5472-68-4

Basic information

• Product Name: 2,4-Dichloro-DL-phenylalanine
• Synonyms: Nsc29445;4-Dichloro-DL-phenylalanine;BOC-2;BOC-D-2;DL-3-(2,4-Dichlorophenyl)alanine;DL-2,4-Dichlorophenylalanine
• CAS NO: 5472-68-4
• Molecular Formula: C₉H₉Cl₂NO₂
• Molecular Weight: 234.08
• Mol File: 5472-68-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 239℃
• Boiling Point: 368.1 °C at 760 mmHg
• Flash Point: 176.4 °C
• Appearance: /
• Density: 1.450
• Storage Temp.: 2-8°C
• PKA: 2.14±0.15(Predicted)
• CAS DataBase Reference: 2,4-Dichloro-DL-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-DL-phenylalanine(5472-68-4)
• EPA Substance Registry System: 2,4-Dichloro-DL-phenylalanine(5472-68-4)

Safety Data

• Hazardous Substances Data: 5472-68-4(Hazardous Substances Data)

Synthetic route

(2,4-dichloro-benzyl)-malonic acid (146882-06-6) → rac-2,4-dichloro-Phe (5472-68-4)

Conditions	Yield
With tris-(2-chloro-ethyl)-amine; sulfuric acid; benzene

acetylamino-(2,4-dichloro-benzyl)-malonic acid diethyl ester (5472-72-0) → rac-2,4-dichloro-Phe (5472-68-4)

Conditions	Yield
With hydrogen bromide

(+-)-2-chloro-3-<2,4-dichloro-phenyl>-propionic acid → rac-2,4-dichloro-Phe (5472-68-4)

Conditions	Yield
With ammonia; ammonium chloride

acetamidomalonate + 2,4-dichloro-benzyl halide → rac-2,4-dichloro-Phe (5472-68-4)

2-(2,4-dichloro-benzyl)-malonic acid diethyl ester (61023-54-9) → rac-2,4-dichloro-Phe (5472-68-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous KOH 2: HN3; H2SO4; benzene View Scheme

2,4-Dichlorobenzyl chloride (94-99-5) → rac-2,4-dichloro-Phe (5472-68-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol 2: concentrated aqueous HBr View Scheme

2,4-dichlorobenzyl bromide (20443-99-6) → rac-2,4-dichloro-Phe (5472-68-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium ethylate; ethanol 2: aqueous KOH 3: HN3; H2SO4; benzene View Scheme

formaldehyd (50-00-0) + methyl 2,4-dichloro-N-(ethoxycarbonyl)phenylalaninate → 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid + rac-2,4-dichloro-Phe (5472-68-4)

Conditions	Yield
With sulfuric acid; acetic acid at 80℃; for 8h; Microwave irradiation;

rac-2,4-dichloro-Phe (5472-68-4) + methylamine (74-89-5) → D,L 2,4-dichlorophenylalanine N-methylamide (215311-39-0)

Conditions	Yield
Stage #1: rac-2,4-dichloro-Phe With chloro-trimethyl-silane In methanol Heating / reflux; Stage #2: methylamine In methanol at -20 - 20℃; for 3h;	85%

rac-2,4-dichloro-Phe (5472-68-4) → 2,4-dichloro-D-phenylalanine (114872-98-9)

Conditions	Yield
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;	49%

rac-2,4-dichloro-Phe (5472-68-4) → 2-(2,4-dichlorobenzyl)-5-(2,4-dichlorophenyl)thiazole

Conditions	Yield
With sulfur; ammonium iodide; potassium phosphate; oxygen; dimethyl sulfoxide In chlorobenzene at 120℃; for 16h; Sealed tube;	48%

rac-2,4-dichloro-Phe (5472-68-4) → (S)-2-amino-3-(2,4-dichlorophenyl)propanoic acid (111119-36-9)

Conditions	Yield
With sodium hydroxide; oxygen at 30℃; for 22h; pH=7.3; aq. buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	46%

Upstream product

• 61023-54-9 2-(2,4-dichloro-benzyl)-malonic acid diethyl ester 
• 20443-99-6 2,4-dichlorobenzyl bromide 
• 50-00-0 formaldehyd 
• 94-99-5 2,4-Dichlorobenzyl chloride 
• 146882-06-6 (2,4-dichloro-benzyl)-malonic acid 
• 5472-72-0 acetylamino-(2,4-dichloro-benzyl)-malonic acid diethyl ester 

Downstream Products

• 111119-36-9 (S)-2-amino-3-(2,4-dichlorophenyl)propanoic acid 
• 114872-98-9 2,4-dichloro-D-phenylalanine 
• 215311-39-0 D,L 2,4-dichlorophenylalanine N-methylamide 

Relevant articles and documents

BORONATES AS ARGINASE INHIBITORS

Compounds according to Formula I are potent inhibitors of Arginase I and II activity: (I) where R1, R2, R3, R4, D, W, X, Y, and Z are defined in the specification. The invention also provides pharmaceutical compositions of the compounds and methods of their use in treating or preventing a disease or a condition associated with arginase activity.