| Identification | More | [Name]
2-Cyano-6-methoxybenzothiazole | [CAS]
943-03-3 | [Synonyms]
2-BENZOTHIAZOLECARBONITRILE, 6-METHOXY-
2-CYANO-6-METHOXYBENZOTHIAZOLE
2-CYANO-6-METHOXYBENZOTIAZOLE
6-METHOXY-1,3-BENZOTHIAZOLE-2-CARBONITRILE
6-METHOXY-2-BENZOTHIAZOLE-CARBONITRILE
6-METHOXY-BENZOTHIAZOLE-2-CARBONITRILE
NSC 377382
6-Methoxy-2-cyanobenzothiazole
2-Benzothiazolecarbonitrile,6-methoxy-(7CI,8CI,9CI)
2-cyano-6-methoxy benzothiozale
2-CYANO-6-METHOXY BENZOTHIAZOLE 98% | [EINECS(EC#)]
231-439-8 | [Molecular Formula]
C9H6N2OS | [MDL Number]
MFCD00010537 | [Molecular Weight]
190.22 | [MOL File]
943-03-3.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light yellow crystalline powder | [Melting point ]
129-131 °C (lit.) | [Boiling point ]
334.9±34.0 °C(Predicted) | [density ]
1.2938 (rough estimate) | [refractive index ]
1.6800 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
chloroform: soluble5%, clear, colorless to faintly yellow | [form ]
Crystalline Powder | [pka]
-1.49±0.10(Predicted) | [color ]
Off-white to light yellow | [InChI]
InChI=1S/C9H6N2OS/c1-12-6-2-3-7-8(4-6)13-9(5-10)11-7/h2-4H,1H3 | [InChIKey]
DEWDWBYQOFXKIH-UHFFFAOYSA-N | [SMILES]
S1C2=CC(OC)=CC=C2N=C1C#N | [CAS DataBase Reference]
943-03-3(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Uses]
2-Cyano-6-methoxybenzothiazole is a key intermediate in the synthesis of fireflys’ luciferol, the light emitting chemical. Also a reactant in the preparation of 1,2,4-Oxadiazole EthR inhibitors used in the effort to improve the sensitivity of the human pathogen mycobacterium tuberculosis. |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302+H312+H332-H315-H319-H335 | [Precautionary statements ]
P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and 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 .
S36:Wear suitable protective clothing .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3439 | [WGK Germany ]
3
| [HS Code ]
29341000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
2-Cyano-6-methoxybenzothiazole is a building block for synthesis of luciferins. | [Chemical Properties]
off-white to light yellow crystalline powder | [Synthesis]
Typical routes to 2-cyano-6-methoxybenzothiazole include the classical Rosenmund-von Braun and Sandmeyer reactions. These methods proceed with low atom economy and require toxic reagents such as KCN, NaCN, Zn(CN)2, or TMSCN, which are also challenging to handle in a large-scale synthesis. Shahmoradi et al. introduced a Cu-catalyzed cyanation of 2-iodo-6-methoxybenzothiazole to synthesize 2-cyano-6-methoxybenzothiazole. K4[Fe(CN)6] was applied as a source of cyanide, and CuI in the presence of N, N N′, N′-tetramethylethylenediamine (TMEDA) was used as part of the catalyst system. 2-Amino-6-methoxybenzothiazole as a starting material was synthesized from p-anisidine as shown below and subsequently converted into 2-iodo-6-methoxybenzothiazole using a simple and efficient one-pot sequential diazotization-iodination method. The one-pot cyanation of 2-iodo-6-methoxybenzothiazole to 2-cyano-6-methoxybenzothiazole was achieved using 0.25 mmol of K4[Fe(CN)6], 0.25 mmol of CuI and 3 mmol of TMEDA in acetonitrile at 160°C. In addition, 1 mmol of mystril trimethyl bromide (MTMAB) was used as a phase transfer agent. The presence of a phase-transfer catalyst is essential for a successful cyanation reaction. Under these conditions, 2-cyano-6-methoxybenzothiazole was produced in a 90% yield[1].
| [References]
[1] Ghasem Shahmoradi, S. Amani. “Synthesis, characterization and computational studies of 2-cyano-6-methoxybenzothiazole as a firefly-luciferin precursor.” Heterocyclic Communications 24 1 (2018): 255–258. |
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