H-DL-Phe(3-F)-OH is a fluorophenylalanine derivative, commonly used in organic synthesis as an intermediate in polypeptide synthesis, enhancing peptide chain stability, and widely applied in drug synthesis.

Synonyms: H-DL-Phe(3-F)-OH

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Quality Control of H-DL-Phe(3-F)-OH Purity: 95% SDS Specification

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Product Details of H-DL-Phe(3-F)-OH

CAS No. :	456-88-2
Formula :	C₉H₁₀FNO₂
M.W :	183.18
SMILES Code :	NC(CC1=CC(F)=CC=C1)C(O)=O
Synonyms :	H-DL-Phe(3-F)-OH
MDL No. :	MFCD00004273
InChI Key :	VWHRYODZTDMVSS-UHFFFAOYSA-N
Pubchem ID :	9976

Safety of H-DL-Phe(3-F)-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of H-DL-Phe(3-F)-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 456-88-2 ]

[ 456-88-2 ] Synthesis Path-Downstream 1~41

1
[ 143051-43-8 ]
[ 456-88-2 ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 1806.

2
[ 456-88-2 ]
[ 404-70-6 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 135,p. 101,113.

3
[ 17607-28-2 ]
[ 456-88-2 ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 1806.

4
[ 587-41-7 ]
[ 456-88-2 ]

References: [1]Chemische Berichte,1932,vol. 65,p. 1439,1441.

5
[ 354-32-5 ]
[ 456-88-2 ]
[ 39801-55-3 ]

References: [1]Journal of Pharmaceutical Sciences,1979,vol. 68,p. 496 - 499.

6
[ 75-44-5 ]
[ 456-88-2 ]
[ 87184-31-4 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

7
[ 67818-94-4 ]
[ 456-88-2 ]
[ 87184-33-6 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

8
[ 58632-95-4 ]
[ 456-88-2 ]
[ 87184-23-4 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

9
[ 80980-62-7 ]
[ 130835-04-0 ]
[ 456-88-2 ]
[ 80980-59-2 ]

References: [1]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 1925 - 1928.

10
[ 456-88-2 ]
[ 103-80-0 ]
[ 151962-25-3 ]

References: [1]Russian Journal of Bioorganic Chemistry,1993,vol. 19,p. 236 - 240.
Bioorganicheskaya Khimiya,1993,vol. 19,p. 478 - 483.

11
[ 456-88-2 ]
(RS)-3-(3'-Fluorophenyl)lactic acid [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2117 - 2120.

Yield	Reaction Conditions	Operation in experiment
7.5 mg	With water; trifluoroacetic acid; In dichloromethane; at 25℃; for 0.5h;	General procedure: 50 mumols of resin 1 was treated with 100 mumols of 0.20 M BTPP in NMP followed by 100 mumols of 0.20 M fluorinated benzyl bromide R1X in NMP. After two days the reaction mixture was filtered and the resulting resin 2 was washed once with 3 mL of THF. To the resin was then added 2.5 mL of 1.0 N HCl in THF (1:2). After 20 minutes the resin was filtered and was washed with 3 mL of THF followed by 2×2.5 mL of 0.20 M diisopropylethylamine in NMP, 2×2.5 mL of NMP, 3×2 mL of THF and 3×3 mL of dichloromethane to give resin 3. Treatment of resin 3 with 2 mL of 35:60:5 TFA/DCM/H2O for 30 minutes was followed by filtering and washing the resin with 2 mL of 35:60:5 TFA/DCM/H2O and 2 mL of DCM. The combined filtrates were evaporated to a residue which was chromatographed on silica gel using iPrOH/MeOH/NH4OH mobile phases to elute the free bases 4.

14
[ 456-88-2 ]
[ 501-53-1 ]
[ 126693-47-8 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 82 - 86.
[2]Canadian Journal of Chemistry,2008,vol. 86,p. 219 - 224.

15
[ 456-88-2 ]
[ 82911-69-1 ]
Fmoc-Phe(3-F)-OH [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 6852 - 6853.

16
[ 67-56-1 ]
[ 456-88-2 ]
[ 64493-16-9 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 259 - 273.
[2]Tetrahedron,2005,vol. 61,p. 10254 - 10261.
[3]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3327 - 3332.

17
[ 78-83-1 ]
[ 456-88-2 ]
2-Amino-3-(3-fluoro-phenyl)-propionic acid isobutyl ester; hydrochloride [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 10254 - 10261.

18
[ 207910-83-6 ]
[ 456-88-2 ]

References: [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2684 - 2691.

19
3-(3-fluorophenyl)-2-oxopropionic acid ethyl ester [ No CAS ]
[ 456-88-2 ]

References: [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2684 - 2691.

20
[ 456-42-8 ]
[ 456-88-2 ]

References: [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2684 - 2691.

21
[ 456-88-2 ]
[ 19883-77-3 ]

References: [1]Tetrahedron,2005,vol. 61,p. 10254 - 10261.
[2]Tetrahedron,2005,vol. 61,p. 10254 - 10261.
[3]Russian Journal of Bioorganic Chemistry,1993,vol. 19,p. 236 - 240.
Bioorganicheskaya Khimiya,1993,vol. 19,p. 478 - 483.

22
[ 456-88-2 ]
[ 110117-84-5 ]

References: [1]Tetrahedron,2005,vol. 61,p. 10254 - 10261.
[2]Russian Journal of Bioorganic Chemistry,1993,vol. 19,p. 236 - 240.
Bioorganicheskaya Khimiya,1993,vol. 19,p. 478 - 483.
[3]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3327 - 3332.
[4]ChemCatChem,2018,vol. 10,p. 470 - 474.

23
[ 456-88-2 ]
[ 49759-56-0 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 82 - 86.

24
[ 456-88-2 ]
[ 127862-80-0 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 82 - 86.

25
[ 456-88-2 ]
Z-(S)-Phe(3F)-(S)-Leu-NH₂ [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 82 - 86.
[2]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 82 - 86.

26
[ 456-88-2 ]
Tropanyl (RS)-3-(3'-fluorophenyl)lactate [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2117 - 2120.

27
[ 456-88-2 ]
(R)-N-phenylacetyl-3-fluorophenylalanine [ No CAS ]

References: [1]Russian Journal of Bioorganic Chemistry,1993,vol. 19,p. 236 - 240.
Bioorganicheskaya Khimiya,1993,vol. 19,p. 478 - 483.

28
[ 456-88-2 ]
[ 87184-34-7 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

29
[ 456-88-2 ]
[ 87184-24-5 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

30
[ 456-88-2 ]
[ 87184-25-6 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

31
[ 456-88-2 ]
[ 87184-28-9 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

32
[ 456-88-2 ]
[ 87184-21-2 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

33
[ 456-88-2 ]
[ 87184-20-1 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

34
[ 456-88-2 ]
[ 87184-17-6 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

35
[ 456-88-2 ]
[ 87184-16-5 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

36
[ 456-88-2 ]
[ 87184-19-8 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

37
[ 456-88-2 ]
[ 87184-18-7 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1725 - 1729.

38
[ 380-70-1 ]
[ 456-88-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride; In water; for 18.0h;Reflux;	The intermediate 231 46 (7.50g, 21.43mmol) was added into 94 HCl (80mL). The reaction mixture was stirred at refluxing for 15h and TLC analysis indicated that the reaction was completed. The mixture was filtered to give the white solid 233 47 in 86percent yield. HRMS (ESI): m/z, calculated for C9H10NO2 184.0715 (M+H)+, found 184.0767.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 143,p. 1325 - 1344.
[2]Journal of the American Chemical Society,1950,vol. 72,p. 1806.
[3]Organic Letters,2018,vol. 20,p. 6298 - 6301.

39
[ 50-00-0 ]
[ 456-88-2 ]
[ 86323-66-2 ]

Yield	Reaction Conditions	Operation in experiment
48%	With hydrogenchloride; In water; for 6.0h;Reflux;	To the solution of 233 47 (16.50g, 0.3mol) in 94 HCl (150mL), 40percent 188 formaldehyde solution (70mL, 1mol) was added. The reaction mixture was stirred at refluxing for 6h and TLC analysis indicated that the reaction was completed. The mixture was cooled to room temperature and filtered to give white solid 235 48 in 48percent yield. HRMS (ESI): m/z, calculated for C10H10FNO2 196.0702 (M+H)+, found 196.0783.
	With hydrogenchloride; In water; at 90℃; for 3.5h;	2 g of m-fluoro-DL-phenylalanine are suspended in 20 ml of conc. hydrochloric acid and 8 ML of aqu. 37percent formaldehyde solution and stirred during 3.5 h at 90° during which a partial solution takes place. Stirring is continued overnight at room temperature and the precipitate filtered off and washed with cold water. Filtrate, combined with the wash solutions are evaporated to dryness, the residue suspended in 50 ml of MEOH saturated with HCI and stirred overnight, during which a clear solution is formed. The solvent is evaporated, the residue dissolved in CH2CI2/MeOH (9: 1) and extracted with 2N NA2CO3 solution and brine. The organic phases are dried over NA2SO4, evaporated and chromatographed on silica gel using MeOtBu. The title compound is obtained as an oil, MS (ES+) : 210 (MH) +.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 143,p. 1325 - 1344.
[2]Patent: WO2004/99206,2004,A1 .Location in patent: Page 7-8.

40
[ 123-91-1 ]
[ 24424-99-5 ]
[ 456-88-2 ]
[ 87184-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water;	L-2-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-propionic acid A mixture of L-2-amino-3-(3-fluoro-phenyl)-propionic acid (20.0 g, 110 mmol, 1 eq) in H2O (100 mL) was treated with Na2CO3 (16.2 g, 153 mmol, 1.4 eq) in H2O (40 mL) followed by 1,4-dioxane (100 mL) and cooled to 0° C. The BOC2O was added and the reaction mixture was stirred at ambient temperature for 5 h after which the dioxane was evaporated. H2O (125 mL) was then added and the mixture then washed with Et2O (2100 mL). The aqueous phase was acidified with 10percent citric acid followed by extraction with EtOAc (2300 mL). The combined EtOAc layers were washed with H2O (2*150 mL), brine (150 mL), dried (Na2SO4) and concentrated to give the acid as a colorless, viscous oil which slowly solidified upon standing (31 g, quant). 1H NMR (CDCl3) 7.33-7.26 (m,1H), 7.00-6.91 (m,3H), 4.96 (s, 1H), 4.62 (bs, 1H), 3.23 (dd, J=14, 5.3, 2H), 1.44 (s, 9H); Anal Calcd for C14H18NO4F: C, 5936; H, 6.40; N, 4.94. Found: C, 59.29; H, 6.34; N, 4.90.

References: [1]Patent: US2004/204591,2004,A1 .

41
[ 456-88-2 ]
(R)-3-amino-3-(3-fluoro-phenyl)-propionic acid [ No CAS ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 6953 - 6959.

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CAS No.: 456-88-2

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CAS No.: 456-88-2

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Product Details of H-DL-Phe(3-F)-OH

Safety of H-DL-Phe(3-F)-OH

Application In Synthesis of H-DL-Phe(3-F)-OH

[ 456-88-2 ] Synthesis Path-Downstream 1~41

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