ChemicalBook Product Catalog Organic Chemistry Organic fluorine compound Fluoro-benzoic acid series 2-Amino-5-fluorobenzoic acid

2-Amino-5-fluorobenzoic acid

Product Name2-Amino-5-fluorobenzoic acid
CAS446-08-2
MFC7H6FNO2
MW155.13
EINECS207-159-7
MOL File446-08-2.mol

Chemical Properties

Melting point	181-183 °C(lit.)
Boiling point	223.67°C (rough estimate)
Density	1.3021 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	DMSO (Slightly), Methanol (Slightly)
pka	1.86±0.10(Predicted)
form	Fine Crystalline Powder
color	Light yellow to light brown
BRN	2803664
Major Application	peptide synthesis
InChI	InChI=1S/C7H6FNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11)
InChIKey	FPQMGQZTBWIHDN-UHFFFAOYSA-N
SMILES	C(O)(=O)C1=CC(F)=CC=C1N
CAS DataBase Reference	446-08-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,T
Risk Statements	36/37/38
Safety Statements	26-36-37/39
WGK Germany	3
HazardClass	IRRITANT
HS Code	29224999
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
5-Fluoroanthranilic acid	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

Used in the synthesis of styrylquinazolinones which are potential anticancer agents.

Uses

2-Amino-5-fluorobenzoic acid is used for the counterselection of TRP1, a commonly used genetic marker in the yeast Saccharoyces Cerevisiae. An antimetabolite for the tryptophan pathway in yeast, and is toxic by virtue of its antimetabolite conversion to 5-Fluorotryptophan. It can be used for the selection of tryptophan auxotroophs.

Definition

ChEBI: An aminobenzoic acid that is anthranilic acid in which the hydrogen at position 5 on the phenyl ring is replaced by fluorine.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

320-98-9

446-08-2

General procedure for the synthesis of 2-amino-5-fluorobenzoic acid from 2-nitro-5-fluorobenzoic acid: 2-nitro-5-fluorobenzoic acid (10 g, 54 mmol) was dissolved in ethanol (100 mL) and 10% Pd/C catalyst (0.5 g) was added. The reaction was stirred at room temperature for 4 h under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration. The filtrate was concentrated under reduced pressure to give 8.2 g (98% yield) of the white solid product 2-amino-5-fluorobenzoic acid. Product melting point: 142 °C. 1H NMR (DMSO-d6) δ: 6.71 (dd, J = 4.9, 8.9 Hz, 1H), 7.15 (dt, J = 2.9, 8.4 Hz, 1H), 7.37 (dd, J = 2.9, 9.8 Hz, 1H), 8.60 (s, 1H).EIMS m/z 156 (M + 1).

References

[1] Patent: WO2004/74218, 2004, A2. Location in patent: Page 106
[2] Patent: US2008/139551, 2008, A1. Location in patent: Page/Page column 43
[3] Patent: US2008/139551, 2008, A1. Location in patent: Page/Page column 44
[4] Patent: US5514676, 1996, A
[5] Journal of Biological Chemistry, 1954, vol. 207, p. 411,412

2-Amino-5-fluorobenzoic acid

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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