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4-Fluoro-L-phenylalanine

4-Fluoro-L-phenylalanine structure

CAS No:
1132-68-9
Formula:
C9H10FNO2
Chemical Name:
4-Fluoro-L-phenylalanine
Synonyms:
L-Phenylalanine,4-fluoro-;Alanine,3-(p-fluorophenyl)-,L-;4-Fluoro-L-phenylalanine;p-Fluoro-L-phenylalanine;L-(p-Fluorophenyl)alanine;S-(-)-p-Fluorophenylalanine;L-4-Fluorophenylalanine;(S)-2-Amino-3-(4-fluorophenyl)propionic acid;(S)-4-Fluorophenylalanine;(2S)-Amino-3-(4-fluorophenyl)propionic acid;(S)-2-Amino-3-(4-fluorophenyl)propanoic acid;(2S)-2-Amino-3-(4-fluorophenyl)propanoic acid;(2S)-2-Azaniumyl-3-(4-fluorophenyl)propanoate
Categories:
Biochemical Engineering > Amino Acids and Derivatives

Description

white to off-white powderChEBI: A L-phenylalanine derivative that is L-phenylalanine in which the hydrogen at position 4 on the benzene ring is replaced by a fluoro group.

4-fluoro-L-phenylalanine is a fluoroamino acid, a L-phenylalanine derivative and a non-proteinogenic L-alpha-amino acid.|3-(p-Fluorophenyl)-alanine.

4-Fluoro-L-phenylalanine Basic Attributes

Molecular Weight：

183.18

Exact Mass：

183.18

BRN：

2416148

EC Number：

200-459-9

UNII：

E2K2VDK6KK

HScode：

29224999

Characteristics

PSA：

63.3

XLogP3：

-1.9

Density：

1.1939 (estimate)

Melting Point：

252-255 °C

Boiling Point：

313.3±32.0 °C(Predicted)

Flash Point：

143.3±25.1 °C

Refractive Index：

1.555

Water Solubility：

Soluble in water and 0.5M HCl (50 mg/ml).

Storage Conditions：

Store at RT.

Specific rotation：

-26.5 º (c=1, H2O 25 ºC)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

23-24/25

RTECS Number：

DW1765000

Hazard note：

Harmful

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

4 Fluorophenylalanine

4-Fluoro-L-phenylalanine Use and Manufacturing

Methods of Manufacturing

General procedure: To a 5 mL vial equipped with a magnetic stirrer bar were added 3-cyclohexyl-2-oxopropanoic acid (1j) (0.0510 g, 0.30 mmol), 2, 2-diphenylglycine (2) (0.0681 g, 0.30 mmol), chiral pyridoxamine 6g (0.0195 g, 0.030 mmol), and MeOH-H2O (8:2) (3.0 mL). The mixture was stirred at 20 °C for 3 days. The reaction mixture was transferred to a 25 mL round-bottom flask and MeOH was added until all the solid was dissolved. Then silica gel (0.50 g) was added. After removal of the solvent in vacuo at 20 °C, the resulting residue was submitted to column chromatography on silica gel (EtOH/ethyl acetate/25-28percent ammonia solution =100:58:16) to give compound 3j (0.0401 g, 78percent yield, 52percent ee) as a white solid. The enantiomeric excesses of 3b-k were deteremined by HPLC analysis after being converted to N-benzoyl methyl esters by treatment with thionyl chloride in methanol and subsequent reaction benzoyl chloride.7 The enantiomeric excess of 3a was deteremined by HPLC analysis after being converted to its methyl ester by treatment with CH2N2 in methanol.

Manufacturing Info：

Phenylalanine, 4-fluoro-: INACTIVE

Computed Properties

Molecular Weight:183.18
XLogP3:-1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:183.06955672
Monoisotopic Mass:183.06955672
Topological Polar Surface Area:63.3
Heavy Atom Count:13
Complexity:179
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 1132-68-9

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L-4-Fluorophenylalanine

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Guide of 4-Fluoro-L-phenylalanine

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
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4-Fluoro-L-phenylalanine

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