METHYL THIOSALICYLATE

METHYL THIOSALICYLATE Property

Melting point:

164 °C

Boiling point:

98-100 °C/2 mmHg (lit.)

Density 

1.223 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.591(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

5.84±0.43(Predicted)

form 

Liquid

Specific Gravity

1.223

color 

Clear colorless to light yellow or light green

Sensitive 

Air Sensitive

Stability:

Air Sensitive

InChI

InChI=1S/C8H8O2S/c1-10-8(9)6-4-2-3-5-7(6)11/h2-5,11H,1H3

InChIKey

BAQGCWNPCFABAY-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC=C1S

CAS DataBase Reference

4892-02-8(CAS DataBase Reference)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

DH3500000

HazardClass 

IRRITANT

HS Code 

29309090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

METHYL THIOSALICYLATE Chemical Properties,Usage,Production

Chemical Properties

clear colorless to light yellow or light green

Uses

Methyl 2-Mercaptobenzoate (cas# 4892-02-8) is a compound useful in organic synthesis.

Uses

Methyl thiosalicylate may be used:

• in the synthesis of thioxanthone, an efficient enantioselective organocatalyst for the intramolecular [2+2] photocycloaddition reaction
• as anionic bidentate ligand, in the preparation of ′2+1′ type complexes of [(99m)Tc]-tricarbonyltechnetium(I) and [(188)Re]-tricarbonylrhenium(I)
• in the synthesis of a series of benzisothiazolone derivatives
• in the synthesis of a new fused benzoheterocyclic compound, [1]benzothieno[3,2-b]furan

General Description

Methyl thiosalicylate may be benefecial in preventing mercury-induced toxicity.

Synthesis

Example 1: Preparation of methyl 2-[6-(1-bromo-ethyl)-5-fluoropyrimidin-4-yl-thioalkyl]benzoate (Preparation of compounds of formula 2 with o-CO2CH3 substitution); Step 1) Preparation of methyl 2-mercaptobenzoate: 40 g of 2-mercaptobenzoic acid was dissolved in 600 mL of methanol, and cooled to 5°C. 42 mL of concentrated sulfuric acid was added slowly and dropwise over a 10 minute period. The reaction mixture was reacted under reflux conditions for 14 hours and then concentrated under reduced pressure. The concentrate was diluted with 400 mL of dichloromethane and 400 mL of pure water and the organic layer was subsequently separated. The organic layer was washed sequentially with 200 mL of saturated sodium bicarbonate solution and 400 mL of saturated brine, and then dried with anhydrous sodium sulfate. After drying, the organic layer was concentrated to give the crude product, which was further purified by fractional distillation (118°C/7 mmHg). Finally, 42 g (yield: 96%) of methyl thiosalicylate was obtained as a clear oil.1H-NMR (200 MHz, CDCl3) δ (ppm): 8.01 (d, 1H), 7.30 (d, 2H), 7.14 (m, 1H), 4.68 (s, 1H), 3.91 (s, 3H).

References

[1] Patent: EP2444398, 2012, A2. Location in patent: Page/Page column 9
[2] Tetrahedron, 2017, vol. 73, # 13, p. 1745 - 1761
[3] Patent: WO2013/64231, 2013, A1. Location in patent: Page/Page column 62
[4] Journal of Medicinal Chemistry, 2018,
[5] Patent: US2007/167497, 2007, A1. Location in patent: Page/Page column 28