2-Amino-6-chlorobenzothiazole Chemical Properties

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 Information

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

MSDS

• Language:English Provider:2-Amino-6-chlorobenzothiazole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2-Amino-6-chlorobenzothiazole Usage And Synthesis

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

2-Amino-6-chlorobenzothiazole (95-24-9)Related Product Information

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• EC 2.6.1.2
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• Aniline
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• Epichlorohydrin
• ALTRENOGEST
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