40963-14-2

Basic information

• Product Name: 2-Amino-2,3-dimethylbutyramide
• Synonyms: 2-AMINO-2,3-DIMETHYL BUTYRAMIDE;2-AMINO-2,3-DIMETHYLBUTACETAMIDE;2-amino-2,3-dimethylbutanamide;2-AMINO-2,3-DIMETHYLBUTACETAMIDE, >93%;2-amino-2，3-dimethy butyramide;2-aMino-2,3-diMethylbutanaMide( raceMic );ButanaMide,2-aMino-2,3-diMethyl-
• CAS NO: 40963-14-2
• Molecular Formula: C₆H₁₄N₂O
• Molecular Weight: 130.19
• Mol File: 40963-14-2.mol

Chemical Properties

• Boiling Point: 242.664 °C at 760 mmHg
• Flash Point: 100.56 °C
• Appearance: /
• Density: 0.983 g/cm³
• Vapor Pressure: 0.034mmHg at 25°C
• Refractive Index: 1.469
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol
• PKA: 16.12±0.50(Predicted)
• CAS DataBase Reference: 2-Amino-2,3-dimethylbutyramide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-2,3-dimethylbutyramide(40963-14-2)
• EPA Substance Registry System: 2-Amino-2,3-dimethylbutyramide(40963-14-2)

Safety Data

• Hazardous Substances Data: 40963-14-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-2,3-dimethylbutyramide is used as an intermediate in the synthesis of potent imidazoline herbicides, which are effective in controlling a wide range of weeds in agricultural settings.
Used in Chemical Research:
2-Amino-2,3-dimethylbutyramide is also used to prepare new chiral ligands, which are essential in various chemical reactions and processes, particularly in asymmetric synthesis and catalysis. These ligands play a vital role in enhancing the selectivity and efficiency of chemical reactions.

InChI:InChI=1/C6H14N2O/c1-4(2)6(3,8)5(7)9/h4H,8H2,1-3H3,(H2,7,9)

Synthetic route

2-amino-2,3-dimethylbutyronitrile (13893-53-3) → 2-amino-2,3-dimethylbutyramide (40963-14-2)

Conditions	Yield
With water In aq. phosphate buffer at 20℃; pH=7; Concentration; pH-value; Temperature; Solvent; Microbiological reaction; Green chemistry; Enzymatic reaction;	97.3%
With ammonium hydroxide; dihydrogen peroxide
With sulfuric acid; water

ammonium hydroxide (1336-21-6) + 2-amino-2,3-dimethylbutyronitrile (13893-53-3) → 2-amino-2,3-dimethylbutyramide (40963-14-2)

Conditions	Yield
With sulfuric acid In ice-acetone
With sulfuric acid In ice-acetone

dimethyl 5-(1-acetyl-3-methyl-2-imidazolidinyl)pyridine-2,3-dicarboxylate + 2-amino-2,3-dimethylbutyramide (40963-14-2) → 5-(1-ACETYL-3-METHYL-2-IMIDAZOLIDINYL)-2-(4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2-YL)NICOTINIC ACID AMMONIUM SALT (136592-75-1)

Conditions	Yield
With ammonium chloride; potassium tert-butylate In chloroform; toluene	100%

5-(1,3-dioxolan-2-yl)-2,3-pyridinedicarboxylic anhydride + 2-amino-2,3-dimethylbutyramide (40963-14-2) → 2-[(1-CARBAMOYL-1,2-DIMETHYLPROPYL)-CARBAMOYL]-5-(1,3-DIOXOLAN-2-YL)NICOTINIC ACID

Conditions	Yield
In tetrahydrofuran	100%

2-amino-2,3-dimethylbutyramide (40963-14-2) + 2-nitrobenzyl chloride (610-14-0) → N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-nitro-benzamide

Conditions	Yield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;	98%

2-amino-2,3-dimethylbutyramide (40963-14-2) + 2,5-dinitrobenzoyl chloride (778-90-5) → N-(1-Carbamoyl-1,2-dimethyl-propyl)-2,5-dinitro-benzamide

Conditions	Yield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;	94%

2-methoxycarbonyl-5-methyl-3-pyridinecarboxylic acid + 2-amino-2,3-dimethylbutyramide (40963-14-2) → imazapic (104098-48-8)

Conditions	Yield
With sodium methylate at 120℃; for 1h; Temperature;	90.8%

pyridine-2,3-dicarboxylic acid 2-methyl ester (24195-07-1) + 2-amino-2,3-dimethylbutyramide (40963-14-2) → 2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid (81334-34-1, 81510-77-2, 81510-78-3)

Conditions	Yield
With sodium methylate at 120℃; for 1h; Temperature;	90.1%

2-amino-2,3-dimethylbutyramide (40963-14-2) + C10H11NO4 → imazapic (104098-48-8)

Conditions	Yield
With sodium ethanolate at 110℃; for 1h; Temperature; Reagent/catalyst;	89.2%

furo[2,3-b]pyridine-5,6-dicarboxylic anhydride + 2-amino-2,3-dimethylbutyramide (40963-14-2) → 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid (94746-47-1)

Conditions	Yield
In tetrahydrofuran	88.6%

2-amino-2,3-dimethylbutyramide (40963-14-2) + C10H11NO4 → 2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid (81334-34-1, 81510-77-2, 81510-78-3)

Conditions	Yield
With sodium n-propoxide at 110℃; for 1h;	88.5%

pyridine-2,3-dicarboxylic acid-2-butyl ester + 2-amino-2,3-dimethylbutyramide (40963-14-2) → 2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid (81334-34-1, 81510-77-2, 81510-78-3)

Conditions	Yield
With potassium n-butoxide at 110℃; for 1h;	88.2%

2-[(ethyloxy)carbonyl]-3-pyridinecarboxylic acid (161522-42-5) + 2-amino-2,3-dimethylbutyramide (40963-14-2) → 2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]nicotinic acid (81334-34-1, 81510-77-2, 81510-78-3)

Conditions	Yield
With sodium ethanolate at 110℃; for 1h; Temperature; Reagent/catalyst;	87.3%

2-amino-2,3-dimethylbutyramide (40963-14-2) + C12H15NO4 → imazapic (104098-48-8)

Conditions	Yield
With potassium n-butoxide at 120℃; for 1h;	87.3%

2-amino-2,3-dimethylbutyramide (40963-14-2) + 2-bromobenzene-1,3-dicarboxylic acid dichloride (151603-30-4) → (+/-)-N,N'-bis(2-carbamoyl-3-methylbut-2-yl)-2-bromobenzene-1,3-dicarboxamide (1276021-20-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 12h;	87%

2-amino-2,3-dimethylbutyramide (40963-14-2) → (S)-α-Methylvaline (4378-19-2, 26287-62-7, 53940-82-2, 53940-83-3) + (+)-(R)-2-amino-2,3-dimethylbutanamide (90376-98-0)

Conditions	Yield
In water at 37℃; Ochrobactrum anthropi NCIMB 40321;	A 86% B 74%
With water at 37℃; for 72h; aminopeptidase from Mycobacterium neoaurum ATCC 25795;

2-amino-2,3-dimethylbutyramide (40963-14-2) + diethyl 5-ethyl-2,3-pyridinedicarboxylate (105151-39-1) → imazethapyr (81335-77-5)

Conditions	Yield
With sodium hydride In toluene at 20℃; for 0.25h;	85.2%

2-amino-2,3-dimethylbutyramide (40963-14-2) + benzaldehyde (100-52-7) → (+/-)-2-N-benzylamino-2,3-dimethylbutanamide (1016561-97-9)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 48h;	85%

3-chlorobenzo[b]thiophen-2-carbonyl chloride (21815-91-8) + 2-amino-2,3-dimethylbutyramide (40963-14-2) → N-(2-carbamoyl-3-methylbut-2-yl)-3-chlorobenzo[b]thiophene-2-carboxamide (1039755-43-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	85%

2-amino-2,3-dimethylbutyramide (40963-14-2) + diethyl quinoline-2,3-dicarboxylate (32413-08-4) → 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-Yl]-3-quinolinecarboxylic acid (81335-37-7)

Conditions	Yield
With sodium hydride In toluene at 20℃; for 0.25h;	83.7%

pentanal (110-62-3) + 2-amino-2,3-dimethylbutyramide (40963-14-2) → 2-butyl-4-methyl-4-(2-methylethyl)-imidazolidin-5-one

Conditions	Yield
In methanol; water	82%

2-amino-2,3-dimethylbutyramide (40963-14-2) + 4-chloro-benzoyl chloride (122-01-0) → N-(1-Carbamoyl-1,2-dimethyl-propyl)-4-chloro-benzamide (40963-06-2)

Conditions	Yield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;	81%

Conditions	Yield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;	81%
In chloroform Yield given;

2-Picolinic acid + 2-amino-2,3-dimethylbutyramide (40963-14-2) → (+/-)-2-{[2-(aminocarbonyl)-3-methylbut-2-yl]aminocarbonyl}pyridine (898529-74-3)

Conditions	Yield
Stage #1: 2-Picolinic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran for 0.5h; Stage #2: 2-amino-2,3-dimethylbutyramide In tetrahydrofuran for 3h;	78%

2-amino-2,3-dimethylbutyramide (40963-14-2) + 2-bromobenzoic acid chloride (7154-66-7) → (+/-)-N-(2-carbamoyl-3-methylbut-2-yl)-2-bromobenzenecarboxamide (1276021-17-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 5h;	77%

2-amino-2,3-dimethylbutyramide (40963-14-2) + diethyl 5-ethyl-2,3-pyridinedicarboxylate (105151-39-1) → 2-[4,5-dihydro-5-methyl-5-(1-methylethyl)-4-oxo-1H-imidazol-2-yl]-5-ethyl nicotinic acid

Conditions	Yield
With sodium methylate In toluene for 1h; Heating;	76.5%
With hydrogenchloride; potassium tert-butylate In water; toluene

2-amino-2,3-dimethylbutyramide (40963-14-2) + o-chlorobenzoyl chloride (609-65-4) → N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-chloro-benzamide

Conditions	Yield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;	75%

2-amino-2,3-dimethylbutyramide (40963-14-2) + ortho-toluoyl chloride (933-88-0) → N-(1-Carbamoyl-1,2-dimethyl-propyl)-2-methyl-benzamide

Conditions	Yield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;	75%

2-amino-2,3-dimethylbutyramide (40963-14-2) + 4-methyl-benzoyl chloride (874-60-2) → (+/-)-N-(1-carbamoyl-1,2-dimethylpropyl)-p-toluamide (100594-41-0, 97712-44-2)

Conditions	Yield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;	70%
With triethylamine In tetrahydrofuran; water
With triethylamine In tetrahydrofuran; water
With triethylamine In acetone

2,3-Dimethylmaleic anhydride (766-39-2)

Conditions	Yield
With sodium ethanolate; triethylamine In ethanol	69.9%

2-amino-2,3-dimethylbutyramide + 2,6-difluorobenzoylchloride → N-(1-Carbamoyl-1,2-dimethyl-propyl)-2,6-difluoro-benzamide

Conditions	Yield
With triethylamine In chloroform 1.) 1 h, 2.) reflux, 30 min;	68%

Upstream product

• 13893-53-3 2-amino-2,3-dimethylbutyronitrile 
• 1336-21-6 ammonium hydroxide 

Downstream Products

• 4378-19-2 (S)-α-Methylvaline 
• 90376-98-0 (+)-(R)-2-amino-2,3-dimethylbutanamide 
• 100594-41-0 (+/-)-N-(1-carbamoyl-1,2-dimethylpropyl)-p-toluamide 
• 40963-06-2 N-(1-Carbamoyl-1,2-dimethyl-propyl)-4-chloro-benzamide 
• 166538-35-8 2-(4-Nitrobenzoylamino)-2,3-dimethylbutanamide 
• 81335-77-5 imazethapyr 
• 81335-37-7 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-Yl]-3-quinolinecarboxylic acid 
• 53940-82-2 (R)-2-amino-2,3-dimethylbutanoic acid 
• 81334-34-1 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid 
• 69969-56-8 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-benzoic acid 
• 100594-35-2 (+/-)-N-(1-carbamoyl-1,2-dimethylpropyl)-m-toluamide 
• 104098-48-8 imazapic 

Relevant articles and documents

Efficient hydration of 2-amino-2,3-dimethylbutyronitrile to 2-amino-2,3-dimethylbutyramide in a biphasic system via an easily prepared whole-cell biocatalyst

From an environmental perspective, utilizing nonconventional solvents (i.e. green solvents) with low ecological footprints is a highly beneficial alternative to using conventional organic solvents to form a reaction system. The nitrile hydratase (NHase, EC 4.2.1.84) catalyzed hydration of 2-amino-2,3-dimethylbutyronitrile (ADBN) to 2-amino-2,3-dimethylbutyramide (ADBA) in various green solvent-aqueous reaction systems was investigated in this study. After systematically optimizing the reaction conditions, the HFE-7100/H2O (v/v, 10%) biphasic system was ultimately identified as a promising reaction system for reducing product inhibition, avoiding substrate hydrolysis, and facilitating product separation and solvent recovery. The average ADBA yield of an entire batch reaction was 97.3%, which is obviously higher than those obtained with previously reported chemical or enzymatic methods. This is the first attempt to apply a fluorous solvent-aqueous biphasic system to a biocatalytic process, and the results suggest that the fluorous solvent employed in the biphasic system satisfies the requirements for green chemistry.

Substituent effect on acidity of substituted 2-(4-nitrobenzoylamino)alkanamidesin methanol-dimethyl sulfoxide mixtures

The dissociation constants of substituted 2-(4-nitrobenzoylamino)alkanamides, N-[2-(4-nitrobenzoylamino)aikanoyl]pyrrolidines, and N-alkyl-4-nitrobenzamides have been measured spectrophotometrically in 60 and 80% v/v DMSO. The pKA values of these N-acids are discussed from the point of view of substituents at the acetamide a-carbon atom.

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.

2-(2-imidazolin-2-yl)-pyridines and quinolines, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents

There are provided novel 2-(2-imidazolin-2-yl)pyridine and quinoline compounds, a process and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.

Method for the preparation of certain pyridine and quinoline 2,3-dicarboxylic anhydrides

The present invention relates to a process for the preparation of substituted pyridine and quinoline-2,3-dicarboxylic anhydrides, and the herbicidally effective imidazolinyl pyridine and quinoline compounds prepared therefrom.

Process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters

There is provided a process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters useful as intermediates in the manufacture of herbicidally active 2-(2-imidazolin-2-yl)pyridine compounds.

Imidazoisoindolediones and the use thereof as herbicidal agents

The invention relates to novel imidazoisoindoledione compounds including the optical isomers thereof. This invention also relates to a method for the control of undesirable plant species with the imidazoisoindolediones and their optical isomers, and further, to a process for the preparation of the compounds.

Dihydroimidaz oisoindolediones and the use thereof as herbicidal agents

The invention relates to novel dihydroimidazoisoindoledione compounds and the optical and stereo isomers thereof. This invention also relates to a method for the control of undesirable plant species with the dihydroimidazoisoindolediones and their optical and stereo isomers, and further, to a process for the preparation of the compounds.