| Identification | More | [Name]
2,4-Dibromothiazole | [CAS]
4175-77-3 | [Synonyms]
2,4-BROMOTHIAZOLE
2,4-DIBROMOTHIAZOLE
2,4-Dibromo-1,3-thiazole
2,4-DIBROMOTHIAZOLE 98%
2,4-Dibromothiazole ,98%
2,4-DIBROMOTHIAZOLE, 97+%
2,4-Dibrmothiazole | [EINECS(EC#)]
629-026-6 | [Molecular Formula]
C3HBr2NS | [MDL Number]
MFCD01318994 | [Molecular Weight]
242.92 | [MOL File]
4175-77-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white crystalline powder | [Melting point ]
80-84 °C | [Boiling point ]
242.8±13.0 °C(Predicted) | [density ]
2.324±0.06 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
-1.93±0.10(Predicted) | [color ]
White to Light yellow | [Detection Methods]
HPLC | [InChI]
InChI=1S/C3HBr2NS/c4-2-1-7-3(5)6-2/h1H | [InChIKey]
MKEJZKKVVUZXIS-UHFFFAOYSA-N | [SMILES]
S1C=C(Br)N=C1Br | [CAS DataBase Reference]
4175-77-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
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 .
S39:Wear eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [Hazard Note ]
Harmful | [HazardClass ]
IRRITANT, KEEP COLD | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white crystalline powder | [Uses]
2,4-Dibromothiazole is an intermediate used in the preparation of various 2,4-disubstituted thiazole derivatives with biologically active properties such as survival motor neuron (SMN) protein modula
tors. | [Synthesis]
General procedure for the synthesis of 2,4-dibromothiazoles from 2,4-thiazolidinediones:
Example 41: Preparation of 2-amino-3-methyl-5-(3-pyrimidin-5-ylphenyl)-5-(1,3-thiazol-4-yl)-3,5-dihydro-4H-imidazol-4-one
Step a) Preparation of compound 2
A mixture of 2,4-thiazolidinedione 1 (2.28 g, 19.5 mmol) with phosphorus tribromide (25.0 g, 87.0 mmol) was heated at 130°C for 30 min and subsequently cooled to room temperature. The reaction mixture was diluted with ice water (300 mL) and neutralized by batchwise addition of solid sodium carbonate. After neutralization was complete, the mixture was extracted with dichloromethane (3 x 150 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by fast column chromatography (silica gel, elution gradient: 0:100 to 5:95 ethyl acetate/hexane) to afford compound 2 (3.34 g, 71%) as light yellow crystals.1H NMR (500 MHz, CDCl3) δ 7.21 (s, 1H). | [References]
[1] Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3754 - 3761
[2] Synthesis, 2012, vol. 44, # 7, p. 1026 - 1029
[3] Journal of Materials Chemistry C, 2017, vol. 5, # 45, p. 11927 - 11936
[4] Patent: US2007/4786, 2007, A1. Location in patent: Page/Page column 21
[5] Tetrahedron, 2006, vol. 62, # 38, p. 9017 - 9037 |
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