Ethyl Cyanoacetate CAS 105-56-6

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  • Appearance: Colorless liquid
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Ethyl Cyanoacetate Supplement
105-56-6

Basic Info of Ethyl Cyanoacetate

What is Ethyl Cyanoacetate?

Ethyl cyanoacetate molecular formula c5h7no2; Structural type ncch2cooch2ch3; The appearance is colorless or slightly yellow liquid with slight smell; Molecular weight 113.12; Steam pressure 2.00kpa (99 ℃); Flash point: 110 ℃; Melting point – 22.5 ℃; Boiling point 206 ~ 208 ℃; Slightly soluble in water, lye and ammonia, miscible in ethanol and ether; The relative density is 1.06. Ethyl cyanoacetate is mainly used as a pharmaceutical intermediate, caffeine and vitamin B, as well as an oil soluble coupler for color films and a raw material for 502 adhesives.

5-Cyano-6-hydroxy-4-methoxymethyl-2-methylpyridine can be prepared by cyclizing ethyl cyanoacetate with methoxyacetylacetone and ammonia. After nitration, chlorination and catalytic hydrogenation, 3-amino-5-aminomethyl-4-methoxymethyl-2-methylpyridine can be obtained. Further diazotization, hydrolysis and salification can obtain biotin B6. Ethyl cyanoacetate is an intermediate for the preparation of diethyl malonate, from which 2-amino-4,6-dimethoxypyrimidine can be prepared as an intermediate for sulfonylurea herbicides, insecticide fipronil, and vitamin B.

Ethyl cyanoacetate is the ethyl ester of cyanoacetate. Ethyl cyanoacetate is rapidly hydrolyzed to cyanoacetic acid and ethanol under neutral and alkaline conditions (the same is true under most physiological and environmental conditions), while the half-life is much longer under acidic pH conditions.

Ethyl cyanoacetate is mainly used in organic synthesis, pharmaceutical industry and dye industry. At low concentration, the experimental animals have shortness of breath, tears, sleepiness, listlessness and slow response; Slightly higher concentration can also cause dyspnea, lateral lying and eyeball protrusion; When the concentration is high, extreme dyspnea, spasm and death occur. It can be absorbed through skin and cause poisoning death. In addition, it is also harmful to the environment.

Ethyl Cyanoacetate Uses

  1. Ethyl cyanoacetate is used as a pharmaceutical intermediate, for caffeine and vitamin B, and as a raw material for oil-soluble couplers for color films and 502 adhesives.
  2. Ethyl cyanoacetate is an intermediate for the preparation of diethyl malonate, from which 2-amino-4,6-dimethoxypyrimidine can be prepared as an intermediate for sulfonylurea herbicides, and also for the insecticide fluphinium Nitrile intermediates.
  3. In Japan, it is mainly used as an intermediate of cyanoacrylate quick-drying adhesives, used in the bonding of auto parts and household appliance assemblies, and also used in fields such as vitamin B6 and synthetic dyes.
  4. 5-Cyano-6-hydroxy-4-methoxymethyl-2-methylpyridine can be obtained by cyclization of ethyl cyanoacetate with methoxyacetylacetone and ammonia. After nitration, chlorination and catalytic hydrogenation, 3-amino-5-aminomethyl-4-methoxymethyl-2-methylpyridine can be obtained. Further diazotization, hydrolysis, and salt formation can obtain micro-vitamin B6.

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Application of Ethyl Cyanoacetate

As a result of its practical cyanoacetate response:

  • On the nitrile team in various methods:
    1. Hydrogenation generation β- amino acid β- alanine.
    2. Nucleophilic strike on carbon as an action in the synthesis of numerous heterocycles as well as various other items.
    3. As a risk-free cyanide contributor reagent.
  • Nucleophilic strike of ester group, as part of acyl substitution: it responds with ammonia to produce cyanoacetamide, which can be converted to malononitrile by dehydration with PCL 5 or POCl 3.
  • Using acidic methylene as nucleophile.

Ethyl cyanoacetate is an essential part of the synthesis of heterocyclic substances, such as drugs:

  • Allopurinol, made use of to deal with chronic gout pain, can be manufactured from Knoevenagel condensation with triethyl orthoformate; The condensation product is cyclized with hydrazine to acquire substituted pyrazole, and then cyclized with formamide to acquire allopurinol, that is, replaced pyrazolopyrimidine.
  • Purine derivatives theophylline, high levels of caffeine and also uric acid can be manufactured from ethyl cyanoacetate and also N, n’- dimethylurea.
  • Pteridine acquired folic acid is designated to vitamin B complex; Ethyl cyanoacetate and also guanidine can be used as starting materials for multistage polymerization synthesis.
  • Pyrrole Ethylsuccinate is utilized to deal with epilepsy, which can be synthesized from ethyl cyanoacetate and also butanone in multiple actions.
  • Trimethoprim, a pyrimidine by-product, is made use of as a taken care of combination of compound sulfamethoxazole as well as sulfamethoxazole as an anti-bacterial representative, and also is synthesized from ethyl cyanoacetate and also 3,4,5-trimethoxybenzaldehyde or its benzyl chloride.

Several other functional heterocycles can also be gotten from ethyl cyanoacetate in good returns, such as 3-substituted coumarin derivatives.
The non distributing products of this starting material include:

  • Anticonvulsant valproic acid
  • Ethyl cyanoacrylate, utilized as a solid adhesive by reacting with formaldehyde.

Ethyl cyanoacetate is additionally used for the prep work of 3,3-diphenylpropan-1-amine, which is a precursor for the synthesis of isoprene amine and dropping aniline

Preparation of Ethyl Cyanoacetate

  • Ethyl chloroacetate cyanation method: This method uses chloroacetic acid and ethanol for esterification to prepare ethyl chloroacetate first, and then cyanide ethyl chloroacetate with sodium cyanide to prepare ethyl cyanoacetate. This reaction process is very complicated, the operating cost is very high, and it is not suitable for industrial production.
  • Methyl cyanoacetate transesterification method: This method prepares ethyl cyanoacetate by transesterifying methyl cyanoacetate with absolute ethanol, but the effect of the transesterification catalyst is not ideal, and the recovery brought by the catalyst The processing cost is high, and the recovered methanol and ethanol mixture is difficult to handle, so this preparation method is also difficult to realize industrialized production.
  • Cyanoacetic acid esterification method: This method uses cyanoacetic acid and ethanol as raw materials, and directly performs esterification to prepare ethyl cyanoacetate. The traditional process uses inorganic acid sulfuric acid as a catalyst to promote the esterification reaction, but Due to the corrosiveness and environmental protection problems brought by sulfuric acid, this preparation method is also being gradually replaced at present.

Reference

  1. Ethyl cyanoacetate – WikiPedia
  2. Ethyl cyanoacetate – PubChem
  3. Liu Xu, Yin Guohua, Wang Jinhua, Cheng Lihua, Chen Guoyu. A new method for the synthesis of ethyl cyanoacetate [J]. Fine and Specialty Chemicals, 2016,24(01):35-37.

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