2-Amino-6-chlorobenzothiazole

2-Amino-6-chlorobenzothiazole Property

Melting point:

199-201 °C (lit.)

Boiling point:

344.3±34.0 °C(Predicted)

Density 

1.4750 (rough estimate)

refractive index 

1.6100 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

Crystalline Powder

pka

3.30±0.10(Predicted)

color 

Off-white to light beige

CAS DataBase Reference

95-24-9(CAS DataBase Reference)

NIST Chemistry Reference

2-Amino-6-chlorobenzothiazole(95-24-9)

EPA Substance Registry System

2-Benzothiazolamine, 6-chloro- (95-24-9)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

DL1575000

Hazard Note 

Harmful/Irritant

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29349990

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

2-Amino-6-chlorobenzothiazole Chemical Properties,Usage,Production

Chemical Properties

off-white to light beige crystalline powder

General Description

2-amino-6-chloro-benzothiazole on microwave irradiation in the presence of 1-butyl-3-methylimidazolium and inorganic anions yields fluorinated benzothiazolo[2,3-b]quinazoline-2H-ones analogues. It has synergistic effect on inhibitive performance of propargyl alcohol during corrosion of mild steel in boiling HCl solution.

Synthesis

GENERAL METHOD: A solution of 4-chloroaniline (2 mmol) in acetonitrile (15 ml) was added to a solution of potassium thiocyanate (8 mmol) in acetonitrile (15 ml). Subsequently, 0.06 g (30 mol% BF3) of BF3/SiO2 nanoparticles was added to the mixture, which was then placed in an ice salt bath and mechanically stirred for 30 min. Next, a solution of bromine (4 mmol, 0.2 ml) in acetonitrile (3 ml) was slowly added through a dropping funnel, controlling the rate of addition to ensure that the reaction temperature did not exceed 0 °C. After the addition of bromine, the reaction mixture continued to be stirred at room temperature for 4 h, during which the progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was poured into water and heated to 70 °C on a steam bath followed by thermal filtration to remove the catalyst. The recovered catalyst was washed with acetone and reused. The filtrate was neutralized with 10% NaOH solution and the resulting precipitate was collected by filtration, dried and recrystallized from ethanol (10 ml) to give the target product 2-amino-6-chlorobenzothiazole. All 2-aminobenzothiazole products were characterized by physical and spectroscopic data including comparison with real samples. Spectral data of selected products: 6-bromo-1,3-benzothiazol-2-amine (2e) is a yellow solid; yield = 93%; melting point = 202-204 °C (literature value mp = 203 °C); FT-IR (KBr) ν/cm?1: 3315, 3012, 2835, 1580, 1476, 1261, 920, 742, 512; 1H NMR (400 MHz. CDCl3) δ ppm: 5.44 (s, 2H, NH2), 7.4-7.5 (d, 2H, Ar-H), 7.71 (s, 1H, Ar-H); 13C NMR (100MHz, DMSO-d6) δ ppm: 119, 120.9, 125.15, 126.07, 133.1, 152.15, 167.75.

References

[1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222
[2] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 7855 - 7868
[3] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9312 - 9320
[4] Patent: CN108623537, 2018, A. Location in patent: Paragraph 0104; 0105
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 6, p. 818 - 825