3-PIPERIDINOPHENOL

3-PIPERIDINOPHENOL Property

Melting point:

123-124 °C

Boiling point:

338.9±25.0 °C(Predicted)

Density 

1.106±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

10.37±0.10(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-PIPERIDINOPHENOL Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 3-piperidinylphenol from hexahydropyridine and m-bromophenol: N-(3-hydroxyphenyl)piperidine Pd(OAc)2 (129 mg, 0.578 mmol) was added to a mixture of piperidine (2.95 g, 34.68 mmol) and 3-bromophenol (5.00 g, 28.90 mmol). Under nitrogen protection, 2,8,9-tri-tert-butyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (397 mg, 1.16 mmol), LiHMDS (66.5 cm3, 1 M in THF), and anhydrous toluene (110 cm3) were added sequentially. The reaction mixture was heated to 80 °C, maintained for 18 h and subsequently cooled to room temperature. Water (50 cm3) was added for partitioning and the aqueous layer was extracted with toluene (3 x 30 cm3). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. Purification by column chromatography [eluent ratio 3:7 ethyl acetate/hexane (Rf = 0.4)] gave an off-white solid product (2.56 g, 50% yield). NMR hydrogen spectrum (250 MHz, CDCl3) δH: 7.11-7.04 (1H, m, aryl ring H), 6.52 (1H, d, J = 8 Hz, aryl ring H), 6.35 (1H, s, aryl ring H), 6.29 (1H, d, J = 8 Hz, aryl ring H), 5.84 (1H, bs, OH), 3.08 (4H, t, J = 5 Hz , 2 × CH2), 1.75-1.62 (4H, m, 2 × CH2), 1.60-1.50 (2H, m, CH2); NMR carbon spectra (62.5 MHz, CDCl3) δC: 156.7, 153.4, 130.0, 109.3, 107.4, 104.6, 51.0, 25.5, 24.2; IR spectra ( KBr) νmax/cm?1: 3064, 2959, 2937, 2921, 2856, 1597, 1503, 1454, 1276, 1201, 1133, 1104, 971, 877; mass spectra (ESI) m/z: 178.12 (100%, [M + H]+).

References

[1] Advanced Synthesis and Catalysis, 2004, vol. 346, # 6, p. 611 - 616
[2] Patent: WO2010/67078, 2010, A2. Location in patent: Page/Page column 91
[3] Chemistry - A European Journal, 2009, vol. 15, # 12, p. 2742 - 2746
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 22, p. 7107 - 7117