| Identification | More | [Name]
2-Amino-6-chlorobenzothiazole | [CAS]
95-24-9 | [Synonyms]
2-AMINO-6-CHLOROBENZOTHIAZOLE
6-CHLORO-1,3-BENZOTHIAZOL-2-AMINE
6-CHLORO-BENZOTHIAZOL-2-YLAMINE
IFLAB-BB F1386-0399
LABOTEST-BB LT00012588
TIMTEC-BB SBB000249
2-amino-6-chloro-benzothiazol
2-Benzothiazolamine, 6-chloro-
6-chloro-2-benzothiazolamin
Benzothiazole, 2-amino-6-chloro-
2-Amino-6-chloro-1,3-benzothiazole
6-Chlorobenzo[d]thiazol-2-amine
2-Amino-6-Chlorolbenzothiazole
2-Benzothiazolamine,6-chloro-(9CI)
6-Chloro-1,3-benzothiazol-2-ylamine
6-Chloro-2-benzothiazolamine
6-Chloro-2-benzothiazolylamine
6-Chlorobenzothiazol-2-amine | [EINECS(EC#)]
202-402-3 | [Molecular Formula]
C7H5ClN2S | [MDL Number]
MFCD00053557 | [Molecular Weight]
184.65 | [MOL File]
95-24-9.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
DL1575000
| [Hazard Note ]
Harmful/Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [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 |
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