| Identification | More | [Name]
4-Chloronicotinic acid | [CAS]
10177-29-4 | [Synonyms]
4-CHLORO-3-PYRIDINECARBOXYLIC ACID
4-CHLORONICOTINIC ACID
4-CHLOROPYRIDINE-3-CARBOXYLIC ACID
IFLAB-BB F1926-0029
4-Chloro-3-pyridinecarboxylic
4-CHLORONICOTINIC ACID,99%
4-Choronicotinic acid
4-Chloronicotinic acid ,97% | [EINECS(EC#)]
628-434-1 | [Molecular Formula]
C6H4ClNO2 | [MDL Number]
MFCD00128860 | [Molecular Weight]
157.55 | [MOL File]
10177-29-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
139-143 °C | [Boiling point ]
301.9±22.0 °C(Predicted) | [density ]
1.470±0.06 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [solubility ]
Soluble in organic solvents at 20 deg C | [form ]
powder | [pka]
0.78±0.25(Predicted) | [color ]
White | [Detection Methods]
HPLC | [BRN ]
9255849 | [InChI]
1S/C6H4ClNO2/c7-5-1-2-8-3-4(5)6(9)10/h1-3H,(H,9,10) | [InChIKey]
IMRGVWZLCZERSQ-UHFFFAOYSA-N | [SMILES]
OC(=O)c1cnccc1Cl | [CAS DataBase Reference]
10177-29-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H319 | [Precautionary statements ]
P264-P280-P305+P351+P338-P337+P313 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT, KEEP COLD | [PackingGroup ]
III | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light brown solid | [Uses]
Building block used in a synthesis of benzocanthinones via tributyltin hydride radical induced cyclization. Also used in a synthesis of heterocyclic analogues of xanthone. | [Uses]
4-Chloronicotinic Acid is a building block used in a synthesis of benzocanthinones via tributyltin hydride radical induced cyclization. It is also used in a synthesis of heterocyclic analogues of xanthone. | [Synthesis]
1. Neutralization reaction: Neutralize 4-chloropyridine hydrochloride using 10% NaOH solution to obtain 4-chloropyridine (1).
2. lithiation reaction: 4-chloropyridine (1) (15 mmol) was dissolved in THF (250 ml) under nitrogen protection, cooled to -78 °C, and 1.2 equivalents of lithium diisopropylammonium was slowly added (1.5 M hexane solution containing 1 equivalent of THF, ALDRICH).
3. carboxylation reaction: the resulting anion is reacted with dry CO? to produce 4-chloropyridine-3-carboxylic acid (3, i.e. 4-chloronicotinic acid).
4. Isolation and purification: The reaction mixture was treated and isolated to obtain 4-chloronicotinic acid as a colorless solid in 60-80% yield. | [References]
[1] Journal of Organic Chemistry, 1995, vol. 60, # 2, p. 292 - 296
[2] Patent: US2011/53975, 2011, A1. Location in patent: Page/Page column 60
[3] Patent: WO2009/87238, 2009, A2. Location in patent: Page/Page column 97; 98-99
[4] Patent: WO2005/21546, 2005, A1. Location in patent: Page/Page column 124-125
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1869 - 1879 |
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