[ CAS No. 499-81-0 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 499-81-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 499-81-0 ]

SDS Specification

Alternatived Products of [ 499-81-0 ]

Product Details of [ 499-81-0 ]

CAS No. :	499-81-0	MDL No. :	MFCD00006393
Formula :	C₇H₅NO₄	Boiling Point :	-
Linear Structure Formula :	(HOOC)₂C₅H₃N	InChI Key :	MPFLRYZEEAQMLQ-UHFFFAOYSA-N
M.W :	167.12	Pubchem ID :	10366
Synonyms :

Calculated chemistry of [ 499-81-0 ] Expand+

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 :	2.0
Molar Refractivity :	38.16
TPSA :	87.49 ?2

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) :	-7.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.21
Log Po/w (XLOGP3) :	-0.1
Log Po/w (WLOGP) :	0.48
Log Po/w (MLOGP) :	-1.47
Log Po/w (SILICOS-IT) :	0.12
Consensus Log Po/w :	-0.15

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.05
Solubility :	14.9 mg/ml ; 0.0889 mol/l
Class :	Very soluble
Log S (Ali) :	-1.28
Solubility :	8.68 mg/ml ; 0.0519 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.77
Solubility :	28.7 mg/ml ; 0.172 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.22

Safety of [ 499-81-0 ]

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

Application In Synthesis of [ 499-81-0 ]

* 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 [ 499-81-0 ]
Downstream synthetic route of [ 499-81-0 ]

[ 499-81-0 ] Synthesis Path-Upstream 1~1

1
[ 499-81-0 ]
[ 20730-07-8 ]

Reference： [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699

[ 499-81-0 ] Synthesis Path-Downstream 1~7

1
[ 67-56-1 ]
[ 499-81-0 ]
[ 4591-55-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sulfuric acid; for 18h;Reflux;	2,6-Pyridine dicarboxylic acid (5.00 g, 29.92 mmol) was dissolved in MeOH (100 ml) and concentrated sulfuric acid (2 ml) was slowly added thereto and refluxed for 18 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the mixture was extracted with sodium bicarbonate and dichloromethane. The dichloromethane layer was washed with a saturated sodium chloride aqueous solution to obtain 5.5 g (94%) of compound l1
89%	With thionyl chloride; at 0℃; for 4h;Inert atmosphere; Reflux;	To a precooled (0 C) solution of pyridine-3,5-dicarboxylic acid (10.0 g, 59.8 mmol) in MeOH (100 mL) under N2 atmosphere was slowly added thionyl chloride (13 mL, 180 mmol). The resulting mixture was allowed to warm to room temperature then heated to reflux and stirred for 4 h. The mixture was then allowed to cool to room temperature and concentrated in vacuo. The resulting white solid was taken up in H2O and the aqueous solution was cooled (0 C) then neutralized with 10 M aq. NaOH (white ppt formed). The heterogenous mixture was diluted with EtOAc and the bisphasic solution was stirred for 5 min. The layers were separated, and the aqueous phase was extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the product as a white solid (10.4 g, 89% yield).1H NMR (500 MHz, Chloroform-d) d 9.35 (d, J = 2.1 Hz, 2H), 8.85 (t, J = 2.1 Hz, 1H), 3.98 (s, 6H); 13C NMR (126 MHz, CDCl3) d 165.05, 154.37, 138.19, 126.15, 52.85; IR (ATR) vmax 3074, 2966, 1713, 1445, 1312, 1256, 1108, 979, 745 cm-1; AMM (ESI) m/z 196.0600 [calc for C9H10NO4 (M+H)+ 196.0610].
82.0%	With sulfuric acid; at 50 - 65℃;	4) To a mixture of pyridine-3,5-dicarboxylic acid (110 g, 0.66 mol) and methanol (660 mL) was added dropwise conc. sulfuric acid (226.0 g, 2.30 mol) at 50 C. or lower. Thereafter, the mixture was heated to 55-65 C. and stirred for 7 hr. The reaction mixture was allowed to cool to 40-50 C., and water (220 mL) was added. Furthermore, 5% aqueous ammonia (about 1.10 L) was added dropwise at 40-50 C. to adjust the mixture to pH 8.0-8.5. After stirring at 40-50 C. for 30 min, the mixture was cooled to 0-10 C. and stirred for 1 hr. The precipitated crystals were collected by filtration, washed successively with methanol-water (1:3, 165 mL) and water (440 mL), and dried under reduced pressure at 50 C. to give dimethyl pyridine-3,5-dicarbonate as a white crystalline powder (105.0 g, yield 82.0%). 1H-NMR (300 MHz, CDCl3) delta 4.00 (s, 6H), 8.87 (s, 1H), 9.37 (s, 2H). Anal. Calcd for C9H9NO4: C, 55.39; H, 4.65; N, 7.18; O, 32.79. Found: C, 55.42; H, 4.65; N, 7.16.

	With sulfuric acid; In methanol; at 120℃; for 2h;Microwave irradiation;	A: Pyridine-3,5-dicarboxylic acid dimethyl ester 3,5-Pyridinedicarboxylic acid (1.5 g, 63 mmol) and conc. H2SO4 (0.9 mL) in MeOH (15 mL) are heated in a microwave oven at 120 C. for 2 h. The solvent is evaporated to give a residue which is partitioned between ethyl acetate and sat. aq. NaHCO3. The organic phase is washed with brine, dried over Na2SO4, filtered and evaporated to give a light yellow solid. MS (LC-MS): 196 [M+H]+ TLC, Rf (ethyl acetate/hexane 1:1)=0.56.
		3,5-Pyridinedicarboxylic acid (1.5 g, 63 mmol) and conc. H2SO4 (0.9 mL) in MeOH (15 mL) are heated in a microwave oven at 120 C. for 2 h. The solvent is evaporated to give a residue with is partitioned between ethyl acetate and sat. aq. NaHCO3. The organic phase is washed with brine, dried over Na2SO4, filtered and evaporated to give a light yellow solid. MS (LC-MS): 196 [M+H]+ TLC, Rf (ethyl acetate/hexane 1:1)=0.56.
	With thionyl chloride; at 10 - 35℃;Reflux;	Reference Example 1dimethyl pyridine-3,5-dicarboxylate Pyridine-3,5-dicarboxylic acid (25.5 g) was suspended in methanol (184 ml), and thionyl chloride (33.8 ml) was added dropwise at room temperature. The reaction mixture was stirred with heating under reflux for 3 hr, and the mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was diluted with water, and the mixture was extracted with ethyl acetate. The aqueous layer was neutralized with 8M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the object product (27.9 g) as a powder.1H-NMR (CDCl3) delta 4.00 (6H, s), 8.88(1H, t), 9.37(2H, d)
		Reference Example 33 dimethyl pyridine-3,5-dicarboxylate [Show Image] Pyridine-3,5-dicarboxylic acid (100 g) was suspended in methanol (1000 ml), and thionyl chloride (130 ml) was added dropwise at room temperature. The reaction mixture was stirred with heating to reflux for 3 hr. The mixture was allowed to cool to room temperature, and concentrated under reduced pressure. The residue was diluted with water, and the mixture was extracted with ethyl acetate. The aqueous layer was neutralized with 8 M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the object compound (117 g) as a powder. 1H-NMR (CDCl3) delta 4.00 (6H, s), 8.88 (1H, t), 9.37 (2H, d).
	With thionyl chloride; at 60℃; for 12h;	Dimethyl pyridine-3,5-dicarboxylateTo a solution of pyridine-3,5-dicarboxylic acid (85.0 g, 508.62 mmol) in MeOH (1 L) was added SOCl2 (61.80 g, 519.46 mmol) dropwise. The reaction mixture was stirred and heated to 60 C for 12 hr. The reaction mixture was concentrated under vacuum to afford the title compound (120.00 g, crude) as a white solid.
		3,5-Pyridinedicarboxylic acid (1.5g, 63 mmol) and cone. H2SO4 (0.9 mL) in MeOH (15 mL) are heated in a microwave oven at 120C for 2 h. The solvent is evaporated to give a residue with is partitioned between ethyl acetate and sat. aq. NaHCO3. The organic phase is washed with brine, dried over Na2SO4, filtered and evaporated to give a light yellow solid. MS (LC-MS): 196 [M+H]+ TLC, Rf (ethyl acetate/hexane 1 :1 ) = 0.56.

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 933 - 938
[2]Patent: KR2018/9249,2018,A .Location in patent: Paragraph 0250; 0251
[3]Angewandte Chemie - International Edition,2004,vol. 43,p. 3914 - 3918
[4]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 2397 - 2400
[5]Patent: WO2020/28482,2020,A1 .Location in patent: Paragraph 0025
[6]Life Sciences,2005,vol. 78,p. 495 - 505
[7]Chemical Communications,2011,vol. 47,p. 4547 - 4549
[8]Patent: US2013/90337,2013,A1 .Location in patent: Paragraph 0086; 0087; 0088
[9]Organic Letters,2004,vol. 6,p. 1033 - 1036
[10]European Journal of Organic Chemistry,2003,p. 4406 - 4412
[11]Angewandte Chemie - International Edition,2014,vol. 53,p. 11660 - 11664
Angew. Chem.,2014,vol. 126,p. 11846 - 11850,5
[12]Journal of the Chemical Society. Perkin transactions I,1990,p. 101 - 103
[13]Phytochemistry,1984,vol. 23,p. 1225 - 1228
[14]Patent: US2008/319018,2008,A1 .Location in patent: Page/Page column 17
[15]Patent: US2009/233920,2009,A1 .Location in patent: Page/Page column 83; 86
[16]Patent: US2010/137587,2010,A1 .Location in patent: Page/Page column 48
[17]Patent: EP2202228,2010,A1 .Location in patent: Page/Page column 90
[18]Photochemistry and Photobiology,2013,vol. 89,p. 1020 - 1028
[19]Dalton Transactions,2013,vol. 42,p. 16255 - 16258
[20]Patent: WO2015/58163,2015,A2 .Location in patent: Paragraph 355
[21]European Journal of Medicinal Chemistry,2016,vol. 108,p. 415 - 422
[22]Patent: WO2006/117183,2006,A1 .Location in patent: Page/Page column 134-135

2
[ 499-81-0 ]
[ 4591-55-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	With thionyl chloride; sodium chloride; sodium hydrogencarbonate; In methanol;	[Step 1] Synthesis of dimethyl pyridine-3,5-dicarboxylate Pyridine-3,5-dicarboxylic acid (8.3 g) was suspended in anhydrous methanol (60 ml), and thionyl chloride (11 ml) was added dropwise at room temperature. The mixture was heated under reflux for 1.5 hours in an argon atmosphere and allowed to cool. The solvent was evaporated under reduced pressure, and extracted with water-ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound (7.5 g, 78%). m.p.: 83.5-84.5 C. IR spectrum (KBr tab.) nucm-1: 1734, 1603, 1315, 1269, 1240, 995, 746. NMR spectrum (*DMSO-d6) delta ppm: 9.30 (2H, s), 8.66 (1H, s), 3.93 (6H, s).

Reference： [1]Patent: US6018046,2000,A
[2]Journal of Materials Chemistry,2002,vol. 12,p. 173 - 180
[3]Patent: WO2008/10964,2008,A1

3
[ 499-81-0 ]
[ 143131-66-2 ]
[ 7732-18-5 ]
silver nitrate [ No CAS ]
[(silver(I))8(pyridine-3,5-dicarboxylate)4(1,4-bis(1,2,4-triazol-1-ylmethyl)benzene)4]*8H₂O [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2009,vol. 362,p. 5023 - 5030

4
[ 499-81-0 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[ 143131-66-2 ]
[cadmium(II)(μ-H2O)2(pyridine-2,6-dicarboxylate)2(1,4-bis(1,2,4-triazol-1-ylmethyl)benzene)] [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2009,vol. 362,p. 5023 - 5030

5
[ 499-81-0 ]
zinc(II) nitrate hexahydrate [ No CAS ]
[ 7732-18-5 ]
[ 69506-85-0 ]
[Zn(1,3-bis(imidazolyl)propane)(pyridine-3,5-dicarboxylate)]·2H2O}n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	at 120℃; for 72h;High pressure; Autoclave;	A mixture of 3,5-pdc (0.10 mmol,16.7 mg), 1,3-<strong>[69506-85-0]bip</strong> (0.10 mmol, 17.6 mg) and Zn(NO3)2.6H2O (0.10 mmol, 30.8 mg) in distilled water (15 mL) was placed in a Teflon-lined stainless steel vessel, heated to 120 C for 3 days, and then cooled to room temperature over 24 h. Colourless block crystals of 1 were obtained. Yield 51%. Anal calcd for C16H19N5O6Zn (Mr = 442.72): C, 43.38; H, 4.29; N, 15.81; found: C, 43.24; H, 3.96; N, 15.90%. IR(cm-1): 3455 (s), 3125 (m),2934 (w), 1668 (s), 1627 (s), 1530 (m), 1353(s),1247 (w), 1103 (s), 946 (w), 835 (w).

Reference： [1]Journal of Chemical Research,2014,vol. 38,p. 726 - 730

6
[ 499-81-0 ]
[ 3452-97-9 ]
C₂₅H₄₁NO₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 3080 - 3090

7
[ 4591-55-3 ]
[ 499-81-0 ]
[ 5027-65-6 ]

Yield	Reaction Conditions	Operation in experiment
		3,5-<strong>[4591-55-3]dimethyl pyridine-3,5-dicarboxylate</strong> (500 mg, 2.56 mmol) was dissolved in methanol (2 ml_) and 1 M NaOH (2.56 ml_, 2.56 mmol) was slowly added. The resulting yellow solution was stirred for 15 mins at RT, then organic solvent was evaporated and the aqueous residue was acidified to pH 2 and extracted with DCM (4 x). Material detected in aqueous phase, therefore aqueous and organic phase were combined and concentrated affording 5- (methoxycarbonyl)pyridine-3-carboxylic acid (561 mg) as yellow solid. Presence of -10% of starting material and 10% dicarboxylic acid detected. Used as such in the next step.

Reference： [1]Patent: WO2016/67043,2016,A1 .Location in patent: Page/Page column 150

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Isomers

Technical Information

? Arndt-Eistert Homologation ? Hunsdiecker-Borodin Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction

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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 499-81-0 ] {[proInfo.proName]}

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