| Identification | More | [Name]
2-Bromo-5-thiazolecarboxylic acid | [CAS]
54045-76-0 | [Synonyms]
2-BROMO-1,3-THIAZOLE-5-CARBOXYLIC ACID
2-BROMO-5-THIAZOLECARBOXYLIC ACID
2-BROMOTHIAZOLE-5-CARBOXYLIC ACID
RARECHEM AL BE 1435
2-BROMO-5-THLAZOLECARBOXYLIC ACID
2-Bromo-1,3-thiazole-5-carboxylic acid 97%
2-BROMOTHAIZOLE-5-CARBOXYLIC ACID | [EINECS(EC#)]
626-804-7 | [Molecular Formula]
C4H2BrNO2S | [MDL Number]
MFCD04115730 | [Molecular Weight]
208.03 | [MOL File]
54045-76-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
182 °C (dec.)
| [Boiling point ]
350.0±15.0 °C(Predicted) | [density ]
2.062±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
2.52±0.10(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C4H2BrNO2S/c5-4-6-1-2(9-4)3(7)8/h1H,(H,7,8) | [InChIKey]
BESGTWHUMYHYEQ-UHFFFAOYSA-N | [SMILES]
S1C(C(O)=O)=CN=C1Br | [CAS DataBase Reference]
54045-76-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R43:May cause sensitization by skin contact. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29341000 |
| Hazard Information | Back Directory | [Chemical Properties]
White to brown solid | [Uses]
2-Bromothiazole-5-carboxylic acid is used as a reagent to synthesize azole-based protein kinase B inhibitors, some of which have anti-cancer properties. | [Synthesis]
General procedure for the synthesis of 2-bromothiazole-5-carboxylic acid from ethyl 2-bromothiazole-5-carboxylate: an aqueous solution (100 mL) of sodium hydroxide (4.1 g, 102 mmol) was added slowly and dropwise at 0 °C to a solution of tetrahydrofuran (THF, 100 mL) of ethyl 2-bromothiazole-5-carboxylate (20 g, 84.7 mmol). The reaction mixture was stirred continuously at 10 °C for 1 hour. Subsequently, the reaction mixture was neutralized with 6 M hydrochloric acid and extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-bromothiazole-5-carboxylic acid (17.7 g, 100% yield) as a yellow solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6) with chemical shift δ 8.21 (s, 1H). | [References]
[1] Patent: WO2015/116663, 2015, A1. Location in patent: Paragraph 0103
[2] Patent: US2011/92475, 2011, A1. Location in patent: Page/Page column 14
[3] Helvetica Chimica Acta, 1954, vol. 37, p. 2057,2064
[4] Patent: US6066639, 2000, A |
|
|