4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
- Product Name
- 4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
- CAS No.
- 29681-42-3
- Chemical Name
- 4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
- Synonyms
- METHYL 4-BROMOPICOLINATE;METHYL 4-BROMOPYRIDINE-2-CARBOXYLATE;Picolinic acid, 4-bro;Methyl 4-broMopyridine-2-...;METHYL 4-BROMO-2-PYRIDINECARBOXYLATE;Picolinic acid, 4-bromo-, methyl ester;4-BROMO-PYRIDINE-2-CARBOXYLIC ACID MET;Methyl 4-bromopyridine-2-carboxylate 97%;Methyl 4-broMopyridine-2-carboxylate, 97+%;4-Bromo-2-pyridinecarboxylic acid methyl ester
- CBNumber
- CB9200016
- Molecular Formula
- C7H6BrNO2
- Formula Weight
- 216.03
- MOL File
- 29681-42-3.mol
4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER Property
- Melting point:
- 54-56
- Boiling point:
- 286.0±20.0 °C(Predicted)
- Density
- 1.579±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,2-8°C
- pka
- -0.25±0.10(Predicted)
- form
- Solid
- Appearance
- Off-white to light yellow Solid
- Water Solubility
- Slightly soluble in water.
- InChI
- InChI=1S/C7H6BrNO2/c1-11-7(10)6-4-5(8)2-3-9-6/h2-4H,1H3
- InChIKey
- JZFLATQBIPILFS-UHFFFAOYSA-N
- SMILES
- C1(C(OC)=O)=NC=CC(Br)=C1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- B687255
- Product name
- 4-Bromopyridine-2-carboxylicAcidMethylEster
- Packaging
- 10g
- Price
- $365
- Updated
- 2021/12/16
- Product number
- J95494
- Product name
- Methyl4-bromopicolinate
- Packaging
- 25g
- Price
- $140
- Updated
- 2021/12/16
- Product number
- OR9577
- Product name
- Methyl4-bromopyridine-2-carboxylate
- Purity
- 97%
- Packaging
- 25g
- Price
- $158
- Updated
- 2021/12/16
- Product number
- 057337
- Product name
- Methyl 4-bromopicolinate
- Purity
- 90+%
- Packaging
- 25g
- Price
- $173
- Updated
- 2021/12/16
- Product number
- OR9577
- Product name
- Methyl4-bromopyridine-2-carboxylate
- Purity
- 97%
- Packaging
- 1g
- Price
- $12
- Updated
- 2021/12/16
4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER Chemical Properties,Usage,Production
Chemical Properties
yellow solid
Uses
It finds its application as a useful synthetic intermediate and in the straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals and agrochemicals. It is used in the synthesis of biaryl mannoside FimH inhibitors for use in urinary infection treatment.
Synthesis
600-22-6
19524-06-2
29681-42-3
Methyl 4-bromopyridine-2-carboxylate (147) was synthesized as follows: first, 4-bromopyridine hydrochloride (595 mg, 3.06 mmol) was dissolved in dichloromethane (DCM, 20 mL), washed with saturated aqueous sodium bicarbonate (NaHCO3) (2 × 20 mL), followed by drying and filtration with anhydrous magnesium sulfate (MgSO4). The filtrate was adjusted to 45 mL by the addition of additional DCM, followed by the addition of water (3 mL), iron(II) sulfate heptahydrate (8.51 g, 30.6 mmol) and concentrated sulfuric acid (H2SO4, 0.95 mL, 9.18 mmol). In another flask, methyl pyruvate (4.15 mL, 46 mmol) was treated with hydrogen peroxide (3.5 mL, 30.6 mmol, 30% aqueous solution) in a mixture at -10 °C, which was subsequently added to the above DCM/water mixture under vigorous stirring, keeping the temperature at -10 °C. After 15 min of reaction, the reaction mixture was diluted with ice water (100 mL) and extracted with DCM (4 x 20 mL). The DCM phases were combined and dried with anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under reduced pressure. Purification by column chromatography (gradient elution conditions: first using 10-40% ethyl acetate (EtOAc) in heptane solution containing 0.5% triethylamine, followed by 0-20% EtOAc/heptane containing 0.5% triethylamine) gave the target compound. Yield: 211 mg (32%). lC/MS retention time (tv) 0.98 min. mass spectra (ES+) m/z 218, 216 ([M+H]+).
References
[1] Patent: WO2007/89669, 2007, A2. Location in patent: Page/Page column 199-200
[2] Patent: WO2008/57469, 2008, A1. Location in patent: Page/Page column 288-289
[3] Patent: WO2008/57468, 2008, A1. Location in patent: Page/Page column 288-289
4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER manufacturers
- Product
- 4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER 29681-42-3
- Price
- US $10.00/IU
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 Tons
- Release date
- 2021-10-18
- Product
- 4-BROMO-PYRIDINE-2-CARBOXYLIC ACID METHYL ESTER 29681-42-3
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.00%
- Supply Ability
- 100 Tons min
- Release date
- 2021-08-19
- Product
- Methyl 4-bromopyridine-2-carboxylate 29681-42-3
- Price
- US $0.00-0.00/Kg
- Min. Order
- 1KG
- Purity
- 99.0%
- Supply Ability
- 500 MT
- Release date
- 2020-05-12