10-METHYLPHENOTHIAZINE Chemical Properties

Melting point:

99-101 °C (lit.)

Boiling point:

341.6±12.0 °C(Predicted)

Density 

1.1168 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

0.56±0.20(Predicted)

color 

White to Light yellow

Water Solubility 

Insoluble in water.

λmax

310nm(CHCl3)(lit.)

InChI

InChI=1S/C13H11NS/c1-14-10-6-2-4-8-12(10)15-13-9-5-3-7-11(13)14/h2-9H,1H3

InChIKey

QXBUYALKJGBACG-UHFFFAOYSA-N

SMILES

C1=C2C(SC3=C(N2C)C=CC=C3)=CC=C1

CAS DataBase Reference

1207-72-3(CAS DataBase Reference)

EPA Substance Registry System

10H-Phenothiazine, 10-methyl- (1207-72-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HS Code 

2934.30.5000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

10-METHYLPHENOTHIAZINE Usage And Synthesis

Chemical Properties

slightly yellow to pale green crystalline powder

Uses

They are used in pharmaceutical manufacturing especially antipsychotic drugs. Also used as a stabilizer against polymerization of acrylates.

Definition

ChEBI: 10-methylphenothiazine is a member of phenothiazines.

Synthesis

General procedure for the synthesis of 10-methylphenothiazine from phenothiazine and iodomethane: NaH (60% purity, 1.0 g, 25.1 mmol) was slowly added to a 50 ml round-bottomed flask containing DMF (10 ml) under ice-water bath conditions. Iodomethane (1.3 g, 11.04 mmol) and phenothiazine (2 g, 10.0 mmol) were then added sequentially. The reaction mixture was transferred to room temperature and stirred for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction was quenched by addition of water and extracted with dichloromethane (50 ml x 3). The organic phases were combined and dried with magnesium sulfate and subsequently concentrated to remove the solvent. Purification by silica gel column chromatography afforded the target product 10-methylphenothiazine (2.1 g, white solid) with a melting point of 96 °C in 97% yield.

Purification Methods

Recrystallise it (three times) from EtOH to give the -form (prisms). Recrystallisation from EtOH/*benzene gives the .-form (needles). It has also been purified by vacuum sublimation and is carefulmax 255nm (log 4.60) (pH 6.3) and 255nm in hexane. [Cymerman-Craig & Warburton Aust J Chem 9 294 1956, Beilstein 27 II 33, 27 III/IV 1215.]

References

[1] Molecular Crystals and Liquid Crystals, 2010, vol. 520, p. 36 - 43
[2] Patent: CN106045986, 2016, A. Location in patent: Paragraph 0039; 0040; 0041
[3] Patent: CN106045987, 2016, A. Location in patent: Paragraph 0039; 0040; 0041
[4] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1053 - 1056
[5] ACS Chemical Neuroscience, 2017, vol. 8, # 4, p. 798 - 806

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