10-Phenyl-10H-phenothiazine

10-Phenyl-10H-phenothiazine Property

Melting point:

94 °C

Boiling point:

411.2±15.0 °C(Predicted)

Density 

1.247±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Acetone

form 

powder to crystal

pka

-3.48±0.20(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C18H13NS/c1-2-8-14(9-3-1)19-15-10-4-6-12-17(15)20-18-13-7-5-11-16(18)19/h1-13H

InChIKey

WSEFYHOJDVVORU-UHFFFAOYSA-N

SMILES

C1=C2C(SC3=C(N2C2=CC=CC=C2)C=CC=C3)=CC=C1

Safety

HS Code 

2934.30.5000

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.

10-Phenyl-10H-phenothiazine Chemical Properties,Usage,Production

Chemical Properties

light yellow powder

Uses

An organic photo-catalyst used in synthesis of small molecules as well as polymerization reactions.

reaction suitability

reagent type: catalyst
reaction type: Photocatalysis

Synthesis

Phenothiazine (500 mg, 2.50 mmol) was dissolved in anhydrous toluene (5 mL) under nitrogen protection, and iodobenzene (310 mg, 2.2 mmol), sodium tert-butanolate (0.5 mL), and tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 46 mg, 0.05 mmol) were added in sequence. The reaction mixture was transferred to a sealed tube and the reaction was stirred at 160 °C for 16 hours. After completion of the reaction, it was cooled to room temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2 x 15 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate= 20:1) to afford 10-phenylphenothiazine (600 mg, 87.3%) as a white solid with a melting point of 205 °C. Nuclear magnetic resonance hydrogen spectrum (1H-NMR, 300 MHz, acetone-d6): δ 7.70 (t, J = 7.5 Hz, 2H), 7.57 (t, J = 7.2 Hz, 1H), 7.44 (d, J = 7.8 Hz, 2H), 7.06 (d, J = 7.5 Hz, 2H), 6.92 (t, J = 7.2 Hz, 2H), 6.89 (t , J = 7.2 Hz, 2H), 6.23 (d, J = 8.1 Hz, 2H). Nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, acetone-d6): δ 144.98, 141.82, 131.64, 131.37, 129.07, 127.31, 123.37, 120.90, 116.96. The electrospray high-resolution mass spectrometry (ESI-HRMS) m/z calculated value of C18H14NS ([M + H] +) was 276.0841 and the measured value was 276.0842.

References

[1] Chinese Chemical Letters, 2015, vol. 26, # 8, p. 951 - 954
[2] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 1, p. 107 - 111
[3] Patent: CN104478870, 2016, B. Location in patent: Paragraph 0052; 0053; 0054
[4] Journal of Materials Chemistry A, 2017, vol. 5, # 16, p. 7586 - 7594
[5] Applied Organometallic Chemistry, 2017, vol. 31, # 11,