2-Methylphenyl-L-alanine supplier

Name
2-Methylphenyl-L-alanine
EINECS 145-896-5
CAS No. 80126-53-0
Article Data7
CAS DataBase
Density 1.165 g/cm³
Solubility
Melting Point
Formula C₁₀H₁₃NO₂
Boiling Point 326.2 °C at 760 mmHg
Molecular Weight 179.219
Flash Point 151.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms (S)-2-Amino-3-o-tolylpropionicacid;L-2-Methylphenylalanine;L-2'-Methylphenylalanine;
PSA 49.33000
LogP 1.95300

Synthetic route

: 2-Oxo-3-o-tolyl-propionic acid anion

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

Conditions

Conditions	Yield
With L-glutamic acid; pyridoxal 5'-phosphate In water at 40℃; for 12h; E.coli Aspartate transaminase, pH 8;	30%

: 939-57-1, 2373-76-4, 41397-71-1
(E)-3-(2-methylphenyl)acrylic acid

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

Conditions

Conditions	Yield
With carbon dioxide; Taxus chinensis phenylalanine aminomutase; ammonia In water pH=10; Kinetics; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
With ammonia at 30℃; for 17h; pH=10; Time; Reagent/catalyst;	n/a

: 1111643-38-9
2-([(18)F]-fluoromethyl)-L-phenylalanine

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

Conditions

Conditions	Yield
With water at 50℃; pH=7;

: 2373-76-4
2-methylcinnamic acid

A: 736131-48-9
(S)-3-amino-3-(2-methylphenyl)propionic acid

B: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

Conditions

Conditions	Yield
With ammonium bisulphate; EncP-E293M variant at 55℃; for 22h; pH=8.3; Enzymatic reaction; stereoselective reaction;	A n/a B n/a

: 2373-76-4
2-methylcinnamic acid

A: (R)-3-amino-3-(2-methylphenyl)propionic acid

B: 736131-48-9
(S)-3-amino-3-(2-methylphenyl)propionic acid

C: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

Conditions

Conditions	Yield
With ammonium bisulphate; EncP wild type enzyme at 55℃; for 22h; pH=8.3; Enzymatic reaction; stereoselective reaction;	A n/a B n/a C n/a

...Expand

: 68208-16-2
3-amino-3-(2-methylphenyl)propanoic acid

A: (R)-3-amino-3-(2-methylphenyl)propionic acid

B: 939-57-1, 2373-76-4, 41397-71-1
(E)-3-(2-methylphenyl)acrylic acid

C: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

Conditions

Conditions	Yield
With phenylalanine ammonia α-lyase from Anabaena variabilis; phenylalanine ammonia lyase from Streptomyces maritimus In aq. buffer at 30℃; for 24h; pH=8; Reagent/catalyst; Resolution of racemate; Enzymatic reaction; enantioselective reaction;

...Expand

: 939-57-1, 2373-76-4, 41397-71-1
(E)-3-(2-methylphenyl)acrylic acid

A: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

B: 2-(fluoromethyl)-D-phenylalanine

Conditions

Conditions	Yield
Stage #1: (E)-3-(2-methylphenyl)acrylic acid With ammonium hydroxide; phenylalanine ammonia-lyase from Anabaena variabilis N347A mutant In aq. buffer at 35℃; for 12h; pH=8.5; Stage #2: With borane-ammonia complex; L-amino acid deaminase from Proteus mirabilis In aq. buffer at 35℃; for 12h; pH=8.5; stereoselective reaction;	A n/a B n/a

: 22888-51-3
2-amino-3-(2-methylphenyl)propanoic acid

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: phenylalanine ammonia-lyase from Pseudozyma antarctica yeast / aq. buffer / 168 h / 30 °C / pH 8.5 / Resolution of racemate 2: ammonia / 17 h / 30 °C / pH 10 View Scheme

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

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 80102-29-0, 139558-50-2, 114873-05-1
Nα-tert-butyloxycarbonyl-2'-methyl-L-phenylalanine

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 20℃; for 2h;	89.2%

: 66-71-7
1,10-Phenanthroline

: sodium perchlorate

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: palladium dichloride

: [Pd(L-(o-methyl)phenylalaninate)(1,10-phenanthroline)]ClO4

Conditions

Conditions	Yield
With NaOH; HCl In hydrogenchloride; methanol addn. of 2 equiv. aminoacid to PdCl2 (in 1 M HCl), pH-adjustment to 6-7 (aq. NaOH), addn. of 1 equiv. phenanthroline (in aq. MeOH), stirring at 40°C overnight, pptn. on addn. of aq. NaClO4;	89%

...Expand

: 66-71-7
1,10-Phenanthroline

: copper(II) perchlorate hexahydrate

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: [Cu(L-(o-methyl)phenylalaninate)(1,10-phenanthroline)]ClO4 * H2O

Conditions

Conditions	Yield
With NaOH In methanol; water addn. of 1 equiv. aminoacid (in 1 M NaOH) to equimolar mixt. of Cu-salt and phenanthroline (in 50% aq. MeOH), stirring at room temp. to dissoln.; crystn., collection, recrystn. (aq. MeOH); elem. anal.;	86%

...Expand

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 2-(fluoromethyl)-D-phenylalanine

Conditions

Conditions	Yield
With D-glucose; nicotinamide adenine dinucleotide phosphate; ammonium chloride In aq. buffer at 20℃; for 24h; pH=9; Microbiological reaction; enantioselective reaction;	83%
With D-glucose; D-amino acid aminotransferase from Bacillus sp mutant T242G; L-aminoacid deaminase from Proteus mirabilis In aq. phosphate buffer at 37℃; for 4h; pH=8; Enzymatic reaction; enantioselective reaction;	n/a

: 590-28-3
potassium cyanate

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: (S)-5-(2-methylbenzyl)imidazolidine-2,4-dione

Conditions

Conditions	Yield
With hydrogenchloride In water for 5h; Reflux;	67%

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: (R)-3-amino-3-(2-methylphenyl)propionic acid

Conditions

Conditions	Yield
With phenylalanine aminomutase at 31℃; for 2h; Enzyme kinetics;

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 943726-70-3
Nα-tert-butyloxycarbonyl-2'-methyl-L-phenylalanyl-L-phenylalanylamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 89.2 percent / triethylamine / dioxane; H2O / 2 h / 20 °C 2: 97 percent / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphonium*PF6 / dimethylformamide / 4 h / 20 °C View Scheme

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: C19H23N3O2*HCl

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 89.2 percent / triethylamine / dioxane; H2O / 2 h / 20 °C 2: 97 percent / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphonium*PF6 / dimethylformamide / 4 h / 20 °C 3: HCl / dioxane / 0.5 h / 20 °C View Scheme

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 943726-76-9
Nα-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-2'-methyl-L-phenylalanyl-L-phenylalanylamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 89.2 percent / triethylamine / dioxane; H2O / 2 h / 20 °C 2: 97 percent / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphoniumPF6 / dimethylformamide / 4 h / 20 °C 3: HCl / dioxane / 0.5 h / 20 °C 4: 289 mg / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphoniumPF6 / dimethylformamide / 4 h / 20 °C View Scheme

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 943726-77-0
Nα-tert-butyloxycarbonyl-2',6'-dimethyl-L-tyrosyl-L-prolyl-2'-methyl-L-phenylalanyl-L-phenylalanylamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 89.2 percent / triethylamine / dioxane; H2O / 2 h / 20 °C 2: 97 percent / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphoniumPF6 / dimethylformamide / 4 h / 20 °C 3: HCl / dioxane / 0.5 h / 20 °C 4: 266 mg / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphoniumPF6 / dimethylformamide / 4 h / 20 °C View Scheme

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: L-tyrosyl-L-prolyl-2'-methyl-L-phenylalanyl-L-phenylalanylamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 89.2 percent / triethylamine / dioxane; H2O / 2 h / 20 °C 2: 97 percent / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphoniumPF6 / dimethylformamide / 4 h / 20 °C 3: HCl / dioxane / 0.5 h / 20 °C 4: 289 mg / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphoniumPF6 / dimethylformamide / 4 h / 20 °C 5: trifluoroacetic acid; anisole / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: 89.2 percent / triethylamine / dioxane; H2O / 2 h / 20 °C
2: 97 percent / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphonium*PF6 / dimethylformamide / 4 h / 20 °C
3: HCl / dioxane / 0.5 h / 20 °C
4: 289 mg / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphonium*PF6 / dimethylformamide / 4 h / 20 °C
5: trifluoroacetic acid; anisole / 1 h / 20 °C
View Scheme

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 2',6'-dimethyl-L-tyrosyl-L-prolyl-2'-methyl-L-phenylalanyl-L-phenylalanylamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 89.2 percent / triethylamine / dioxane; H2O / 2 h / 20 °C 2: 97 percent / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphoniumPF6 / dimethylformamide / 4 h / 20 °C 3: HCl / dioxane / 0.5 h / 20 °C 4: 266 mg / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphoniumPF6 / dimethylformamide / 4 h / 20 °C 5: trifluoroacetic acid; anisole / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: 89.2 percent / triethylamine / dioxane; H2O / 2 h / 20 °C
2: 97 percent / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphonium*PF6 / dimethylformamide / 4 h / 20 °C
3: HCl / dioxane / 0.5 h / 20 °C
4: 266 mg / diisopropylethylamine; benzotriazol-1-yloxytrispyrrolidinophosphonium*PF6 / dimethylformamide / 4 h / 20 °C
5: trifluoroacetic acid; anisole / 1 h / 20 °C
View Scheme

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: palladium dichloride

: [Pd(L-(o-methyl)phenylalaninate)2]

Conditions

Conditions	Yield
With NaOH; HCl In hydrogenchloride addn. of 2 equiv. ligand to PdCl2, pH-adjustment to 6-7 (aq. NaOH);

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 939-57-1, 2373-76-4, 41397-71-1
(E)-3-(2-methylphenyl)acrylic acid

Conditions

Conditions	Yield
With Taxus phenylalanine aminomutase at 31℃; for 1h; Kinetics; Enzymatic reaction;

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 3-(4-methoxybenzyl)-5-(2-methylbenzyl)imidazolidine-2,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 5 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C View Scheme

: 540-88-5
acetic acid tert-butyl ester

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: (S)-tert-butyl 2-amino-3-(o-tolyl)propanoate

Conditions

Conditions	Yield
With perchloric acid In water at 20 - 30℃; for 16h; Inert atmosphere;

: 64-17-5
ethanol

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: 1212275-99-4
C12H17NO2

Conditions

Conditions	Yield
With thionyl chloride at 0 - 75℃; for 3h;

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: N-((2S)-4-chloro-3-hydroxy-1-(o-tolyl)butan-2-yl)benzamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / 3 h / 0 - 75 °C 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 - -70 °C 3.2: -78 - -65 °C 4.1: sodium tetrahydroborate View Scheme

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: N-((2S,3R)-4-chloro-3-hydroxy-1-(o-tolyl)butan-2-yl)benzamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / 3 h / 0 - 75 °C 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 - -70 °C 3.2: -78 - -65 °C 4.1: C38H40ClN2O3RhS; / dichloromethane / 1 h / 25 °C / Schlenk technique View Scheme

: 80126-53-0
(S)-2-amino-3-(o-tolyl)propanoic acid

: (S)-N-(4-chloro-3-oxo-1-(o-tolyl)butan-2-yl)benzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 3 h / 0 - 75 °C 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 - -70 °C 3.2: -78 - -65 °C View Scheme

2-Methylphenyl-L-alanine Specification

The 2-Methylphenyl-L-alanine, also known as L-2-Methylphenylalanine, is the organic compound with the formula C₁₀H₁₃NO₂. It belongs to the product categories of Amino Acids; Phenylalanine Analogs and Other Aromatic Alpha Amino Acids; Amino Acid Derivatives; a-Amino. With the CAS registry number 80126-53-0, its IUPAC name is called (2S)-2-amino-3-(2-methylphenyl)propanoic acid. When you are using this chemical, please be cautious about it. This chemical may cause inflammation to the skin or other mucous membranes. The product should be sealed and stored in cool and dry place. What's more, it should be protected from strong oxides.

Physical properties of 2-Methylphenyl-L-alanine: (1)ACD/LogP: 1.57; (2)ACD/LogD (pH 5.5): -0.93; (3)ACD/LogD (pH 7.4): -0.93; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.568; (12)Molar Refractivity: 50.31 cm³; (13)Molar Volume: 153.7 cm³; (14)Surface Tension: 50.3 dyne/cm; (15)Density: 1.165 g/cm³; (16)Flash Point: 151.1 °C; (17)Enthalpy of Vaporization: 60 kJ/mol; (18)Boiling Point: 326.2 °C at 760 mmHg; (19)Vapour Pressure: 8.9E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=CC=CC=C1CC(C(=O)O)N
(2)Isomeric SMILES: CC1=CC=CC=C1C[C@@H](C(=O)O)N
(3)InChI: InChI=1S/C10H13NO2/c1-7-4-2-3-5-8(7)6-9(11)10(12)13/h2-5,9H,6,11H2,1H3,(H,12,13)/t9-/m0/s1
(4)InChIKey: NHBKDLSKDKUGSB-VIFPVBQESA-N

Product Name

2-Methylphenyl-L-alanine

Synthetic route

2-Methylphenyl-L-alanine Specification

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