N-Methyl-L-alanine supplier

Name
N-Methyl-L-alanine
EINECS 1533716-785-6
CAS No. 3913-67-5
Article Data47
CAS DataBase
Density 1.048 g/cm³
Solubility
Melting Point 315-317 °C (decomp)
Formula C₄H₉NO₂
Boiling Point 190.1 °C at 760 mmHg
Molecular Weight 103.121
Flash Point 68.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Alanine,N-methyl-, L- (7CI,8CI);(S)-N-Methylalanine;2-(Methylamino)propanoic acid;N-Methylalanine;a-(Methylamino)propionic acid;
PSA 49.33000
LogP 0.06980

Synthetic route

: (2R,2'R)-N-<2'-(methylamino)propionyl>bornane-10,2-sultam

A: 3913-67-5
N-methylalanine

B: 29475-64-7
N-methyl-D-alanine

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran at 0℃; Title compound not separated from byproducts;	A n/a B 94%

: (2S,2'S)-N-<2'-(methylamino)propionyl>bornane-10,2-sultam

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran at 0℃;	91%

: (S)-2-(Benzhydryl-methyl-amino)-propionic acid benzhydryl ester

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol	91%

: 50-00-0
formaldehyd

: 56-41-7
L-alanin

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With sodium dihydrogenphosphate; zinc at 30℃; for 0.25h;	85%

: 130368-69-3
(2R)-2-(4-Toluenesulfonyloxy)propionic Acid

: 74-89-5
methylamine

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
In water at 15 - 30℃; Autoclave; Sealed tube;	81.4%

: 10009-70-8
R-(+)-2-bromopropionic acid

: 74-89-5
methylamine

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
In water
With lead(II) hydroxide on calcium carbonate; water

: 16948-16-6
N-(tert-butoxycarbonyl)-N-methyl-L-alanine

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With trifluoroacetic acid

: 79821-69-5
Nα-4-toluenesulfonyl-Nα-methylalanine

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid

: 60522-13-6
(S)-2-[Methyl-(toluene-4-sulfonyl)-amino]-propionic acid isopropyl ester

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogen bromide; phenol
With hydrogen bromide; phenol In water for 0.5h; Heating;

: 63238-82-4
(-)-N-methyl-N-benzyl-(S)-Ala

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In acetic acid

: 138062-74-5
N-Chloracetyl-N-methyl-DL-alanin

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
In water at 30℃; N-Acyl-L-prolin-Acylase; other substrates, enantioselectivity;
With hydrogenchloride In water at 30℃; N-Acyl-L-prolin-Acylase, pH 7.0;

: 105091-14-3, 119816-11-4
theonellamine B

A: 3913-67-5
N-methylalanine

B: 72-18-4
L-valine

C: 72-19-5
L-threonine

D: 2480-23-1
N-methyl-L-valine

Conditions

Conditions	Yield
With hydrogenchloride at 110℃; for 40h; Further byproducts given;

...Expand

: 105091-14-3, 119816-11-4
theonellamine B

A: 3913-67-5
N-methylalanine

B: 72-18-4
L-valine

C: 72-19-5
L-threonine

D: 2480-23-1
N-methyl-L-valine

E: 328-38-1
(R)-leucine

F: 107-95-9
3-amino propanoic acid

Conditions

Conditions	Yield
With hydrogenchloride at 110℃; for 4h;

...Expand

: 105091-14-3, 119816-11-4
theonellamine B

A: 3913-67-5
N-methylalanine

B: 72-18-4
L-valine

C: 2480-23-1
N-methyl-L-valine

D: 107-95-9
3-amino propanoic acid

Conditions

Conditions	Yield
With hydrogenchloride at 110℃; for 40h; Further byproducts given;

...Expand

: 138062-73-4
(S)-2-[(2-Chloro-acetyl)-methyl-amino]-propionic acid

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogenchloride In water at 30℃; N-Acyl-L-prolin-Acylase, pH 7.0;

: (S)-2-[Methyl-(2,2,5,7,8-pentamethyl-chroman-6-sulfonyl)-amino]-propionic acid benzyl ester

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid

: 37661-60-2
phenylmethyl (4S)-5-oxo-4-methyl-1,3-oxazolidine-3-carboxylate

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol Yield given;

N-p-toluenesulfonyl-N-methyl-d-alanine: N-p-toluenesulfonyl-N-methyl-d-alanine

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogenchloride at 100℃;

: 7647-01-0
hydrogenchloride

: 79821-69-5
Nα-4-toluenesulfonyl-Nα-methylalanine

A: 3913-67-5
N-methylalanine

B: 104-15-4
toluene-4-sulfonic acid

Conditions

Conditions	Yield
at 100℃;

...Expand

: 352199-36-1
N-benzyloxycarbonyl-L-phenylalanyl-N-methyl-L-alanine

A: 3913-67-5
N-methylalanine

B: 1161-13-3
N-Cbz-L-Phe

Conditions

Conditions	Yield
With carboxypeptidase-Y In water at 37℃; pH=6.5; Kinetics;
With hydrogenchloride; carboxypeptisae-A In water at 37℃; pH=6.5; Enzyme kinetics; Kinetics; Further Variations:; Reagents;

: 21691-41-8
(2S)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid

: 3913-67-5
N-methylalanine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol; water at 20℃; for 20h;
With ethylenediaminetetraacetic acid; phenylmethylsulphonyl fluoride; water In aq. phosphate buffer at 30℃; Kinetics; Reagent/catalyst; Microbiological reaction; Enzymatic reaction;

: apratoxin E

A: 3913-67-5
N-methylalanine

B: 4125-98-8
N-methyl-L-isoleucine

C: 6230-11-1
O-Methyltyrosine

D: 60-18-4
L-tyrosine

E: 147-85-3
L-proline

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 18h;

...Expand

: 1187486-24-3
itralamide A

A: 56-41-7
L-alanin

B: 3913-67-5
N-methylalanine

C: 2480-23-1
N-methyl-L-valine

D: 2812-28-4
(2S,3R)-3-hydroxy-2-(methylamino)butanoic acid

E: N-methylvalylalanine

F: N-methylphenylalanylalanine

G: 56564-52-4
N-methyl-D-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 18.5h;

...Expand

: 1187486-25-4
itralamide B

A: 3913-67-5
N-methylalanine

B: 640-68-6
D-Val-OH

C: 2812-28-4
(2S,3R)-3-hydroxy-2-(methylamino)butanoic acid

D: N-methylalanylvaline

E: N-methylphenylalanylvaline

F: 56564-52-4
N-methyl-D-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 18.5h;

...Expand

: aspochracin

A: 3913-67-5
N-methylalanine

B: 2480-23-1
N-methyl-L-valine

C: 70-26-8
L-ornithine

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 20h;

...Expand

: 1232889-28-9
sclerotiotide A

A: 3913-67-5
N-methylalanine

B: 72-18-4
L-valine

C: 70-26-8
L-ornithine

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 20h;

...Expand

: 1232889-32-5
sclerotiotide B

A: 3913-67-5
N-methylalanine

B: 2480-23-1
N-methyl-L-valine

C: 70-26-8
L-ornithine

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 20h;

...Expand

: 1232889-36-9
sclerotiotide C

A: 3913-67-5
N-methylalanine

B: 2480-23-1
N-methyl-L-valine

C: 56-87-1
L-lysine

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 20h;

...Expand

: 1255709-51-3
7,39-epi-Lagunamide A

A: 56-41-7
L-alanin

B: 3913-67-5
N-methylalanine

C: 1509-34-8
D-allo-isoleucine

D: 73-32-5
L-isoleucine

E: 488-15-3, 51576-04-6, 59653-35-9, 86540-81-0, 86630-77-5, 70748-47-9
(2R,3S)-2-hydroxy-3-methylpentanoic acid

F: 56564-52-4
N-methyl-D-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 18h; sealed vial;

...Expand

: 64-17-5
ethanol

: 3913-67-5
N-methylalanine

: 117856-39-0
(S)-2-methylaminopropionic acid ethyl ester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride for 22h; Ambient temperature;	100%
With hydrogenchloride In 1,4-dioxane for 18h;
With thionyl chloride In neat (no solvent) at 0 - 25℃; for 16h;
With thionyl chloride at 0 - 25℃; for 16h;	1.8 g
With thionyl chloride at 0 - 25℃; for 16h;

: 67-56-1
methanol

: 3913-67-5
N-methylalanine

: 19914-41-1, 20045-77-6, 114079-50-4
N-methyl-L-alanine methyl ester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 96h;	100%
With thionyl chloride

: 3913-67-5
N-methylalanine

: 19914-41-1, 20045-77-6, 114079-50-4
N-methyl-L-alanine methyl ester hydrochloride

Conditions

Conditions	Yield
In methanol	100%

: 3913-67-5
N-methylalanine

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 3,4-dimethyl-2-thioxo-oxazolidin-5-one

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; Inert atmosphere;	91%

: 3913-67-5
N-methylalanine

: C45H62N4O13

: C49H69N5O14

Conditions

Conditions	Yield
Stage #1: C45H62N4O13 With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.166667h; Stage #2: N-methylalanine In N,N-dimethyl-formamide for 1h;	91%

: 3913-67-5
N-methylalanine

: 67-64-1
acetone

: 1105044-89-0
N-isopropyl-N-methyl-L-alanine

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In methanol under 775.743 Torr; for 18h;	88%
With hydrogen; palladium 10% on activated carbon In methanol under 775.743 Torr; for 18h;	88%

: 3913-67-5
N-methylalanine

A: 124-38-9
carbon dioxide

B: 75-07-0
acetaldehyde

C: 74-89-5
methylamine

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium perchlorate; chlorine at 24.9℃; Mechanism; Rate constant; Equilibrium constant; multistep reaction: 1.) water, 298 deg K, 2.) water, 298 deg K; reactions under var. conditions;	A n/a B 87% C n/a

...Expand

: 3913-67-5
N-methylalanine

: 2937-50-0
Allyl chloroformate

: Alloc-Me-Ala

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 3h;	87%

: 3913-67-5
N-methylalanine

: 24424-99-5
di-tert-butyl dicarbonate

: 16948-16-6
N-(tert-butoxycarbonyl)-N-methyl-L-alanine

Conditions

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 20℃; for 16h;	86%
With sodium hydroxide In 1,4-dioxane; water for 5h; Ambient temperature;	42.3%

: 3913-67-5
N-methylalanine

: 79-22-1
methyl chloroformate

: 1085528-19-3
2-(methoxycarbonylmethylamino)propionic acid

Conditions

Conditions	Yield
Stage #1: N-methylalanine With sodium hydroxide In water at 3℃; for 0.5h; Inert atmosphere; Stage #2: methyl chloroformate In water at 3℃; for 6.5h; Stage #3: With hydrogenchloride In water at 20℃; pH=1;	86%
With sodium carbonate; sodium hydroxide In water at 0 - 20℃; for 7.25h;	77%

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: 3913-67-5
N-methylalanine

: 675141-34-1
[(p-cymene)RuCl(η(2)-N,O-NH(CH3)CH(CH3)COO]

Conditions

Conditions	Yield
With sodium methylate In methanol; dichloromethane byproducts: NaCl; soln. of 2 equiv. of N-Me-alanine and 1 equiv. of NaOMe in MeOH added dropwise to soln. 1 equiv. of complex in CH2Cl2, mixt. stirred for 3 h at room temp.; solvent distd. in vac., residue dissolved in CH2Cl2, NaCl centrifuged, soln. added dropwise to pentane, ppt. washed twice with Et2O then pentane, elem. anal.;	81%

: 3913-67-5
N-methylalanine

: 69113-59-3
3-iodobenzonitrile

: 1335533-53-3
N-(3-cyanophenyl)-methyl-L-alanine

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 160℃; for 0.75h; Microwave irradiation;	81%

: 3913-67-5
N-methylalanine

: 2,4-dichloro-6-isopropylpyrimidin-5-amine

: (7S)-2-chloro-4-isopropyl-7,8-dimethyl-7,8-dihydropteridin-6(5H)-one

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol at 90℃; for 16h;	81%

: 3913-67-5
N-methylalanine

: 103979-54-0
1H,2H,4H-thieno[2,3-d][1,3]oxazine-2,4-dione

: 1140528-73-9
(S)-3,4-dihydro-3,4-dimethyl-1H-thieno[2,3-e][1,4]diazepine-2,5-dione

Conditions

Conditions	Yield
In water Reflux; regioselective reaction;	80%

: 75-44-5
phosgene

: 3913-67-5
N-methylalanine

: 58311-53-8
(L)-3,4-dimethyl-1,3-oxazolidine-2,5-dione

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃; for 4h; Inert atmosphere;	77.6%
Product distribution / selectivity;

: 13162-27-1
5-amino-2,4-dichloro-6-methylpyrimidine

: 3913-67-5
N-methylalanine

: (7S)-2-chloro-4,7,8-trimethyl-7,8-dihydropteridin-6(5H)-one

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water Reflux;	77%

: 12354-84-6, 12354-85-7
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

: 3913-67-5
N-methylalanine

: 675585-20-3, 675141-32-9
[Cp(*)IrCl(η(2)-N,O-NH(CH3)CH(CH3)COO]

Conditions

Conditions	Yield
With sodium methylate In methanol; dichloromethane byproducts: NaCl; soln. of 2 equiv. of N-Me-alanine and 1 equiv. of NaOMe in MeOH added dropwise to soln. 1 equiv. of complex in CH2Cl2, mixt. stirred for 3 h at room temp.; solvent distd. in vac., residue dissolved in CH2Cl2, NaCl centrifuged, soln. added dropwise to pentane, ppt. washed twice with Et2O then pentane, elem. anal.; isomers detected by (1)H and (13)C NMR;	76%

Yield

With sodium methylate In methanol; dichloromethane byproducts: NaCl; soln. of 2 equiv. of N-Me-alanine and 1 equiv. of NaOMe in MeOH added dropwise to soln. 1 equiv. of complex in CH2Cl2, mixt. stirred for 3 h at room temp.; solvent distd. in vac., residue dissolved in CH2Cl2, NaCl centrifuged, soln. added dropwise to pentane, ppt. washed twice with Et2O then pentane, elem. anal.; isomers detected by (1)H and (13)C NMR;

76%

: 5177-27-5
5-amino-2,4-dichloropyrimidine

: 3913-67-5
N-methylalanine

: (7S)-2-chloro-7,8-dimethyl-7,8-dihydropteridin-6(5H)-one

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 80℃; for 3h;	75%

: 3913-67-5
N-methylalanine

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 84000-07-7
N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-alanine

Conditions

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 20℃; for 6h;	74.9%

: {(nBu3P)(Cl)Pd(μ-Cl)}2

: 3913-67-5
N-methylalanine

: 675141-35-2, 675585-26-9
[(nBu3P)PdCl(η(2)-N,O-NH(CH3)CH(CH3)COO]

Conditions

Conditions	Yield
With sodium methylate In methanol; dichloromethane byproducts: NaCl; soln. of 2 equiv. of N-Me-alanine and 1 equiv. of NaOMe in MeOH added dropwise to soln. 1 equiv. of complex in CH2Cl2, mixt. stirred for 3 h at room temp.; solvent distd. in vac., residue dissolved in CH2Cl2, NaCl centrifuged, soln. added dropwise to pentane, ppt. washed twice with Et2O then pentane, elem. anal.;	71%

: 3913-67-5
N-methylalanine

: 73179-67-6
2-<(3-phenyl-2-propynyl)oxy>benzaldehyde

: 637759-97-8
1,2-dimethyl-3-phenyl-1,2,4,9b-tetrahydro-5-oxa-1-aza-cyclopenta[a]naphthalene

Conditions

Conditions	Yield
lk In toluene for 4h; Heating;	68%

: dichlorobis(triethyl phosphine)-μ-dichloro dipalladium (II)

: 3913-67-5
N-methylalanine

: 675141-36-3, 675585-28-1
[(Et3P)PdCl(η(2)-N,O-NH(CH3)CH(CH3)COO]

Conditions

Yield

68%

: 3913-67-5
N-methylalanine

: (4-nitrophenyl) N-[4-(trifluoromethyl)-2-pyridyl]carbamate

: (5S)-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidine-2,4-dione

Conditions

Conditions	Yield
In 1,4-dioxane at 80℃; Inert atmosphere;	67%

: 138148-62-6
N-methyl-N-[(3-methyldithio)-1-oxopropyl]-L-alanine

: 138148-67-1
5-methyldithio-pentanoic acid

: 3913-67-5
N-methylalanine

: 543-27-1
isobutyl chloroformate

: N-methyl-N-(5-methyldithio-pentanoyl)-L-alanine

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; water	66%
With triethylamine In tetrahydrofuran; water	66%

...Expand

: 112-16-3
n-dodecanoyl chloride

: 3913-67-5
N-methylalanine

: N-n-Dodecanoyl-N-methyl-(S)-alanine

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide	64%
With triethylamine In N,N-dimethyl-formamide at 0℃; for 6h;	64%

N-Methyl-L-alanine Specification

The IUPAC name of N-Methyl-L-alanine is (2S)-2-(methylamino)propanoic acid. With the CAS registry number 3913-67-5, it is also named as L-Alanine, N-methyl-. The product's categories are Amino Acid Derivatives; N-Methyl Amino Acids; N-Methyl Amino Acids; Peptide Synthesis; Unnatural Amino Acid Derivatives. Besides, it should be sealed in dark, ventilated and dry place. This chemical is apharmaceutical intermediate and fine industrial chemical. In addition, its molecular formula is C₄H₉NO₂ and molecular weight is 103.12.

The other characteristics of N-Methyl-L-alanine can be summarized as: (1)ACD/LogP: -0.45; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.94; (4)ACD/LogD (pH 7.4): -2.95; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 29.54 Å²; (13)Index of Refraction: 1.435; (14)Molar Refractivity: 25.69 cm³; (15)Molar Volume: 98.3 cm³; (16)Polarizability: 10.18×10^-24cm³; (17)Surface Tension: 34.4 dyne/cm; (18)Density: 1.048 g/cm³; (19)Flash Point: 68.8 °C; (20)Enthalpy of Vaporization: 46.99 kJ/mol; (21)Boiling Point: 190.1 °C at 760 mmHg; (22)Vapour Pressure: 0.244 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(O)[C@@H](NC)C
(2)InChI: InChI=1/C4H9NO2/c1-3(5-2)4(6)7/h3,5H,1-2H3,(H,6,7)/t3-/m0/s1
(3)InChIKey: GDFAOVXKHJXLEI-VKHMYHEABL
(4)Std. InChI: InChI=1S/C4H9NO2/c1-3(5-2)4(6)7/h3,5H,1-2H3,(H,6,7)/t3-/m0/s1
(5)Std. InChIKey: GDFAOVXKHJXLEI-VKHMYHEASA-N

Product Name

N-Methyl-L-alanine

Synthetic route

N-Methyl-L-alanine Specification

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