2-AMINO-3-FLUOROPHENOL

2-AMINO-3-FLUOROPHENOL Property

Melting point:

126-127°

Boiling point:

221.9±25.0 °C(Predicted)

Density 

1.347±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

solid

pka

8.76±0.10(Predicted)

color 

Light yellow to brown

InChI

InChI=1S/C6H6FNO/c7-4-2-1-3-5(9)6(4)8/h1-3,9H,8H2

InChIKey

QOZLOYKAFDTQNU-UHFFFAOYSA-N

SMILES

C1(O)=CC=CC(F)=C1N

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

RIDADR 

2512

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2908990000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H228Flammable solid

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

P403Store in a well-ventilated place.

2-AMINO-3-FLUOROPHENOL Chemical Properties,Usage,Production

Uses

2-Amino-3-fluorophenol is a reagent that is used in the preparation of benzimidazole- and benzoxazole-pyrimidone selective PI3Kβ inhibitors for the treatment of phosphatase and TENsin homologue (PTEN) deficient cancers.

Synthesis

Step 1. General procedure for the synthesis of 2-amino-3-fluorophenol from 3-fluoro-2-nitrophenol: Stannous chloride dihydrate (0.724 g, 3.18 mmol) was added to a solution of tetrahydrofuran (THF, 5.0 mL) of 3-fluoro-2-nitrophenol (0.100 g, 0.636 mmol, SynQuest), followed by water ( 5.0 mL). The reaction mixture was heated to 80 °C and maintained for 40 min. After the reaction was completed, it was cooled to room temperature and the reaction mixture was diluted with ethyl acetate and saturated sodium bicarbonate solution. The insoluble material was removed by filtration and the organic and aqueous layers were separated. The aqueous layer was extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product 2-amino-3-fluorophenol (65 mg, 80% yield), which could be used in the subsequent reaction without further purification.LCMS (M + H)+: 128.0.

References

[1] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 7, p. 623 - 634
[3] Patent: US5886044, 1999, A
[4] Patent: US5780483, 1998, A
[5] Patent: US6262113, 2001, B1