2-(BROMOMETHYL)-1,3-BENZOTHIAZOLE

2-(BROMOMETHYL)-1,3-BENZOTHIAZOLE Property

Melting point:

47 °C

Boiling point:

288℃

Density 

1.680

Flash point:

128℃

storage temp. 

Inert atmosphere,2-8°C

pka

0.38±0.10(Predicted)

form 

crystalline powder

color 

Pale yellow

CAS DataBase Reference

106086-78-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,C,Xn

Risk Statements 

34-41-37/38-22

Safety Statements 

26-36/37/39-36/37/3945-39

RIDADR 

3261

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

2934208090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

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

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

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P405Store locked up.

2-(BROMOMETHYL)-1,3-BENZOTHIAZOLE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2-(bromomethyl)benzothiazole using 2-hydroxymethylbenzothiazole as starting material was as follows: 2-hydroxymethylbenzothiazole (1.00 g, 6.05 mmol) was dissolved in an appropriate amount of CH2Cl2 according to Attardo's method 1. Phosphorus tribromide (1.15 mL, 12.1 mmol) was slowly added dropwise to the above solution under argon protection. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent ratio hexane:ethyl acetate = 5:1) to afford 2-(bromomethyl)benzothiazole (786 mg, 57% yield) as a brown solid. The structure of the product was confirmed by the following characterization data: 1H NMR (300 MHz, CDCl3) δ 4.81 (s, 2H), 7.42 (td, 1H, J = 8.1 Hz, 1.1 Hz), 7.50 (td, 1H, J = 8.1 Hz, 1.1 Hz), 7.87 (dd, 1H, J = 8.1 Hz, 1.1 Hz), 8.02 ( dd, 1H, J = 8.1 Hz, 1.1 Hz); 13C NMR (75 MHz, CDCl3) δ 27.1, 121.8, 123.5, 125.9, 126.5, 136.2, 152.8, 166.2; mass spectrometry (EI) showed molecular ion peaks at m/z 227, 229 (M+); and thin-layer chromatography (TLC) showed Rf value of 0.60 (unfolding agent ratio of hexane:ethyl acetate=5:1).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 1, p. 43 - 45
[2] Patent: WO2017/66606, 2017, A1. Location in patent: Page/Page column 95; 96
[3] Journal of the American Chemical Society, 2017, vol. 139, # 21, p. 7318 - 7334
[4] Patent: WO2018/191394, 2018, A1. Location in patent: Page/Page column 135-136
[5] Zhurnal Obshchei Khimii, 1951, vol. 21, p. 2055,2056, 2061; engl. Ausg. S. 2295, 2301