Methyl 4-bromopyrrole-2-carboxylate Chemical Properties

Melting point:

100-101°C

Boiling point:

290.5±20.0 °C(Predicted)

Density 

1.674±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

13.49±0.50(Predicted)

color 

White to Orange to Green

λmax

271nm(MeOH)(lit.)

InChI

InChI=1S/C6H6BrNO2/c1-10-6(9)5-2-4(7)3-8-5/h2-3,8H,1H3

InChIKey

ZXFCRVGOHJHZNF-UHFFFAOYSA-N

SMILES

N1C=C(Br)C=C1C(OC)=O

CAS DataBase Reference

934-05-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

29339900

Methyl 4-bromopyrrole-2-carboxylate Usage And Synthesis

Chemical Properties

Off-white powder

Uses

4-Bromo-1H-pyrrole-2-carboxylic Acid Methyl Ester is a useful synthetic intermediate. It is used to synthesize potent melanin-concentrating hormone (MCH-R1) antagonists based on pyrazolopiperazinone.

Synthesis

Example 1C. Synthesis of 4-bromo-2-methoxycarbonylpyrrole: To a solution of methanol (100 mL) containing 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroacetophenone (20 g, 68 mmol) was added slowly and dropwise sodium methanol (1M solution in methanol, 34 mL, 34 mmol). The reaction mixture was stirred at room temperature for 1 hour and then diluted with water (300 mL) to separate the organic layer. The aqueous phase was extracted with dichloromethane (CH2Cl2), and the combined organic layer and extract were washed with water (2 x 50 mL), dried over anhydrous magnesium sulfate (MgSO4), and concentrated under reduced pressure. The residue was recrystallized by hexane to give 4-bromo-2-methoxycarbonylpyrrole (12 g, 85% yield) as a white solid.LC-MS analysis showed [M-H]+ peak at 203.1.1.1H NMR (DMSO-d6, 400 MHz) data were as follows: δ 12.31 (broad single peak, 1H), 7.16 (single peak, 1H), 6.81 (single peak, 1H ), 3.75 (single peak, 3H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4412 - 4418
[2] Patent: WO2010/42682, 2010, A1. Location in patent: Page/Page column 50
[3] Patent: US2006/293320, 2006, A1. Location in patent: Page/Page column 25; 35

Methyl 4-bromopyrrole-2-carboxylate(934-05-4)Related Product Information

• Acetonitrile
• Methyl 4-(bromomethyl)benzoate
• Polyvinylpyrrolidone
• Pyrrolidine
• RESMETHRIN
• N-Vinyl-2-pyrrolidone
• Methyl acrylate
• N-Methyl-2-pyrrolidone
• Methanol
• Methyl 2-bromo-2-methylpropionate
• Kresoxim-methyl
• Methylparaben
• Paraquat dichloride
• Methyl bromoacetate
• Basic Violet 1
• Methyl 2-bromobenzoate
• methyl 3-bromopyrazine-2-carboxylate
• Methyl