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673-06-3

Basic Information
CAS No.: 673-06-3
Name: D-Phenylalanine
Molecular Structure:
Molecular Structure of 673-06-3 (D-Phenylalanine)
Formula: C9H11NO2
Molecular Weight: 165.21
Synonyms: Alanine, phenyl-, D-;NCI-C60195;phenylalanine D-form;D-alpha-Amino-beta-phenylpropionic acid;CPD-216;Sabiden;D-.beta.-Phenylalanine;(2R)-2-amino-3-phenylpropanoic acid;D-Phenylalanine(673-06-3);H-D-Phe-OH;D-Phenylalanine, (R)-2-Amino-3-phenyl- propionic acid;D-alpha-aminohydrocinnamic acid;
EINECS: 211-603-5
Density: 1.201 g/cm3
Melting Point: 273-276 °C(lit.)
Boiling Point: 307.5 °C at 760 mmHg
Flash Point: 139.8 °C
Solubility: water: 27 g/L (20 °C)
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 34
Safety: 24/25-45-36/37/39-27-26
Transport Information:
PSA: 63.32000
LogP: 1.34130
Synthetic route
174591-38-9

(3R,6S)-4-N-((S)-1-phenethyl)-3-benzyl-6-methyl-1,4-morpholin-2,5-dione

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogen iodide for 1h; Heating;100%
247259-40-1

N-Cbz-O-benzyl phenylalanine

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With 10% Pd/C; cyclohexa-1,4-diene In methanol at 100℃; for 0.0833333h; Microwave irradiation;100%

C46H34ClN3NiO3

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 40℃; for 6h;100%
With hydrogenchloride In methanol; water at 40℃; for 6h;96%
108321-83-1

phenylalanine amide hydrochloride

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate monohydrate In aq. buffer at 40℃; for 6h; pH=8.0; Enzymatic reaction;99%
118460-00-7

(R)-2-azido-3-phenylpropanoic acid

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In water; acetic acid under 7757.2 Torr; for 1h;97%
16367-71-8

t-butyl (RS)-phenylalaninate

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
95%
136707-23-8

(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogen; palladium dichloride In tetrahydrofuran; ethanol under 2585.7 Torr; for 20h;93%
1202-30-8

D-α-Hydrazino-β-phenyl-propionsaeure

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide89%
129568-84-9

(2R,2'R)-N-(2'-amino-3'-phenylpropanoyl)bornane-10,2-sultam

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran at 20℃;87%
With lithium hydroxide; ion exchange 1.) THF; Yield given. Multistep reaction;
With lithium hydroxide; Amberlite IR-120 1) THF, room temperature, 2) H2O, room temperature, 15 h; Yield given. Multistep reaction;
1004755-20-7

C32H38N2O3

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
Stage #1: C32H38N2O3 With hydrogenchloride; hydrogen; palladium(II) hydroxide/carbon In tetrahydrofuran; water at 50℃; for 48h;
Stage #2: With hydrogenchloride; water for 3.5h; Heating / reflux;
Stage #3: With sodium hydroxide; water pH=2.5; Product distribution / selectivity;
87%
1374035-93-4

(R)-2-(benzhydrylamino)-3-phenylpropanenitrile

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride; water for 3h; Reflux; optical yield given as %ee;87%
5619-07-8

methyl 2-amino-3-phenylpropanoate hydrochloride

A

63-91-2

L-phenylalanine

B

673-06-3

D-(R)-phenylalanine

C

21685-51-8

D-phenylalanine methyl ester

Conditions
ConditionsYield
at 30℃; for 0.333333h; enzyme alcalase from Bacillus licheniforms; pH 8.0; Yields of byproduct given;A n/a
B n/a
C 85%
at 30℃; for 0.333333h; enzyme alcalase from Bacillus licheniforms, pH 8.0; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
85114-36-9

(R)-N-benzyl-phenylalanine

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetic acid for 24h;85%

C15H15N3*C16H13Cl2NO3

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
Stage #1: C15H15N3*C16H13Cl2NO3 With hydrogenchloride In acetonitrile at 20℃; for 1h;
Stage #2: With triethylamine In ethanol; dichloromethane at 20℃; for 1h;
85%
154738-07-5

N-triphenylmethylsulfenyl-D-phenylalanine

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With tri-n-butyl-tin hydride In toluene at 115℃; for 0.0833333h;82%
422570-19-2

(1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
Stage #1: (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one With hydrogenchloride at 87℃; for 2h;
Stage #2: With methyloxirane In ethanol at 20℃; for 0.5h; Further stages.;
82%
170899-07-7

(S,S)-pseudoephedrine D-phenylalaninamide

A

90-82-4

pseudoephedrine

B

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With water for 18h; Heating;A n/a
B 77%
170899-07-7

(S,S)-pseudoephedrine D-phenylalaninamide

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
In water for 18h; Heating; other reagent;77%
With water Heating;70%
63-91-2

L-phenylalanine

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With D-glucose; nicotinamide adenine dinucleotide phosphate; ammonium chloride In aq. buffer at 20℃; for 24h; pH=9; Microbiological reaction; enantioselective reaction;76%
In water at 140℃; Rate constant; pH 8.0;
Stage #1: L-phenylalanine With (S)-2-hydroxy-2'-(3-(N-phenylcarbamoylamino)benzyl)-1,1'-binaphthyl-3-carboxaldehyde; triethylamine In dimethylsulfoxide-d6 at 40℃; for 24h;
Stage #2: With hydrogenchloride; water In chloroform enantioselective reaction;
156-06-9

2-oxo-3-(phenyl)propionic acid

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With D-glucose; nicotinamide adenine dinucleotide phosphate; ammonium chloride In methanol at 20℃; for 24h; pH=9; Solvent; Microbiological reaction; enantioselective reaction;72%
With meso-2,6-D-diaminopimelic acid dehydrogenase mutant BC621; ammonium chloride; NADPH In various solvent(s) for 24h;
With D-glucose; pyridoxal 5'-phosphate; D-amino acid aminotransferase from Bacillus sp mutant T242G In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 12h; pH=8; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;n/a

C34H33N3NiO3

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
Stage #1: C34H33N3NiO3 With hydrogenchloride In methanol at 70℃;
Stage #2: In water
71%
152507-71-6

(R)-(N-allyloxycarbonyl)phenylalanine

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 20℃; for 0.166667h;70%
501-52-0

3-Phenylpropionic acid

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With D-Alanine; meso-diaminopimelate dehydrogenase; pyridoxal 5'-phosphate; alcohol dehydrogenases from Bacillus stearothermophilus; alcohol dehydrogenases from Thermoanaerobacter brockii; NADH In isopropyl alcohol at 35℃; for 9h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;43.4%
155385-83-4

(-)-1-<(1-cyano-2-phenylethyl)amino>-2R-methyl-5R-(1-methylethenyl)cyclohexane-1R,3R-dicarbonitrile

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride at 110℃; for 12h;41%
150-30-1

Phenylalanine

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide; oxygen; 2-amino-2-hydroxymethyl-1,3-propanediol In water at 30℃; for 5h; pH=7.3; Resolution of racemate; Enzymatic reaction; enantioselective reaction;38%
durch partielle Vergaerung mit lebender Hefe bei Gegenwart von Zucker;

3-phenyl-(2R)-[(1'R)-phenylethylamino]propionic acid

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogen; palladium on carbon In water at 50℃; for 25h; Product distribution / selectivity;31%
10172-89-1

(R)-N-acetylphenylalanin

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
In water at 37℃; for 0.166667h; Rate constant; D-aminocyclase from Alcaligenes denitrificans DA181, pH 7.8, bovine serum albumin;
With hydrogenchloride
With hydrogenchloride
With hydrogen bromide
137503-97-0

N-Chloroacetyl-D-phenylalanine

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride
2566-22-5, 2901-76-0, 37002-52-1

DL-N-benzoylphenylalanine

A

2566-22-5

N-benzoyl-L-phenylalanine

B

673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With D-amidase-substance from pseudomonas-cultures at 37℃;
85-44-9

phthalic anhydride

673-06-3

D-(R)-phenylalanine

3588-64-5, 5123-55-7, 32150-90-6, 38229-08-2

(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid

Conditions
ConditionsYield
for 0.05h; microwave irradiation;100%
With pyridine for 12h; Heating;93%
With triethylamine In toluene Heating;88%
67-56-1

methanol

673-06-3

D-(R)-phenylalanine

13033-84-6

D-phenylalanine methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride100%
With chloro-trimethyl-silane100%
With thionyl chloride at 0 - 75℃; for 2h;100%
64-17-5

ethanol

673-06-3

D-(R)-phenylalanine

63060-94-6

D-phenylalanine ethyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride for 4h; Reflux;100%
With hydrogenchloride In toluene
With hydrogenchloride for 2h; Heating;
With thionyl chloride at 80℃; Cooling with ice;
With thionyl chloride at 20℃;
67-56-1

methanol

673-06-3

D-(R)-phenylalanine

21685-51-8

D-phenylalanine methyl ester

Conditions
ConditionsYield
Stage #1: methanol With acetyl chloride at 0℃; for 0.5h;
Stage #2: D-(R)-phenylalanine for 3h; Reflux;
100%
With hydrogenchloride for 0.166667h; Heating;88%
With chlorosulfonic acid at 20℃; for 2h;76%
673-06-3

D-(R)-phenylalanine

13033-84-6

D-phenylalanine methyl ester hydrochloride

Conditions
ConditionsYield
With acetyl chloride at 70℃; Cooling;100%
With thionyl chloride In methanol31.2 g (97%)
673-06-3

D-(R)-phenylalanine

64-19-7

acetic acid

146235-25-8

(2R)-2-acetoxy-3-phenylpropanoic acid

Conditions
ConditionsYield
With sodium nitrite at 20℃; for 1.5h; Inert atmosphere;100%
With sodium nitrite In water
673-06-3

D-(R)-phenylalanine

75-36-5

acetyl chloride

13033-84-6

D-phenylalanine methyl ester hydrochloride

Conditions
ConditionsYield
In methanol at 0 - 20℃; for 16h; Inert atmosphere;100%
Stage #1: acetyl chloride In methanol Cooling with ice;
Stage #2: D-(R)-phenylalanine In methanol at 70℃; for 24h; Reflux;
673-06-3

D-(R)-phenylalanine

5267-64-1

(R)-2-amino-3-phenylpropanol

Conditions
ConditionsYield
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.25h; Reduction;99%
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; Reflux;99%
With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran at 20℃;98%
673-06-3

D-(R)-phenylalanine

501-53-1

benzyl chloroformate

2448-45-5

Cbz-D-Phe

Conditions
ConditionsYield
With sodium carbonate99%
With sodium hydrogencarbonate In water at 20℃; for 12h;99%
With sodium hydrogencarbonate; sodium hydroxide In water at 0 - 20℃;74%
673-06-3

D-(R)-phenylalanine

2937-50-0

Allyl chloroformate

152507-71-6

(R)-(N-allyloxycarbonyl)phenylalanine

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 2h; Inert atmosphere;99%
With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane80%
With sodium carbonate In water; acetonitrile at 0 - 20℃;74%
673-06-3

D-(R)-phenylalanine

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite at 0 - 20℃; for 18h;98.5%
With sulfuric acid; sodium nitrite for 36h;98%
Stage #1: D-(R)-phenylalanine With sulfuric acid; sodium nitrite In water at 0 - 10℃; for 3h;
Stage #2: With water at 10 - 20℃;
87%
673-06-3

D-(R)-phenylalanine

128-69-8

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

N,N′-bis-(D)-phenylalanyl perylenebisimide

Conditions
ConditionsYield
Stage #1: D-(R)-phenylalanine; perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride With 1H-imidazole at 120℃; for 0.5h;
Stage #2: With hydrogenchloride In water at 85℃; pH=3 - 4;
98%
With 1H-imidazole at 140℃; for 1h;97%
383-63-1

ethyl trifluoroacetate,

673-06-3

D-(R)-phenylalanine

7656-14-6

(R)-N-(trifluoroacetyl)phenylalanine

Conditions
ConditionsYield
With triethylamine In methanol at 20℃;98%
24424-99-5

di-tert-butyl dicarbonate

673-06-3

D-(R)-phenylalanine

18942-49-9

Boc-D-Phe-OH

Conditions
ConditionsYield
Stage #1: D-(R)-phenylalanine With sodium hydroxide In tetrahydrofuran; water for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 20℃; for 24h; pH=Ca. 10.5; Inert atmosphere; Cooling with ice;
97.2%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 6.5h;93%
With amberlyst-15 In ethanol at 20℃; for 20h; chemoselective reaction;93%
673-06-3

D-(R)-phenylalanine

2719-27-9

cyclohexanylcarbonyl chloride

85856-40-2

(R)-2-(cyclohexanecarboxamido)-3-phenylpropanoic acid

Conditions
ConditionsYield
With potassium phosphate In tetrahydrofuran for 24h; Inert atmosphere;97%
With sodium hydroxide In acetone65%
108-31-6

maleic anhydride

673-06-3

D-(R)-phenylalanine

889096-99-5

N-maleyl-D-phenylalanine

Conditions
ConditionsYield
In acetic acid at 20℃;96%

(S)-1-benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one

673-06-3

D-(R)-phenylalanine

(R)-3-phenyl-2-((S)-3,3,3-trifluoro-2-methoxy-2-phenylpropionylamino)propionic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 12h;96%
942130-82-7

(R)-1-benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one

673-06-3

D-(R)-phenylalanine

126191-13-7

(R)-3-phenyl-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionylamino)propionic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 12h;96%
673-06-3

D-(R)-phenylalanine

3674-06-4

Boc-Phe-ONSu

93397-22-9

Boc-L-Phe-D-Phe-OH

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water; acetone at 20℃; for 5h;96%
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

673-06-3

D-(R)-phenylalanine

101-83-7

N-cyclohexyl-cyclohexanamine

Z-D-phenylalanine DCHA salt

Conditions
ConditionsYield
Stage #1: N-(Benzyloxycarbonyloxy)succinimide; D-(R)-phenylalanine With sodium hydrogencarbonate; sodium carbonate In water; acetone at 20℃; for 3.5h;
Stage #2: N-cyclohexyl-cyclohexanamine In water; ethyl acetate; acetone at 20℃;
96%
673-06-3

D-(R)-phenylalanine

321-23-3

4-bromo-2-fluoronitrobenzene

(5-bromo-2-nitrophenyl)-d-phenylalanine

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 100℃; for 10h;96%
673-06-3

D-(R)-phenylalanine

98-59-9

p-toluenesulfonyl chloride

86117-53-5

Nα-(4-methylbenzenesulfonyl)-D-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide In water at 60℃; for 6h;95%
With sodium hydroxide In diethyl ether at 20℃; for 6h;81%
With sodium hydroxide In diethyl ether at 20℃;79%
24165-03-5

tritylsulfenyl chloride

673-06-3

D-(R)-phenylalanine

154738-07-5

N-triphenylmethylsulfenyl-D-phenylalanine

Conditions
ConditionsYield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;95%
673-06-3

D-(R)-phenylalanine

82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

86123-10-6

Fmoc-D-Phe-OH

Conditions
ConditionsYield
With sodium hydrogencarbonate In acetone Ambient temperature;95%
With sodium carbonate In aq. buffer at 37℃; for 10h; pH=8.0 - 9.0;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

D-Phenylalanine is an essential amino acid. With cas registry number of 673-06-3, it also has other registry number which is 10549-11-8. Its EINECS registry number is 211-603-5. This chemical is also known as Phenylalanine D-form with appearance of white crystalline powder. It is stable, but incompatible with strong oxidizing agents, acids, bases. It belongs to the categories in Benzene derivatives; Aromatic Propionic Acids; Phenylalanine [Phe, F]; Amino Acids and Derivatives; alpha-Amino Acids; Amino Acids; Biochemistry; Amino Acids; chemicals; organic acids; pharmaceutical intermediate; phenlalnine.

Physical properties about this chemical are: (1)ACD/LogP: 1.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.39; (4)ACD/LogD (pH 7.4): -1.39; (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)Index of Refraction: 1.576; (13)Molar Refractivity: 45.49 cm3; (14)Molar Volume: 137.4 cm3; (15)Surface Tension: 53.5 dyne/cm; (16)Density: 1.201 g/cm3; (17)Flash Point: 139.8 °C; (18)Enthalpy of Vaporization: 57.87 kJ/mol; (19)Boiling Point: 307.5 °C at 760 mmHg; (20)Vapour Pressure: 0.000313 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
Mildly toxic by intraperitoneal route. Human systemic effects by ingestion: nausea, hypermotility, diarrhea. When heated to decomposition, it emits toxic fumes of NOx. It can causes burns. Wear suitable protective clothing, gloves and eye/face protection during using it. Avoid contact with skin and eyes. Take off immediately all contaminated clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Or if you feel unwell, seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@H](N)Cc1ccccc1;
(2)InChI: InChI=1/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m1/s1;
(3)InChIKey: COLNVLDHVKWLRT-MRVPVSSYBE

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 500mg/kg/5W-I (500mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of the American College of Toxicology. Vol. 1(3), Pg. 124, 1982.
rat LD50 intraperitoneal 5452mg/kg (5452mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives of Biochemistry and Biophysics. Vol. 64, Pg. 319, 1956.