| Identification | More | [Name]
2-Chlorobenzothiazole | [CAS]
615-20-3 | [Synonyms]
2-BENZOTHIAZOLYL CHLORIDE
2-CHLORO-1,3-BENZOTHIAZOLE
2-CHLOROBENZO[D]THIAZOLE
2-CHLOROBENZOTHIAZOLE
2-Chlorobenzophiazole
2-chloro-benzothiazol
USAF ek-2784
usafek-2784
Benzothiazole, 2-chloro-(6CI,7CI,8CI,9CI)
2-Chlorobenzothiazole,98+%
2-CHLOROBENZOTHIOAZOLE
Benzothiazole, 2-chloro-
2-Chlorbenzothiazol | [EINECS(EC#)]
210-415-0 | [Molecular Formula]
C7H4ClNS | [MDL Number]
MFCD00005776 | [Molecular Weight]
169.63 | [MOL File]
615-20-3.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR YELLOW TO YELLOW-BROWNISH LIQUID | [Melting point ]
21-23 °C (lit.) | [Boiling point ]
141 °C/30 mmHg (lit.) | [density ]
1.303 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.637(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid | [pka]
-0.23±0.10(Predicted) | [color ]
Clear yellow to yellow-brownish | [Specific Gravity]
1.3711.303 | [Water Solubility ]
insoluble | [BRN ]
116316 | [InChI]
1S/C7H4ClNS/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H | [InChIKey]
BSQLQMLFTHJVKS-UHFFFAOYSA-N | [SMILES]
Clc1nc2ccccc2s1 | [CAS DataBase Reference]
615-20-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzothiazole, 2-chloro-(615-20-3) | [EPA Substance Registry System]
615-20-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS07,GHS06 | [Signal word ]
Warning | [Hazard statements ]
H302-H301 | [Precautionary statements ]
P264-P270-P301+P312+P330-P501-P301+P310a-P321-P405-P501a | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
2810 | [WGK Germany ]
3
| [RTECS ]
DL3150000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [REACH Registrations]
Inactive | [HS Code ]
29342080 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Inhalation
Acute Tox. 3 Oral
Aquatic Chronic 2
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR YELLOW TO YELLOW-BROWNISH LIQUID | [Uses]
2-Chloro-1,3-benzothiazole is used in the synthesis of CBTs which are good building blocks for bioluminescent compounds for imaging. | [Synthesis]
The general procedure for the synthesis of 2-chlorobenzothiazole from benzothiazole was as follows: benzothiazole (1 mmol, 135.9 mg) and carbon tetrachloride (1.1 mmol, 169.2 mg) were placed in a 10 mL round bottom flask. 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg) were added to the reaction system and stirred thoroughly to ensure that the reactants were homogeneously mixed. The reaction was carried out at room temperature for 3 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was poured into water and extracted with dichloromethane. The organic phase was separated and dried with anhydrous sodium sulfate. Subsequently, the dichloromethane was removed by rotary evaporator to obtain the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate as eluent (30:1, v/v). 2-Chlorobenzothiazole (brown oily liquid, 149.2 mg) was finally obtained in 88% yield. | [Purification Methods]
It is purified by fractional distillation in vacuo. The 2-chloro-3-methylbenzothiazolinium 2,4-dinitrobenzenesulfonate crystallises from Ac2O, m 162-163o(dec). [Young & Amstutz J Am Chem Soc 73 4773 1951, Brower et al. J Org Chem 19 1830 1954, Hunter & Jones J Chem Soc 2190 1930, Beilstein 27 H 44, 27 II 18, 27 III/IV 1072.] | [References]
[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 6, p. 886 - 890
[2] Patent: CN107501023, 2017, A. Location in patent: Paragraph 0063; 0064
[3] Organic Letters, 2009, vol. 11, # 2, p. 421 - 423
[4] Journal of Organic Chemistry, 2009, vol. 74, # 21, p. 8309 - 8313
[5] Chemische Berichte, 1880, vol. 13, p. 16 |
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