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4-Chloronicotinic acid

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Name

4-Chloronicotinic acid

EINECS -0
CAS No. 10177-29-4 Density 1.47 g/cm3
PSA 50.19000 LogP 1.43320
Solubility N/A Melting Point 139-143 °C
Formula C6H4ClNO2 Boiling Point 301.9 °C at 760 mmHg
Molecular Weight 157.556 Flash Point 136.4 °C
Transport Information N/A Appearance yellow powder
Safety 26-36 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 10177-29-4 (4-Chloronicotinic acid) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

4-chloro-3-pyridine carboxylic acid;4-chloro-pyridine-3-carboxylic acid;4-chloro-Nicotinic acid;4-Chloro-3-pyridinecarboxylic acid;4-Chloropyridine-3-carboxylic acid;3-Pyridinecarboxylic acid, 4-chloro-;

Article Data 22

4-Chloronicotinic acid Synthetic route

626-61-9

4-Chloropyridine

124-38-9

carbon dioxide

10177-29-4

4-chloronicotinic acid

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 20 min, 2.) 18 h;96%
Stage #1: 4-Chloropyridine With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran; hexane
80%
Stage #1: 4-Chloropyridine With lithium diisopropyl amide In tetrahydrofuran; hexanes at -78℃; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran; hexanes
Stage #1: 4-Chloropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: carbon dioxide In tetrahydrofuran at -78 - 20℃; Product distribution / selectivity;
Stage #1: 4-Chloropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: carbon dioxide In tetrahydrofuran at -78℃;

lithium; 4-chloro-nicotinate

10177-29-4

4-chloronicotinic acid

Conditions
ConditionsYield
With Amberlyst(R) IR-200 In methanol at 20℃; for 0.25h;75%
1681-36-3

4-chloro-3-methylpyridine

10177-29-4

4-chloronicotinic acid

Conditions
ConditionsYield
With potassium permanganate In water at 80 - 90℃; for 4h;65%
124-38-9

carbon dioxide

10177-29-4

4-chloronicotinic acid

Conditions
ConditionsYield
Stage #1: 4-Chloropyridine With lithium diisopropyl amide In tetrahydrofuran; hexanes at -78℃; for 1h;
Stage #2: carbon dioxide In tetrahydrofuran; hexanes at -78 - 20℃;
61%
Stage #1: 4-Chloropyridine With lithium diisopropyl amide In tetrahydrofuran; hexanes at -78℃; for 1h;
Stage #2: carbon dioxide In tetrahydrofuran; hexanes
61%
124-38-9

carbon dioxide

7379-35-3

4-chlorpyridine hydrochloride

10177-29-4

4-chloronicotinic acid

Conditions
ConditionsYield
Stage #1: 4-chlorpyridine hydrochloride With sodium carbonate In water
Stage #2: With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #3: carbon dioxide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
57%
114077-82-6

4-chloronicotinaldehyde

10177-29-4

4-chloronicotinic acid

Conditions
ConditionsYield
With potassium permanganate In water for 3h; Heating / reflux;56%
With potassium permanganate In water; acetonitrile
609-70-1

4-hydroxynicotinic acid

10177-29-4

4-chloronicotinic acid

Conditions
ConditionsYield
With thionyl chloride anschliessende Hydrolyse;
2398-81-4

Nicotinic acid N-oxide

10026-13-8, 874483-75-7

phosphorus pentachloride

A

2942-59-8

2-chloronicotinic acid

B

10177-29-4

4-chloronicotinic acid

nicotinic acid-1-oxide

nicotinic acid-1-oxide

A

2942-59-8

2-chloronicotinic acid

B

10177-29-4

4-chloronicotinic acid

Conditions
ConditionsYield
With phosphorus pentachloride; trichlorophosphate
59-67-6

nicotinic acid

potassium

potassium

A

10177-29-4

4-chloronicotinic acid

B

Nα-Fmoc-Nim-tert-butyloxycarbonyl-L-tryptophan 4-hydroxymethylphenoxy resin

Nα-Fmoc-Nim-tert-butyloxycarbonyl-L-tryptophan 4-hydroxymethylphenoxy resin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: BuLi; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran; hexane / 0.67 h / -75 - -55 °C
1.2: 79 percent / hexachloroethane / tetrahydrofuran; hexane / -55 - 20 °C
2.1: 75 percent / Amberlyst(R) IR-200 / methanol / 0.25 h / 20 °C
View Scheme

4-Chloronicotinic acid Specification

The IUPAC name of 4-Chloronicotinic acid is 4-chloropyridine-3-carboxylic acid. With the CAS registry number 10177-29-4, it is also named as 3-Pyridinecarboxylic acid, 4-chloro-. The product's categories are Blocks; Carboxes; Pyridines; Pyridines, Pyrimidines, Purines and Pteredines; Pharmacetical; Pyridine Series; Carboxylic Acids; Chiral Chemicals. It is yellow powder which should be sealed in the container and kept cold in the dry place.

The other characteristics of 4-Chloronicotinic acid can be summarized as: (1)ACD/LogP: 0.14; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 39.19 Å2; (11)Index of Refraction: 1.59; (12)Molar Refractivity: 36.16 cm3; (13)Molar Volume: 107.1 cm3; (14)Polarizability: 14.33×10-24 cm3; (15)Surface Tension: 61 dyne/cm; (16)Enthalpy of Vaporization: 57.24 kJ/mol; (17)Vapour Pressure: 0.000454 mmHg at 25°C; (18)Rotatable Bond Count: 1; (19)Exact Mass: 156.993056; (20)MonoIsotopic Mass: 156.993056; (21)Topological Polar Surface Area: 50.2; (22)Heavy Atom Count: 10; (23)Complexity: 140.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing. 

People can use the following data to convert to the molecule structure.
1. SMILES:c1cncc(c1Cl)C(=O)O
2. InChI:InChI=1/C6H4ClNO2/c7-5-1-2-8-3-4(5)6(9)10/h1-3H,(H,9,10)
3. InChIKey:IMRGVWZLCZERSQ-UHFFFAOYAL

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