[ CAS No. 4433-01-6 ] {[proInfo.proName]}

Name: 4433-01-6|[2,2'-Bipyridine]-3,3'-dicarboxylic acid|97%
Brand: Ambeed
SKU: A241343
Price: 8.0 USD
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Quality Control of [ 4433-01-6 ]

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Product Details of [ 4433-01-6 ]

CAS No. :	4433-01-6	MDL No. :	MFCD00226068
Formula :	C₁₂H₈N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KNVZVRWMLMPTTJ-UHFFFAOYSA-N
M.W :	244.20	Pubchem ID :	681885
Synonyms :

Calculated chemistry of [ 4433-01-6 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	2.0
Molar Refractivity :	61.39
TPSA :	100.38 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) :	-7.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.66
Log Po/w (XLOGP3) :	0.53
Log Po/w (WLOGP) :	1.54
Log Po/w (MLOGP) :	-0.99
Log Po/w (SILICOS-IT) :	1.22
Consensus Log Po/w :	0.59

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.98
Solubility :	2.54 mg/ml ; 0.0104 mol/l
Class :	Very soluble
Log S (Ali) :	-2.21
Solubility :	1.51 mg/ml ; 0.00618 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.92
Solubility :	0.292 mg/ml ; 0.00119 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.1

Safety of [ 4433-01-6 ]

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 [ 4433-01-6 ]

* 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 [ 4433-01-6 ]
Downstream synthetic route of [ 4433-01-6 ]

[ 4433-01-6 ] Synthesis Path-Upstream 1~12

1
[ 2942-59-8 ]
[ 4433-01-6 ]

Yield	Reaction Conditions	Operation in experiment
48%	With hydrogenchloride; sodium hydroxide In methanol; water	Example 4 9.50 g of 2-chloronicotinic acid and 5.30 g of sodium hydroxide are dissolved in a mixture of 40 ml of water and 40 ml of methanol. Following the addition of 4 g of palladium (5percent by weight on activated carbon) as catalyst, the mixture is stirred for 30 h at 80-85° C. at 0.1 MPa. The catalyst is then filtered off. Following acidification to pH 1 using hydrochloric acid, the product, 2,2'-bipyridyl-3,3'-dicarboxylic acid, precipitates out as a white solid. This gives 3.5 g (48percent yield).

Reference： [1] Patent: US6500956, 2002, B1,

2
[ 66-71-7 ]
[ 4433-01-6 ]

Reference： [1] European Journal of Organic Chemistry, 2013, # 26, p. 5893 - 5901
[2] Synthetic Communications, 2003, vol. 33, # 18, p. 3159 - 3164
[3] New Journal of Chemistry, 2016, vol. 40, # 8, p. 7148 - 7156
[4] Journal of the Chemical Society. Perkin Transactions 1, 2002, # 14, p. 1688 - 1692
[5] Russian Journal of Organic Chemistry, 2005, vol. 41, # 11, p. 1690 - 1693
[6] Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 275,278
[7] Journal of the American Chemical Society, 1930, vol. 52, p. 397,400
[8] Journal of the American Chemical Society, 1950, vol. 72, p. 842
[9] Organic Letters, 2002, vol. 4, # 16, p. 2799 - 2801
[10] Journal of Physical Chemistry B, 2004, vol. 108, # 50, p. 19541 - 19549
[11] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 69, # 1, p. 49 - 55
[12] Dalton Transactions, 2008, # 28, p. 3701 - 3708
[13] Journal of Chemical Crystallography, 2009, vol. 39, # 6, p. 423 - 427
[14] Monatshefte fur Chemie, 2010, vol. 141, # 2, p. 157 - 168
[15] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374

3
[ 27318-90-7 ]
[ 4433-01-6 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1601 - 1606
[2] Synlett, 2013, vol. 24, # 10, p. 1225 - 1228

4
[ 136869-49-3 ]
[ 4433-01-6 ]

Reference： [1] Journal of Organometallic Chemistry, 1995, vol. 486, # 1-2, p. 115 - 122

5
[ 66-71-7 ]
[ 50890-67-0 ]
[ 4433-01-6 ]
[ 143825-63-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1601 - 1606
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1601 - 1606
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1601 - 1606
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 13, p. 1601 - 1606

6
[ 41673-52-3 ]
[ 4433-01-6 ]

Reference： [1] Journal and Proceedings of the Royal Society of New South Wales, 1947, vol. 80, p. 212 - 216
[2] , Gmelin Handbook: Ru: SVol., 169, page 458 - 461,

7
[ 66-71-7 ]
[ 50890-67-0 ]
[ 4433-01-6 ]
[ 143825-63-2 ]

8
[ 186581-53-3 ]
[ 4433-01-6 ]
[ 39775-31-0 ]

Reference： [1] Journal of Organometallic Chemistry, 1995, vol. 486, # 1-2, p. 115 - 122
[2] Canadian Journal of Research, Section B: Chemical Sciences, 1950, vol. 28, p. 26,30

9
[ 4433-01-6 ]
[ 79-22-1 ]
[ 39775-31-0 ]

Reference： [1] Russian Journal of Organic Chemistry, 2005, vol. 41, # 11, p. 1690 - 1693

10
[ 67-56-1 ]
[ 4433-01-6 ]
[ 39775-31-0 ]

Reference： [1] New Journal of Chemistry, 2016, vol. 40, # 8, p. 7148 - 7156
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 5, p. 593 - 601
[3] Synlett, 2013, vol. 24, # 10, p. 1225 - 1228
[4] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374

11
[ 67-56-1 ]
[ 4433-01-6 ]
[ 39775-31-0 ]

Reference： [1] Molecules, 2002, vol. 7, # 8, p. 628 - 640

12
[ 4433-01-6 ]
[ 39775-31-0 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 1, 2002, # 14, p. 1688 - 1692

[ 4433-01-6 ] Synthesis Path-Downstream 1~55

1
[ 66-71-7 ]
[ 4433-01-6 ]

Yield	Reaction Conditions	Operation in experiment
82.8%	With potassium permanganate; sodium hydroxide In water for 6h; Reflux;
80%	With potassium permanganate; sodium hydroxide In water Reflux;	3.2. Synthesis of [2,2'-Bipyridine]-3,3'-Dicarboxylic Acid(1) 1,10-Phenanthroline (6 g), water (400 mL), sodium hydroxide(2.4 g) were mixed in a 1000 mL flask. After thesodium hydroxide dissolved, KMnO4 (10 g) was added inbatches under vigorously stirring. Then the resulting mixturewas refluxed to colorless. The mixture was filtered when hot.The filtrate was evaporated to 50 mL and then cooled toroom temperature. The pH was adjusted to 2-3 by addingconcentrated hydrochloric acid (10 mL) dropwise. The whitesolid product was obtained with a yield of 80%.
78%	With sodium hydroxide; potassium permanganate In water for 6h; Heating;

72%	With potassium permanganate; water for 6h; Reflux;
67%	With sodium hydroxide; potassium permanganate
61.1%	With sodium hydroxide; potassium permanganate In water for 2h; Heating;
	With potassium hydroxide; potassium permanganate
	With sodium hydroxide; potassium permanganate
	With potassium permanganate; sodium periodate
	With hydrogenchloride; potassium permanganate
	With sodium hydroxide; potassium permanganate
	With hydrogenchloride; potassium permanganate In water at 120℃;
	Stage #1: 1,10-Phenanthroline With potassium permanganate; potassium hydroxide Stage #2: With hydrogenchloride In water
	With potassium permanganate; sodium hydroxide
1.50 g	With potassium permanganate; sodium hydroxide In water at 20 - 105℃; for 6.5h;

Reference： [1]Yu, Xiaoguang; Jin, Xueliang; Tang, Guipeng; Zhou, Jun; Zhang, Wei; Peng, Dahai; Hu, Jiaomei; Zhong, Chaofan [European Journal of Organic Chemistry, 2013, # 26, p. 5893 - 5901]
[2]Zhang, Lei-Yang; Geng, Jing-Bo; Wang, Nai-Xing; Wu, Yue-Hua; Yan, Zhan; Xu, Bao-Cai; Xing, Yalan [Letters in Organic Chemistry, 2022, vol. 19, # 1, p. 41 - 45]
[3]Kanungo; Baral, Minati; Bhattacharya; Sahoo [Synthetic Communications, 2003, vol. 33, # 18, p. 3159 - 3164]
[4]Ashokkumar, Veeramanoharan; Duraimurugan, Kumaraguru; Siva, Ayyanar [New Journal of Chemistry, 2016, vol. 40, # 8, p. 7148 - 7156]
[5]Sam, Najat; Elkadiri, Sghir; Le Bozec, Hubert; Toupet, Loic; Daoudi, Maria; Bitit, Najib; Hadda, Taibi Ben; Dixneuf, Pierre H. [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 14, p. 1688 - 1692]
[6]Denisova; Degtyareva; Dem'yanchuk; Simanova [Russian Journal of Organic Chemistry, 2005, vol. 41, # 11, p. 1690 - 1693]
[7]Willink; Wibaut [Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 275,278] Smith [Journal of the American Chemical Society, 1930, vol. 52, p. 397,400]
[8]Inglett; Smith [Journal of the American Chemical Society, 1950, vol. 72, p. 842]
[9]Shimada, Toyoshi; Kina, Asato; Ikeda, Syushiro; Hayashi, Tamio [Organic Letters, 2002, vol. 4, # 16, p. 2799 - 2801]
[10]Liu, Yu; Li, Xue-Qing; Chen, Yong; Guan, Xu-Dong [Journal of Physical Chemistry B, 2004, vol. 108, # 50, p. 19541 - 19549]
[11]Song, Xue-Qin; Zheng, Jiang-Rong; Liu, Wei-Sheng; Ju, Zheng-Hua [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 69, # 1, p. 49 - 55]
[12]Location in patent: scheme or table Geary, Elaine A. M.; McCall, Keri L.; Turner, Andrew; Murray, Paul R.; McInnes, Eric J. L.; Jack, Lorna A.; Yellowlees, Lesley J.; Robertson, Neil [Dalton Transactions, 2008, # 28, p. 3701 - 3708]
[13]Location in patent: scheme or table Toupet, Loic; Dixneuf, Pierre H.; Akkurt, Mehmet; Daoudi, Maria; Sam, Najat; Kerbal, Abdelali; Chohan, Zahid H.; Hadda, Taibi Ben [Journal of Chemical Crystallography, 2009, vol. 39, # 6, p. 423 - 427]
[14]Location in patent: scheme or table Kanungo, Bikram Kishore; Baral, Minati; Bera, Rati Kanta; Sahoo, Suban Kumar [Monatshefte fur Chemie, 2010, vol. 141, # 2, p. 157 - 168]
[15]Ganesan, Vinothkumar; Sivanesan, Dharmalingam; Yoon, Sungho [Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374]

2
[ 186581-53-3 ]
[ 4433-01-6 ]
[ 39775-31-0 ]

Reference： [1]Journal of Organometallic Chemistry,1995,vol. 486,p. 115 - 122
[2]Canadian Journal of Research, Section B: Chemical Sciences,1950,vol. 28,p. 26,30

3
[ 136869-49-3 ]
[ 4433-01-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In acetonitrile

Reference： [1]Baxter, Paul N. W.; Connor, Joseph A. [Journal of Organometallic Chemistry, 1995, vol. 486, # 1-2, p. 115 - 122]

4
[ 4433-01-6 ]
[ 169873-17-0 ]

Yield	Reaction Conditions	Operation in experiment
92.8%	With dihydrogen peroxide; acetic acid at 105 - 110℃; for 3h;
	With dihydrogen peroxide; acetic acid at 105 - 110℃;	(8.2 mmol) ofraw material H2bpda) was added into the mixture of 16 mL aceticacid and 16 mL 30% hydrogen peroxide, placed in a 50 mL roundbottom flask, heated at 105-110 °C, refluxed for 8 h, cooled at roomtemperature, filtered and washed to obtain a white powderedsolid, namely H2bpdado ligand.

Reference： [1]Tichy, Milos; Zavada, Jiri; Podlaha, Jaroslav; Vojtisek, Pavel [Tetrahedron Asymmetry, 1995, vol. 6, # 6, p. 1279 - 1282]
[2]Zhang, Wen-Qian [Polyhedron, 2021, vol. 193]

5
[ 64-17-5 ]
[ 4433-01-6 ]
[ 1762-36-3 ]
ethyl (7RS,8RS,9SR)-7,8,9-trichloro-5,7,8,9-tetrahydro-5-oxopyrido[2,3-a]indolizine-10-carboxylate [ No CAS ]
ethyl (7SR,8RS,9SR)-7,8,9-trichloro-5,7,8,9-tetrahydro-5-oxopyrido[2,3-a]indolizine-10-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 81% 2: 4% 3: 12%	Stage #1: 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine With thionyl chloride; chlorine for 1h; Heating; Stage #2: ethanol In toluene for 3h; Heating;
1: 45% 2: 12% 3: 39%	With thionyl chloride; chlorine for 5h; Heating;

Reference： [1]Zunino, Franco; Kotchevar, Ann T.; Waring, Michael; Daoudi, Maria; Larbi, Najib Ben; Mimouni, Mostafa; Sam, Najat; Zahidi, Assou; Ben-Hadda, Taibi [Molecules, 2002, vol. 7, # 8, p. 628 - 640]
[2]Sam, Najat; Elkadiri, Sghir; Le Bozec, Hubert; Toupet, Loic; Daoudi, Maria; Bitit, Najib; Hadda, Taibi Ben; Dixneuf, Pierre H. [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 14, p. 1688 - 1692]

6
[ 4433-01-6 ]
[ 173032-82-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With thionyl chloride for 1h; Heating;
	With thionyl chloride for 5h; Heating;
	With thionyl chloride

	With thionyl chloride Heating;
	With thionyl chloride for 5h; Reflux;
	With thionyl chloride at 78℃; for 5h;	2,20-Bipyridine-3,30-dicarboxylic acid (0.525 g, 2.15 mmol) andthionyl chloride (8 mL) were refluxed (78 C) for 5 h. The excessof thionyl chloride was distilled and the residue vacuum driedfor 2 h. The resulting yellow powder was dissolved in dry toluene(10 mL) and the solution was added drop wise to a solution of 3-(perfluorohexyl)propanol (1.1 mL, 6.9 mmol) and triethylamine(1.2 mL, 8.6 mmol) in 5 mL of dry dichloromethane. The mixture was refluxed (85 C) for 20 h. After removal of the solvent, the obtained powder was dissolved in chloroform (10 mL) and the mixture was extracted with a cold blank solution of saturated sodium bicarbonate (5 5 mL). The organic layer was dried onMgSO4 and the solvent removed in vacuum to obtain a solid product,which was purified by chromatography on silica gel using diethyl ether as eluent. A spectroscopically pure white solid was obtained after trituration with pentane.
	With thionyl chloride In dichloromethane at 0 - 20℃; for 1h;

Reference： [1]Kanungo; Baral, Minati; Bhattacharya; Sahoo [Synthetic Communications, 2003, vol. 33, # 18, p. 3159 - 3164]
[2]Sam, Najat; Elkadiri, Sghir; Le Bozec, Hubert; Toupet, Loic; Daoudi, Maria; Bitit, Najib; Hadda, Taibi Ben; Dixneuf, Pierre H. [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 14, p. 1688 - 1692]
[3]Liu, Yu; Li, Xue-Qing; Chen, Yong; Guan, Xu-Dong [Journal of Physical Chemistry B, 2004, vol. 108, # 50, p. 19541 - 19549]
[4]Song, Xue-Qin; Zheng, Jiang-Rong; Liu, Wei-Sheng; Ju, Zheng-Hua [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 69, # 1, p. 49 - 55]
[5]Location in patent: experimental part Toupet, Loic; Dixneuf, Pierre H.; Akkurt, Mehmet; Daoudi, Maria; Sam, Najat; Kerbal, Abdelali; Chohan, Zahid H.; Hadda, Taibi Ben [Journal of Chemical Crystallography, 2009, vol. 39, # 6, p. 423 - 427]
[6]Campos-Carrasco, Ariadna; Bruce, Marlene; Reguero, Mar; Masdeu-Bultó, Anna M. [Inorganica Chimica Acta, 2014, vol. 409, # PART B, p. 285 - 295]
[7]Zhang, Lei-Yang; Geng, Jing-Bo; Wang, Nai-Xing; Wu, Yue-Hua; Yan, Zhan; Xu, Bao-Cai; Xing, Yalan [Letters in Organic Chemistry, 2022, vol. 19, # 1, p. 41 - 45]

7
[ 67-56-1 ]
[ 4433-01-6 ]
[ 39775-31-0 ]
methyl (7RS,8RS,9SR)-7,8,9-trichloro-5,7,8,9-tetrahydro-5-oxopyrido[2,3-a]indolizine-10-carboxylate [ No CAS ]
methyl (7SR,8RS,9SR)-7,8,9-trichloro-5,7,8,9-tetrahydro-5-oxopyrido[2,3-a]indolizine-10-carboxylate [ No CAS ]

Reference： [1]Molecules,2002,vol. 7,p. 628 - 640

8
[ 78-83-1 ]
[ 4433-01-6 ]
3,3'-bis(isobutyloxycarbonyl)-2,2'-bipyridine [ No CAS ]
iso-butyl (7RS,8RS,9SR)-7,8,9-trichloro-5,7,8,9-tetrahydro-5-oxopyrido[2,3-a]indolizine-10-carboxylate [ No CAS ]
iso-butyl (7SR,8RS,9SR)-7,8,9-trichloro-5,7,8,9-tetrahydro-5-oxopyrido[2,3-a]indolizine-10-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 3% 3: 16%	Stage #1: 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine With thionyl chloride; chlorine for 1h; Heating; Stage #2: 2-methyl-propan-1-ol In toluene for 3h; Heating;

9
[ 4433-01-6 ]
[ 67-63-0 ]
[ 39775-34-3 ]
iso-propyl (7RS,8RS,9SR)-7,8,9-trichloro-5,7,8,9-tetrahydro-5-oxopyrido[2,3-a]indolizine-10-carboxylate [ No CAS ]
iso-propyl (7SR,8RS,9SR)-7,8,9-trichloro-5,7,8,9-tetrahydro-5-oxopyrido[2,3-a]indolizine-10-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 12% 3: 6%	Stage #1: 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine With thionyl chloride; chlorine for 1h; Heating; Stage #2: isopropyl alcohol In toluene for 3h; Heating;

10
[ 4433-01-6 ]
[ 79-22-1 ]
[ 39775-31-0 ]

Reference： [1]Russian Journal of Organic Chemistry,2005,vol. 41,p. 1690 - 1693

11
[ 4433-01-6 ]
[ 39775-31-0 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1688 - 1692

12
[ 4433-01-6 ]
[ 1762-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / 5 h / Heating 2: SOCl₂ / 3 h / Heating

Reference： [1]Sam, Najat; Elkadiri, Sghir; Le Bozec, Hubert; Toupet, Loic; Daoudi, Maria; Bitit, Najib; Hadda, Taibi Ben; Dixneuf, Pierre H. [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 14, p. 1688 - 1692]

13
[ 2942-59-8 ]
[ 4433-01-6 ]

Yield	Reaction Conditions	Operation in experiment
48%	With hydrogenchloride; sodium hydroxide In methanol; water	4 Example 4 Example 4 9.50 g of 2-chloronicotinic acid and 5.30 g of sodium hydroxide are dissolved in a mixture of 40 ml of water and 40 ml of methanol. Following the addition of 4 g of palladium (5% by weight on activated carbon) as catalyst, the mixture is stirred for 30 h at 80-85° C. at 0.1 MPa. The catalyst is then filtered off. Following acidification to pH 1 using hydrochloric acid, the product, 2,2'-bipyridyl-3,3'-dicarboxylic acid, precipitates out as a white solid. This gives 3.5 g (48% yield).

Reference： [1]Current Patent Assignee: MERCK KGAA - US6500956, 2002, B1

14
[ 10025-99-7 ]
[ 4433-01-6 ]
[ 197641-99-9 ]

Yield	Reaction Conditions	Operation in experiment
94.8%	In water reflux a mixt. of ligand and platinum complex in water for 18 h, cooling; elem. anal.;
84%	In water N2-atmosphere, absence of light; slow warming to 50°C, stirring for 8 h; cooling, collection (filtration), washing (cold water, EtOH, Et2O; in air), drying over CaCl2;

Reference： [1]Geary, Elaine A. M.; Yellowlees, Lesley J.; Jack, Lorna A.; Oswald, Iain D. H.; Parsons, Simon; Hirata, Narukuni; Durrant, James R.; Robertson, Neil [Inorganic Chemistry, 2005, vol. 44, # 2, p. 242 - 250]
[2]Yoo, Jeongsoo; Kim, Jae-Hak; Sohn, Youn Soo; Youngkyu, Do [Inorganica Chimica Acta, 1997, vol. 263, # 1-2, p. 53 - 60]

15
ferrous(II) sulfate heptahydrate [ No CAS ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[Fe(2,2'-bipyridyl-3,3'-dicarboxylate)(H₂O)3]*3H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With NaOH In water ligand soln. added dropwise to soln. of metal compd. (1:1), pH 8 (NaOH),heated at 40°C for 12 h, cooled to room temp.; crystd. on storage, filtered off, washed (MeOH), dried in air, elem. anal.;

Reference： [1]Kwak, Ock Keum; Min, Kil Sik; Kim, Bong Gon [Inorganica Chimica Acta, 2007, vol. 360, # 5, p. 1678 - 1683]

16
[ 64-17-5 ]
[ 4433-01-6 ]
[ 1762-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid at 115℃;
	With hydrogenchloride Heating;

Reference： [1]Location in patent: scheme or table Geary, Elaine A. M.; McCall, Keri L.; Turner, Andrew; Murray, Paul R.; McInnes, Eric J. L.; Jack, Lorna A.; Yellowlees, Lesley J.; Robertson, Neil [Dalton Transactions, 2008, # 28, p. 3701 - 3708]
[2]Location in patent: experimental part Kanungo, Bikram Kishore; Baral, Minati; Bera, Rati Kanta; Sahoo, Suban Kumar [Monatshefte fur Chemie, 2010, vol. 141, # 2, p. 157 - 168]

17
[ 67-56-1 ]
[ 4433-01-6 ]
[ 39775-31-0 ]

Reference： [1]New Journal of Chemistry,2016,vol. 40,p. 7148 - 7156
[2]Tetrahedron Asymmetry,2009,vol. 20,p. 593 - 601
[3]Synlett,2013,vol. 24,p. 1225 - 1228
[4]Inorganic Chemistry,2017,vol. 56,p. 1366 - 1374
[5]Journal of the American Chemical Society,2019,vol. 141,p. 13253 - 13260

18
[ 4711-00-6 ]
[ 4433-01-6 ]
[ 1163299-46-4 ]

Yield	Reaction Conditions	Operation in experiment
26%	With triethylphosphine In tetrahydrofuran; toluene at 80℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Assalit, Aurelie; Billard, Thierry; Chambert, Stephane; Langlois, Bernard R.; Queneau, Yves; Coe, Diane [Tetrahedron Asymmetry, 2009, vol. 20, # 5, p. 593 - 601]

19
[ 160677-41-8 ]
[ 4433-01-6 ]
2,2'-bipyridinyl-3,3'-dicarboxylic acid bis-[6-(1,3-dibocguanidinohexyl)amide] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Berni, Emanuela; Gosse, Isabelle; Badocco, Denis; Pastore, Paolo; Sojic, Neso; Pinet, Sandra [Chemistry - A European Journal, 2009, vol. 15, # 20, p. 5145 - 5152]

20
samarium(III) chloride hexahydrate [ No CAS ]
[ 4433-01-6 ]
Sm₂(2,2'-bipyridine-3,3'-dicarboxylate)3(H₂O)2*5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.8%	With NaOH In water High Pressure; mixt. of SmCl3*6H2O, 2,2'-bipyridine-3,3'-dicarboxylic acid (1:3) and NaOH stirred in H2O in air for 30 min, heated in an autoclave at 165°C for 96 h; slowly cooled to room temp. over 45 h, filtered, washed (H2O, Et2O), elem. anal.;

Reference： [1]Hu, Ming; Li, Hong-Feng; Yao, Jing-Ya; Gao, Ya; Liu, Zhi-Liang; Su, Hai-Quan [Inorganica Chimica Acta, 2010, vol. 363, # 2, p. 368 - 374]

21
[ 4433-01-6 ]
[ 6080-56-4 ]
[Pb₄(2,2'-bipyridine-3,3'-dicarboxylato)4(H₂O)2]*3H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With NaOH In water High Pressure; a mixt. of Pb salt, ligand, NaOH, and H2O sealed, heated at 160°Cfor 6 d; cooled to room temp.; elem. anal.;

Reference： [1]Sun, Jia-Yin; Wang, Wei; Wang, Li; Zhang, Dao-Jun; Chen, Yan-Li; Ji, Xiang-Dong; Fan, Yong; Song, Tian-You [Journal of Molecular Structure, 2011, vol. 990, # 1-3, p. 204 - 208]

22
copper(II) perchlorate hexahydrate [ No CAS ]
[ 4433-01-6 ]
[ 1415246-59-1 ]
[Ni(dioxime)2Cu₂(3,3'-dicarboxy-2,2'-bipyridine)2](ClO₄)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine In ethanol for 7h; Reflux;	Synthesis of the [Ni(dioxime)2Cu2(N-N)2](ClO4)2 (3-7) complexes General procedure: The mononuclear [Ni(dioxime)2] complex (0.4 g, 0.91 mmol) was added to Et3N (0.30 mmol) in absolute ethanol (70 ml) and the mixture was stirred for 2 h. A solution of Cu(ClO4)2·6H2O (0.69 g, 1.82 mmol) in absolute ethanol (20 ml) was added to the stirred ethanol mixture of [Ni(dioxime)2] (2) complex and Et3N. Then an ethanolic solution (15 mL) of the N-N ligand [2,2′-bipyridine (0.29 g, 1.82 mmol), 1,10-phenanthroline monohydrate (0.36 g, 1.82 mmol), 3,3′-dicarboxy-2,2′-bipyridine (0.44 g, 1.82 mmol), 4,5-diazafluoren-9-one (0.35 g, 1.82 mmol) or 1,10-phenanthroline-5,6-dione (0.38 g, 1.82 mmol)] was added and stirred under reflux for 5 h. After boiling under reflux for 5 h, the mixture was left to precipitate up to 2 days. The solvent was slowly evaporated at room temperature, and the products were recrystallized from EtOH/H2O (1:2). Different color crystals obtained were filtered, washed with EtOH, MeOH and Et2O, and dried in air.

Reference： [1]Kilic, Ahmet; Palali, Ahmet Arif; Durgun, Mustafa; Tasci, Zeynep; Ulusoy, Mahmut; Dagdevren, Metin; Yilmaz, Ismail [Inorganica Chimica Acta, 2013, vol. 394, p. 635 - 644]

23
magnesium(II) nitrate hexahydrate [ No CAS ]
[ 4433-01-6 ]
[Mg(bpda)(H₂O)4]n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In N,N-dimethyl-formamide at 100℃; for 72h;	A mixture of Mg(NO3)2·6H2O (0.1282 g, 0.5 mmol) and H2bpda (0.1221 g,0.5 mmol) in DMF (10 mL) was sealed in a Teflon-lined stainless steel vessel and heated at 100 °C for 3 d, and then cooled to room temperature. C12H14MgN2O8 (338.56): calcd. C 42.57, H 4.17, N 8.27; found C42.60, H 4.15, N 8.29.

Reference： [1]Zhang, Qingfu; Hao, Hongguo; Zhang, Haina; Wang, Suna; Jin, Juan; Sun, Dezhi [European Journal of Inorganic Chemistry, 2013, # 7, p. 1123 - 1126]

24
[ 100125-12-0 ]
[ 4433-01-6 ]
[ 5970-45-6 ]
[ 1460349-92-1 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 5893 - 5901

25
[ 100125-12-0 ]
[ 4433-01-6 ]
[ 6147-53-1 ]
[ 1460349-93-2 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 5893 - 5901

26
copper(II) perchlorate hexahydrate [ No CAS ]
[ 4433-01-6 ]
[ 1564244-02-5 ]
[{(dimethylglyoxime)Cu(3,3′-dicarboxy-2,2′-bipyridine)}₂ClCo-(4,4′-bipyridine)-CoCl{(dimethylglyoxime)Cu(3,3′-dicarboxy-2,2′-bipyridine)}₂](ClO₄)₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine In ethanol; water; N,N-dimethyl-formamide for 6h; Reflux;	General procedure: The complexes [{dmgCu(N-N)}2ClCo-(4,4′-bpy)-CoCl{dmgCu(N-N)}2](ClO4)4 (3-9) and as linked ligands, N-N=2,2′-bipyridine (bpy), 1,10-phenanthroline (phen), 3,3′-dicarboxy-2,2′-bipyridine (dcbpy), 4,5-diazafluoren-9-one (dafo), 1,10-phenanthroline-5,6-dione (dione), 4,4′-ditertbutyl-2,2′-bipyridine (dtbpy) and 4,5-diazafluorene-9-oxime (dafoxi) containing these multinuclear complexes were synthesized according to the reported analogous procedure with some modifications. The complex (1) (0.5 g, 0.62 mmol) was added to Et3N (5 mL) in absolute ethanol-DMF-H2O (80:5:3 mL) and the mixture was stirred for 1 h. The separated solution of Cu(ClO4)2·6H2O (0.94g, 2.48mmol) for all of multinuclear [{dmgCu(N-N)}2ClCo-(4,4′-bpy)-CoCl{dmgCu(N-N)}2](ClO4)4 in absolute ethanol (20 mL) and 2,2′-bipyridine (0.40 g, 2.48 mmol), 1,10-phenanthroline monohydrate (0.49 g, 2.48 mmol), 3,3′-dicarboxy-2,2′-bipyridine (0.60 g, 2.48 mmol), 4,5-diazafluoren-9-one (0.48 g, 2.48 mmol), 1,10-phenanthroline-5,6-dione (0.52 g, 2.48 mmol), 4,4′-ditertbutyl-2,2′-bipyridine (0.67 g, 2.48 mmol) and 4,5-diazafluorene-9-oxime (0.49 g, 2.48 mmol) in absolute ethanol (15 mL) was successively added to the resulting mixture, which was boiled under reflux for 6 h. Then, the mixtures left to 48 h for precipitating. The solvent was evaporated slowly at room temperature and the products were recrystallized from EtOH/H2O (1:2) to give different color crystals which were filtered, then washed with EtOH, MeOH and Et2O and dried in air. Color: green; Yield (%): 68, m.p: 210°C, Anal. Calc. for [C74H64N18O40Cl6Cu4Co2] (F.W: 2430.2g/mol): C, 36.57; H, 2.65; N, 10.38. Found: C, 36.52; H, 2.61; N, 10.45%. ΛM=258Ω-1cm2mol-1, μeff=1.59 [B.M]. (for per Cu(II) ion), LC-MS (Scan ES+): m/z (%) 2431.3 (18) [M+H]+, FT-IR (KBr pellets, νmax/cm-1): 3564-3114 ν(COOH), 3087 ν(Ar-CH), 2983-2871 ν(Aliph-CH), 1681 ν(C=O), 1609 ν(C=N of oxime), 1573 ν(C=N of pyridine), 1493-1417 ν(C=C), 1241 ν(N-O), 1099 and 624 ν(ClO4), 518 ν(Co-N) and 466 ν(Cu-O). UV-Vis (λmax, nm, FontWeight="Bold" FontSize="10" = shoulder peak): 239, 269 FontWeight="Bold" FontSize="10" and 320 (in C2H5OH); 248, 283, 318 FontWeight="Bold" FontSize="10" and 412 FontWeight="Bold" FontSize="10" (in DMSO).

Reference： [1]Kilic, Ahmet; Ulusoy, Mahmut; Durgun, Mustafa; Aytar, Emine [Inorganica Chimica Acta, 2014, vol. 411, p. 17 - 25]

27
[ 4433-01-6 ]
silver nitrate [ No CAS ]
[Ag(2,2'-bipyridine)]NO₃*5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With europium(III) oxide In water at 170℃; for 72h; Autoclave; High pressure;

Reference： [1]Zhou, Yunshan; Li, Xiaomin; Zhang, Lijuan; Guo, Yan; Shi, Zonghai [Inorganic Chemistry, 2014, vol. 53, # 7, p. 3362 - 3370]

28
[ 125370-09-4 ]
[ 4433-01-6 ]
C₅₂H₈₈Ga₄N₄O₈Si₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In tetrahydrofuran at 20℃; for 17h; Inert atmosphere; Schlenk technique;

Reference： [1]Uhl, Werner; Stefaniak, Christina; Hepp, Alexander; Kösters, Jutta [European Journal of Inorganic Chemistry, 2014, # 22, p. 3521 - 3526] Uhl, Werner; Stefaniak, Christina; Hepp, Alexander; Kösters, Jutta [European Journal of Inorganic Chemistry, 2014, vol. 2014, # 22, p. 3521 - 3526]

29
[ 7791-07-3 ]
zinc(II) nitrate hexahydrate [ No CAS ]
[ 27318-90-7 ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[ 75-05-8 ]
[Zn₂(2,2'-bipyridine-3,3'-dicarboxylate)(1,10-phenanthroline-5,6-dione)₂(H₂O)₆]*(ClO₄)₂*(H₂O)₆*(CH₃CN) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: zinc(II) nitrate hexahydrate; 1,10-phenanthroline-5,6-dione; 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine; water; acetonitrile In methanol for 2h; Reflux; Stage #2: sodium perchlorate monohydrate In methanol	2.5. Preparation of [Zn2(bpy-3,30-dc)(ptd)2(H2O)6](ClO4)2(H2O)6(CH3CN)(4) The way was similar to that described for the preparation of 3,except that was Zn(NO3)26H2O instead of Cd(OAc)22H2O. Slowevaporation of the reaction solution at room temperature yieldedyellow crystals suitable for X-ray diffraction determination. Yield:53%. Anal. Calc. for C38H41N7O28Zn2Cl2: C, 36.65; H, 3.32; N, 7.87.Found: C, 37.74; H, 3.42; N, 7.63%. IR (cm1): 3325(m), 3071(m),1689(s), 1571(s), 1465(m), 1439(s), 1323(m), 1235(w), 1128(w),1022(w), 938(w), 837(w), 734(w), 704(w), 635(w), 545(w).

Reference： [1]Xie, Lixia; Feng, Wenhua; Li, Xin; Meng, Lei; Zheng, Xianfu [Inorganica Chimica Acta, 2014, vol. 423, # PART A, p. 79 - 86]

30
zinc(II) nitrate hexahydrate [ No CAS ]
[ 942512-94-9 ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[Zn(2,2'-bipyridine-3,3'-dicarboxylic acid(-2H))(2,2'-bis(imidazol-1-ylmethyl)biphenyl)(H₂O)_2.5] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With sodium hydroxide at 120℃; for 72h;	2.3. Preparation of [Zn(bpy-3,30-dc)(bibp)(H2O)2.5]n (2) The synthesis was similar to that described for 1 except usingZn(NO3)26H2O (0.5 mmol) instead of CdCl22H2O (yield: 32% basedon Zn). Anal. Calc. for C32H29N6O6.5Zn: C, 57.62; H, 4.38; N, 12.60.Found: C, 57.45; H, 4.73; N, 12.35%. IR spectrum (cm1):3547(m), 3395(m), 3115(m), 1630(s), 1573(s), 1444(m), 1368(s),1234(m), 1155(m), 1109(s), 1095(s), 1058(w), 951(w), 847(m),804(w), 774(s), 704(s), 657(m), 631(w), 556(w).

Reference： [1]Xie, Lixia; Feng, Wenhua; Li, Xin; Meng, Lei; Zheng, Xianfu [Inorganica Chimica Acta, 2014, vol. 423, # PART A, p. 79 - 86]

31
[ 7791-07-3 ]
[ 27318-90-7 ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[ 5743-04-4 ]
[Cd₂(2,2'-bipyridine-3,3'-dicarboxylate)(1,10-phenanthroline-5,6-dione)₂(H₂O)₆]*(ClO₄)₂*(H₂O)₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: 1,10-phenanthroline-5,6-dione; 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine; water; cadmium(II) acetate dihydrate In methanol; acetonitrile for 2h; Reflux; Stage #2: sodium perchlorate monohydrate In methanol; acetonitrile	2.4. Preparation of [Cd2(bpy-3,30-dc)(ptd)2(H2O)6](ClO4)2(H2O)5 (3) The ligand H2bpy-3,30-dc (0.24 mmol), ptd (0.12 mmol) andCd(OAc)22H2O (0.24 mmol) were mixed in methanol/acetonitrile/H2O (15 mL/10 mL/5 mL). After refluxing for 2 h, the resultantsolution was added to a saturated solution (5 mL) of NaClO4H2O.Slow evaporation of the resulting yellow solution at room temperatureyielded yellow crystals suitable for X-ray diffraction determination.Yield: 26%. Anal. Calc. for C36H40Cl2N6O27Cd2: C, 33.66; H,3.14; N, 6.54. Found: C, 34.03; H, 3.28; N, 6.76%. IR spectrum(cm1): 3329(m), 3067(m), 3012(m), 1695(s), 1575(s), 1470(m),1426(s), 1313(m), 1258(w), 1210(w), 1128(w), 1073(w), 933(w),840(w), 737(w), 692(w), 634(w). Anal. Calc. for C37H38N6O25Cd2Cl2(30): C, 35.20; H, 3.03; N, 6.66. Found: C, 34.66; H, 3.25; N, 6.83%.

Reference： [1]Xie, Lixia; Feng, Wenhua; Li, Xin; Meng, Lei; Zheng, Xianfu [Inorganica Chimica Acta, 2014, vol. 423, # PART A, p. 79 - 86]

32
cadmium(II) chloride dihydrate [ No CAS ]
[ 942512-94-9 ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[Cd(2,2'-bipyridine-3,3'-dicarboxylic acid(-2H))(2,2'-bis(imidazol-1-ylmethyl)biphenyl)(H₂O)₃] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium hydroxide at 120℃; for 72h;	2.2. Preparation of [Cd(bpy-3,3’-dc)(bibp)(H2O)3] A mixture of CdCl22H2O (0.5 mmol), H2bpy-3,3’-dc (0.5 mmol),bibp (0.5 mmol), NaOH (1 mmol), and H2O (6 mL) was placed in aParr Teflon-lined stainless steel vessel (25 cm3), and then the vesselwas sealed and heated at 120 C for 3 days. After the mixturewas slowly cooled to room temperature, colorless crystals of 1were obtained (yield: 45% based on Cd). Anal. Calc. for C32H30N6O7-Cd: C, 53.16; H, 4.18; N, 11.62. Found: C, 53.38; H, 4.62; N, 11.85%.IR (cm1): 3575(m), 3504(m), 3124(m), 1614(s), 1564(s), 1449(w),1393(s), 1288(w), 1236(w), 1159(w), 1109(m), 1083(m), 936(w),861(m), 796(m), 775(w), 701(w), 656(w).

Reference： [1]Xie, Lixia; Feng, Wenhua; Li, Xin; Meng, Lei; Zheng, Xianfu [Inorganica Chimica Acta, 2014, vol. 423, # PART A, p. 79 - 86]

33
[ 27318-90-7 ]
[ 4433-01-6 ]
[ 5743-04-4 ]
[Cd₂(2,2'-bipyridine-3,3'-dicarboxylic acid(-2H))(1,10-phenanthroline-5,6-dione)₂(H₂O)₆](ClO₄)₂(H₂O)₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	In methanol; water; acetonitrile for 2h; Reflux;	2.4. Preparation of [Cd2(bpy-3,30-dc)(ptd)2(H2O)6](ClO4)2(H2O)5 (3) The ligand H2bpy-3,30-dc (0.24 mmol), ptd (0.12 mmol) andCd(OAc)22H2O (0.24 mmol) were mixed in methanol/acetonitrile/H2O (15 mL/10 mL/5 mL). After refluxing for 2 h, the resultantsolution was added to a saturated solution (5 mL) of NaClO4H2O.Slow evaporation of the resulting yellow solution at room temperatureyielded yellow crystals suitable for X-ray diffraction determination.Yield: 26%. Anal. Calc. for C36H40Cl2N6O27Cd2: C, 33.66; H,3.14; N, 6.54. Found: C, 34.03; H, 3.28; N, 6.76%. IR spectrum(cm1): 3329(m), 3067(m), 3012(m), 1695(s), 1575(s), 1470(m),1426(s), 1313(m), 1258(w), 1210(w), 1128(w), 1073(w), 933(w),840(w), 737(w), 692(w), 634(w). Anal. Calc. for C37H38N6O25Cd2Cl2(30): C, 35.20; H, 3.03; N, 6.66. Found: C, 34.66; H, 3.25; N, 6.83%.

Reference： [1]Xie, Lixia; Feng, Wenhua; Li, Xin; Meng, Lei; Zheng, Xianfu [Inorganica Chimica Acta, 2014, # PA, p. 79 - 86]

34
cadmium(II) chloride dihydrate [ No CAS ]
[ 942512-94-9 ]
[ 4433-01-6 ]
[Cd(2,2'-bipyridine-3,3'-dicarboxylic acid(-2H))(2,2'-bis(imidazol-1-ylmethyl)biphenyl)(H₂O)₃] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium hydroxide In water at 120℃; for 72h; Autoclave;	2.2. Preparation of [Cd(bpy-3,3’-dc)(bibp)(H2O)3]n (1) A mixture of CdCl22H2O (0.5 mmol), H2bpy-3,3’-dc (0.5 mmol),bibp (0.5 mmol), NaOH (1 mmol), and H2O (6 mL) was placed in aParr Teflon-lined stainless steel vessel (25 cm3), and then the vesselwas sealed and heated at 120 C for 3 days. After the mixturewas slowly cooled to room temperature, colorless crystals of 1were obtained (yield: 45% based on Cd). Anal. Calc. for C32H30N6O7-Cd: C, 53.16; H, 4.18; N, 11.62. Found: C, 53.38; H, 4.62; N, 11.85%.IR (cm1): 3575(m), 3504(m), 3124(m), 1614(s), 1564(s), 1449(w),1393(s), 1288(w), 1236(w), 1159(w), 1109(m), 1083(m), 936(w),861(m), 796(m), 775(w), 701(w), 656(w).

Reference： [1]Xie, Lixia; Feng, Wenhua; Li, Xin; Meng, Lei; Zheng, Xianfu [Inorganica Chimica Acta, 2014, # PA, p. 79 - 86]

35
zinc(II) nitrate hexahydrate [ No CAS ]
[ 942512-94-9 ]
[ 4433-01-6 ]
[Zn(2,2'-bipyridine-3,3'-dicarboxylic acid(-2H))(2,2'-bis(imidazol-1-ylmethyl)biphenyl)(H₂O)_2.5] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With sodium hydroxide In water at 120℃; Autoclave;	2.3. Preparation of [Zn(bpy-3,30-dc)(bibp)(H2O)2.5]n (2) General procedure: A mixture of CdCl22H2O (0.5 mmol), H2bpy-3,3’-dc (0.5 mmol),bibp (0.5 mmol), NaOH (1 mmol), and H2O (6 mL) was placed in aParr Teflon-lined stainless steel vessel (25 cm3), and then the vesselwas sealed and heated at 120 C for 3 days. After the mixturewas slowly cooled to room temperature

Reference： [1]Xie, Lixia; Feng, Wenhua; Li, Xin; Meng, Lei; Zheng, Xianfu [Inorganica Chimica Acta, 2014, # PA, p. 79 - 86]

36
zinc(II) nitrate hexahydrate [ No CAS ]
[ 27318-90-7 ]
[ 4433-01-6 ]
[Zn₂(2,2'-bipyridine-3,3'-dicarboxylic acid(-2H))(1,10-phenanthroline-5,6-dione)₂(H₂O)₆](ClO₄)₂(H₂O)₆(CH₃CN) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	In methanol; water; acetonitrile for 2h; Reflux;	2.5. Preparation of [Zn2(bpy-3,30-dc)(ptd)2(H2O)6](ClO4)2(H2O)6(CH3CN)(4) General procedure: The ligand H2bpy-3,30-dc (0.24 mmol), ptd (0.12 mmol) andCd(OAc)22H2O (0.24 mmol) were mixed in methanol/acetonitrile/H2O (15 mL/10 mL/5 mL). After refluxing for 2 h, the resultantsolution was added to a saturated solution (5 mL) of NaClO4H2O.Slow evaporation of the resulting yellow solution at room temperatureyielded yellow crystals suitable for X-ray diffraction determination.

Reference： [1]Xie, Lixia; Feng, Wenhua; Li, Xin; Meng, Lei; Zheng, Xianfu [Inorganica Chimica Acta, 2014, # PA, p. 79 - 86]

37
[ 4433-01-6 ]
[2,2′-bipyridine]-3,3′-dicarbonyl dichloride dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With thionyl chloride at 20℃; for 12h; Inert atmosphere;	2.2. Synthesis of [2,2′-Bipyridine]-3,3′-dicarbonyl dichloride hydrochloride (D) A solution of 1.0 g (4.1 mM) of 3,3′-dicarboxybipyridine acid in 4 mL of thionyl chloride was stirred under argon at room temperature for 12 h. Thionyl chloride was removed under reduced pressure and 5 mL of diethyl ether was added to the flask. The precipitate was filteredoff and washed three times with diethyl ether to eliminate residues of SOCl2. The white solid was dried under vacuum. Yield: 94% (1.36 g). 1H NMR (DMSO-d6) 8.85 (dd, 2 H, 2J = 5.0, 3J = 1.5, H1), 8.54 (dd, 2 H, 2J = 7.9, 3J = 1.5, H3), 7.78 (dd, 2 H, 2J = 7.9, 2J = 5.0, H2). FT-IR (cm-1) 2454 (NH), 1711 (CO).

Reference： [1]Saavedra Díaz, Rafael Omar; Le Lagadec, Ronan; Shen, Longzhu Q.; Ryabov, Alexander D. [Journal of Coordination Chemistry, 2015, vol. 67, # 23-24, p. 3909 - 3919]

38
[ 4433-01-6 ]
[ 18531-95-8 ]
C₃₂H₂₀N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: (S)-2,2'-diamino-1,1'-binaphthalene In N,N-dimethyl-formamide Inert atmosphere;

Reference： [1]Ashokkumar, Veeramanoharan; Duraimurugan, Kumaraguru; Siva, Ayyanar [New Journal of Chemistry, 2016, vol. 40, # 8, p. 7148 - 7156]

39
dysprosium((III) oxide [ No CAS ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[ 144-62-7 ]
[Dy₄(μ₃-OH)₄(2,2'-bipyridine-3,3'-dicarboxyliclato)₃(oxalate)(H₂O)₅]·13H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	at 170℃; for 3h; Autoclave; High pressure;	2.2. Synthesis of [Dy4(m3-OH)4(bpdc)3(ox)(H2O)5]·13H2O 1 H2bpdc (0.15 mmol, 0.0733 g), H2ox (0.05 mmol, 0.0063 g) andDy2O3 (0.2 mmol, 0.0746 g) were added in 10 mL distilled water.The reaction mixture was sealed in a 25 mL Teflon-lined stainlesssteel vessel and heated at 170 °C for 3 days, then cooled by 10 C/hto room temperature. The product was washed with distilled waterand air dried. White block-shaped crystals were obtained with theyield of 58% based on Dy. Anal. Calcd (%) for C38H34O26N6Dy4 1′ (aformula after loss of 12 lattice water molecules): C, 27.81%; H,2.09%; N, 5.12%. Found: C, 27.31%; H, 1.89%; N, 5.03%. IR(KBr, cm-1):3440(vs), 1597(s),1456(s), 1397(s), 1160(m), 778(s), 693(m), 576(m).
	at 170℃; for 72h;	1 Preparation of Dy4 (μ3-OH) 4 (bpdc) 3 (ox) (H2O) 5] · 13H2O Will be dysprosium oxide,I.e. Dy2O3 (0.2 mmol, 0.0746 g),2,2'-bipyridine-3,3'-dicarboxylic acid (0.15 mmol, 0.0733 g)And oxalic acid (0.05 mmol, 0.0063 g) were added to 10 ml of deionized water,Magnetic stirring for 30 minutes;And then transferred to the hydrothermal reactor in the PTFE liner,Pack a good reactor into the oven,Heated at 170 ° C for 3 days,The solution was cooled to room temperature at 1 ° C /After removal of the product, the solid was separated,Get white lumps of crystals,Which is a functional metal-organic skeleton based on rare earth clusters.

Reference： [1]Li, Chao; Yue, Qing; Xu, Yan; Ping, Enming; Zhang, Lijuan; Zhou, Yunshan [Journal of Molecular Structure, 2020, vol. 1209]
[2]Current Patent Assignee: BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY - CN103965230, 2016, B Location in patent: Paragraph 0028; 0029; 0030

40
erbium(III) oxide [ No CAS ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[ 144-62-7 ]
[Er₄(μ₃-OH)₄(2,2'-bipyridine-3,3'-dicarboxyliclato)₃(oxalate)(H₂O)₅]·13H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	at 170℃; for 3h; Autoclave; High pressure;	2.3. Synthesis of [Er4(m3-OH)4(bpdc)3(ox)(H2O)5]·11H2O 2 H2bpdc (0.15 mmol, 0.0733 g), H2ox (0.05 mmol, 0.0063 g) andEr2O3 (0.2 mmol, 0.0765 g) were added in 10 mL distilled water. Thereaction mixture was sealed in a 25 mL Teflon-lined stainless steelvessel and heated at 170° C for 3 days, then cooled by 10 C/h toroom temperature. The product was washed with distilled waterand air dried. Pink block-shaped crystals were obtained with theyield of 62% based on Er. Anal. Calcd (%) for C38H36O27N6Er4 2′ (aformula after loss of 9 lattice water molecules): C, 27.20%; H, 2.16%;N, 5.01%. Found: C, 26.93%; H, 2.01%; N, 5.13%. IR (KBr, cm-1):3430(v), 1599(s), 1454(s), 1395(s), 1161(m), 778(s), 693(m), 576(m).
	In N,N-dimethyl-formamide at 170℃; for 72h;	2 Preparation of Er₄(μ3-OH)₄(bpdc)₃(ox)(H2O)₅]·11H₂O Erbium oxide,I.e. Er2O3 (0.2 mmol, 0.0778 g),2,2'-bipyridine-3,3'-dicarboxylic acid (0.15 mmol, 0.0733 g) and oxalic acid (0.05 mmol,0.0063 g) was added to 5 ml of deionized water and 5 ml of DMF,Magnetic stirring for 30 minutes;And then transferred to the hydrothermal reactor in the PTFE liner,Pack a good reactor into the oven,Heated at 170 ° C for 3 days,The temperature was lowered to room temperature at 20 ° C /After removal of the product, the solid was separated,To obtain pink lumpy crystals,

41
[ 111-26-2 ]
[ 4433-01-6 ]
2,2′-bipyridine-3,3′-dicarboxylic acid bis(N-hexylamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

Reference： [1]Berni, Emanuela; Le Henaff, Laurent; Jarrige, Lucie; Girard, Emeline; Jonusauskas, Gediminas; Gosse, Isabelle; Pinet, Sandra [European Journal of Organic Chemistry, 2017, vol. 2017, # 25, p. 3620 - 3630]

42
[ 4433-01-6 ]
silver nitrate hexahydrate [ No CAS ]
[Ag₄(2,2′-bipyridyl-3,3′-dicarboxylate)₂·(H₂O)]·3H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium hydroxide In methanol; water at 105℃; for 60h; Autoclave; High pressure;

Reference： [1]Li, Quan-Quan; Chao, Zeng-Yin; Liu, Cong-Yan; Zhang, Wen-Qian; Liu, Qing; Cai, Wang-Zhao; Liu, Ping; Wang, Yao-Yu [Crystal Growth and Design, 2018, vol. 18, # 5, p. 2784 - 2794]

43
[ 1148-79-4 ]
[ 4433-01-6 ]
[ 6046-93-1 ]
uranyl(VI) acetate dihydrate [ No CAS ]
C₂₇H₁₇N₅O₆U*H₂O [ No CAS ]
C₃₀H₂₃CuN₆⁽²⁺⁾*3H₂O*C₂₄H₁₂N₄O₁₀U^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.6%	With sodium hydroxide In water; isopropyl alcohol at 130℃; for 120h; Autoclave;

Reference： [1]Gomez, Germán E.; Ridenour, J. August; Byrne, Nicole M.; Shevchenko, Alexander P.; Cahill, Christopher L. [Inorganic Chemistry, 2019, vol. 58, # 11, p. 7243 - 7254]

44
nickel(II) chloride hexahydrate [ No CAS ]
[ 4433-01-6 ]
C₁₂H₁₄N₂NiO₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.3%	Stage #1: 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine With potassium hydroxide In methanol for 0.5h; Reflux; Stage #2: nickel(II) chloride hexahydrate In methanol for 2h; Reflux;	Stage one: Preparation of [Ni(κ2-bpdc)( H2O)4] A solution of KOH (0.6 millimole, 0.0336 g) in methanol (5 milliliter) was placed to a solution of bpdc (0.3 millimole, 0.0732 g) in methanol (10 milliliter) and refluxed for (30 minutes). The subsequent mixture was refluxed for a further(2 h) after addition of a methanol solution (5 milliliter) of NiCl2.6H2O (0.3 millimole, 0.0713 g) and filtered. When the solution was evaporated at room temperature the dark-green solid was formed. (Chemical formula: C12H14NiN2O8; Yield: 0.13 g, 94.3%; Melting point: 230-232°C; Color: dark-green).

Reference： [1]Mohammad, Hikmat Ali; Saber, Salim Najm Aldin; Saleh, Rezan Ali [Oriental Journal of Chemistry, 2020, vol. 36, # 5, p. 834 - 842]

45
cobalt(II) chloride hexahydrate [ No CAS ]
[ 4433-01-6 ]
C₁₂H₁₄CoN₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.7%	Stage #1: 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine With potassium hydroxide In methanol for 0.5h; Reflux; Stage #2: cobalt(II) chloride hexahydrate In methanol for 2h; Reflux;	Stage one: Preparation of [Co(κ2-bpdc)(H2O)4] 2, 2'-bipyridine-3, 3'-dicarboxylic acid (bpdc) (0.3 millimole, 0.0732 g) was dissolved in methanol (10 milliliter) and (5 milliliter) methanol solution of KOH (0.6 millimole, 0.0336 gram) was added. After refluxing for (30 min), a solution of CoCl2.6H2O(0.3 millimole, 0.0713 g) in methanol (5 milliliter) was added dropwise. The resulted solution was heated under reflux for 2 h and filtered. The light brown precipitate was produced when the filtrate was evaporated at room temperature. (Chemical formula: C12H14CoN2O8; Yield: 0.09 gram, 65.7%; decomposition point: 296°C; Color: light brown).

Reference： [1]Mohammad, Hikmat Ali; Saber, Salim Najm Aldin; Saleh, Rezan Ali [Oriental Journal of Chemistry, 2020, vol. 36, # 5, p. 834 - 842]

46
copper(II) choride dihydrate [ No CAS ]
[ 4433-01-6 ]
C₁₂H₁₄CuN₂O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.9%	Stage #1: 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine With potassium hydroxide In methanol for 0.5h; Reflux; Stage #2: copper(II) choride dihydrate In methanol for 2h; Reflux;	Stage one: Preparation of [Cu(κ2-bpdc)(H2O)4] To a methanol solution (10 mL) of bpdc (0.3 millimole, 0.0732 g), a methanol solution(5 milliliter) of KOH (0.6 millimole, 0.0336 g) was added and refluxed for (30 min) then a solution of CuCl2.2H2O (0.3 millimole, 0.0514 g) dissolved in (5 milliliter) methanol was added and the resultant solution was refluxed for a further 2 h and filtered. The green solid was achieved when the solvent was evaporated at room temperature. (Chemical formula: C12H14CuN2O8; Yield: 0.07 g, 61.9 %; Melting point: 236-238°C; Color: green).

Reference： [1]Mohammad, Hikmat Ali; Saber, Salim Najm Aldin; Saleh, Rezan Ali [Oriental Journal of Chemistry, 2020, vol. 36, # 5, p. 834 - 842]

47
uranyl nirate hexahydrate [ No CAS ]
[ 4433-01-6 ]
[ 33513-42-7 ]
[H₂N(CH₃)₂]₂[UO₂(2,2′-bipyridine-3,3′-dicarboxylate)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Methyltriphenylphosphonium bromide In water at 140℃;	[H2N(CH3)2]2[UO2(bpdc)2] (1) 2,2′-bipyridine-3,3′-dicarboxylic acid (24 mg, 0.10 mmol),[UO2(NO3)2(H2O)2]·4H2O (35 mg, 0.07 mmol), andPPh3MeBr(36 mg, 0.10 mmol) were dissolved in a mixtureof water (0.8 mL) and DMF (0.2 mL). The solution wasplaced in a 10 mL tightly closed glass vessel and heated at140 °C in a sand bath, under autogenous pressure, giving afew yellow crystals of complex 1 within one month.

Reference： [1]Atoini, Youssef; Harrowfield, Jack; Kim, Yang; Thuéry, Pierre [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2021, vol. 100, # 1-2, p. 89 - 98]

48
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 4433-01-6 ]
catena-poly[[diaquacobalt(II)]-μ-(2,2'-dipyridyl-3,3'-dicarboxylato-κ(4)N,N':O,O')] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In aq. acetate buffer at 79.99℃; for 72h;	Synthesis of [Co(3,3′-BDA)(H2O)2]n (1) Complex 1 was synthesized in the high-pressure reactor ofmicrocalorimetry under the simulated hydrothermal conditionat different holding temperatures of 353.15 K, 393.15 K,413.15 K, 433.15 K. A mixture of Co(NO3)2· 6H2O(0.032 g,0.05 mmol), 3,3′-BDA (0.012 g, 0.05 mmol) was added to a3 mL HAc-NaAc buffer solution (pH = 4). The mixture wasstirred for 10 min and was placed in the high-pressure reactorheated at holding temperature for 72 h. The reactor wascooled at a cooling rate of 5 K·min-1 to room temperature.The wine block-like crystals of 1 were collected by filtration,washed with ethanol and dried in air (yield 65%-82%based on Co). Elemental analyses: calcd for C12H10CoN2O6(1): C: 43.02, H:2.61, N:8.19%; Found for C: 42.75, H:2.99,N:8.31%.

Reference： [1]Ren, Yixia; Yang, Xue; Wang, Zhixiang; Wu, Yue; Xu, Xunpeng; Wang, Hang; Huang, Peipei [Journal of Thermal Analysis and Calorimetry, 2021, vol. 145, # 6, p. 3293 - 3299]

49
sodium tetrachloroaurate(III) dihyrate [ No CAS ]
[ 4433-01-6 ]
[ 55310-46-8 ]
C₂₇H₂₂AuN₃O₄S₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: sodium tetrachloroaurate(III) dihyrate; 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine In ethanol for 3h; Stage #2: sodium dibenzyldithiocarbamate In ethanol for 0.166667h;	3.4. Synthesis of Complexes 1-3 General procedure: In the first step, 0.122 g (0.5 mmol) 2,20-bipyridine-3,30-dicarboxylic acid in 10 mL ofethanol was added to 0.200 g (0.5 mmol) Na[AuCl4]2H2O in 10 mL of ethanol, and themixture was stirred for 3 h, generating a yellow product. In the second step, 0.5 mmolof the respective sodium dithiocarbamate in 5 mL of ethanol was added dropwise to theabove mixture. The mixture was stirred for an additional 10 min. For complexes 1 and2, yellow precipitates were obtained, while in the case of 3, it was an orange color. Theproducts were collected by filtration, washed with distilled water (3 10 mL), and driedunder vacuum. Yield: 0.215 g, 68% for 1; 0.245 g, 74.2% for 2; 0.278 g, 71% for 3.

Reference： [1]Ahmad, Saeed; Alhazzani, Khalid; Alhoshani, Ali; Alotaibi, Moureq; Isab, Anvarhusein A.; Monim-Ul-mehboob, Muhammad; Qamar, Wajhul; Sobeai, Homood M. As; Sulaiman, Adam A. A. [Molecules, 2021, vol. 26, # 13]

50
sodium tetrachloroaurate(III) dihyrate [ No CAS ]
[ 4433-01-6 ]
C₁₂H₈AuCl₂N₂O₄⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.6%	In ethanol at 20℃; for 3h;	3.3. Synthesis of [Au(Bipydc))Cl2]Cl (A) It was prepared by combining 0.122 g (0.5 mmol) 2,20-bipyridine-3,30-dicarboxylic acidin 10 mL of ethanol and 0.20 g (0.5 mmol) NaAuCl42H2O in 10 mL of ethanol. The mixturewas stirred for 3 h at room temperature and then filtered. The yellow product was washedtwice with ethanol (5 mL) and three times with diethyl ether (10 mL), then dried in thedark and stored in a fridge. Yield = 0.212 g, 77.6%. Analysis (C12H8AuCl3N2O4, 547.52):Calcd. C 26.32, H 1.47, N 5.11; found C 25.98, H 1.53, N 5.54.

51
sodium tetrachloroaurate(III) dihyrate [ No CAS ]
[ 4433-01-6 ]
[ 128-04-1 ]
C₁₅H₁₄AuN₃O₄S₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: sodium tetrachloroaurate(III) dihyrate; 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine In ethanol for 3h; Stage #2: sodium dimethyldithiocarbamate In ethanol for 0.166667h;	3.4. Synthesis of Complexes 1-3 General procedure: In the first step, 0.122 g (0.5 mmol) 2,20-bipyridine-3,30-dicarboxylic acid in 10 mL ofethanol was added to 0.200 g (0.5 mmol) Na[AuCl4]2H2O in 10 mL of ethanol, and themixture was stirred for 3 h, generating a yellow product. In the second step, 0.5 mmolof the respective sodium dithiocarbamate in 5 mL of ethanol was added dropwise to theabove mixture. The mixture was stirred for an additional 10 min. For complexes 1 and2, yellow precipitates were obtained, while in the case of 3, it was an orange color. Theproducts were collected by filtration, washed with distilled water (3 10 mL), and driedunder vacuum. Yield: 0.215 g, 68% for 1; 0.245 g, 74.2% for 2; 0.278 g, 71% for 3.

52
sodium tetrachloroaurate(III) dihyrate [ No CAS ]
[ 4433-01-6 ]
[ 148-18-5 ]
C₁₇H₁₈AuN₃O₄S₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.2%	Stage #1: sodium tetrachloroaurate(III) dihyrate; 3,3'-bis(hydroxycarbonyl)-2,2'-bipyridine In ethanol for 3h; Stage #2: sodium N,N-diethyldithiocarbamate In ethanol for 0.166667h;	3.4. Synthesis of Complexes 1-3 General procedure: In the first step, 0.122 g (0.5 mmol) 2,20-bipyridine-3,30-dicarboxylic acid in 10 mL ofethanol was added to 0.200 g (0.5 mmol) Na[AuCl4]2H2O in 10 mL of ethanol, and themixture was stirred for 3 h, generating a yellow product. In the second step, 0.5 mmolof the respective sodium dithiocarbamate in 5 mL of ethanol was added dropwise to theabove mixture. The mixture was stirred for an additional 10 min. For complexes 1 and2, yellow precipitates were obtained, while in the case of 3, it was an orange color. Theproducts were collected by filtration, washed with distilled water (3 10 mL), and driedunder vacuum. Yield: 0.215 g, 68% for 1; 0.245 g, 74.2% for 2; 0.278 g, 71% for 3.

53
[ 66-71-7 ]
europium sesquioxide [ No CAS ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[Eu₂(1,10-phenanthroline)₂(2,2′-bipyridine-3,3′-dicarboxylate)₃(H₂O)₂]_n*6nH₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With perchloric acid at 160℃; for 144h; Autoclave; Sealed tube;	2.2. Synthesis of [Ln2(phen)2(bpdc)3(H2O)2]n6nH2O [Ln = Eu (1), Tb(2), Gd (3)] General procedure: A mixture of H2bpdc (0.0241 g, 0.1 mmol), phen (0.0191 g, 0.1mmol), Ln2O3 {Ln = Eu (0.0351 g, 0.1 mmol), Tb (0.0361 g, 0.1 mmol)and Gd (0.0361 g, 0.1 mmol)} and water (5 mL) was stirred for 10 min,and then the pH value of the mixed solution was adjusted to 3 by HClO4acid. The final mixture was sealed in a 25 mL Teflonlined autoclave andheated at 160 C for 6 days. After cooling to room temperature slowly,colorless-block crystals of 1-3 were isolated. The yield of 1 is 52% basedon Eu2O3. Anal. calcd. for 1, C30H25EuN5O10, C 46.95%, H 3.28%, N9.12%, found: C 47.03%, H 3.34%, N 9.06%. IR (cm 1):3593(w), 3054(w), 1631(s), 1568(vs), 1375(vs), 1155(m), 1097(w), 1058(m), 854(m),769(s), 729(vs), 684(m), 633(s), 547(s). The yield of 2 is 56% based onTb2O3. Anal. calcd. for 2, C30H25TbN5O10, C 46.52%, H 3.25%, N 9.04%,found: C 46.45%, H 3.31%, N 9.11%. IR (cm 1): 3591(w), 3066(w),1641(vs), 1571(s), 1514(w), 1377(vs), 1231(w), 1158(m), 1100(w),1055(m), 958(w), 848(s), 769(s), 729(vs), 627(m), 552(m). The yield of3 is 52% based on Gd2O3. Anal. calcd. for 3, C30H25GdN5O10, C 46.63%,H 3.26%, N 9.06%, found: C 46.57%, H 3.32%, N 9.12%. IR (cm 1):3597(w), 3057(w), 1638(vs), 1579(vs), 1380(vs), 1225(w), 1152(m),1098(w), 1057(m), 958(w), 848(s), 767(s), 731(vs), 626(s), 554(s). TheCCDC reference numbers are 2164586-2164588.

Reference： [1]Huang, Chun-Mei; Liu, Xing; Ouyang, Congrui; Zhang, Lu; Zhou, Jian [Dyes and Pigments, 2022, vol. 203]

54
[ 66-71-7 ]
terbium sesquioxide [ No CAS ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[Tb₂(1,10-phenanthroline)₂(2,2′-bipyridine-3,3′-dicarboxylate)₃(H₂O)₂]_n*6nH₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With perchloric acid at 160℃; for 144h; Autoclave; Sealed tube;	2.2. Synthesis of [Ln2(phen)2(bpdc)3(H2O)2]n6nH2O [Ln = Eu (1), Tb(2), Gd (3)] General procedure: A mixture of H2bpdc (0.0241 g, 0.1 mmol), phen (0.0191 g, 0.1mmol), Ln2O3 {Ln = Eu (0.0351 g, 0.1 mmol), Tb (0.0361 g, 0.1 mmol)and Gd (0.0361 g, 0.1 mmol)} and water (5 mL) was stirred for 10 min,and then the pH value of the mixed solution was adjusted to 3 by HClO4acid. The final mixture was sealed in a 25 mL Teflonlined autoclave andheated at 160 C for 6 days. After cooling to room temperature slowly,colorless-block crystals of 1-3 were isolated. The yield of 1 is 52% basedon Eu2O3. Anal. calcd. for 1, C30H25EuN5O10, C 46.95%, H 3.28%, N9.12%, found: C 47.03%, H 3.34%, N 9.06%. IR (cm 1):3593(w), 3054(w), 1631(s), 1568(vs), 1375(vs), 1155(m), 1097(w), 1058(m), 854(m),769(s), 729(vs), 684(m), 633(s), 547(s). The yield of 2 is 56% based onTb2O3. Anal. calcd. for 2, C30H25TbN5O10, C 46.52%, H 3.25%, N 9.04%,found: C 46.45%, H 3.31%, N 9.11%. IR (cm 1): 3591(w), 3066(w),1641(vs), 1571(s), 1514(w), 1377(vs), 1231(w), 1158(m), 1100(w),1055(m), 958(w), 848(s), 769(s), 729(vs), 627(m), 552(m). The yield of3 is 52% based on Gd2O3. Anal. calcd. for 3, C30H25GdN5O10, C 46.63%,H 3.26%, N 9.06%, found: C 46.57%, H 3.32%, N 9.12%. IR (cm 1):3597(w), 3057(w), 1638(vs), 1579(vs), 1380(vs), 1225(w), 1152(m),1098(w), 1057(m), 958(w), 848(s), 767(s), 731(vs), 626(s), 554(s). TheCCDC reference numbers are 2164586-2164588.

Reference： [1]Huang, Chun-Mei; Liu, Xing; Ouyang, Congrui; Zhang, Lu; Zhou, Jian [Dyes and Pigments, 2022, vol. 203]

55
gadolinium(III) oxide [ No CAS ]
[ 66-71-7 ]
[ 4433-01-6 ]
[ 7732-18-5 ]
[Gd₂(1,10-phenanthroline)₂(2,2′-bipyridine-3,3′-dicarboxylate)₃(H₂O)₂]_n*6nH₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With perchloric acid at 160℃; for 144h; Autoclave; Sealed tube;	2.2. Synthesis of [Ln2(phen)2(bpdc)3(H2O)2]n6nH2O [Ln = Eu (1), Tb(2), Gd (3)] General procedure: A mixture of H2bpdc (0.0241 g, 0.1 mmol), phen (0.0191 g, 0.1mmol), Ln2O3 {Ln = Eu (0.0351 g, 0.1 mmol), Tb (0.0361 g, 0.1 mmol)and Gd (0.0361 g, 0.1 mmol)} and water (5 mL) was stirred for 10 min,and then the pH value of the mixed solution was adjusted to 3 by HClO4acid. The final mixture was sealed in a 25 mL Teflonlined autoclave andheated at 160 C for 6 days. After cooling to room temperature slowly,colorless-block crystals of 1-3 were isolated. The yield of 1 is 52% basedon Eu2O3. Anal. calcd. for 1, C30H25EuN5O10, C 46.95%, H 3.28%, N9.12%, found: C 47.03%, H 3.34%, N 9.06%. IR (cm 1):3593(w), 3054(w), 1631(s), 1568(vs), 1375(vs), 1155(m), 1097(w), 1058(m), 854(m),769(s), 729(vs), 684(m), 633(s), 547(s). The yield of 2 is 56% based onTb2O3. Anal. calcd. for 2, C30H25TbN5O10, C 46.52%, H 3.25%, N 9.04%,found: C 46.45%, H 3.31%, N 9.11%. IR (cm 1): 3591(w), 3066(w),1641(vs), 1571(s), 1514(w), 1377(vs), 1231(w), 1158(m), 1100(w),1055(m), 958(w), 848(s), 769(s), 729(vs), 627(m), 552(m). The yield of3 is 52% based on Gd2O3. Anal. calcd. for 3, C30H25GdN5O10, C 46.63%,H 3.26%, N 9.06%, found: C 46.57%, H 3.32%, N 9.12%. IR (cm 1):3597(w), 3057(w), 1638(vs), 1579(vs), 1380(vs), 1225(w), 1152(m),1098(w), 1057(m), 958(w), 848(s), 767(s), 731(vs), 626(s), 554(s). TheCCDC reference numbers are 2164586-2164588.

Reference： [1]Huang, Chun-Mei; Liu, Xing; Ouyang, Congrui; Zhang, Lu; Zhou, Jian [Dyes and Pigments, 2022, vol. 203]

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P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
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

[ CAS No. 4433-01-6 ] {[proInfo.proName]}

Quality Control of [ 4433-01-6 ]

Related Doc. of [ 4433-01-6 ]

Product Details of [ 4433-01-6 ]

Calculated chemistry of [ 4433-01-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4433-01-6 ]

Application In Synthesis of [ 4433-01-6 ]

[ 4433-01-6 ] Synthesis Path-Upstream 1~12

[ 4433-01-6 ] Synthesis Path-Downstream 1~55

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry