2-AMINO-4,6-DICHLOROPHENOL Chemical Properties

Melting point:

97 °C

Boiling point:

286.5±40.0 °C(Predicted)

Density 

1.2549 (rough estimate)

refractive index 

1.5680 (estimate)

RTECS 

SJ5774000

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

7.85±0.23(Predicted)

form 

Solid

color 

Yellow to brown

Merck 

14,437

CAS DataBase Reference

527-62-8(CAS DataBase Reference)

EPA Substance Registry System

2-Amino-4,6-dichlorophenol (527-62-8)

Safety Information

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

2922290090

2-AMINO-4,6-DICHLOROPHENOL Usage And Synthesis

Chemical Properties

Off-white or light brown crystals

Uses

2-Amino-4,6-dichlorophenol is used in preparation of novel heteroaryl-substituted Aminoalkyl Azole compounds as pesticides.

General Description

Long needles (from carbon disulfide). Sublimes (at 0.06 mm Hg) at 158-176°F.

Air & Water Reactions

May be sensitive to prolonged exposure to air/or light.

Reactivity Profile

2-AMINO-4,6-DICHLOROPHENOL may react with strong oxidizers and mineral acids or bases .

Fire Hazard

Flash point data for 2-AMINO-4,6-DICHLOROPHENOL are not available. 2-AMINO-4,6-DICHLOROPHENOL is probably combustible.

Synthesis

General procedure for the synthesis of 2,4-dichloro-6-aminophenol from 2,4-dichloro-6-nitrophenol: To a suspension of 2,4-dichloro-6-nitrophenol (60.0 g, 288 mmol) in ethanol (250 mL) and water (250 mL) was added sodium bisulfite (251 g, 1.44 mol) in batches. The reaction mixture was stirred at 65 °C for 4 hours. Upon completion of the reaction, the mixture was concentrated under vacuum and subsequently diluted with saturated aqueous sodium bicarbonate (500 mL) and extracted with ethyl acetate (200 mL x 4). The extracted organic layer was washed with brine and then dried with anhydrous magnesium sulfate. The dried organic layer was filtered and concentrated in vacuum. The residue was purified by silica gel EPO fast column chromatography with an eluent of 0-50% ethyl acetate/hexane gradient mixture. The target fractions were collected and the filtrate was concentrated in vacuum to give a solid product. The solid was washed with hexane to give a final 2,4-dichloro-6-aminophenol (30.6 g, 172 mmol, 60% yield) as a colorless powder. The product was confirmed by 1H NMR (CDCl3): δ 3.92 (s, 2H), 5.36 (s, 1H), 6.59 (d, J = 2.1Hz, 1H), 6.71 (d, J = 2.1Hz, 1H). Results of mass spectrometry analysis: MS Calcd.: 177; MS measured value: 178 (M + H).

Purification Methods

Crystallise the phenol from CS2 or *benzene. It sublimes at 0.06mm. The hydrochloride has m 280-285o from EtOH. [Meyer Helv Chim Acta 41 1890 1958, Beilstein 13 II 185, 13 III 856, 13 IV 889.]

References

[1] Liebigs Annalen der Chemie, 1994, # 3, p. 269 - 276
[2] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 14, p. 1923 - 1928
[3] Patent: WO2008/51533, 2008, A2. Location in patent: Page/Page column 79-80
[4] Patent: US2002/156081, 2002, A1
[5] Patent: US6921763, 2005, B2

2-AMINO-4,6-DICHLOROPHENOL(527-62-8)Related Product Information

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