diMethyl 5-broMopyridine-2,3-dicarboxylate

diMethyl 5-broMopyridine-2,3-dicarboxylate Property

Boiling point:

315.0±37.0 °C(Predicted)

Density 

1.569±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-3.18±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H8BrNO4/c1-14-8(12)6-3-5(10)4-11-7(6)9(13)15-2/h3-4H,1-2H3

InChIKey

JYRYOIMMYLBBNZ-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=C(Br)C=C1C(OC)=O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

diMethyl 5-broMopyridine-2,3-dicarboxylate Chemical Properties,Usage,Production

Synthesis

Concentrated sulfuric acid (10 mL) was slowly added to a methanolic (500 mL) suspension of 2,3-pyridinedicarboxylic acid (50 g, 300 mmol). The reaction mixture was heated to reflux for 48 hours and subsequently cooled to 40 °C and bromine (38 mL, 750 mmol) was added slowly and dropwise over 2 hours. The reaction mixture was continued to be heated at 55 °C for 48 h, followed by vacuum concentration. The concentrated residue was dissolved in isopropyl acetate (500 mL), and the resulting solution was washed sequentially with saturated aqueous sodium thiosulfate (200 mL x 4) and brine (400 mL), dried over anhydrous sodium sulfate, filtered, and concentrated again under vacuum. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, v/v=5/1) to afford dimethyl 5-bromo-pyridine-2,3-dicarboxylate as a yellow solid (52 g, 63% yield). Mass spectrum (ESI, positive ion mode) m/z: 274.0 [M + H]+; 1H NMR (400 MHz, CDCl3) δ (ppm): 8.75-8.76 (d, J = 2.2 Hz, 1H), 8.23-8.24 (d, J = 2.2 Hz, 1H), 3.93 (s, 3H), 3.89 (s, 3H).

References

[1] Patent: WO2014/89324, 2014, A1. Location in patent: Paragraph 0284
[2] Patent: CN104016979, 2017, B. Location in patent: Paragraph 0800; 0801; 0802; 0803
[3] Patent: US2012/122899, 2012, A1. Location in patent: Page/Page column 18
[4] Patent: WO2012/129013, 2012, A1. Location in patent: Page/Page column 29-30
[5] Patent: WO2013/169563, 2013, A1. Location in patent: Page/Page column 69; 70