13893-53-3

Basic information

• Product Name: 2-Amino-2,3-dimethylbutyronitrile
• Synonyms: 2-AMINO-2,3-DIMETHYL-BUTYRONITRILE;2-AMINO-2,3-DIMETHYLBUTANENITRILE;2-AMino-2,3-diMethyl-butyronitril;2-Amino-2,3-dimethylbutyronitrile, 1-Amino-1,2-dimethylprop-1-yl cyanide;Butanenitrile, 2-aMino-2,3-diMethyl-
• CAS NO: 13893-53-3
• Molecular Formula: C₆H₁₂N₂
• Molecular Weight: 112.17
• Mol File: 13893-53-3.mol

Chemical Properties

• Boiling Point: 43 °C
• Flash Point: 58.8 °C
• Appearance: colourless to light yellow liquid
• Density: 0.896 g/cm³
• Vapor Pressure: 1.26mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 5.18±0.25(Predicted)
• CAS DataBase Reference: 2-Amino-2,3-dimethylbutyronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-2,3-dimethylbutyronitrile(13893-53-3)
• EPA Substance Registry System: 2-Amino-2,3-dimethylbutyronitrile(13893-53-3)

Safety Data

• Hazardous Substances Data: 13893-53-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-2,3-dimethylbutyronitrile is used as a key intermediate for the biosynthesis of 2-Amino-2,3-dimethylbutyramide by Rhodococcus qingshengii. This amide is an important intermediate in the synthesis of potent imidazoline herbicides, which are widely used in agriculture for controlling weed growth.
Used in Chemical Industry:
2-Amino-2,3-dimethylbutyronitrile is also used in the preparation of new chiral ligands, which are essential in various chemical reactions, particularly in asymmetric synthesis. These ligands play a crucial role in enhancing the selectivity and efficiency of chemical reactions, leading to the production of enantiomerically pure compounds with desired properties.

InChI:InChI=1/C6H12N2/c1-5(2)6(3,8)4-7/h5H,8H2,1-3H3/p+1/t6-/m0/s1

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 773837-37-9 sodium cyanide 
• 87-69-4 L-Tartaric acid 
• 151-50-8 potassium cyanide 
• 74-90-8 hydrogen cyanide 
• 90376-97-9 (R)2-amino-2,3-dimethibutyronitrile 
• 143-33-9 sodium cyanide 

Downstream Products

• 81334-34-1 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid 
• 81335-37-7 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-Yl]-3-quinolinecarboxylic acid 
• 90377-00-7 (-)-(S)-2-amino-2,3-dimethylbutanamide 
• 63081-72-1 N-(1-cyano-1,2-dimethylpropyl)phthalamic acid 
• 40963-14-2 2-amino-2,3-dimethylbutyramide 
• 81334-34-1 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid 
• 880133-98-2 C₁₇H₂₃IN₂O 
• 115852-48-7 N-(1-cyano-1,2-dimethyl-propyl)-2-(2,4-dichlorophenoxy)-propionamide 
• 203314-42-5 C₁₆H₂₂N₂O 
• 110863-17-7 (S,S)-ammonium hydrogen tartrate 
• 166538-35-8 2-(4-Nitrobenzoylamino)-2,3-dimethylbutanamide 
• 107640-56-2 N-(1-cyano-1,2-dimethylpropyl)benzamide 

Relevant articles and documents

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 synthesizing 2-amino-2, 3-dimethylbutyronitrile by using micro-channel reactor

The invention relates to a method for synthesizing 2-amino-2, 3-dimethylbutyronitrile by using a micro-channel reactor. The method comprises the steps that methyl isopropyl ketone, a sodium cyanide solution, ammonia water and an ammonium chloride solution are introduced into the micro-channel reactor, the molar ratio of methyl isopropyl ketone to sodium cyanide to ammonium chloride is lower, a reaction is conducted through a pipeline reactor, a reaction solution is cooled to be subjected to solvent extraction and decompression desolvation, and 2-amino-2, 3-dimethylbutyronitrile is obtained. According to the method, the micro-channel reactor is used for synthesizing 2-amino-2, 3-dimethylbutyronitrile; compared with the existing production process adopting a conventional reaction kettle, themethod has the advantages of uniform heat and mass transfer process, no amplification effect, no use of a phase transfer catalyst, reduction of the use amount of sodium cyanide, shortening of the reaction time, improvement of the conversion rate of the raw materials, high production efficiency and reduction of the production cost.

Fenoxanil original drug synthesis method

The invention relates to a fenoxanil original drug synthesis method. The method includes: employing an organic solvent to synthesize an intermediate 2-(2, 4-dichlorophenoxy)propionic acid by one step, and then synthesizing fenoxanil. Therefore, the condensation yield reaches more than 96%. The method provided by the invention can substantially reduce wastewater and realize clean production, and has very good practical application effect.

Recyclable Enantioselective Catalysts Based on Copper(II) Complexes of 2-(Pyridine-2-yl)imidazolidine-4-thione: Their Application in Asymmetric Henry Reactions

This paper describes the preparation of enantioselective catalysts based on derivatives of imidazolidine-4-thione and their subsequent anchoring by means of a sulfur atom on a polymeric carrier. First, we verified the catalytic activity and enantioselecti

Synthesis of enantiopure fmoc-#-methylvaline

An efficient synthesis of enantiopure Fmoc-α-methylvaline has been developed. The racemate was prepared in two steps from 3-methyl-2-butanone and was resolved using a chiral amine, (S)- 1,2,3,4-tetrahydro-1-naphthylamine to give the desired, enantiopure S

PROCESS FOR THE RACEMISATION OF ENANTIOMERICALLY ENRICHED ALPHA-AMINO NITRILES

Process for the racemisation of an enantiomerically enriched α-amino nitrile characterized in that the enantiomerically enriched α-amino nitrile is contacted with a lewis acid catalyst. Preferably an aprotic solvent is used. The lewis acid catalyst preferably comprises a metal chosen from main group elements IA-IVA of the Periodic Table (CAS version), the transition metals and the lanthanides, in particular Al, Ti, Zr, or lanthanides. The catalsyt for example has the general structure MnXpSqLr, and preferably is chosen from the group of aluminum alkoxides, aluminum alkyls, lanthanide alkoxydes and lanthanocenes. The racemisation may be performed in combination with a resolution process, for instance in combination with an enzymatic or a crystallization induced resolution process, preferably in situ, for instance in situ in a crystallization induced asymmetric transformation process.

Process for the preparation of enantiomerically enriched compounds

1. Process for the preparation of enantiomerically enriched amino aldehydes and amino alcohols, wherein a corresponding enantiomerically enriched amino nitrile is subjected to hydrogenation in the presence of hydrogen, a hydrogenation catalyst, preferably a Pd-catalyst and a mineral acid. For the preparation of an amino aldehyde hydrogen preferably is present at a hydrogen-pressure between 0.1 and 2 MPa, in particular between 0.5 and 1 MPa. The amino aldehyde preferably is isolated in the form of a chemically and configurationally stable derivative. For the preparation of an amino alcohol, preferably at least during part of the hydrogenation hydrogen is present at a hydrogen-pressure between 2 and 10 MPa, in particular between 4 and 6 MPa. In a preferred embodiment the hydrogen-pressure initially is between 0,5 and 2 MPa and subsequently, after most of the nitrile starting material is converted, the hydrogen pressure is increased to a value between 2 and 10 MPa. The enantiomerically enriched nitrile starting material may a.o. be prepared by enzymatic resolution, classical resolution, resolution via preferential crystallization, diastereomeric synthesis, catalytic asymmetric synthesis or dehydratation of amino acid amides.

Studies on phosphoroheterocycle chemistry II: A simple and new route to 1,3,2-diazaphospholidine-4-thione 2-sulfide derivatives

A simple and new method for the synthesis of phosphoroheterocycles 1,3,2-diazaphospholidine-4-thione 2-sulfide derivatives by treatment of Lawesson's reagent (LR) with a variety of α-aminonitriles has been developed. The same methodology was also used in the preparation of fused phosphoroheterocycle 6 from 5-amino-4-cyano-3-methylthia-l-phenylpyrazole. The possible mechanism of the reaction involving addition of P-SH to the nitrile and subsequent rearrangement is proposed.

Process for the resolution of certain racemic amino nitriles

The invention is a process for the selective and concomitant resolution-racemization-resolution of certain substituted, racemic amino nitriles via their respective tartrate salts. The invention further relates to certain resolved (optically active) amino amides prepared from said amino nitriles, and to the herbicidal substituted oxo-imidazolinyl nicotinic acids and 3-quinoline carboxylic acids prepared therefrom.

Synthesis of 4,4-Disubstituted 1,3-Thiazol-5(4H)-thiones

An easy synthesis for the 1,3-thiazol-5(4H)-thiones 5, a class of heterocycles which have hitherto only been available with difficulty, is described.Reaction of 3-amino-2H-azirines 25 with thiocarboxylic acids at 0 deg yields monothiodiamides of type 20 (Scheme 6) which, on treatment with Lawesson reagent at 100 deg, undergo thiation and cyclization to give 5 in good yield.