Ethyl 5-bromonicotinate Chemical Properties

Melting point:

39-42 °C

Boiling point:

86-92°C 0,5mm

Density 

1.501±0.06 g/cm3(Predicted)

Flash point:

86-92°C/0.5mm

storage temp. 

Inert atmosphere,2-8°C

pka

0.94±0.20(Predicted)

form 

solid

color 

Red/brown

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-3637/39

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl 5-bromonicotinate Usage And Synthesis

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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