5-Bromopyridine-2-carboxylic acid
- Iupac Name：5-bromopyridine-2-carboxylic acid
- CAS No.: 30766-11-1
- Molecular Weight：202.00546
- Modify Date.: 2022-11-22 16:50
- Introduction: 5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate. Store in cool, dry place in a well sealed container. Store away from oxidizing agents.
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1. Names and Identifiers
- 1.1 Name
- 5-Bromopyridine-2-carboxylic acid
- 1.2 Synonyms
2-Pyridinecarboxylic acid, 5-bromo- 5-Bromo-2- Pyridinecarboxylic Acid 5-bromo-2-carboxypyridine 5-bromo-2-picolinic acid 5-bromo-2-pyridine carboxlic acid 5-bromo-2-pyridinecarboxlic acid 5-Bromo-2-pyridinecarboxylic acid 5-bromoisonicotinic acid 5-Bromopicolinic Acid 5-bromo-picolinic acid 5-Bromo-pyridine-2-carboxylic acid 5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER 5-Brom-pyridin-2-carbonsaeure METHYL 5-BROMO-2-PYRIDINECARBOXYLATE METHYL 5-BROMOPICOLINATE MFCD04112493
- 1.3 CAS No.
- 30766-11-1
- 1.4 CID
- 608544
- 1.5 EINECS(EC#)
- 640-263-4
- 1.6 Molecular Formula
- C6H4BrNO2 (isomer)
- 1.7 Inchi
- InChI=1S/C6H4BrNO2/c7-4-1-2-5(6(9)10)8-3-4/h1-3H,(H,9,10)
- 1.8 InChkey
- MNNQIBXLAHVDDL-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC(=NC=C1Br)C(=O)O
- 1.10 Isomers Smiles
- C1=CC(=NC=C1Br)C(=O)O
2. Properties
- 2.1 Density
- 1.813
- 2.1 Melting point
- 173-175°C
- 2.1 Boiling point
- 319.5°Cat760mmHg
- 2.1 Refractive index
- 1.617
- 2.1 Flash Point
- 147 °C
- 2.1 Precise Quality
- 200.94300
- 2.1 PSA
- 50.19000
- 2.1 logP
- 1.54230
- 2.1 Solubility
- Soluble in methanol.
- 2.2 Appearance
- White to off-white Powder
- 2.3 Storage
- Ambient temperatures.
- 2.4 Chemical Properties
- white Cryst 5-Bromopyridine-2-carboxylic acid Preparation Products And Raw materials Raw materials
- 2.5 Color/Form
- Pale-yellow to Yellow-brown Solid
- 2.6 pKa
- 3.41±0.10(Predicted)
- 2.7 Water Solubility
- soluble in methanol.
- 2.8 StorageTemp
- Keep in dark place,Sealed in dry,Room Temperature
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- 4.1.7 Toluene (114 mL) was cooled to -78 °C, n-BuLi (79.7 mL, 127 mmol) was added dropwise at the same temperature followed by 2, 5-dibromopyridine (30 g, 120 mmol) in toluene (60 mL) and stirred for 2 h. The Reaction mixture was bubbled with dry carbon dioxide gas for 1 h at -78 °C. Progress of the reaction was monitored by TLC. On completion of the reaction, reaction contents were warmed to room temperature and toluene was distilled under reduced pressure. Then water (200 mL) was added to the reaction mixture and filtered on celite bed. The filtrate was acidified with diluted HCI solution, solid was precipitated out which was filtered and dried over sodium sulphate to yield 5-bromopicolinic acid (12 g, 47 percent yield) as a brown colored solid.Step 1 General procedure: Ester (FAE, 4a-m, 2a or 2b) (500 mg scale, 1 equiv.) was dissolvedin 6 ml THF at 0 °C in a 25 ml round-bottom flask. ThenNaOH(aq) (5 equiv.) was added dropwise and stirred for 15 h atroom temperature. After starting materials were consumed (byTLC), water (20 ml) was added. The reaction mixture was washedwith ethyl acetate (2 x 20 ml). The aqueous solution was acidified(pH 2-3) with 1 M HCl(aq) causing precipitation of a solid, whichwas filtered and dried under vacuum. Recrystallization in ethanolafford clean compound.Preparation 245-Bromopyridine-2-carboxylic acidAdd 5-bromopicolinonitrile (1 g, 5.46 mmol) to concentrated HC1 (13.4 mL, 139.66 mmol) in a round bottomed flask. Heat the mixture to reflux with stirring overnight. Cool the mixture to room temperature. Filter the resulting white solid, washing with water. Dry the solid under reduced pressure to give 5-bromopyridine-2- carboxylic acid (0.707 g, 64percent) as a white solid. LC-ES/MS m/z 202 [M+H]
- 3.2 Usage
- 5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate. Store in cool, dry place in a well sealed container. Store away from oxidizing agents.
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- 24/25-36-26
- 4.1 Hazard Class
- IRRITANT
- 4.1 Hazard Declaration
- H315
- 4.1 Caution Statement
- P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
30766-11-1Total: 18 Synthesis Route
8. Other Information
- 8.0 Uses
-
5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate. Store in cool, dry place in a well sealed container. Store away from oxidizing agents.
- 8.1 Chemical Properties
- white Cryst
- 8.2 Usage
- 5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate.
9. Computational chemical data
- Molecular Weight: 202.00546g/mol
- Molecular Formula: C6H4BrNO2
- Compound Is Canonicalized: True
- XLogP3-AA: 1.4
- Exact Mass: 200.94254
- Monoisotopic Mass: 200.94254
- Complexity: 140
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 50.2
- Heavy Atom Count: 10
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBiMAAAEAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHgBACAABqAjBlgQ8iJIIEgCoATT3TASCgCA3AiQI2CG4bPgKJvLAlbGEcQhkwAHY25eYSAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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