 55 - 60 ℃; for 3h;

DOI:10.1248/cpb.28.2374

Reference yield: 69.0%

formylglycine (2491-15-8) → Ethyl isocyanoacetate (2999-46-4)

Guidance literature:

With triethylamine; trichlorophosphate; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1039/b807278g

upstream raw materials:

ethyl N-formylglycinate

methyl isocyanate

Diethyl carbonate

potassium 2-isocyanoacetate

Downstream raw materials:

ethyl-5‐phenyl‐1,3‐thiazole‐4‐carboxylate

ethyl 5-benzyloxazole-4-carboxylate

oxazole-4-carboxylic acid ethyl ester

4-Cyano-2-methyleneamino-3-phenyl-butyric acid ethyl ester

Refernces

Simple and efficient copper(I)-catalyzed access to three versatile aminocoumarin-based scaffolds using isocyanoacetate

10.1002/adsc.201000895

The study presents an efficient method for the one-pot copper(I)-catalyzed synthesis of 3-aminocoumarin and its derivatives, which are biologically and pharmaceutically significant compounds. The researchers utilized salicylaldehyde, ethyl isocyanoacetate, and 2-aminopyridine as the primary starting materials, along with copper(I) salts (CuI, Cu(OTf)2, etc.) as catalysts, and pyridine as a base. These chemicals served to construct molecular scaffolds that are valuable in medicinal chemistry due to their potential applications as CNS depressants, antitumor, anti-inflammatory, and antimicrobial agents, as well as their use as fluorescent markers. The study aimed to develop a straightforward and efficient approach to these molecular scaffolds, which are considered "privileged structures" in the pharmaceutical and agrochemical industries.