[ CAS No. 13509-19-8 ] {[proInfo.proName]}

Name: 13509-19-8|4-Nitropicolinic acid|98%
Brand: Ambeed
SKU: A109851
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Quality Control of [ 13509-19-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13509-19-8 ]

SDS Specification

Alternatived Products of [ 13509-19-8 ]

Product Details of [ 13509-19-8 ]

CAS No. :	13509-19-8	MDL No. :	MFCD00191562
Formula :	C₆H₄N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	USTVSOYPMQZLSA-UHFFFAOYSA-N
M.W :	168.11	Pubchem ID :	2762825
Synonyms :

Calculated chemistry of [ 13509-19-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.02
TPSA :	96.01 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.34
Log Po/w (XLOGP3) :	0.54
Log Po/w (WLOGP) :	0.69
Log Po/w (MLOGP) :	-2.16
Log Po/w (SILICOS-IT) :	-1.37
Consensus Log Po/w :	-0.39

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.46
Solubility :	5.82 mg/ml ; 0.0346 mol/l
Class :	Very soluble
Log S (Ali) :	-2.13
Solubility :	1.25 mg/ml ; 0.00745 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.77
Solubility :	28.4 mg/ml ; 0.169 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 13509-19-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13509-19-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 13509-19-8 ]
Downstream synthetic route of [ 13509-19-8 ]

[ 13509-19-8 ] Synthesis Path-Upstream 1~6

1
[ 19235-88-2 ]
[ 13509-19-8 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With sodium sulfite In ice-water; sulfuric acid; water	III-2-2: Synthesis of 4-nitropicolinic acid A solution of 5.00 g (34 mmol) of 2-cyano-4-nitropyridine dissolved in 50 g of 90percent sulfuric acid was stirred at 120° C. for 2 hours. Then, at 20° to 25° C., a solution of 5.60 g of sodium sulfite in 10 ml of water was dropwise added, and the mixture was stirred at the same temperature for one hour, and further, at 80° C. for one hour under heating. After cooling, 100 g of ice-water was added, and the mixture was adjusted to a pH of about 2 with sodium carbonate. The mixture was left to stand in a refrigerator, resulting in precipitation of the solid. The solid was collected by filtration and recrystallized from a water-acetone mixture to obtain 3.50 g of pale yellow crystals (yield 62.1percent). m.p.: 157°-158° C. (decompd.). IR (KBr): 1710, 1600, 1585, 1535 cm^-1.

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 47, p. 19366 - 19369
[2] Patent: US5219847, 1993, A,
[3] Journal of Organometallic Chemistry, 1997, vol. 544, # 2, p. 163 - 174

2
[ 13508-96-8 ]
[ 13509-19-8 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3167

3
[ 18437-58-6 ]
[ 13509-19-8 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3167

4
[ 1124-33-0 ]
[ 13509-19-8 ]

Reference： [1] Journal of Organometallic Chemistry, 1997, vol. 544, # 2, p. 163 - 174
[2] Journal of the American Chemical Society, 2012, vol. 134, # 47, p. 19366 - 19369

5
[ 694-59-7 ]
[ 13509-19-8 ]

Reference： [1] Journal of Organometallic Chemistry, 1997, vol. 544, # 2, p. 163 - 174

6
[ 67-56-1 ]
[ 13509-19-8 ]
[ 29681-41-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	at 25℃; for 18 h;	Methyl 4-nitropicolinate (1f) was prepared in 65percent yield by esterification of 4-nitropicolinic acid using catalytic conc. H2SO4 in dry MeOH at 25°C for 18 h. A solution of methyl 4-nitro-2-picolinate (1f) (1.0 g, 6.62 mmol) and acetone (0.195 mL,2.65 mmol) in DME (5 mL) was added dropwise to a stirred suspensionof NaH (60percent suspension in oil, 0.5 g, 13.23 mmol) in DME (5 mL) under an atmosphere of argon at room temperature. Stirringat 30°C for 2 h or 18 h followed by refluxing the mixture for 2 h did not result in the evolution of gas and work up resulted in recoveryof starting material.

Reference： [1] Tetrahedron, 2014, vol. 70, # 45, p. 8520 - 8531

[ 13509-19-8 ] Synthesis Path-Downstream 1~88

1
[ 13509-19-8 ]
[ 14933-78-9 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 155,158

2
[ 4418-61-5 ]
[ 13509-19-8 ]
[ 83282-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-carbonyldiimidazole;	EXAMPLE 28 0.48 g of <strong>[13509-19-8]4-nitro-2-pyridinecarboxylic acid</strong>, 0.48 g of N,N'-carbonyldiimidazole and 0.27 g of 5-aminotetrazole are treated in the same manner as described in Example 2. The crude product thus obtained is recrystallized from ethanol, whereby 0.38 g of N-(5-tetrazolyl)-4-nitro-2-pyridinecarboxamide is obtained. M.p. 250-270 C. (decomp.) Sodium salt: M.p. 260-280 C. (decomp.)

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 125 - 128
[2]Patent: US4404214,1983,A

3
[ 19235-88-2 ]
[ 13509-19-8 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With sodium sulfite; In ice-water; sulfuric acid; water;	III-2-2: Synthesis of 4-nitropicolinic acid A solution of 5.00 g (34 mmol) of 2-cyano-4-nitropyridine dissolved in 50 g of 90% sulfuric acid was stirred at 120 C. for 2 hours. Then, at 20 to 25 C., a solution of 5.60 g of sodium sulfite in 10 ml of water was dropwise added, and the mixture was stirred at the same temperature for one hour, and further, at 80 C. for one hour under heating. After cooling, 100 g of ice-water was added, and the mixture was adjusted to a pH of about 2 with sodium carbonate. The mixture was left to stand in a refrigerator, resulting in precipitation of the solid. The solid was collected by filtration and recrystallized from a water-acetone mixture to obtain 3.50 g of pale yellow crystals (yield 62.1%). m.p.: 157-158 C. (decompd.). IR (KBr): 1710, 1600, 1585, 1535 cm-1.

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 19366 - 19369
[2]Patent: US5219847,1993,A
[3]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174

4
[ 13509-19-8 ]
[ 541-41-3 ]
C₉H₈N₂O₆ [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 7143 - 7146

5
[ 13509-19-8 ]
4-nitro-pyridine-2-carboxylic acid methyl-pyridin-2-yl-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 7143 - 7146

6
[ 13509-19-8 ]
4-amino-pyridine-2-carboxylic acid thiazol-2-ylamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 635 - 638

7
[ 13509-19-8 ]
4-benzylamino-pyridine-2-carboxylic acid thiazol-2-ylamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 635 - 638

8
[ 13509-19-8 ]
4-{2-[(4-nitro-pyridine-2-carbonyl)-amino]-phenoxy}-phthalic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4125 - 4128

9
[ 13509-19-8 ]
4-{4-fluoro-2-[(4-nitro-pyridine-2-carbonyl)-amino]-phenoxy}-phthalic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4125 - 4128

10
[ 13509-19-8 ]
4-{3-fluoro-2-[(4-nitro-pyridine-2-carbonyl)-amino]-phenoxy}-phthalic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4125 - 4128

11
[ 694-59-7 ]
[ 13509-19-8 ]

Reference： [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174

12
[ 1124-33-0 ]
[ 13509-19-8 ]

Reference： [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174
[2]Journal of the American Chemical Society,2012,vol. 134,p. 19366 - 19369

13
C₆H₇N₂O₃⁽¹⁺⁾*CH₃O₄S^(1-) [ No CAS ]
[ 13509-19-8 ]

Reference： [1]Journal of Organometallic Chemistry,1997,vol. 544,p. 163 - 174

14
[ 13509-19-8 ]
[ 62150-49-6 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 155,158

15
[ 13509-19-8 ]
[ 35895-54-6 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 155,158

16
[ 13509-19-8 ]
[ 90048-09-2 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 155,158

17
[ 13509-19-8 ]
[ 98142-21-3 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 155,158

18
[ 18437-58-6 ]
[ 13509-19-8 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 3167

19
[ 13509-19-8 ]
zinc(II) acetate tetrahydrate [ No CAS ]
zinc 4-nitropicolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.2%	In ethanol; water;	III-2-3: Synthesis of zinc 4-nitropicolinate To a solution of 2.00 g (12 mmol) of <strong>[13509-19-8]4-nitropicolinic acid</strong> dissolved in 150 ml of ethanol at 70 C. was dropwise added a solution of 1.30 g (5.9 mmol) of zinc acetate.dihydrate dissolved in 5 ml of water. After the dropwise addition, the mixture was stirred at the same temperature for one hour. The solid obtained after leaving the mixture to stand in a refrigerator for 3 days was collected by filtration, and recrystallized from water to obtain 2.05 g of pale yellow crystals (yield 79.2%). m.p.: 258-269 C. IR (KBr): 3250, 1665, 1580, 1525, 1350 cm-1. Elemental analysis: for 312 H6 N4 O8 Zn.2H2 O Calcd. C 33.09 H 2.31 N 12.86. Found C 33.11 H 2.27 N 12.65.

Reference： [1]Patent: US5219847,1993,A

20
[ 13509-19-8 ]
[ 57260-73-8 ]
[ 530-62-1 ]
[ 103878-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	EXAMPLE 2 6.0 g of <strong>[13509-19-8]4-nitro-2-pyridinecarboxylic acid</strong> were stirred at 60 bath temperature for 4 hours in 300 ml of absolute tetrahydrofuran and 5.9 g of 1,1'-carbonyldiimidazole. Thereafter, 6.0 g of t-butyl (2-aminoethyl)carbamate were added thereto and the mixture was heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure and thereafter partitioned between ethyl acetate and water. The combined organic phases were dried over magnesium sulfate and concentrated. The residue was crystallized from ethyl acetate, whereby there was obtained t-butyl [2-(4-nitropyridine-2-carboxamido)ethyl]carbamate as white crystals, m.p. 130-131.

Reference： [1]Patent: US4764522,1988,A

21
[ 13509-19-8 ]
[ 1158975-01-9 ]
[ 1254364-60-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5839 - 5842

22
[ 13509-19-8 ]
[ 1414851-44-7 ]