Product Name

  • Name

    D-4-Chlorophenylalanine

  • EINECS
  • CAS No. 14091-08-8
  • Article Data20
  • CAS DataBase
  • Density 1.336 g/cm3
  • Solubility Slightly soluble in water.
  • Melting Point 260℃
  • Formula C9H10ClNO2
  • Boiling Point 339.5 °C at 760 mmHg
  • Molecular Weight 199.637
  • Flash Point 159.1 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance
  • Safety 36/37-45
  • Risk Codes 25-43
  • Molecular Structure Molecular Structure of 14091-08-8 (D-4-Chlorophenylalanine)
  • Hazard Symbols ToxicT,IrritantXi
  • Synonyms Alanine,3-(p-chlorophenyl)-, D- (8CI);4-Chloro-D-phenylalanine;D-p-Chlorophenylalanine;p-Chloro-D-phenylalanine;p-Cl-D-Phe-OH;
  • PSA 63.32000
  • LogP 1.99470

Synthetic route

C46H33Cl2N3NiO3

C46H33Cl2N3NiO3

A

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

(S)-N-(2-benzoyl-4-chlorophenyl)-2-[3,5-dihydro-4H-dinaphth[2,1-c:1′,2′-e]azepin-4-yl]acetamide

(S)-N-(2-benzoyl-4-chlorophenyl)-2-[3,5-dihydro-4H-dinaphth[2,1-c:1′,2′-e]azepin-4-yl]acetamide

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 40℃; for 6h;A 95%
B 97%
With hydrogenchloride In methanol; water at 40℃; for 6h;A n/a
B 96%
C46H33Cl2N3NiO3

C46H33Cl2N3NiO3

A

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

B

C37H27ClN2O2

C37H27ClN2O2

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 40℃; for 6h;A 96%
B 96%
DL-Phe(4Cl)
7424-00-2

DL-Phe(4Cl)

A

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

B

β-(4-chlorophenyl)pyruvic acid
3617-01-4

β-(4-chlorophenyl)pyruvic acid

Conditions
ConditionsYield
With diaphorase; 2,6-Dichlorophenolindophenol; potassium chloride; oxygen; nicotiamide adenine dinucleotide at 15 - 20℃; pH=9.5; aq. buffer; Enzymatic reaction;A 78%
B n/a
DL-Phe(4Cl)
7424-00-2

DL-Phe(4Cl)

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
With sodium hydroxide; oxygen; 2-amino-2-hydroxymethyl-1,3-propanediol In water at 30℃; for 3h; pH=7.3; Resolution of racemate; Enzymatic reaction; enantioselective reaction;44%
With (S)-2-hydroxy-2'-(3-(N-phenylcarbamoylamino)benzyl)-1,1'-binaphthyl-3-carboxaldehyde In dimethyl sulfoxide Resolution of racemate; stereoselective reaction;n/a
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
tert-butyl (R)-3-(4-chlorophenyl)-2-(diphenylmethanediylamino)propanoate
119244-26-7

tert-butyl (R)-3-(4-chlorophenyl)-2-(diphenylmethanediylamino)propanoate

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
With hydrogenchloride Yield given;
β-(4-chlorophenyl)pyruvic acid
3617-01-4

β-(4-chlorophenyl)pyruvic acid

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
With meso-2,6-D-diaminopimelic acid dehydrogenase mutant BC621; ammonium chloride; NADPH In various solvent(s) for 24h;
(±)-ethyl 2-amino-3-(4-chlorophenyl)propanoate
29622-19-3

(±)-ethyl 2-amino-3-(4-chlorophenyl)propanoate

A

L-4-chlorophenylalanine ethyl ester

L-4-chlorophenylalanine ethyl ester

B

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

C

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

D

D-4-chlorophenylalanine ethyl ester
166449-97-4

D-4-chlorophenylalanine ethyl ester

Conditions
ConditionsYield
With Bacillus licheniformis; sodium hydrogencarbonate; 1-ethyl-3-methylimidazolium acetate In water; water-d2 at 30℃; for 1h;
...Expand
4-chlorobenzyl bromide
622-95-7

4-chlorobenzyl bromide

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50percent aq. NaOH / cinchonidine catalyst / CH2Cl2 / 12 h / 25 °C
2: 6N HCl
View Scheme
DL-Phe(4Cl)
7424-00-2

DL-Phe(4Cl)

Benzeneacetamide
103-81-1

Benzeneacetamide

A

phenylacetic acid
103-82-2

phenylacetic acid

B

N-phenylacetyl-4-chloro-L-phenylalanine
482281-07-2

N-phenylacetyl-4-chloro-L-phenylalanine

C

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
Stage #1: DL-Phe(4Cl); Benzeneacetamide With recombinant Alcaligenes faecalis penicillin G acylase immobilized on oxirane acrylic carrier; potassium hydroxide In water at 35℃; for 3.66667h; pH=10; Enzymatic reaction;
Stage #2: With hydrogenchloride In water pH=1; optical yield given as %ee; enantioselective reaction;
...Expand
4-chloro-(RS)-phenylalaninamide hydrochloride
1428149-31-8

4-chloro-(RS)-phenylalaninamide hydrochloride

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate monohydrate In aq. buffer at 40℃; for 24h; pH=8.0; Enzymatic reaction; Overall yield = > 99 %;A n/a
B n/a
With pyridoxal 5'-phosphate monohydrate; cobalt(II) chloride In aq. buffer at 40℃; for 36h; pH=7.0; Enzymatic reaction; Overall yield = > 99 %;A n/a
B n/a
DL-Phe(4Cl)
7424-00-2

DL-Phe(4Cl)

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 0 °C
2: ammonia / methanol / 0 °C
3: pyridoxal 5'-phosphate monohydrate; cobalt(II) chloride / aq. buffer / 36 h / 40 °C / pH 7.0 / Enzymatic reaction
View Scheme
With (S)-2-hydroxy-2'-(3-(N-phenylcarbamoylamino)benzyl)-1,1'-binaphthyl-3-carboxaldehyde In dimethyl sulfoxide Resolution of racemate; stereoselective reaction;A n/a
B n/a
With (R)-2-hydroxy-2'-(3-phenylurylbenzyl)-1,1'-binaphthyl-3-carboxaldehyde In dimethyl sulfoxide Resolution of racemate; stereoselective reaction;A n/a
B n/a
With phenylalanine ammonia-lyase from Pseudozyma antarctica yeast In aq. buffer at 30℃; for 17h; pH=8.5; Resolution of racemate; stereoselective reaction;A n/a
B n/a
2-amino-3-(4-chlorophenyl)propionic acid methyl ester hydrochloride
14173-40-1, 23434-91-5, 33965-47-8, 60594-65-2

2-amino-3-(4-chlorophenyl)propionic acid methyl ester hydrochloride

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonia / methanol / 0 °C
2: pyridoxal 5'-phosphate monohydrate; cobalt(II) chloride / aq. buffer / 36 h / 40 °C / pH 7.0 / Enzymatic reaction
View Scheme
N-Boc-D-(4-Cl)Phe-OH
57292-44-1

N-Boc-D-(4-Cl)Phe-OH

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 0.5h;
DL-Phe(4Cl)
7424-00-2

DL-Phe(4Cl)

A

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

B

(S)-β-amino-β-(4-chlorophenyl)propionic acid
131690-60-3

(S)-β-amino-β-(4-chlorophenyl)propionic acid

Conditions
ConditionsYield
With phenylalanine 2,3-aminomutase from Pantoea agglomerans; ammonium carbonate at 20℃; for 20h; pH=8; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
β-(4-chlorophenyl)pyruvic acid
3617-01-4

β-(4-chlorophenyl)pyruvic acid

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; ethylenediaminetetraacetic acid; sodium diphenylglycine In aq. buffer at 50℃; pH=8; Overall yield = 24 %; enantioselective reaction;A n/a
B n/a
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ethanolamine
1.2: Alkaline conditions
2.1: sodium diphenylglycine; pyridoxal 5'-phosphate; ethylenediaminetetraacetic acid / aq. buffer / 50 °C / pH 8
View Scheme
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
With L-amino acid deaminase from Proteus mirabilis; Burkholderia stabilis formate dehydrogenase; meso-diaminopimelate dehydrogenase from Symbiobacterium thermophilum mutant H227V; sodium formate; ammonium chloride; NADPH In aq. phosphate buffer at 45℃; pH=9; Enzymatic reaction;
DL-Phe(4Cl)
7424-00-2

DL-Phe(4Cl)

A

3-(4-chlorophenyl)prop-2-enoic acid
1615-02-7

3-(4-chlorophenyl)prop-2-enoic acid

B

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

Conditions
ConditionsYield
With phenylalanine ammonia-lyase from Pseudozyma antarctica yeast In aq. buffer at 30℃; for 168h; pH=8.5; Reagent/catalyst; Time; Resolution of racemate; stereoselective reaction;A n/a
B n/a
para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

(R)-2-amino-3-(4-chlorophenyl)propan-1-ol
201863-99-2

(R)-2-amino-3-(4-chlorophenyl)propan-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; Inert atmosphere;99%
para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

N-Boc-D-(4-Cl)Phe-OH
57292-44-1

N-Boc-D-(4-Cl)Phe-OH

Conditions
ConditionsYield
With triethylamine In water; acetone at 25℃; for 14h;90%
para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

N-Boc-D-(4-Cl)Phe-OH
57292-44-1

N-Boc-D-(4-Cl)Phe-OH

Conditions
ConditionsYield
With triethylamine In water; acetone at 20℃; for 44h;87.3%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

N-Boc-D-(4-Cl)Phe-OH
57292-44-1

N-Boc-D-(4-Cl)Phe-OH

Conditions
ConditionsYield
With triethylamine In water; acetone at 20℃; for 44h;87.3%
C31H45N5O5

C31H45N5O5

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

C40H53ClN6O6

C40H53ClN6O6

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide) at 20℃;
N-(spiro[5.5]undecan-3-yl)ethylenediamine

N-(spiro[5.5]undecan-3-yl)ethylenediamine

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

trifluoroacetic acid
76-05-1

trifluoroacetic acid

(2S)-2-amino-N-(2-aminoethyl)-3-(4-chlorophenyl)-N-(spiro[5.5]undecan-3-yl)propanamide trifluoroacetic acid salt
949590-07-2

(2S)-2-amino-N-(2-aminoethyl)-3-(4-chlorophenyl)-N-(spiro[5.5]undecan-3-yl)propanamide trifluoroacetic acid salt

Conditions
ConditionsYield
Stage #1: N-(spiro[5.5]undecan-3-yl)ethylenediamine In N,N-dimethyl-formamide at 20℃; for 24h;
Stage #2: para-Chloro-D-phenylalanine With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h;
Stage #3: trifluoroacetic acid With chlorotriisopropylsilane; ethane-1,2-dithiol In water at 20℃; for 1h; Further stages.;
...Expand
2-[(2,1,3-benzothiadiazol-4-ylsulfonyl)amino]-4-chlorobenzoic acid
791098-17-4

2-[(2,1,3-benzothiadiazol-4-ylsulfonyl)amino]-4-chlorobenzoic acid

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

C22H16Cl2N4O5S2
1202359-16-7

C22H16Cl2N4O5S2

Conditions
ConditionsYield
With pyridine; 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate In N,N-dimethyl-formamide for 1h;
4-chloroisatoic anhydride
40928-13-0

4-chloroisatoic anhydride

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

C16H14Cl2N2O3

C16H14Cl2N2O3

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 50℃; for 12h;
4-chloro-2-nitro-benzoic acid
6280-88-2

4-chloro-2-nitro-benzoic acid

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

C16H12Cl2N2O5

C16H12Cl2N2O5

Conditions
ConditionsYield
With pyridine; 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate In N,N-dimethyl-formamide for 1h;
para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

4-chloro-2-nitro-benzoyl chloride
41995-04-4

4-chloro-2-nitro-benzoyl chloride

C16H12Cl2N2O5

C16H12Cl2N2O5

Conditions
ConditionsYield
In N,N-dimethyl-formamide
para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

A

N-(N-benzoyl-L-tryptophanyl)-para-chloro-D-phenylalanine methyl ester
1435265-79-4

N-(N-benzoyl-L-tryptophanyl)-para-chloro-D-phenylalanine methyl ester

B

N-(N-benzoyl-D-tryptophanyl)-para-chloro-D-phenylalanine methyl ester

N-(N-benzoyl-D-tryptophanyl)-para-chloro-D-phenylalanine methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / dichloromethane; trifluoroacetic acid / 2 h / Reflux
2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C
View Scheme
methanol
67-56-1

methanol

para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

D-p-chlorophenylalanine methyl ester
134166-72-6

D-p-chlorophenylalanine methyl ester

Conditions
ConditionsYield
With sulfuric acid In dichloromethane; trifluoroacetic acid for 2h; Reflux;
para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

2,2'-(propane-2,2-diyl)bis[(R)-4-(4-chlorobenzyl)-4,5-dihydrooxazole]
1487438-24-3

2,2'-(propane-2,2-diyl)bis[(R)-4-(4-chlorobenzyl)-4,5-dihydrooxazole]

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux; Inert atmosphere
2: zinc trifluoromethanesulfonate / toluene / 48 h / 20 °C / Inert atmosphere; Reflux
View Scheme

D-4-Chlorophenylalanine Specification

The IUPAC name of D-4-Chlorophenylalanine is (2R)-2-amino-3-(4-chlorophenyl)propanoic acid. With the CAS registry number 14091-08-8, it is also named as 4-Chloro-3-phenyl-D-alanine. The product's categories are Amino Acids; Phenylalanine Analogs and other Aromatic Alpha Amino Acids; Phenylalanine [Phe, F]; Amino Hydrochloride; A-Amino. Besides, it is used as a pharmaceutical intermediate, which should be stored at -20 °C. In addition, its molecular formula is C9H10ClNO2 and molecular weight is 199.64.

The other characteristics of D-4-Chlorophenylalanine can be summarized as: (1)ACD/LogP: 1.71; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 29.54 Å2; (11)Index of Refraction: 1.589; (12)Molar Refractivity: 50.38 cm3; (13)Molar Volume: 149.3 cm3; (14)Polarizability: 19.97×10-24cm3; (15)Surface Tension: 55.4 dyne/cm; (16)Density: 1.336 g/cm3; (17)Flash Point: 159.1 °C; (18)Enthalpy of Vaporization: 61.53 kJ/mol; (19)Boiling Point: 339.5 °C at 760 mmHg; (20)Vapour Pressure: 3.54E-05 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following: it is toxic if swallowed. And it also may cause sensitization by skin contact. You should wear suitable protective clothing and gloves when use it. Moreover, 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)SMILES: Clc1ccc(cc1)C[C@H](C(=O)O)N
(2)InChI: InChI=1/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1
(3)InChIKey: NIGWMJHCCYYCSF-MRVPVSSYBK
(4)Std. InChI: InChI=1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1 
(5)Std. InChIKey: NIGWMJHCCYYCSF-MRVPVSSYSA-N

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