3198-47-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-(methylthio)-butyronitrile is used as a key intermediate for the production of various pharmaceuticals. Its role in the synthesis of medicinal compounds is crucial due to its ability to form complex organic structures that contribute to the therapeutic effects of drugs.
Used in Agricultural Chemical Production:
2-Amino-4-(methylthio)-butyronitrile also serves as an intermediate in the production of agricultural chemicals. Its application in this industry is significant for developing substances that can enhance crop protection and improve agricultural yields.
Used in Heterocyclic Compound Synthesis:
2-Amino-4-(methylthio)-butyronitrile has been studied for its potential as a precursor in the synthesis of various heterocyclic compounds. Its unique structure allows it to participate in multiple chemical reactions, leading to the creation of diverse heterocyclic compounds with potential applications in various fields.

Upstream product

• 3268-49-3 3-(methylsulfenyl)propanal 
• 143-33-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 17773-41-0 2-hydroxy-4-(methylthio)butyronitrile 
• 74-90-8 hydrogen cyanide 
• 74-93-1 methylthiol 
• 107-02-8 acrolein 
• 19298-72-7 DL-methionine amide 
• 65707-55-3 4-Methylsulfanyl-2-(2-nitro-phenylsulfanylamino)-butyramide 

Downstream Products

• 7536-72-3 methioninamide sulfoxyde 
• 59-51-8 DL-methionine 
• 19298-72-7 DL-methionine amide 
• 7349-78-2 DD/LL/LD/DL-methionylmethionine 
• 36963-02-7 3,6-bis[2-(methylthio)ethyl]-2,5-piperazinedione 
• 56830-84-3 5-(2-(methylthio)ethyl)-2-thioxoimidazolidin-4-one 
• 65055-13-2 3-Chloro-N-(1-cyano-3-methylsulfanyl-propyl)-benzamide 
• 65055-10-9 3,5-Dichloro-N-(1-cyano-3-methylsulfanyl-propyl)-benzamide 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF METHIONINE

The present invention relates to a process for the preparation of methionine comprising the step of contacting a solution or suspension comprising 2-amino-4-(methylthio)butanenitrile and/or 2-amino- 4-(methylthio)butaneamide with water in the presence of a catalyst to give a methionine comprising mixture, wherein the catalyst comprises CeO2 comprising particles, wherein the CeO2 comprising particles have a BET surface area of from 175 to 300 +/- 10% m2/g measured according to DIN ISO 9277-5 (2003), a mean maximum Feret diameter xFmax, mean of from 3 +/- 10% to 40 +/- 10% nm and a mean minimum Feret diameter xFmin, mean of from 2 +/- 10% to 30 +/- 10% nm, both measured according to DIN ISO 9276-6 (2012).

METHOD FOR PRODUCING METHIONINE

The present invention pertains to a method for producing methionine or salts or derivatives thereof from hydrogen cyanide (HCN), the method comprising a step of producing 2-hydroxy-4-(methylthio)butyronitrile (MMP-CN), or a crude product mixture comprising MMP-CN, by contacting a hydrogen cyanide (HCN) process gas mixture prepared according to the Andrussow process from methane, ammonia and oxygen, with 3-methylmercaptopropionaldehyde (MMP), wherein the HCN process gas mixture is obtained from the crude HCN process gas mixture by adjusting the amount of ammonia to between 20 % (v/v) and 60% (v/v) of the amount of the ammonia in the crude HCN process gas mixture.

SALT-FREE PRODUCTION OF METHIONINE FROM METHIONINE NITRILE

The invention refers to the use of a particulate catalyst containing 60.0 to 99.5 wt.% ZrO2 stabilised with an oxide of the element Hf and at least one oxide of the element M, wherein M = Ce, Si, Ti, or Y, for the hydrolysis reaction of methionine amide to methionine, wherein the median particle size x50 of the particulate catalyst is in the range of from 0.8 to 9.0 mm, preferably of from 1.0 to 7.0 mm. The invention also refers to a process for preparing methionine comprising a step of contacting a solution or suspension comprising methionine amide and water with said particulate catalyst to provide a reaction mixture comprising methionine and/or its ammonium salt from which methionine can be isolated.

METHOD FOR PRODUCING alpha-AMINO ACID

The present invention relates to a method for producing a specified α-amino acid, the method including allowing a specified α-amino acid amide and water to react with each other in the presence of a zirconium compound which contains zirconium and at least one metal element selected from the group consisting of lithium, nickel, copper, zinc, cesium, barium, hafnium, tantalum, cerium, and dysprosium.

Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia

α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.

Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures

A central problem for the prebiotic synthesis of biological amino acids and nucleotides is to avoid the concomitant synthesis of undesired or irrelevant by-products. Additionally, multistep pathways require mechanisms that enable the sequential addition of reactants and purification of intermediates that are consistent with reasonable geochemical scenarios. Here, we show that 2-aminothiazole reacts selectively with two- and three-carbon sugars (glycolaldehyde and glyceraldehyde, respectively), which results in their accumulation and purification as stable crystalline aminals. This permits ribonucleotide synthesis, even from complex sugar mixtures. Remarkably, aminal formation also overcomes the thermodynamically favoured isomerization of glyceraldehyde into dihydroxyacetone because only the aminal of glyceraldehyde separates from the equilibrating mixture. Finally, we show that aminal formation provides a novel pathway to amino acids that avoids the synthesis of the non-proteinogenic α,α-disubstituted analogues. The common physicochemical mechanism that controls the proteinogenic amino acid and ribonucleotide assembly from prebiotic mixtures suggests that these essential classes of metabolite had a unified chemical origin.

METHOD FOR PRODUCING METHIONINE

A method for producing methionine involves contacting 2-amino-4-(methylthio)butanenitrile with water in the presence of an oxide catalyst containing cerium. The 2-amino-4-(methylthio)butanenitrile may be 2-amino-4-(methylthio)butanenitrile, produced by contacting 2-hydroxy-4-(methylthio)butanenitrile with ammonia water or 2-amino-4-(methylthio)butanenitrile, produced by contacting 3-(methylthio)propionaldehyde with hydrocyanic acid and ammonia water.

Prebiotic synthesis of aminooxazoline-5′-phosphates in water by oxidative phosphorylation

RNA is essential to all life on Earth and is the leading candidate for the first biopolymer of life. Aminooxazolines have recently emerged as key prebiotic ribonucleotide precursors, and here we develop a novel strategy for aminooxazoline-5′-phosphate synthesis in water from prebiotic feedstocks. Oxidation of acrolein delivers glycidaldehyde (90%), which directs a regioselective phosphorylation in water and specifically affords 5′-phosphorylated nucleotide precursors in upto 36% yield. We also demonstrated a generational link between proteinogenic amino acids (Met, Glu, Gln) and nucleotide synthesis.

Clean production method of methionine

The present invention belongs to the technical field of organic compound production, separation and purification, and particularly relates to a clean production method of methionine. According to the method, 2-amino-4-methylthiobutyronitrile is subjected to hydrolysis by using calcium hydroxide and/or barium hydroxide to prepare methionine calcium/barium, the calcium/barium salt of the byproduct 2,2'-bis-(2-methylthioethyl)iminodiacetic acid is insoluble in water so as to easily separate and purify the methionine calcium/barium and the insoluble byproduct, then the methionine calcium/barium aqueous solution is neutralized by using carbon dioxide to produce the insoluble calcium carbonate/barium and other insoluble precipitates at a high temperature so as to achieve the methionine separation purpose, and the calcium carbonate/barium salt is subjected to calcination to decompose into the carbon dioxide and the oxides, wherein the carbon dioxide and the oxides can be recycled. Compared with the method in the prior art, the method of the present invention has characteristics of low methionine loss rate, high product purity, simple operation, low cost, no low-value inorganic salt production, no emission of a lot of acidic and odor wastewater, and green environmental protection.

Carbohydrates as efficient catalysts for the hydration of α-amino nitriles

Directed hydration of α-amino nitriles was achieved under mild conditions using simple carbohydrates as catalysts exploiting temporary intramolecularity. A broadly applicable procedure using both formaldehyde and NaOH as catalysts efficiently hydrated a variety of primary and secondary susbtrates, and allowed the hydration of enantiopure substrates to proceed without racemization. This work also provides a rare comparison of the catalytic activity of carbohydrates, and shows that the simple aldehydes at the basis of chemical evolution are efficient organocatalysts mimicking the function of hydratase enzymes. Optimal catalytic efficiency was observed with destabilized aldehydes, and with difficult substrates only simple carbohydrates such as formaldehyde and glycolaldehyde proved reliable.