2566-34-9

Basic information

• Product Name: N-ME-AIB-OH HCL
• Synonyms: N-ME-ALPHA-AMINOISOBUTYRIC ACID;N-ME-ALPHA-ME-ALA-OH;N-ME-AIB-OH;N-ME-AIB-OH HCL;N-METHYL-ALPHA-AMINOISOBUTYRIC ACID;N-METHYL-ALPHA-AMINOISOBUTYRIC ACID HYDROCHLORIDE;N-METHYL-ALPHA-METHYL-ALANINE;N-METHYL-ALPHA-METHYLALANINE HYDROCHLORIDE
• CAS NO: 2566-34-9
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 117.15
• EINECS: 219-898-2
• Mol File: 2566-34-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 192.5 °C at 760 mmHg
• Flash Point: 70.2 °C
• Appearance: White Crystalline powder
• Density: 1.2000 (estimate)
• Vapor Pressure: 0.213mmHg at 25°C
• Refractive Index: 1.4650 (estimate)
• Storage Temp.: −20°C
• PKA: 2.17±0.10(Predicted)
• Water Solubility: almost transparency in Water
• BRN: 1746984
• CAS DataBase Reference: N-ME-AIB-OH HCL(CAS DataBase Reference)
• NIST Chemistry Reference: N-ME-AIB-OH HCL(2566-34-9)
• EPA Substance Registry System: N-ME-AIB-OH HCL(2566-34-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 2566-34-9(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

InChI:InChI=1/C5H11NO2/c1-5(2,6-3)4(7)8/h6H,1-3H3,(H,7,8)

Synthetic route

methylamine hydrochloride (593-51-1) + potassium cyanide (151-50-8) + acetone (67-64-1) → 2-(methylamino)isobutyric acid (2566-34-9)

Conditions	Yield
With water at 50 - 55℃; im geschlossenen Gefaess und verseift man das entstandene α-Methylamino-isobuttersaeurenitril mit Salzsaeure;

potassium cyanide (151-50-8) + acetone (67-64-1) + methylamine (74-89-5) → 2-(methylamino)isobutyric acid (2566-34-9)

Conditions	Yield
Verseifung des erhaltenen Nitrils;

2-bromo-2-methylpropionic acid (2052-01-9) + methylamine (74-89-5) → 2-(methylamino)isobutyric acid (2566-34-9)

Conditions	Yield
at 100℃;
With water

2-{[(R)-6-Hydroxy-2,7,8-trimethyl-2-((4R,8R)-4,8,12-trimethyl-tridecyl)-chroman-5-ylmethyl]-amino}-2-methyl-propionic acid; hydrobromide + MeHal → 2-(methylamino)isobutyric acid (2566-34-9)

Conditions	Yield
With sodium hydroxide 1.) CH2Cl2, -20 deg C, 10 min, 2.) room temperature, 30 min, 3.) 70 deg C, 1 h; Yield given. Multistep reaction;

2-(methylamino)isobutyric acid (2566-34-9) + chloroacetyl chloride (79-04-9) → 2-[(2-Chloro-acetyl)-methyl-amino]-2-methyl-propionic acid (138062-82-5)

Conditions	Yield
With hydroxide	98%

2-(methylamino)isobutyric acid (2566-34-9) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-N-methyl-α-aminoisobutyric acid (146000-39-7)

Conditions	Yield
With tetramethyl ammoniumhydroxide In acetonitrile for 72h; Ambient temperature;	95%

2-(methylamino)isobutyric acid (2566-34-9) + La2 in [80-Ih]fullerene + 3,5-diethoxy-4-pyridinecarboxyaldehyde (164077-50-3) → 2La*C94H22N2O2

Conditions	Yield
In toluene for 0.183333h; Inert atmosphere; Reflux;	95%

2-(methylamino)isobutyric acid (2566-34-9) + AmBisome (1397-89-3) → N-(N-methyl-α-methylalanyl)amphotericin B

Conditions	Yield
With dicyclohexyl-carbodiimide	91.1%

2-(methylamino)isobutyric acid (2566-34-9) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) + 3,5-diethoxy-4-pyridinecarboxyaldehyde (164077-50-3) → N-methyl-2-(3,5-diethoxypyridin-4-yl)-5,5-dimethyl-fulleropyrrolidine of C60 (1454319-81-3)

Conditions	Yield
In toluene for 1h; Inert atmosphere; Reflux;	80%

[2,2]bipyridinyl (366-18-7) + copper(II) perchlorate hexahydrate + 2-(methylamino)isobutyric acid (2566-34-9) → [CuII(bpy)(MAIB)]ClO4·H2O (1628897-45-9)

Conditions	Yield
With triethylamine In methanol at 20℃; for 1h;	77%

[2,2]bipyridinyl (366-18-7) + copper(II) perchlorate hexahydrate + 2-(methylamino)isobutyric acid (2566-34-9) → [CuII(2,2'-bipyridine)(α-(methylamino)isobutyric acid(H-))]ClO4*H2O

Conditions	Yield
With triethylamine In methanol at 20℃; for 1h; Inert atmosphere;	77%

2-(methylamino)isobutyric acid (2566-34-9) + C82*La + 2,6-dimethoxybenzaldehyde (3392-97-0) → C94H18N2O2*La

Conditions	Yield
In toluene for 0.25h; Inert atmosphere; Reflux;	76%

2-(methylamino)isobutyric acid (2566-34-9) + benzoyl chloride (98-88-4) → N-benzoyl-N-methyl-α-amino-2-methylpropionic acid (409108-28-7)

Conditions	Yield
With sodium hydroxide for 2h;	72.69%
With pyridine; acetone

2-(methylamino)isobutyric acid (2566-34-9) + C82*La + thioacetic acid S-[4-(4-formyl-phenoxy)-butyl] ester (383424-14-4) → La*C82CMe2NMeCHC6H4OC4H8SCOMe + La*C82CMe2NMeCHC6H4OC4H8SCOMe

Conditions	Yield
In 1,2-dichloro-benzene at 145℃; for 0.3h; Inert atmosphere;	A 21% B 67%

2-(methylamino)isobutyric acid (2566-34-9) + C82*La + 3,5-diethoxy-4-pyridinecarboxyaldehyde (164077-50-3) → C96H22N2O2*La

Conditions	Yield
In toluene for 0.25h; Inert atmosphere; Reflux;	64%

2-(methylamino)isobutyric acid (2566-34-9) → acetone (67-64-1)

Conditions	Yield
With ammonium hydroxide; [CuII(2,2'-bipyridine)(α-(methylamino)isobutyric acid(H-))]ClO4*H2O; dihydrogen peroxide In water; N,N-dimethyl-formamide at 35℃; Kinetics;	47%
With ammonium hydroxide; dihydrogen peroxide; copper dichloride In water; N,N-dimethyl-formamide at 35℃; Kinetics; Catalytic behavior;

2-(methylamino)isobutyric acid (2566-34-9) + 4-Ethynylbenzaldehyde (63697-96-1) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → C73H15N

Conditions	Yield
In toluene for 12h; Inert atmosphere; Reflux;	40%

2-(methylamino)isobutyric acid (2566-34-9) + 6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid (88574-06-5) → 2-(6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-N-methylhexanamido)-2-methylpropanoic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere;	30%

2-(methylamino)isobutyric acid (2566-34-9) + 2-(5-amino-2',4'-dioxo-2,3-dihydrospiro[indene-1,5'-oxazolidine]-3'-yl)-N-((S)-1-cyclopropylethyl)-N-(4-fluorobenzyl)acetamide → N-[4’-({[(1S)-1-cyclopropylethyl][(4-fluorophenyl)methyl]carbamoyl}methyl)-3‘,5’-dioxo-2,3-dihydrospiro[indene-1,2’-[1,4]oxazolidine]-5-yl]-2-methyl-2-(methylamino)propanamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	25%

2-(methylamino)isobutyric acid (2566-34-9) + 3-(3-(bromomethyl)-2-ethylphenyl)-5-(4-isopropoxy-3-(trifluoromethyl)-phenyl)-1,2,4-thiadiazole (1344997-55-2) → 2-((2-ethyl-3-(5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-thiadiazol-3-yl)benzyl)(methyl)amino)-2-methylpropanoic acid (1373522-34-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	21%

2-(methylamino)isobutyric acid (2566-34-9) + benzyl N-(4-aminophenethyl)-N-methyl-L-valinate dihydrochioride (82333-93-5) → N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-N,2-dimethylalanine (1438853-27-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	16%

2-(methylamino)isobutyric acid (2566-34-9) + C35H55N5O6S → C40H64N6O7S + C40H64N6O7S

Conditions	Yield
With diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 5℃; Inert atmosphere;	A 15% B 13%

2-(methylamino)isobutyric acid (2566-34-9) + 2-nitrobenzyl chloride (610-14-0) → 2-methyl-2-(N-methyl-2-nitrobenzamido)propanoic acid

Conditions	Yield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 18h; Schlenk technique;	15%

2-(methylamino)isobutyric acid (2566-34-9) → α-(benzyloxycarbonyl-methyl-amino)-isobutyric acid (144332-60-5)

Conditions	Yield
With sodium hydroxide; benzyl chloroformate

2-(methylamino)isobutyric acid (2566-34-9) + acetic anhydride (108-24-7) → α-(acetyl-methyl-amino)-isobutyric acid

Conditions	Yield
With acetic acid

2-(methylamino)isobutyric acid (2566-34-9) + acetic anhydride (108-24-7) → α-(acetyl-methyl-amino)-isobutyric acid + α-[methyl-(1,2,5,5-tetramethyl-4-oxo-4,5-dihydro-pyrrole-3-carbonyl)-amino]-isobutyric acid

Conditions	Yield
With acetic acid

2-(methylamino)isobutyric acid (2566-34-9) + 2-methoxy-phenylamine (90-04-0) → N-(2-Methoxy-phenyl)-2-methyl-2-methylamino-propionamide (23559-09-3)

Conditions	Yield
(i) SOCl2, DMF, (ii) /BRN= 386210/; Multistep reaction;

2-(methylamino)isobutyric acid (2566-34-9) + p-toluidine (106-49-0) → 2-Methyl-2-methylamino-N-p-tolyl-propionamide (23558-82-9)

Conditions	Yield
(i) SOCl2, DMF, (ii) /BRN= 471281/; Multistep reaction;

2-(methylamino)isobutyric acid (2566-34-9) + aniline (62-53-3) → 2-Methyl-2-methylamino-N-phenyl-propionamide (23559-01-5)

Conditions	Yield
(i) SOCl2, DMF, (ii) /BRN= 605631/; Multistep reaction;

2-(methylamino)isobutyric acid (2566-34-9) + 2-Chloroaniline (95-51-2) → N-(2-Chloro-phenyl)-2-methyl-2-methylamino-propionamide (23557-45-1)

Conditions	Yield
(i) SOCl2, DMF, (ii) /BRN= 606077/; Multistep reaction;

2-(methylamino)isobutyric acid (2566-34-9) + 1-amino-3-methylbenzene (108-44-1) → 2-Methyl-2-methylamino-N-m-tolyl-propionamide (23558-87-4)

Conditions	Yield
(i) SOCl2, DMF, (ii) /BRN= 635944/; Multistep reaction;

Upstream product

• 593-51-1 methylamine hydrochloride 
• 151-50-8 potassium cyanide 
• 67-64-1 acetone 
• 74-89-5 methylamine 
• 2052-01-9 2-bromo-2-methylpropionic acid 

Downstream Products

• 409108-28-7 N-benzoyl-N-methyl-α-amino-2-methylpropionic acid 
• 23559-09-3 N-(2-Methoxy-phenyl)-2-methyl-2-methylamino-propionamide 
• 23558-82-9 2-Methyl-2-methylamino-N-p-tolyl-propionamide 
• 144332-60-5 α-(benzyloxycarbonyl-methyl-amino)-isobutyric acid 
• 67-64-1 acetone 
• 1438853-27-0 N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-N,2-dimethylalanine 
• 1373522-34-9 2-((2-ethyl-3-(5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-thiadiazol-3-yl)benzyl)(methyl)amino)-2-methylpropanoic acid 
• 15414-89-8 1,3,5,5-tetramethylhydantoin 
• 553667-80-4 2-methyl-2-(1'-methyl-3'-(4-nitrophenyl)ureido)propionamide 
• 146000-39-7 N-tert-butoxycarbonyl-N-methyl-α-aminoisobutyric acid 
• 138062-82-5 2-[(2-Chloro-acetyl)-methyl-amino]-2-methyl-propionic acid 

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