| Identification | More | [Name]
Ethyl 5-bromonicotinate | [CAS]
20986-40-7 | [Synonyms]
3-PYRIDINECARBOXYLIC ACID, 5-BROMO-, ETHYL ESTER
5-BROMONICOTINIC ACID ETHYL ESTER
AURORA KA-3028
ETHYL 5-BROMO-3-PYRIDINECARBOXYLATE
ETHYL 5-BROMONICOTINATE
ETHYL 5-BROMOPYRIDINE-3-CARBOXYLATE
TIMTEC-BB SBB005820
Ethyl 5-bromopyridine-3-carboxylic acid
Ethyl-5-Bromonicotinate98%
5-Bromonicotinicacidethylester~Ethyl5-bromopyridine-3-carboxylate
5-Bromo Nitinic Acid Ethyl Ester
5-Bromonicotinic acid ethyl ester 97%
Ethyl 5-bromonicotinate 97%
5-BROMONICOTIC ACID ETHYL ESTER
Ethyl 5-Bromonicotinic acid ethyl ester
5-Bromopyridine-3-carboxylic acid ethyl ester | [EINECS(EC#)]
674-614-8 | [Molecular Formula]
C8H8BrNO2 | [MDL Number]
MFCD00040366 | [Molecular Weight]
230.06 | [MOL File]
20986-40-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystal powder | [Melting point ]
39-42 °C
| [Boiling point ]
86-92°C 0,5mm | [density ]
1.501±0.06 g/cm3(Predicted) | [Fp ]
86-92°C/0.5mm | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
solid | [pka]
0.94±0.20(Predicted) | [color ]
Red/brown | [Detection Methods]
HPLC,NMR | [BRN ]
131473 | [InChI]
InChI=1S/C8H8BrNO2/c1-2-12-8(11)6-3-7(9)5-10-4-6/h3-5H,2H2,1H3 | [InChIKey]
PCPIANOJERKFJI-UHFFFAOYSA-N | [SMILES]
C1=NC=C(Br)C=C1C(OCC)=O | [CAS DataBase Reference]
20986-40-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
white crystal powder | [Uses]
Ethyl 5-bromonicotinate is used as a key starting material for the preparation of 5-bromonicotinic acid hydrazide via reaction with a hydrazine hydrate. | [Application]
Ethyl 5-bromonicotinate is a carboxylate derivative and can be used as a pharmaceutical intermediate. | [Synthesis]
a) Synthesis of ethyl 5-bromonicotinate: Concentrated H2SO4 (9.0 mL) was slowly added dropwise to an ethanol (30.0 mL) suspension of 5-bromonicotinic acid (3.00 g, 14.9 mmol) under stirring, with the dropwise addition time controlled over 5 minutes until a clarified solution was formed. Subsequently, the reaction mixture was heated to reflux for 22 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction was quenched with water (30 mL) and then extracted with dichloromethane (75 mL). The organic layer was washed sequentially with 10% Na2CO3 solution (20 mL) and water (20 mL), dried over anhydrous MgSO4, and concentrated by filtration through a sintered glass funnel to give 2.8 g of ethyl 5-bromonicotinate as a white solid in 82% yield. The structure of the product was confirmed by 1H NMR (CDCl3): δ 9.13 (d, J = 1.7 Hz, 1H), 8.84 (d, J = 2.2 Hz, 1H), 8.42 (m, J = 2.2, 1.7 Hz, 2H), 4.40 (q, J = 7.1 Hz, 2H), 1.43 (t, J = 7.1 Hz, 3H). | [References]
[1] Patent: WO2008/151073, 2008, A1. Location in patent: Page/Page column 39-40; 44
[2] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4115 - 4121
[3] Patent: US2016/375131, 2016, A1. Location in patent: Paragraph 0080
[4] ACS Combinatorial Science, 2017, vol. 19, # 5, p. 286 - 298
[5] Organic Preparations and Procedures International, 1992, vol. 24, # 2, p. 143 - 146 |
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