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14173-39-8

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14173-39-8 Usage

Chemical Properties

white powder

Uses

4-Chloro-L-phenylalanine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals.

Definition

ChEBI: A non-proteinogenic L-alpha-amino acid that is L-phenylalanine in which the meta-hydrogen of the phenyl group has been replaced by a chlorine.

Biochem/physiol Actions

4-Chloro-L-phenylalanine (L-PCPA) inhibits the synthesis of 5-hydroxytryptamine (5-HT). 4-Chloro-DL-phenylalanine (PCPA) depletes the serotonin levels in the brain by its inhibitory effect on tryptophan hydroxylase (Tph). Studies support the protective effects of PCPA against monocrotaline-induced pulmonary vascular remodeling as well as in lung inflammation.

Check Digit Verification of cas no

The CAS Registry Mumber 14173-39-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,1,7 and 3 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 14173-39:
(7*1)+(6*4)+(5*1)+(4*7)+(3*3)+(2*3)+(1*9)=88
88 % 10 = 8
So 14173-39-8 is a valid CAS Registry Number.
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)

14173-39-8 Well-known Company Product Price

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  • Alfa Aesar

  • (H63573)  4-Chloro-L-phenylalanine, 97%   

  • 14173-39-8

  • 250mg

  • 437.0CNY

  • Detail
  • Alfa Aesar

  • (H63573)  4-Chloro-L-phenylalanine, 97%   

  • 14173-39-8

  • 1g

  • 1313.0CNY

  • Detail
  • Alfa Aesar

  • (H63573)  4-Chloro-L-phenylalanine, 97%   

  • 14173-39-8

  • 5g

  • 5253.0CNY

  • Detail
  • Sigma

  • (C8655)  4-Chloro-L-phenylalanine  

  • 14173-39-8

  • C8655-250MG

  • 3,072.42CNY

  • Detail
  • Sigma

  • (C8655)  4-Chloro-L-phenylalanine  

  • 14173-39-8

  • C8655-1G

  • 5,748.21CNY

  • Detail

14173-39-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Chloro-Phe-OH

1.2 Other means of identification

Product number -
Other names L-4-Chlorophenylalanine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14173-39-8 SDS

14173-39-8Synthetic route

p-chlorocinnamic acid
1615-02-7

p-chlorocinnamic acid

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

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

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

Conditions
ConditionsYield
With ammonia at 25℃; pH=9; Kinetics; aq. buffer; Enzymatic reaction; regioselective reaction;A n/a
B 86%
(±)-ethyl 2-amino-3-(4-chlorophenyl)propanoate
29622-19-3

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

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

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

D-4-chlorophenylalanine ethyl ester

Conditions
ConditionsYield
With lithium hydroxide at 37℃; for 24h; α-chymotrypsin;A 61%
B 83%
N-acetyl-4-chlorophenylalanine
14091-10-2

N-acetyl-4-chlorophenylalanine

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
With hydrogenchloride In water at 95 - 100℃; for 6h;73.2%
Stage #1: N-acetyl-4-chlorophenylalanine; acylase; cobalt(II) chloride In water at 37℃; pH=7;
Stage #2: With hydrogenchloride at 15℃; pH=6;
41.4%
With sodium hydroxide; acylase Amano 30000 from Aspergillus spp. (30 u/mg); water; cobalt(II) chloride at 37 - 40℃; for 42h;40.4%
With phosphate buffer; acylase I from porcine kidney at 24.9℃; for 2h;
3-(4-chlorophenyl)prop-2-enoic acid
1615-02-7

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

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
With ammonium hydroxide; Petroselinum crispum phenylalanine ammonialyase (1U) at 37℃; for 24h; pH=10; Addition;59%
With ammonium hydroxide at 30℃; for 6h; pH=9.5; Reagent/catalyst; Enzymatic reaction;n/a
With ammonium hydroxide; carbon dioxide In dimethyl sulfoxide at 37℃; for 12h; pH=10; Reagent/catalyst; Enzymatic reaction; stereoselective reaction;n/a
With ammonium carbamate at 30℃; for 168h; pH=9.1; Time;n/a
DL-Phe(4Cl)
7424-00-2

DL-Phe(4Cl)

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
With sodium hydroxide; oxygen at 30℃; for 22h; pH=7.3; aq. buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;49%
Multi-step reaction with 2 steps
1.1: thionyl chloride / cooling
1.2: 50 °C
2.1: Aspergillus oryzae protease; aq. NaOH / aq. phosphate buffer / 0.5 h / 30 °C / pH 7.0
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / 15 h / Heating
View Scheme
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: ammonium carbamate / 168 h / 30 °C / pH 9.1
View Scheme
Multi-step reaction with 4 steps
1.1: sodium carbonate / water; acetone / 3 h
1.2: 2 h / 0 °C
2.1: sodium hydrogencarbonate / water; N,N-dimethyl-formamide / 4 h / 37 °C / pH 9
3.1: sodium hydroxide / methanol
4.1: palladium 10% on activated carbon; formic acid / methanol
View Scheme
2-amino-3-(4-chlorophenyl)propionic acid ethyl ester hydrochloride
52031-05-7

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

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

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

D-4-chlorophenylalanine ethyl ester

Conditions
ConditionsYield
Yield given. Yields of byproduct given;
(2S,5S)-2-tert-Butyl-5-(4-chloro-benzyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester
123052-81-3

(2S,5S)-2-tert-Butyl-5-(4-chloro-benzyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
With hydrogenchloride; Dowex 50-WX8; acetic acid; trifluoroacetic acid 1.) CH2Cl2, 30 min, 0 deg C; 12 h, room temperature; 2.) 100-105 deg C, toluene, water, 72 h; Yield given. Multistep reaction;
4-amino-L-phenylalanine
943-80-6

4-amino-L-phenylalanine

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
(i) NaNO2, aq. HCl, (ii) CuCl, Cu; Multistep reaction;
2-Amino-3-(4-chloro-phenyl)-propionic acid isobutyl ester; hydrochloride

2-Amino-3-(4-chloro-phenyl)-propionic acid isobutyl ester; hydrochloride

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

(Z)-3-(4-chlorophenyl)-2-hydroxyacrylic acid
127273-12-5

(Z)-3-(4-chlorophenyl)-2-hydroxyacrylic acid

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; potassium chloride; ammonium chloride; hydrogenchloride; Bacillus sphaericus wild type phenylalanine dehydrogenase In various solvent(s) at 25℃; for 0.666667h; pH=8.0;
(±)-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;
3-(4-chlorophenyl)-2-oxopropionic acid ethyl ester

3-(4-chlorophenyl)-2-oxopropionic acid ethyl ester

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 33 percent / aq. H2SO4 / acetic acid / 1 h / Heating
2: NH4Cl; KCl; NADH / Bacillus sphaericus wild type phenylalanine dehydrogenase; aq. HCl / various solvent(s) / 0.67 h / 25 °C / pH 8.0
View Scheme
1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Mg / diethyl ether / 0.17 h / Heating
1.2: 87 percent / diethyl ether / 2 h / 20 °C
2.1: 33 percent / aq. H2SO4 / acetic acid / 1 h / Heating
3.1: NH4Cl; KCl; NADH / Bacillus sphaericus wild type phenylalanine dehydrogenase; aq. HCl / various solvent(s) / 0.67 h / 25 °C / pH 8.0
View Scheme
(4-chlorophenyl)acetaldehyde
4251-65-4

(4-chlorophenyl)acetaldehyde

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / H2SO4, LiBr / (PPh3)2PdBr2 / various solvent(s) / 12 h / 120 °C / 45003.6 Torr
2: 40.4 percent / H2O, NaOH, CoCl2*6H2O, acylase Amano 30000 from Aspergillus spp. (30 u/mg) / 42 h / 37 - 40 °C
View Scheme
4-chlorobenzyl bromide
622-95-7

4-chlorobenzyl bromide

(+-)-2-(4-<2-(4-chloro-benzhydryloxy)-ethyl>-piperazino)-ethanol

(+-)-2-(4-<2-(4-chloro-benzhydryloxy)-ethyl>-piperazino)-ethanol

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min: 2.) THF, hexane, -78 deg C
2: 1.) trifluoroacetic acid; 2.) 0.75M HCl, Dowex 50-WX8, acetic acid / 1.) CH2Cl2, 30 min, 0 deg C; 12 h, room temperature; 2.) 100-105 deg C, toluene, water, 72 h
View Scheme
3-(4-chlorophenyl)prop-2-enoic acid
1615-02-7

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

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

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

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

Conditions
ConditionsYield
With carbon dioxide; Taxus chinensis phenylalanine aminomutase; ammonia In water pH=10; Kinetics; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
N-acetyl-4-chlorophenylalanine
14091-10-2

N-acetyl-4-chlorophenylalanine

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

(2R)-2-(acetylamino)-3-(4-chlorophenyl)propanoic acid

(2R)-2-(acetylamino)-3-(4-chlorophenyl)propanoic acid

Conditions
ConditionsYield
With lipase AS 'Amano' at 35℃; for 24h; pH=6.5; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
DL-Phe(4Cl)
7424-00-2

DL-Phe(4Cl)

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

(2R)-2-(acetylamino)-3-(4-chlorophenyl)propanoic acid

(2R)-2-(acetylamino)-3-(4-chlorophenyl)propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / water; N,N-dimethyl-formamide / 20 °C
2: lipase AS 'Amano' / 24 h / 35 °C / pH 6.5 / Enzymatic reaction
View Scheme
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
p-chlorocinnamic acid
1615-02-7

p-chlorocinnamic acid

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

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

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

Conditions
ConditionsYield
With ammonium bisulphate; EncP wild type enzyme at 55℃; for 22h; pH=8.3; Enzymatic reaction; stereoselective reaction;A n/a
B n/a
p-chlorocinnamic acid
1615-02-7

p-chlorocinnamic acid

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

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

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

C

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

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

Conditions
ConditionsYield
With ammonium bisulphate; EncP-E293M variant at 55℃; for 22h; pH=8.3; Enzymatic reaction; stereoselective reaction;A n/a
B n/a
C n/a
p-chlorocinnamic acid
1615-02-7

p-chlorocinnamic acid

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
With recombinant cyanobacterium Anabaena variabilis phenylalanine ammonia lyase; ammonium carbamate In water at 30℃; for 48h; Enzymatic reaction; stereoselective reaction;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
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

A

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

B

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate / ethanol / 4 h / Reflux
2: phenylalanine ammonia lyase from Streptomyces maritimus; phenylalanine ammonia α-lyase from Anabaena variabilis / aq. buffer / 24 h / 30 °C / pH 8 / Resolution of racemate; Enzymatic reaction
View Scheme
3-amino-3-(4-chlorophenyl)propionic acid
19947-39-8

3-amino-3-(4-chlorophenyl)propionic acid

A

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

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

B

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

C

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

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

Conditions
ConditionsYield
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; Time; Resolution of racemate; Enzymatic reaction; enantioselective reaction;
para-Chloro-D-phenylalanine
14091-08-8

para-Chloro-D-phenylalanine

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
With L-phenylalanine dehydrogenase; D-amino acid aminotransferase In aq. buffer at 37℃; for 2h; pH=8.5; Enzymatic reaction; stereoselective reaction;
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

(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

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

C46H33Cl2N3NiO3

C46H33Cl2N3NiO3

Conditions
ConditionsYield
With potassium carbonate In methanol at 70℃; for 2h; stereoselective reaction;99%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

(R)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-2-pyrrolidinecarboxamide
1644308-43-9

(R)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-2-pyrrolidinecarboxamide

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

C34H27Cl4N3NiO3

C34H27Cl4N3NiO3

Conditions
ConditionsYield
With potassium carbonate In methanol at 60℃; for 2.5h; Temperature;97%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

(1S)-1-(4-chlorophenylmethyl)-2-hydroxyethylamine
201864-00-8

(1S)-1-(4-chlorophenylmethyl)-2-hydroxyethylamine

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran for 5h; Reflux;89%
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 0 - 20℃;88%
Stage #1: p-chlorophenylalanine With dimethylsulfide borane complex In tetrahydrofuran at 0℃; Reflux;
Stage #2: With hydrogenchloride In water for 1.5h; Reflux;
87%
With dimethylsulfide borane complex In tetrahydrofuran at 0℃; Reflux;87%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; Inert atmosphere;72%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

(S)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)-methyl]-2-pyrrolidinecarboxamide hydrochloride

(S)-N-(2-benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)-methyl]-2-pyrrolidinecarboxamide hydrochloride

nickel dichloride

nickel dichloride

C34H25(2)H2Cl4N3NiO3

C34H25(2)H2Cl4N3NiO3

Conditions
ConditionsYield
With d(4)-methanol; potassium carbonate Reflux; diastereoselective reaction;88%
N-tertiarybutoxycarbonyl-D-alanine N-hydroxysuccinimide ester
34404-33-6

N-tertiarybutoxycarbonyl-D-alanine N-hydroxysuccinimide ester

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Boc-D-Ala-p-ClPhe-OH

Boc-D-Ala-p-ClPhe-OH

Conditions
ConditionsYield
With 4-methyl-morpholine In N,N-dimethyl-formamide for 4h; Ambient temperature;85%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

N-Methylisatoic anhydride
10328-92-4

N-Methylisatoic anhydride

(S)-3-(4-chlorobenzyl)-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

(S)-3-(4-chlorobenzyl)-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Conditions
ConditionsYield
With acetic acid for 16h; Reflux;83%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
With aqueous 27percent NaOH In methanol; water at 30℃; for 4h;81.6%
With sodium hydroxide In water; acetone at 0 - 20℃;80%
Stage #1: di-tert-butyl dicarbonate; p-chlorophenylalanine With sodium hydroxide In water; acetone at 0 - 20℃;
Stage #2: With hydrogenchloride In water pH=2;
80%
With sodium hydroxide In water; acetone at 0 - 20℃;80%
With sodium hydroxide In tert-butyl alcohol for 24h; Ambient temperature;
N-(tert-butyloxycarbonyl) azide
1070-19-5

N-(tert-butyloxycarbonyl) azide

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

Conditions
ConditionsYield
In 1,4-dioxane; water for 48h; Ambient temperature; pH=10;81%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

isobutene
115-11-7

isobutene

p-Chloro-L-phenylalanine t-butyl ester hydrochloride
401791-64-8

p-Chloro-L-phenylalanine t-butyl ester hydrochloride

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid In 1,4-dioxane; water at -78 - 20℃; pH=10;75%
Boc-Val-ONSu
3392-12-9

Boc-Val-ONSu

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

N-(t-butoxycarbonyl)-L-valyl-4-chloro-L-phenylalanine

N-(t-butoxycarbonyl)-L-valyl-4-chloro-L-phenylalanine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water at 20℃; Condensation;67%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

6-chloro-N-methylisatoic anhydride
14529-12-5

6-chloro-N-methylisatoic anhydride

(S)-7-chloro-3-(4-chlorobenzyl)-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

(S)-7-chloro-3-(4-chlorobenzyl)-1-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Conditions
ConditionsYield
With acetic acid for 18h; Reflux;67%
With acetic acid for 16h; Reflux;67%
methanol
67-56-1

methanol

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

(S)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride
14173-40-1, 23434-91-5, 33965-47-8, 60594-65-2

(S)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 0℃;66%
With thionyl chloride
With thionyl chloride at 0℃;
With thionyl chloride In methanol Reflux;
Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

A

(3S,5S)-5-(4-Chloro-benzyl)-6-oxo-morpholine-3-carboxylic acid benzylamide

(3S,5S)-5-(4-Chloro-benzyl)-6-oxo-morpholine-3-carboxylic acid benzylamide

B

(3R,5S)-5-(4-Chloro-benzyl)-6-oxo-morpholine-3-carboxylic acid benzylamide

(3R,5S)-5-(4-Chloro-benzyl)-6-oxo-morpholine-3-carboxylic acid benzylamide

Conditions
ConditionsYield
With trifluoroacetic acid at -40 - 20℃; Ugi reaction;A 21%
B 53%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

(S)-3-(4-chlorophenyl)-2-hydroxypropionic acid
494796-54-2

(S)-3-(4-chlorophenyl)-2-hydroxypropionic acid

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite In water at 0 - 20℃;42.9%
With sulfuric acid; sodium nitrite at 0 - 20℃;20%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

5-(2'-cloro)fenil-7-metilpirazolo-<4,3-c><1,2,4>-oxadiazin-3-one
81198-32-5

5-(2'-cloro)fenil-7-metilpirazolo-<4,3-c><1,2,4>-oxadiazin-3-one

(S)-3-(4-Chloro-phenyl)-2-{3-[2-(2-chloro-phenyl)-5-methyl-4-nitroso-2H-pyrazol-3-yl]-ureido}-propionic acid

(S)-3-(4-Chloro-phenyl)-2-{3-[2-(2-chloro-phenyl)-5-methyl-4-nitroso-2H-pyrazol-3-yl]-ureido}-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water for 1.5h;40%
bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]

bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

sodium methylate
124-41-4

sodium methylate

((η5-pentamethylcyclopentadienyl)(η6-L-p-chlorophenylaniline)ruthenium) chloride

((η5-pentamethylcyclopentadienyl)(η6-L-p-chlorophenylaniline)ruthenium) chloride

Conditions
ConditionsYield
In methanol addn. of amino acid to Ru-complex in methanol and 1 M NaOMe, refluxing for 3 h with stirring under Ar; removal of solvent, dissolution in EtOH, addn. of CH2Cl2, pptn., filtn., drying under vacuum, recrystn. from MeOH, elem. anal.;38%
6-bromoisoatoic anhydride

6-bromoisoatoic anhydride

p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

D,L-N-(2-Amino-5-bromobenzoyl)-4-chlorophenylalanine

D,L-N-(2-Amino-5-bromobenzoyl)-4-chlorophenylalanine

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; pyridine27%
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

p-Chlor-m-nitrophenylalanin
57213-15-7

p-Chlor-m-nitrophenylalanin

Conditions
ConditionsYield
With sulfuric acid; nitric acid
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

potassium thioacetate
10387-40-3

potassium thioacetate

(S)-2-Acetylsulfanyl-3-(4-chloro-phenyl)-propionic acid
177741-56-9

(S)-2-Acetylsulfanyl-3-(4-chloro-phenyl)-propionic acid

Conditions
ConditionsYield
With hydrogen bromide; sodium nitrite 2.) DMF; Yield given. Multistep reaction;
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

4-uulfamoyl-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester
154715-61-4

4-uulfamoyl-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester

(S)-3-(4-Chloro-phenyl)-2-(4-sulfamoyl-benzoylamino)-propionic acid

(S)-3-(4-Chloro-phenyl)-2-(4-sulfamoyl-benzoylamino)-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide for 24h; Ambient temperature;
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

(4-Sulfamoyl-benzoylamino)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester
176170-33-5

(4-Sulfamoyl-benzoylamino)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

(S)-3-(4-Chloro-phenyl)-2-[2-(4-sulfamoyl-benzoylamino)-acetylamino]-propionic acid

(S)-3-(4-Chloro-phenyl)-2-[2-(4-sulfamoyl-benzoylamino)-acetylamino]-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide for 24h; Ambient temperature;
p-chlorophenylalanine
14173-39-8

p-chlorophenylalanine

[2-(4-Sulfamoyl-benzoylamino)-acetylamino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester
67460-24-6

[2-(4-Sulfamoyl-benzoylamino)-acetylamino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester

(S)-3-(4-Chloro-phenyl)-2-{2-[2-(4-sulfamoyl-benzoylamino)-acetylamino]-acetylamino}-propionic acid

(S)-3-(4-Chloro-phenyl)-2-{2-[2-(4-sulfamoyl-benzoylamino)-acetylamino]-acetylamino}-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide for 24h; Ambient temperature;

14173-39-8Relevant articles and documents

A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids

Varga, Andrea,Csuka, Pál,Sonesouphap, Orlavanah,Bánóczi, Gergely,To?a, Monica Ioana,Katona, Gabriel,Molnár, Zsófia,Bencze, László Csaba,Poppe, László,Paizs, Csaba

, p. 185 - 194 (2020/04/28)

A novel phenylalanine ammonia-lyase of the psychrophilic yeast Pseudozyma antarctica (PzaPAL) was identified by screening microbial genomes against known PAL sequences. PzaPAL has a significantly different substrate binding pocket with an extended loop (26 aa long) connected to the aromatic ring binding region of the active site as compared to the known PALs from eukaryotes. The general properties of recombinant PzaPAL expressed in E. coli were characterized including kinetic features of this novel PAL with L-phenylalanine (S)-1a and further racemic substituted phenylalanines rac-1b-g,k. In most cases, PzaPAL revealed significantly higher turnover numbers than the PAL from Petroselinum crispum (PcPAL). Finally, the biocatalytic performance of PzaPAL and PcPAL was compared in the kinetic resolutions of racemic phenylalanine derivatives (rac-1a-s) by enzymatic ammonia elimination and also in the enantiotope selective ammonia addition reactions to cinnamic acid derivatives (2a-s). The enantiotope selectivity of PzaPAL with o-, m-, p-fluoro-, o-, p-chloro- and o-, m-bromo-substituted cinnamic acids proved to be higher than that of PcPAL.

Biocatalytic stereoinversion of d-: Para -bromophenylalanine in a one-pot three-enzyme reaction

Khorsand, Fahimeh,Murphy, Cormac D.,Whitehead, Andrew J.,Engel, Paul C.

, p. 503 - 510 (2017/08/14)

Halogenated derivatives of phenylalanine can be used as cross-coupling reagents for making drug-like molecules, and pure enantiomers of these precursors are therefore highly desirable. In our exploration of enzymatic routes to simplify the deracemisation process, the application of two enzymes, d-amino acid transaminase and phenylalanine dehydrogenase, both from Lysinibacillus sphaericus, has given promising results for the stereo-inversion of d-enantiomers of para-bromophenylalanine as the model substrate and also p-chloro/fluorophenylalanine and tyrosine. The addition of a coenzyme recycling system using ethanol and alcohol dehydrogenase reduced the amount of coenzyme needed for the reaction catalysed by phenylalanine dehydrogenase, reducing cost and permitting efficient and complete conversion of the racemic amino acids to the l-enantiomer. Relative proportions of the enzymes were optimized. The high purity of the l-enantiomer, with an ee over 99%, and the ease of the process make it an ideal alternative for deracemisation of the studied compounds.

Bio-inspired enantioselective full transamination using readily available cyclodextrin

Zhang, Shiqi,Li, Guangxun,Liu, Hongxin,Wang, Yingwei,Cao, Yuan,Zhao, Gang,Tang, Zhuo

, p. 4203 - 4208 (2017/02/05)

The mimics of vitamin B6-dependent enzymes that catalyzed an enantioselective full transamination in the pure aqueous phase have been realized for the first time through the establishment of a new “pyridoxal 5′-phosphate (PLP) catalyzed non-covalent cyclodextrin (CD)-keto acid inclusion complexes” system, and various optically active amino acids have been obtained.

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