Conditions | Yield |
---|---|
With hydrogenchloride; water at 90℃; for 0.166667h; Microwave irradiation; | 98% |
With water; hydrogen cation Heating; | 82% |
With hydrogen bromide anschliessend Erwaermen mit wss. Schwefelsaeure; | |
With sodium hydroxide anschliessend Erwaermen mit wss. Schwefelsaeure; | |
With hydrogenchloride In water at 110℃; Microwave irradiation; |
Conditions | Yield |
---|---|
salicylaldehyde In acetic acid at 100℃; for 1h; | 94% |
With barium dihydroxide; water at 155 - 160℃; | |
With hydrogenchloride; ethanethiol at 110℃; Rate constant; various times; |
Conditions | Yield |
---|---|
With potassium hydroxide; C-7 In dichloromethane at 20℃; | 90% |
2-(Benzhydryl-amino)-3-phenyl-propionic acid tert-butyl ester
Phenylalanine
Conditions | Yield |
---|---|
palladium on activated charcoal In acetic acid Heating; | 89% |
Multi-step reaction with 2 steps 1: 60 percent / formic acid / 10percent Pd/C / methanol 2: trifluoroacetic acid View Scheme |
Phenylalanine
Conditions | Yield |
---|---|
With water; hydrogen cation Heating; | 88% |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether Yields of byproduct given; | A n/a B 69% |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether | A n/a B 63% |
(±)-N-Boc-2-amino-2-benzylacetonitrile
Phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 6h; Heating; | 50% |
N-(diphenylmethylene)glycine tert-butyl ester
benzyl bromide
Phenylalanine
Conditions | Yield |
---|---|
Stage #1: N-(diphenylmethylene)glycine tert-butyl ester; benzyl bromide With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl In dichloromethane at 20℃; for 1h; Stage #2: With hydrogenchloride In methanol; water Heating; | 50% |
Conditions | Yield |
---|---|
With ammonium bicarbonate Ambient temperature; detonation; also with (NH4)2CO3; | 45% |
With ammonium bicarbonate Ambient temperature; detonation; also with (NH4)2CO3; | 45% |
With ammonium hydroxide; Anabaena variabilis phenylalanine ammonia lyase at 30℃; pH=9.5; Kinetics; Enzymatic reaction; | |
With ammonium hydroxide; phenylalanine ammonia-lyase from Anabaena variabilis N347A mutant In aq. buffer at 35℃; for 12h; | |
With phenylalanine ammonia lyase from Anabaena variabilis; ammonium carbamate at 30℃; for 22h; pH=9.9; Catalytic behavior; pH-value; Enzymatic reaction; | 99 %Chromat. |
Conditions | Yield |
---|---|
With hydrogenchloride; lithium hydroxide; n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water | 45% |
Conditions | Yield |
---|---|
Stage #1: 2-oxo-3-(phenyl)propionic acid With ammonia; hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis[[bis(3-sulfophenyl)phosphino]methyl]-4,4',7,7'-tetrasulfo-1,1'-binaphthyl octasodium salt In ethanol; water at 60℃; under 31503.2 Torr; for 24h; Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity; | A 15% B 43% |
4-benzyl-2-phenyl-2-oxazolin-5-one
A
Phenylalanine
B
benzoic acid
Conditions | Yield |
---|---|
With potassium In tetrahydrofuran for 4h; | A 37% B 33% |
Conditions | Yield |
---|---|
With ammonium hydroxide; hydrogen at 219.84℃; under 7500.75 Torr; for 2h; Autoclave; | 30% |
With ammonium hydroxide; hydrogen at 180℃; under 7500.75 Torr; for 2h; Autoclave; | 51.5 %Spectr. |
Phenylalanine
Conditions | Yield |
---|---|
at 19.9℃; under 37503000 Torr; Product distribution; under shear deformation (360 deg); | 0.95% |
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With hydrogen iodide | |
With phosphorus; iodine | |
With barium dihydroxide; water |
2-bromo-3-phenylpropanoic acid
Phenylalanine
Conditions | Yield |
---|---|
With ammonia | |
With ammonia; water | |
With ammonia; water at 100℃; im Druckrohr; | |
With ammonia |
Conditions | Yield |
---|---|
With acetic anhydride at 20℃; for 1h; | 100% |
With acetic anhydride at 20℃; for 19h; | 87% |
In N,N-dimethyl-formamide for 0.166667h; Heating; | 81% |
Phenylalanine
rac-phenylalaninol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; iodine | 100% |
With zirconium(IV) borohydride In tetrahydrofuran at 25℃; Reduction; | 90% |
With sodium tetrahydroborate; iodine In tetrahydrofuran for 15h; Heating; | 60% |
Conditions | Yield |
---|---|
Stage #1: ethanol; Phenylalanine With thionyl chloride Reflux; Stage #2: With sodium hydrogencarbonate | 100% |
With toluene-4-sulfonic acid In toluene at 80℃; for 16h; | 83% |
With hydrogenchloride |
Conditions | Yield |
---|---|
With thionyl chloride at 5 - 50℃; for 25h; | 100% |
With thionyl chloride at 50℃; for 25h; Cooling with ice; | 100% |
With thionyl chloride at 0 - 20℃; for 20h; | 99% |
Phenylalanine
di-tert-butyl dicarbonate
2-(tert-butoxycarbonylamino)-3-phenylpropionic acid
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; | 100% |
With tetramethyl ammoniumhydroxide | 91% |
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 5h; | 81% |
Phenylalanine
bis(2,4-dinitrophenyl) carbonate
4-benzyl-oxazolidine-2,5-dione
Conditions | Yield |
---|---|
In tetrahydrofuran at 60℃; for 91h; Product distribution / selectivity; | 100% |
Phenylalanine
2-chloro-4-fluorobenzonitrile
N-(3-chloro-4-cyanophenyl)phenylalanine
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 90℃; | 100% |
Conditions | Yield |
---|---|
at 160℃; for 0.05h; Product distribution / selectivity; Microwave irradiation (300 W); | 100% |
Phenylalanine
benzoyl chloride
DL-N-benzoylphenylalanine
Conditions | Yield |
---|---|
With sodium hydroxide; N-ethyl-N,N-diisopropylamine In water 1.) 0 deg C, 30 min; 2.) up to RT, 30 min; | 99% |
With sodium hydroxide In water; acetonitrile at 0℃; for 2h; | 88% |
With sodium hydroxide In water for 0.5h; | 79% |
Conditions | Yield |
---|---|
With thionyl chloride at -20℃; for 3.66667h; Reflux; | 99% |
With thionyl chloride for 3h; Heating; | 98% |
With sulfuric acid Reflux; | 92% |
Phenylalanine
1-benzylisatin
(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester
Conditions | Yield |
---|---|
In methanol at 30℃; for 4h; Solvent; Time; Concentration; diastereoselective reaction; | 99% |
1-benzyl-5-chloroisatin
Phenylalanine
(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester
Conditions | Yield |
---|---|
In methanol at 30℃; for 24h; diastereoselective reaction; | 99% |
Phenylalanine
1-benzyl-7-fluoroindoline-2,3-dione
(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester
Conditions | Yield |
---|---|
In methanol at 30℃; for 24h; diastereoselective reaction; | 99% |
Phenylalanine
2,2-dimethoxy-propane
methyl 2-amino-3-phenylpropanoate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 18h; | 99% |
formaldehyd
Phenylalanine
(R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water for 4.5h; Heating / reflux; | 98.9% |
With hydrogenchloride | 69% |
With hydrogenchloride In water for 6h; Reflux; | 33% |
Conditions | Yield |
---|---|
at 170℃; for 2h; | 98% |
In acetonitrile at 145℃; Sealed tube; | 96% |
at 170℃; for 2.5h; | 93% |
Conditions | Yield |
---|---|
In acetic acid at 20℃; | 98% |
In acetic acid for 0.166667h; Heating; | 81% |
Conditions | Yield |
---|---|
With sodium hydroxide In water; butan-1-ol Ambient temperature; | 98% |
m-carborane-1,7-dicarboxylic acid dichloride
Phenylalanine
C2B10H10(CONHCH(CH2C6H5)COOH)2
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide In water byproducts: NaCl; stirring (20-30°C, 2-3 h), aq. HCl addn.; washing (water), drying (vac.); elem. anal.; | 98% |
(S)-benzyl 4-(1-benzo[d][1m2m3]triazol-1-yl)-3-(benzyloxycarbonylamino)-4-oxobutanoate
Phenylalanine
2-((S)-4-(benzyloxy)-2-(benzyloxycarbonylamino)-4-oxobutanamido)-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With triethylamine In water; acetonitrile at 20℃; for 2h; | 98% |
formaldehyd
Phenylalanine
1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ; hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water for 4.5h; Reflux; | 98% |
Phenylalanine
((S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide)
nickel(II) acetate tetrahydrate
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 60℃; for 3h; Temperature; diastereoselective reaction; | 98% |
Phenylalanine
nickel diacetate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60℃; for 72h; | 98% |
With potassium carbonate In methanol at 60℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; diastereoselective reaction; | 98% |
Phenylalanine
N-benzyl-5-fluoroisatin
(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester
Conditions | Yield |
---|---|
In methanol at 30℃; for 24h; diastereoselective reaction; | 98% |
benzoic acid N-hydroxysuccinimide ester
Phenylalanine
DL-N-benzoylphenylalanine
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane; water at 20℃; for 2h; | 97% |
Phenylalanine
4-chloro-benzoyl chloride
dimethyl acetylenedicarboxylate
C21H18ClNO4
Conditions | Yield |
---|---|
With [bmIm]OH In water Heating; | 97% |
Phenylalanine
indole-2,3-dione
(3E)-3-benzylidene-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
In methanol at 60℃; for 3h; diastereoselective reaction; | 97% |
Conditions | Yield |
---|---|
In toluene Reflux; | 97% |
Stage #1: 1-dodecyl alcohol; Phenylalanine In neat (no solvent) at 120℃; for 0.0833333h; Green chemistry; Stage #2: toluene-4-sulfonic acid In neat (no solvent) at 130 - 135℃; Green chemistry; | 82% |
N-benzyloxycarbonyl-3-aminopropionic acid succinimide ester
Phenylalanine
(±)-Cbz-βAla-Phe-OH
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water; acetone at 20℃; for 5h; | 97% |
The IUPAC name of DL-Phenylalanine is 2-amino-3-phenylpropanoic acid. With the CAS registry number 150-30-1, it is also named as Phenylalanine DL-form. The product's categories are Food & Feed Additives; Amino Acids Series; Amino Acids; Chiral; Organic Acids; Phenylalanine [Phe, F]; alpha-Amino Acids; Biochemistry; Amino Acids; Phenlalnine; Amino Acid; Food Additive; Pharmaceutical Intermediate. Besides, it is white crystalline powder, which should be sealed in a cool, dry place. It is stable, and incompatible with strong oxidizing agents. In addition, its molecular formula is C9H11NO2 and molecular weight is 165.19.
The other characteristics of this product can be summarized as: (1)EINECS: 205-756-7; (2)ACD/LogP: 0.24; (3)# of Rule of 5 Violations: 0; (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: 1.576; (12)Molar Refractivity: 45.493 cm3; (13)Molar Volume: 137.437 cm3; (14)Surface Tension: 53.597 dyne/cm; (15)Density: 1.202 g/cm3; (16)Flash Point: 139.771 °C; (17)Melting point: 266-267 °C; (18)Water solubility: 14.11 g/L (25 °C); (19)Enthalpy of Vaporization: 57.873 kJ/mol; (20)Boiling Point: 307.5 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.
Preparation of DL-Phenylalanine: this chemical can be prepared by the reaction of Acetyl-L-phenylalanine with HCl. Furthermore, it is produced by acetylamino-benzyl-malonic acid diethyl ester.
This reaction needs H+, water by heating. The yield is 82 %.
Uses of DL-Phenylalanine: this chemical is used as a dietary supplement and as a nutritional supplement for its supposed analgesic and antidepressant activities. Additionally, it can react with acetic acid anhydride to get N-(1-benzyl-2-oxo-propyl)-acetamide.
This reaction needs pyridine by heating. The yield is 76 %.
When you are using this chemical, please be cautious about it as the following: it may cause burns. It is also irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin and eyes. Moreover, please take off immediately all contaminated clothing. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)N
(2)InChI: InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
(3)InChIKey: COLNVLDHVKWLRT-UHFFFAOYSA-N
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