[ CAS No. 216018-58-5 ] {[proInfo.proName]}

Name: 216018-58-5|[2,2':6',2''-Terpyridine]-4,4',4''-tricarboxylic acid|95%
Brand: Ambeed
SKU: A114832
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Quality Control of [ 216018-58-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 216018-58-5 ]

CAS No. :	216018-58-5	MDL No. :	MFCD06796963
Formula :	C₁₈H₁₁N₃O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NTXWAWVRPLVLKC-UHFFFAOYSA-N
M.W :	365.30	Pubchem ID :	11233869
Synonyms :

Calculated chemistry of [ 216018-58-5 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.0
Num. rotatable bonds :	5
Num. H-bond acceptors :	9.0
Num. H-bond donors :	3.0
Molar Refractivity :	91.58
TPSA :	150.57 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-8.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.3
Log Po/w (XLOGP3) :	0.69
Log Po/w (WLOGP) :	2.3
Log Po/w (MLOGP) :	-1.05
Log Po/w (SILICOS-IT) :	1.69
Consensus Log Po/w :	0.99

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.11

Water Solubility

Log S (ESOL) :	-2.7
Solubility :	0.724 mg/ml ; 0.00198 mol/l
Class :	Soluble
Log S (Ali) :	-3.43
Solubility :	0.136 mg/ml ; 0.000372 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.39
Solubility :	0.015 mg/ml ; 0.0000411 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.76

Safety of [ 216018-58-5 ]

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 [ 216018-58-5 ]

* 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 [ 216018-58-5 ]
Downstream synthetic route of [ 216018-58-5 ]

[ 216018-58-5 ] Synthesis Path-Upstream 1~5

1
[ 33354-77-7 ]
[ 216018-58-5 ]

Reference： [1] Journal of the American Chemical Society, 2001, vol. 123, # 8, p. 1613 - 1624
[2] Green Chemistry, 2011, vol. 13, # 12, p. 3337 - 3340

2
[ 33354-75-5 ]
[ 216018-58-5 ]

Reference： [1] Chemical Communications, 1997, # 18, p. 1705 - 1706

3
[ 330680-46-1 ]
[ 216018-58-5 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8702 - 8705

4
[ 98-01-1 ]
[ 25028-32-4 ]
[ 216018-58-5 ]

Reference： [1] Green Chemistry, 2011, vol. 13, # 12, p. 3337 - 3340

5
[ 67-56-1 ]
[ 216018-58-5 ]
[ 330680-46-1 ]

Yield	Reaction Conditions	Operation in experiment
3.42 g	for 6 h; Reflux	2,2 ': 6', 2 "-terpyridyl-4,4 ', 4" -tricarboxylic acid3.65 g (10.0 mmol) of the compound (manufactured by Tateyama Kasei)Was placed in a 500 mL eggplant flask. continue,2,2 ': 6', 2 "-terpyridyl-4,4 ', 4" -tricarboxylic acid,5 mL of concentrated sulfuric acid and 300 mL of methanol were added,The resulting solution was heated to reflux for 6 hours.The reaction solution thus obtained was filtered off and the resulting solid was dried under vacuum to give 3.42 g ofTo obtain trimethyl 2,2 ': 6', 2 "-terpyridyl-4,4 ', 4" -tricarboxylate.

Reference： [1] Dalton Transactions, 2011, vol. 40, # 17, p. 4497 - 4504
[2] Chemical Communications, 1997, # 18, p. 1705 - 1706
[3] Journal of the American Chemical Society, 2001, vol. 123, # 8, p. 1613 - 1624
[4] RSC Advances, 2013, vol. 3, # 48, p. 26035 - 26046
[5] Inorganica Chimica Acta, 2016, vol. 442, p. 158 - 166
[6] Patent: JP5901496, 2016, B2, . Location in patent: Paragraph 0058

[ 216018-58-5 ] Synthesis Path-Downstream 1~26

1
[ 67-56-1 ]
[ 216018-58-5 ]
[ 330680-46-1 ]

Yield	Reaction Conditions	Operation in experiment
3.42 g	With sulfuric acid; for 6h;Reflux;	2,2 ': 6', 2 "-terpyridyl-4,4 ', 4" -tricarboxylic acid3.65 g (10.0 mmol) of the compound (manufactured by Tateyama Kasei)Was placed in a 500 mL eggplant flask. continue,2,2 ': 6', 2 "-terpyridyl-4,4 ', 4" -tricarboxylic acid,5 mL of concentrated sulfuric acid and 300 mL of methanol were added,The resulting solution was heated to reflux for 6 hours.The reaction solution thus obtained was filtered off and the resulting solid was dried under vacuum to give 3.42 g ofTo obtain trimethyl 2,2 ': 6', 2 "-terpyridyl-4,4 ', 4" -tricarboxylate.

Reference： [1]Dalton Transactions,2011,vol. 40,p. 4497 - 4504
[2]Chemical Communications,1997,p. 1705 - 1706
[3]RSC Advances,2013,vol. 3,p. 26035 - 26046
[4]Inorganica Chimica Acta,2016,vol. 442,p. 158 - 166
[5]Patent: JP5901496,2016,B2 .Location in patent: Paragraph 0058

2
[ 33354-75-5 ]
[ 216018-58-5 ]

Yield	Reaction Conditions	Operation in experiment
41%	With chromium(VI) oxide; sulfuric acid at 75℃;

Reference： [1]Nazeeruddin; Pechy; Graetzel [Chemical Communications, 1997, # 18, p. 1705 - 1706]

3
[ 33354-77-7 ]
[ 216018-58-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With chromium(VI) oxide; sulfuric acid; periodic acid In water at 20 - 60℃; for 19h;	Synthesis of 4,4’,4”-tricarboxy-2,2’:6’,2”-terpyridine 11 General procedure: H5IO6 (1.20g, 5.25 mmol) was dissolved in the mixture of conc. H2SO4 (5 mL) and H2O (2.5 mL) with stirring at room temperature. CrO 3 (0.15g, 1.5 mmol) was added to the solution and dissolved with stirring. Powdered 4,4’,4”-triethyl-2,2’:6’,2”-terpyridine 10(0.159g, 0.50 mmol) was added in one portion to the solution. The resulted mixture was stirred vigorously (600-700 rpm) at room temperature. The temperature of the flask rose to 60°C within a few minutes, and then decreased to room temperature. After stirring for 19hat room temperature, the solution was poured slowly into ice-water (100 mL) with stirring, and the mixture was stirred for 2h, and then stood at room temperature overnight. The precipitate was collected by filtration, and washed well with H 2 O. Vacuum drying at 110°C for 4h gave 0.146g (80%) 4,4’,4”-tricarboxy-2,2’:6’,2”-terpyridine 11 S5 as yellow powder. 1 H NMR (400 MHz, D 2 O/NaOD(1%), TSP) ppm: 7.80 (2H, dd, J=5.0 Hz, 1.6 Hz), 8.42 (2H, s), 8.63 (2H, s), 8.73 (2H, dd, J=5.0 Hz, 0.9 Hz); 13 C NMR (100 MHz, D 2 O/NaOD(1%), relative to external dioxane at 67.4) ppm: 120.7, 121.6, 124.1, 145.6, 147.1, 149.9, 154.8, 154.9, 172.2, 172.5.
36%	Stage #1: 4,4’,4”-triethyl-2,2’:6’,2”-terpyridine With potassium dichromate; sulfuric acid Stage #2: for 5h; Heating; Further stages.;
36%	With potassium dichromate; sulfuric acid

Reference： [1]Yamazaki, Shigekazu [Synthetic Communications, 2019, vol. 49, # 17, p. 2210 - 2218]
[2]Nazeeruddin; Pechy; Renouard; Zakeeruddin; Humphry-Baker; Cointe; Liska; Cevey; Costa; Shklover; Spiccia; Deacon; Bignozzi; Graetzel [Journal of the American Chemical Society, 2001, vol. 123, # 8, p. 1613 - 1624]
[3]Location in patent: scheme or table Dehaudt, Jeremy; Husson, Jerome; Guyard, Laurent [Green Chemistry, 2011, vol. 13, # 12, p. 3337 - 3340]

4
[ CAS Unavailable ]
[ 216018-58-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide for 0.0833333 - 0.25h; Irradiation;

Reference： [1]Current Patent Assignee: NEOMAT SA - EP1178084, 2002, A1 Location in patent: Page 4

5
[ CAS Unavailable ]
[ 216018-58-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol for 6h; Heating / reflux;	6.c The RuCl3 3H2O salt was reacted in n-butanol with a stoichiometric amount of (H3tcterpy) at reflux for 6h. A solution of the intermediate [RuII(H3tcterpy)(Cl)3] complex in n-butanol was obtained.
	In ethanol for 3h; Reflux; Inert atmosphere;	1 4,4',4"-tricarboxy terpyridine and ruthenium trichloride were subjected to thermal reflux for 3 hours in ethanol under an argon atmosphere. After cooling, the medium was removed by means of distillation by using a rotary evaporator, two equivalents of ethylenediamine were added to the obtained N,N-dimethylformamide solution of trichloro (4,4',4"-tricarboxy terpyridine)ruthenium (II), five equivalents of trimethoxyphosphine were additionally added thereto, and the solution was heated for five minutes at 70 °C. The reaction mixture was cooled to room temperature and, after adding trifluoroacetic acid, was agitated for five minutes; the medium was subsequently removed by means of distillation by using a rotary evaporator; and, after adding diethyl ether thereto, the residue was left to stand overnight at 0 °C. By separating the solid product by means of filtering, the desired complex, i.e., dichloro (trimethoxyphosphine)(4,4',4"-tricarboxy terpyridine)ruthenium (II), was obtained. The structure thereof is shown in Fig. 2.. (0066) This complex was a black solid, and the measurement taken by using an electrospray mass spectrometer was 660.9, which corresponds to the molecular mass of C21H20Cl2N3O9PRu. 1H-NMR data were as described below. 1H-NMR(δ, 500 MHz), medium: (DMSO-d6), 9.44 (d, J = 6 Hz, 2H), 9.05 (s, 2H), 8.90 (s, 2H), 7.93 (dd, J = 2, 6 Hz, 2H), and 3.85 (d, J = 10 Hz, 9H).

Reference： [1]Current Patent Assignee: AISIN CORPORATION - EP1424340, 2004, A1 Location in patent: Page/Page column 9
[2]Current Patent Assignee: THE UNIVERSITY OF TOKYO - EP2685553, 2015, B1 Location in patent: Paragraph 0065-0067

6
[ CAS Unavailable ]
[ 216018-58-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol for 7h; Heating / reflux;	1.c The intermediate complex (TBA)2Os(Cl)6 (where TBA means tetrabutylammonium (+1) cation) was prepared from commercial (NH4)2[Os(Cl)6], which was converted into the corresponding TBA salt by precipitation with TBACl from an aqueous solution. The solid product was filtered and dried under vacuum. The (TBA)2[Os(Cl)6] salt was reacted in n-butanol with a stoichiometric amount of (H3tcterpy) at reflux for 7h. A solution of [OsII(H3tcterpy)(Cl)3](TBA) in n-butanol was obtained.

Reference： [1]Current Patent Assignee: AISIN CORPORATION - EP1424340, 2004, A1 Location in patent: Page/Page column 7

7
[ CAS Unavailable ]
[ 216018-58-5 ]
[ CAS Unavailable ]
[ 695229-93-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₆H₃₆N⁽¹⁺⁾*C₁₈H₁₁Cl₃N₃O₆Os^(1-); 4,4',4"-tricarboxy-2,2':6',2"-terpyridine In butan-1-ol for 25h; Heating / reflux; Stage #2: With tetra(n-butyl)ammonium hydroxide In water Stage #3: With hexafluorophosphoric acid In water	1.d The solution [OsII(H3tcterpy)(Cl)3](TBA) in n-butanol prepared before was reacted with a stoichiometric amount of (bpyq) for 25h at reflux. The solution was rotary evaporated to dryness. The solid was then dissolved in water at pH 12 by addition of TBAOH and re-precipitated at pH 2 by addition of HPF6. The precipitate was filtered, washed with dichloromethane and dried. The complex was further purified on Sephadex LH 20 column by using water at pH 7 as eluant and re-precipitated at pH 2 with HPF6. H-NMR of the anionic complex [Os(tcterpy)(bpyq)Cl](TBA)2 (300 MHz, CD3OD) δ ppm: 6.88 (1H, d,H7a), 7.25 (1H,t,H8a), 7.44 (1H, t,H9a), 7.6 (2H, d,H5,5"), 7.66 (2H, d,H6,6"), 7.78 (1H, d,H10a), 7.96 (1H, t,H3a), 8.17 (2H, m,H4a,5a), 8.67 (1H, d,H6a) 8.98 (2H, s,H3,3"), 9.12 (1H, d,H2a), 9.2 (2H, s,H3',5'), 10.26 (1H, d,H1a). Elemental analysis of [OsII(H3tcterpy)(bpyq)(Cl)](PF6), OsC32N5H21O6ClPF6: calculated: C=40.79%, N=7.43%, H=2.25%; found: C=40.35%, N=7.13%, H=2.40% Cyclic voltammetry (glassy carbon working electrode, Pt counter electrode, SCE reference electrode, methanol solvent, 0.1M TBAPF6 inert electrolyte) showed peaks at 1.1 V and 1.24 V versus SCE, corresponding to irreversible reduction of ligands, and reversible peak with E½ at 0.65 V versus SCE, corresponding to the OsII/OsIII transition. UV-vis-NIR spectroscopy from 200 to 1100nm (ethanolic solutions) gives absorption peaks at 270, 290, 325, 380, 450, 530, 630 and 830 nm with extinction coefficients higher than 1000 m-1cm-1.

Reference： [1]Current Patent Assignee: AISIN CORPORATION - EP1424340, 2004, A1 Location in patent: Page column 7

8
[ 20759-14-2 ]
tetra-n-butylammonium hydroxide [ No CAS ]
[ 333-20-0 ]
[ 216018-58-5 ]
[ 552301-47-0 ]

Reference： [1]Journal of the Electrochemical Society,2001,vol. 148,p. E97-E104

9
[ 98-01-1 ]
[ 25028-32-4 ]
[ 216018-58-5 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	Stage #1: furfural; ethyl 2-acetylpyridine-4-carboxylate With ammonia; potassium hydroxide In ethanol; water at 20℃; for 24h; Stage #2: With potassium permanganate; potassium hydroxide In water at 20℃; for 24h; Stage #3: With hydrogenchloride In water

Reference： [1]Dehaudt, Jeremy; Husson, Jerome; Guyard, Laurent [Green Chemistry, 2011, vol. 13, # 12, p. 3337 - 3340]

10
[ CAS Unavailable ]
[ 7732-18-5 ]
[ 216018-58-5 ]
[ CAS Unavailable ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
88%	for 2h; Reflux;

Reference： [1]Yamauchi, Kosei; Sakai, Ken [Dalton Transactions, 2015, vol. 44, # 18, p. 8685 - 8696]

11
[ 1762-95-4 ]
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 1428875-51-7 ]
[ 216018-58-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; 4,4'-bis((E)-2-(9-ethyl-9H-carbazol-3-yl)vinyl)-2,2'-bipyridine In N,N-dimethyl-formamide at 90℃; for 4h; Inert atmosphere; Stage #2: 4,4',4"-tricarboxy-2,2':6',2"-terpyridine In N,N-dimethyl-formamide at 90 - 145℃; for 10h; Inert atmosphere; Stage #3: ammonium thiocyanate; hexafluorophosphoric acid Further stages;	2.3. Synthesis of (DH-1): reaction of 4,4'-bis((E)-2-(9-ethyl-9H-carbazol-3-yl)vinyl)-2,2'-bipyridine with 2,2':6',2''-terpyridine]-4,4',4''-tricarboxylic acid and dichloro(p-cymene)ruthenium(II) dimer In a three neck round bottom flask, (0.2 g, 3.27 x 10-4 mol) of dichloro(p-cymene)ruthenium(II) dimer and (0.388 g, 6.52 x 10-4 mol) of 4,4'-bis((E)-2-(9-ethyl-9H-carbazole-3-yl)-1-yl)vinyl-2,2'-bipyridiyl) were stirred in 50 ml DMF for 4 hrs under argon at 90 °C. A total of (0.2387 g, 6.52 x 10-4 mol) of 2,2:6,2-terpyridine-4,4',4''-tricarboxylic acid was then added and the temperature was increased to 145 °C and allowed to run for 10 hrs. After 10 hrs, excess of NH4NCS (0.5 g) was added to the reaction mixture and allowed to run for another 4 h at 140 °C. The DMF was removed under vacuum and the solid was then dissolved in water at pH 12 by addition of tetrabutylammonium hydroxide and reprecipitated at pH 2 by addition of HPF6. The precipitate was filtered, washed with dichloromethane and dried to yield 0.9 g. The complex was purified on a Sephadex LH-20 column using methanol as an eluent and reprecipitated at pH 2 with HPF6. The precipitate was washed with dichloromethane to remove the excess of HPF6. Three successive chromatographic separations were necessary to obtain the desired purity.

Reference： [1]El-Sherbiny, Dalia; Cheema, Hammad; El-Essawy, Farag; Abdel-Megied, Ahmed; El-Shafei, Ahmed [Dyes and Pigments, 2015, vol. 115, p. 81 - 87]

12
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 1428875-51-7 ]
[ 216018-58-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; 4,4'-bis((E)-2-(9-ethyl-9H-carbazol-3-yl)vinyl)-2,2'-bipyridine In N,N-dimethyl-formamide at 90℃; for 4h; Inert atmosphere; Stage #2: 4,4',4"-tricarboxy-2,2':6',2"-terpyridine In N,N-dimethyl-formamide at 90 - 145℃; for 10h; Inert atmosphere; Stage #3: hexafluorophosphoric acid Inert atmosphere;	2.4. Synthesis of (DH-2) In a three neck round bottom flask, (0.2 g, 3.27 x 10-4 mol) of dichloro(p-cymene)ruthenium(II) dimer and (0.388 g, 6.52 x 10-4 mol) of 4,4'-bis((E)-2-(9-ethyl-9H-carbazole-3-yl)-1-yl)vinyl]-2,2'-bipyridiyl) were stirred in 50 ml DMF for 4 h under argon at 90 °C. A total of (0.2387 g, 6.52 x 10-4 mol) of 2,2:6,2-terpyridine-4,4',4''-tricarboxylic acid was then added and the temperature was increased to 145 °C and allowed to run for 10 hrs. The DMF was removed under vacuo and the solid was reprecipitated at pH 2 by addition of HPF6. Three successive chromatographic separations were necessary to obtain the desired purity.

Reference： [1]El-Sherbiny, Dalia; Cheema, Hammad; El-Essawy, Farag; Abdel-Megied, Ahmed; El-Shafei, Ahmed [Dyes and Pigments, 2015, vol. 115, p. 81 - 87]

13
[ 216018-58-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol / 3 h / Reflux; Inert atmosphere 2: N,N-dimethyl-formamide / 0.08 h / 70 °C