2-Amino-2-methyl-3-phenylpropionic acid supplier

Name
2-Amino-2-methyl-3-phenylpropionic acid
EINECS
CAS No. 1132-26-9
Article Data23
CAS DataBase
Density 1.166 g/cm³
Solubility slightly soluble in water
Melting Point 293-294 °C (dec.)(lit.)
Formula C₁₀H₁₃NO₂
Boiling Point 312.8 °C at 760 mmHg
Molecular Weight 179.219
Flash Point 143 °C
Transport Information
Appearance white crystalline powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Methyl-3-phenylalanine;
PSA 63.32000
LogP 1.73140

Synthetic route

: 100-39-0
benzyl bromide

: C16H13N3O3(2-)*Ni(2+)

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With potassium hydroxide; C-9 In dichloromethane at 20℃;	95%

: 100-39-0
benzyl bromide

: 117470-83-4
ethyl N-<(4-chlorophenyl)methylene>-DL-alanate

A: 1132-26-9
2-methyl-3-phenylalanine

B: 302-72-7
rac-Ala-OH

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In acetonitrile for 48h; Product distribution; Heating; further alkylation method;	A 94% B 7%

...Expand

: 100-39-0
benzyl bromide

: 126402-81-1
isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Stage #1: benzyl bromide; isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate With cesium hydroxide; (R,R)-TADDOL In toluene at 15 - 20℃; for 12h; Alkylation; benzylation; Stage #2: With hydrogenchloride In water; toluene Hydrolysis; Heating;	94%

: 86778-91-8
(+/-)-N-(tert-butoxycarbonyl)-α-methylphenylalanine

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 2h; Ambient temperature;	89%
With ammonium hydroxide; silica gel; trifluoroacetic acid 1.) MeOH; Yield given. Multistep reaction;

: 100-39-0
benzyl bromide

: N-benzylidene-D,L-alanine isopropyl ester

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Stage #1: benzyl bromide; N-benzylidene-D,L-alanine isopropyl ester With sodium hydroxide; tetraethylammonium bromide; (R,R)-TADDOL In toluene at 15 - 20℃; for 12h; Substitution; Stage #2: With hydrogenchloride In water for 0.25h; Hydrolysis; Further stages.;	83%

: 100-39-0
benzyl bromide

: 69555-16-4
ethyl 2-(diphenylmethyleneamino)propanoate

A: 1132-26-9
2-methyl-3-phenylalanine

B: 302-72-7
rac-Ala-OH

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In acetonitrile for 48h; Product distribution; Heating; further alkylation method;	A 23% B 63%

...Expand

: 5874-61-3, 21453-79-2, 51127-19-6, 75658-67-2
4-benzyl-2-phenyl-2-oxazolin-5-one

: 74-88-4
methyl iodide

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
(i) iPr2NEt, (ii) aq. HCl, AcOH; Multistep reaction;

: 64298-85-7
methyl-2-benzylideneamino-2-methyl-3-phenylpropanoate

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride 1.) ether, 12 h, room temp.; 2.) reflux, 4 h; Yield given. Multistep reaction;

: 46438-07-7
α-methyl-α-carbethoxy-β-phenethylamine

A: 1132-26-9
2-methyl-3-phenylalanine

B: 164453-67-2
ethyl (S)-2-amino-2-methyl-3-phenylpropanoate

C: 22435-99-0
ethyl (R)-2-amino-2-methyl-3-phenylpropanoate

Conditions

Conditions	Yield
With phosphate buffer; Humicola amino esterase Ambient temperature; Title compound not separated from byproducts;

...Expand

: 27993-44-8
5-benzyl-5-methyl-imidazolidine-2,4-dione

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With sodium hydroxide Heating;

: 55686-06-1
rac-4-benzyl-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid at 95℃; for 5.5h; Heating; Yield given;

(+-)-4-methyl-4-benzyl-imidazolidinedione-(2.5): (+-)-4-methyl-4-benzyl-imidazolidinedione-(2.5)

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With barium dihydroxide; water

: 100-97-0
hexamethylenetetramine

(+-)-2-chloro-2-methyl-3-phenyl-propionic acid: (+-)-2-chloro-2-methyl-3-phenyl-propionic acid

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With 1,4-dioxane

: 151-50-8
potassium cyanide

: 103-79-7
1-phenyl-acetone

A: 1132-26-9
2-methyl-3-phenylalanine

B (+-)-2-amino-2-methyl-3-phenyl-propionitrile hydrochloride: (+-)-2-amino-2-methyl-3-phenyl-propionitrile hydrochloride

Conditions

Conditions	Yield
With water; ammonium chloride at 55 - 60℃; Behandeln der in Aether loeslichen Anteile des Reaktionsprodukts mit HCl;

...Expand

: 100-39-0
benzyl bromide

: 2-{[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-propionic acid benzyl ester

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Stage #1: 2-{[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-propionic acid benzyl ester With (R,R)-dicyclohexyl tartrate; lithium diisopropyl amide In tetrahydrofuran at -60℃; for 0.5h; Stage #2: benzyl bromide In tetrahydrofuran at 25℃; for 12h; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 10h; Heating;	98 % Chromat.

: 100-39-0
benzyl bromide

: 120328-90-7
methyl (E)-N-benzylidenealaninate

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With sodium hydroxide; N,N'-ethylenebis(salicylideneiminato)copper(II) In toluene at 20℃; for 48h;

: 100-39-0
benzyl bromide

CO: CO

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 70 percent / CF3CO2Ag / CH2Cl2 / 2 h / 0 °C 2: 96 percent / 2,6-dimethylpyridine / CH2Cl2 / 1 h / Ambient temperature 3: 66 percent / CF3CO2H / CH2Cl2 / 2 h / 0 °C 4: KMnO4, dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature 6: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature View Scheme

: 171898-22-9
(+/-)-5-benzyl-1-(tert-butoxycarbonyl)-2,5-dihydropyrrol-2-one

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 96 percent / 2,6-dimethylpyridine / CH2Cl2 / 1 h / Ambient temperature 2: 66 percent / CF3CO2H / CH2Cl2 / 2 h / 0 °C 3: KMnO4, dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature 5: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature View Scheme

: 171898-27-4
(+/-)-5-benzyl-1-(tert-butoxycarbonyl)-5-methyl-2,5-dihydropyrrol-2-one

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: KMnO4, dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature 3: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature View Scheme

: 1059698-59-7
2-Benzyl-3,4-dihydroxy-2-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature View Scheme

: 171898-25-2
5-benzyl-1-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 66 percent / CF3CO2H / CH2Cl2 / 2 h / 0 °C 2: KMnO4, dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature 4: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature View Scheme

: 100-44-7
benzyl chloride

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / K2CO3, KOH / benzyl triethylammonium chloride / CH2Cl2 / 6 h / Ambient temperature 2: 1.) hydrochloric acid (1N); 2.) hydrochloric acid (6N) / 1.) ether, 12 h, room temp.; 2.) reflux, 4 h View Scheme

: 64384-47-0
2-amino-3-phenyl-2-methylpropanenitrile

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride for 3h; Heating;
With hydrogenchloride; water

: 103-79-7
1-phenyl-acetone

: 1132-26-9
2-methyl-3-phenylalanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia 2: hydrogenchloride; water View Scheme

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

: 1132-26-9
2-methyl-3-phenylalanine

: 86778-91-8
(+/-)-N-(tert-butoxycarbonyl)-α-methylphenylalanine

Conditions

Conditions	Yield
Stage #1: di-tert-butyl dicarbonate; 2-methyl-3-phenylalanine With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; pH=9; Stage #2: With hydrogenchloride In 1,4-dioxane; water pH=2;	88%
Stage #1: di-tert-butyl dicarbonate; 2-methyl-3-phenylalanine With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; Stage #2: With hydrogenchloride In 1,4-dioxane; water pH=2;	88%
With triethylamine In N,N-dimethyl-formamide at 25℃; for 18h;	46%
Stage #1: di-tert-butyl dicarbonate; 2-methyl-3-phenylalanine With sodium hydroxide In 1,4-dioxane; water for 14h; Stage #2: With hydrogenchloride In 1,4-dioxane; water pH=~ 1;
Stage #1: di-tert-butyl dicarbonate; 2-methyl-3-phenylalanine With sodium hydroxide In 1,4-dioxane; water for 14h; Stage #2: With hydrogenchloride In 1,4-dioxane; water pH=~ 1;

: 1132-26-9
2-methyl-3-phenylalanine

: 79-04-9
chloroacetyl chloride

: 121703-95-5
N-Chloroacetyl-α-methylphenylalanine

Conditions

Conditions	Yield
In acetonitrile for 1.5h; Heating;	76%

: 85-44-9
phthalic anhydride

: 1132-26-9
2-methyl-3-phenylalanine

: 21878-65-9
α-Methyl-N-phthaloylphenylalanin

Conditions

Conditions	Yield
at 140℃; for 0.5h;	75%

: 1132-26-9
2-methyl-3-phenylalanine

: 2-(boc-oxyimino)-2-phenylacetonitrile

: 86778-91-8
(+/-)-N-(tert-butoxycarbonyl)-α-methylphenylalanine

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide; acetone at 20℃; for 16h;	64%

: 50-00-0
formaldehyd

: 1132-26-9
2-methyl-3-phenylalanine

: 100486-34-8
3-carboxy-3-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride 1.) reflux, 1 h, 2.) RT, 16 h;	63.3%

: 1132-26-9
2-methyl-3-phenylalanine

: 21394-84-3
2-amino-2-methyl-3-phenylpropan-1-ol

Conditions

Conditions	Yield
With borane In tetrahydrofuran 1.) 0 deg C, 4 h, 2.) 25 deg C, 17 h;	51%
	10%
With sodium hydroxide; sodium tetrahydroborate; sulfuric acid 1.) THF, 1 h; 2.) 0 deg C, Et2O, r.t., overnight; 3.) MeOH, 2 h, reflux; Yield given. Multistep reaction;

: 1132-26-9
2-methyl-3-phenylalanine

: 53120-53-9
2-adamantyl chloroformate

: 150871-35-5
N-<(2-adamantyloxy)carbonyl>-DL-α-methyl-3-phenylalanine

Conditions

Conditions	Yield
	38%

: 64-17-5
ethanol

: 1132-26-9
2-methyl-3-phenylalanine

: 46438-07-7
α-methyl-α-carbethoxy-β-phenethylamine

Conditions

Conditions	Yield
With thionyl chloride

: 67-56-1
methanol

: 1132-26-9
2-methyl-3-phenylalanine

: 64665-60-7
DL-α-methylphenylalanine methyl ester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride for 20h; Heating;

: 70110-24-6
(S)-2-chloropropionyl chloride

: 1132-26-9
2-methyl-3-phenylalanine

: 113509-63-0
2-((S)-2-Chloro-propionylamino)-2-methyl-3-phenyl-propionic acid

Conditions

Conditions	Yield
With potassium hydroxide at -10℃; for 0.166667h;

: 1132-26-9
2-methyl-3-phenylalanine

: 1638-63-7
2-acetoxy-2-phenylacetyl chloride

: 2-(2-Hydroxy-2-phenyl-acetylamino)-2-methyl-3-phenyl-propionic acid

Conditions

Conditions	Yield
With sodium hydroxide for 4h; Ambient temperature;

: 1132-26-9
2-methyl-3-phenylalanine

: 22156-89-4
Di<(R)-(-)-sec-butyl> phosphite

: 142421-47-4, 142507-05-9
2-[Bis-((R)-sec-butoxy)-phosphorylamino]-2-methyl-3-phenyl-propionic acid

Conditions

Conditions	Yield
With triethylamine In tetrachloromethane; ethanol; water at 20℃; for 2h;

: 1132-26-9
2-methyl-3-phenylalanine

: 60-15-1, 156-34-3, 51-64-9, 300-62-9
2-amino-1-phenylpropane

Conditions

Conditions	Yield
With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate at 30℃; for 0.5h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;

: 1132-26-9
2-methyl-3-phenylalanine

A: 60-15-1, 156-34-3, 51-64-9, 300-62-9
2-amino-1-phenylpropane

B: 103-79-7
1-phenyl-acetone

Conditions

Conditions	Yield
With pyridixamine phosphate at 30℃; for 20h; pH 9.0. aromatic L-amino acid decarboxylase from Micrococcus percitreus;

: 1132-26-9
2-methyl-3-phenylalanine

: 7148-74-5
2-Bromopropionyl chloride

: 84570-56-9
N-(2-Brompropionyl)-α-methylphenylalanin

Conditions

Conditions	Yield
With sodium hydroxide Yield given;

: 1132-26-9
2-methyl-3-phenylalanine

: 161853-73-2
(2S,4R)-5,5-Dimethyl-4-phenyl-[1,3,2]dioxaphosphinane 2-oxide

: 2-((2R,4R)-5,5-Dimethyl-2-oxo-4-phenyl-2λ5-[1,3,2]dioxaphosphinan-2-ylamino)-2-methyl-3-phenyl-propionic acid

Conditions

Conditions	Yield
With water; triethylamine In tetrachloromethane; ethanol for 2h; Ambient temperature;

: 64-18-6
formic acid

: 1132-26-9
2-methyl-3-phenylalanine

: 23082-21-5
2-Benzyl-2-(formylamino)-propionsaeure

Conditions

Conditions	Yield
With acetic anhydride

: 1132-26-9
2-methyl-3-phenylalanine

: 100-51-6
benzyl alcohol

: 55456-42-3
benzyl 2-amino-2-methyl-3-phenylpropanoate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene

: 1132-26-9
2-methyl-3-phenylalanine

: 137795-35-8
CR 2194

: 2-[(R)-5-(8-Aza-spiro[4.5]dec-8-yl)-4-(3,5-dichloro-benzoylamino)-5-oxo-pentanoylamino]-2-methyl-3-phenyl-propionic acid

Conditions

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1.) THF, -10 deg C, 15 min, 2.) THF, DMF, H2O, a) -10 deg C, 1 h, b) RT, overnight; Multistep reaction;

2-Amino-2-methyl-3-phenylpropionic acid Specification

This chemical is called 2-Amino-2-methyl-3-phenylpropionic acid, and its systematic name is α-methylphenylalanine. The CAS registry number is 1132-26-9. In addition, this chemical is white crystalline powder, and it's soluble in 80% acetic acid, slightly soluble in water. However, it should be stored at the temperature of RT.

Other characteristics of the 2-Amino-2-methyl-3-phenylpropionic acid can be summarised as followings: (1)ACD/LogP: 1.46; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.03; (4)ACD/LogD (pH 7.4): -1.05; (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: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 29.54 Å²; (13)Index of Refraction: 1.566; (14)Molar Refractivity: 50.13 cm³; (15)Molar Volume: 153.6 cm³; (16)Polarizability: 19.87×10^-24cm³; (17)Surface Tension: 50.4 dyne/cm; (18)Density: 1.166 g/cm³; (19)Flash Point: 143 °C; (20)Enthalpy of Vaporization: 58.47 kJ/mol; (21)Boiling Point: 312.8 °C at 760 mmHg; (22)Vapour Pressure: 0.000221 mmHg at 25°C.

Production method of this chemical: The 2-Amino-2-methyl-3-phenylpropionic acid could be obtained by the reactant of (+/-)-N-(tert-butoxycarbonyl)-a-methylphenylalanine. This reaction needs the reagent of aq. HCl, and the solvent of tetrahydrofuran. The yield is 89 %. In addition, this reaction should be taken for 2 hours at the ambient temperature.

Uses of this chemical: The 2-Amino-2-methyl-3-phenylpropionic acid could react with phthalic acid anhydride, and obtain the 2-methyl-3-phenyl-2-phthalimido-propionic acid. The yield is 75 %. In addition, this reaction should be taken for 30 minutes at the temperature of 140 °C.

When you are using this chemical, please be cautious about it as the following: Do not breathe dust. Avoid contacting with skin and eyes.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(O)C(N)(Cc1ccccc1)C
2.InChI: InChI=1/C10H13NO2/c1-10(11,9(12)13)7-8-5-3-2-4-6-8/h2-6H,7,11H2,1H3,(H,12,13)
3.InChIKey: HYOWVAAEQCNGLE-UHFFFAOYAP

Product Name

2-Amino-2-methyl-3-phenylpropionic acid

Synthetic route

2-Amino-2-methyl-3-phenylpropionic acid Specification

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