[ CAS No. 69-89-6 ] {[proInfo.proName]}

Name: 69-89-6|1H-Purine-2,6(3H,7H)-dione|98%
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Quality Control of [ 69-89-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 69-89-6 ]

Product Details of [ 69-89-6 ]

CAS No. :	69-89-6	MDL No. :	MFCD00078453
Formula :	C₅H₄N₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LRFVTYWOQMYALW-UHFFFAOYSA-N
M.W :	152.11	Pubchem ID :	1188
Synonyms :	2,6-Dihydroxypurine;NSC 14664	Chemical Name :	1H-Purine-2,6(3H,7H)-dione

Calculated chemistry of [ 69-89-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	37.34
TPSA :	94.4 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) :	-7.75 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.07
Log Po/w (XLOGP3) :	-0.73
Log Po/w (WLOGP) :	-1.06
Log Po/w (MLOGP) :	-1.25
Log Po/w (SILICOS-IT) :	1.46
Consensus Log Po/w :	-0.3

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.93
Solubility :	17.9 mg/ml ; 0.118 mol/l
Class :	Very soluble
Log S (Ali) :	-0.78
Solubility :	25.5 mg/ml ; 0.167 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.96
Solubility :	1.66 mg/ml ; 0.0109 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 69-89-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 69-89-6 ]

* 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 [ 69-89-6 ]
Downstream synthetic route of [ 69-89-6 ]

[ 69-89-6 ] Synthesis Path-Upstream 1~8

1
[ 58-55-9 ]
[ 3240-72-0 ]
[ 1076-22-8 ]
[ 127091-92-3 ]
[ 69-89-6 ]

Reference： [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5611 - 5620

2
[ 69-89-6 ]
[ 2002-59-7 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 5633,5635,5636

3
[ 69-89-6 ]
[ 2382-10-7 ]

Reference： [1] Patent: WO2018/137036, 2018, A1,

4
[ 58-55-9 ]
[ 3240-72-0 ]
[ 1076-22-8 ]
[ 127091-92-3 ]
[ 69-89-6 ]

Reference： [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5611 - 5620

5
[ 69-89-6 ]
[ 10357-68-3 ]

Yield	Reaction Conditions	Operation in experiment
18.4 g	With bromine In water at 100℃;	Take xanthine 15g, was added 250mL ofwater, 7.6mL bromine, and heated to 100 ° C, i.e. the bromine color disappearsto stop the reaction, washed with a small amount of water, the reaction mixturewas cooled to room temperature, suction filtered, the filter cake was dried invacuo , the products 18.4g;

Reference： [1] Justus Liebigs Annalen der Chemie, 1883, vol. 221, p. 344
[2] Patent: CN103172633, 2016, B, . Location in patent: Paragraph 0145-0147

6
[ 69-89-6 ]
[ 87-42-3 ]

Reference： [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 7, p. 1053 - 1055

7
[ 69-89-6 ]
[ 5451-40-1 ]

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 10, p. 4149 - 4153

8
[ 69-89-6 ]
[ 5451-40-1 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 7, p. 534 - 537
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 4, p. 332 - 334
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984, vol. 23, # 12, p. 1286 - 1288
[4] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 414 - 422

[ 69-89-6 ] Synthesis Path-Downstream 1~88

1
[ 290-87-9 ]
[ 3240-72-0 ]
[ 69-89-6 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 6559

2
[ 83-39-6 ]
[ 69-89-6 ]

Reference： [1]Journal of the Chemical Society,1945,p. 229
[2]Journal of the Chemical Society,1954,p. 232

3
[ 5442-24-0 ]
[ 77287-34-4 ]
[ 69-89-6 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1954,vol. 74,p. 420
Chem.Abstr.,1955,p. 5305
[2]Patent: DE834105,1949,
DRP/DRBP Org.Chem.,

4
[ 69-93-2 ]
[ 627-45-2 ]
[ 69-89-6 ]

Reference： [1]Patent: DE836803,1949,
DRP/DRBP Org.Chem.,

5
[ 69-93-2 ]
[ 544-17-2 ]
[ 69-89-6 ]

Reference： [1]Skandinavisches Archiv fur Physiologie,vol. 25,p. 256
Chemisches Zentralblatt,1911,vol. 82,p. 1411

6
[ 69-93-2 ]
[ 144-62-7 ]
[ 56-81-5 ]
[ 645-93-2 ]
[ 69-89-6 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1911,vol. 76,p. 487

7
[ 69-93-2 ]
[ 77287-34-4 ]
[ 69-89-6 ]

Reference： [1]Chemische Berichte,1950,vol. 83,p. 201,209
[2]Chemische Berichte,1950,vol. 83,p. 201,209
[3]Patent: DE804210,1950,
DRP/DRBP Org.Chem.,

8
[ 64-18-6 ]
[ 69-93-2 ]
[ 56-81-5 ]
[ 69-89-6 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),vol. <2>118,p. 168

9
[ 69-93-2 ]
[ 103-70-8 ]
[ 69-89-6 ]

Reference： [1]Patent: DE836803,1949,
DRP/DRBP Org.Chem.,

11
[ 69-93-2 ]
[ 645-93-2 ]
[ 69-89-6 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1911,vol. 76,p. 487

12
[ 10184-00-6 ]
[ 77287-34-4 ]
[ 69-89-6 ]

Reference： [1]Chemische Berichte,1953,vol. 86,p. 325

13
[ 10184-01-7 ]
[ 77287-34-4 ]
[ 69-89-6 ]

Reference： [1]Chemische Berichte,1953,vol. 86,p. 325
[2]Chemische Berichte,1953,vol. 86,p. 325

14
[ 5435-16-5 ]
[ 77287-34-4 ]
[ 69-89-6 ]

Reference： [1]Chemische Berichte,1952,vol. 85,p. 752,759

15
[ 73-40-5 ]
[ 69-89-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 426 - 429

16
[ 1774-47-6 ]
[ 81980-39-4 ]
[ 938-85-2 ]
[ 73-40-5 ]
[ 578-76-7 ]
[ 69-89-6 ]
[ 2958-98-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 861 - 869

17
[ 69-89-6 ]
[ 69-89-6 ]

Reference： [1]Journal of Physical Chemistry,1986,vol. 90,p. 974 - 978

18
[ 124-38-9 ]
[ 5098-11-3 ]
[ 69-89-6 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 1051 - 1053

19
[ 98541-64-1 ]
[ 69-89-6 ]
[ 391612-16-1 ]
(S)-N-[(tert-butoxy)carbonyl]-β-(xanthin-7-yl)alanine [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2000,vol. 83,p. 2580 - 2593

20
[ 124-38-9 ]
[ 5098-11-3 ]
[ 69-89-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 3155 - 3158

21
[ 20710-47-8 ]
[ 69-89-6 ]
1-[2H₃,13C]methylxanthine [ No CAS ]

Reference： [1]Clinical Pharmacology and Therapeutics,2001,vol. 70,p. 415 - 424

22
C₁₀H₁₃N₅O₂ [ No CAS ]
[ 69-89-6 ]

Reference： [1]European Journal of Organic Chemistry,2007,p. 4056 - 4064

23
[ 69-89-6 ]
[(2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-acetyl]-[2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-ethyl]-amino}-acetic acid [ No CAS ]

Reference： [1]Synlett,2005,p. 1442 - 1446

24
[ 69-89-6 ]
[ 861204-49-1 ]

Reference： [1]Synlett,2005,p. 1442 - 1446

25
[ 69-89-6 ]
[ 61959-50-0 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3341 - 3349

26
[ 69-89-6 ]
7-Butylxanthine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3341 - 3349

27
[ 69-89-6 ]
7,9-diallylxanthinium bromide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3341 - 3349

28
[ 69-89-6 ]
[ 18552-88-0 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 3508

29
5-ureido-1⁽³⁾<i>H</i>-imidazole-4-carboxylic acid methyl ester [ No CAS ]
[ 69-89-6 ]

Reference： [1]Journal of the Chemical Society,1942,p. 232,233

Yield	Reaction Conditions	Operation in experiment
0.78 g (8.2%)		A. 1-(4-Chlorobenzyl)-3-ethyl-8-isopropyl-xanthine 3.17 g (28.2 mM) of potassium t-butoxide (t-BuOK) were added to a solution of 6.11 g (27.5 mM) of 6-amino-1-ethyl-5-isobutyrylamino-uracil. At 0 C., 4.90 g (30.4 mM) of 4-chlorobenzylclhloride were added. After 3 hours at 0-5 C., further 1.22 g t-BuOK and 2.45 g of 4-chloro-benzylchloride were added. After further 3 hours another 2.45 g of benzylchloride are supplemented. After 3 days, the solution was neutralized with 1N HCl and the solvents evaporated. The residue was suspended in water, the solid collected and washed. The crude intermediate amide was heated under reflux in 100 ml of 1N NaOH and 10 ml of 1-propanol. After 1 hour, the mixture was neutralized to pH 7 and extracted with chloroform. Crystallization from dichloromethane (mainly evaporated)--methanol gave 2.99 g (31.3%) of the title xanthine, mp 194-5 C. The mother liquors gave 6.33 g of impure material which was separated on 15 g of silica gel elutions with dichloromethane and gave additional 0.78 g (8.2%) of the xanthine.

31
[ 7440-44-0 ]
[ 69-89-6 ]
[ 34626-84-1 ]

Yield	Reaction Conditions	Operation in experiment
6.80 g (98.7%)	With diphosphorus pentasulfide; In pyridine; sodium hydroxide; water; isopropyl alcohol;	6.59 g (19 mM) of <strong>[69-89-6]xanthin</strong>e and 5.07 g (22.8 mM) of phosphorus pentasulfide were heated under reflux in 102 ml of pyridine for 3 days. At 0 C., 25.1 ml of 2N NaOH were added. The solid was filtered off and washed with pyridine. The solvents were evaporated in vacuo, the residue suspended in water, collected, redissolved in 100 ml of 1N NaOH and 50 ml of isopropanol, treated twice with 0.3 g of charcoal, filtered and neutralized with 5N HCl to pH 7. The isopropanol was removed in vacuo and the solid collected, washed and dried to give 6.80 g (98.7%) of 6-thio<strong>[69-89-6]xanthin</strong>e, mp 188-9 C. Elemental analysis for C17 H19 Cl N4 OS: Calculated: C 56.27 H 5.28 N 15.44 0 4.41 Found: C 56.25 H 5.33 N 15.47 0 4.41

Reference： [1]Patent: US6025361,2000,A

32
[ 2969-81-5 ]
[ 76194-10-0 ]
[ 69-89-6 ]

Yield	Reaction Conditions	Operation in experiment
9.2 g (60%)	In sodium hydroxide; (CH2)3 COOEt; N,N-dimethyl-formamide;	EXAMPLE 2 1-(4-hydroxybutyl)-3-butyl xanthine (Method B, xanthine no. 21) 11.3 g (0. 05 mole) of 1-butyl-5-formylamino-6-aminouracil (II) (R1 =butyl, R8 =H) are dissolved under nitrogen in 200 ml of DMF. 10.6 ml (0.075 mole) of ethyl 4-bromobutyrate are added, after which 2 g (0.05 mole) of solid powder-form NaOH is added with thorough stirring in portions of 0.5 g at intervals of 1 hour. On completion of the addition, the mixture is left to react overnight. The solvent is then evaporated and the oily residue of (IV) (substituent in the 1-position=(CH2)3 COOEt) is dissolved in 100 ml of 10% NaOH. This solution is then heated under reflux for 0.5 hour and then cooled, neutralized to pH 5 with acetic acid and filtered. The precipitate formed is dried. Yield: 9.2 g (60%) of crude xanthine (V) (substituent in the 1-position=(CH2)3 COOH, R3 =butyl, R8 =H).
9.2 g (60%)	In sodium hydroxide; N,N-dimethyl-formamide;	EXAMPLE 2 1-(4-Hydroxybutyl)-3-butylxanthine (Method B, compound No. 21) 11.3 g (0.05 mole) of 1-butyl-5-formylamino-6-aminouracil (II) (R3 =butyl, R2 =H) are dissolved under nitrogen in 200 ml of DMF. 10.6 ml (0.075 mole) of ethyl 4-bromobutyrate are added, followed, with good stirring, by 2 g of (0.05 mole) of powdered solid NaOH in hourly 0.5 g portions. When the addition has been completed, the mixture is left to react overnight again. The solvent is evaporated off and the oily residue of (IV) (substituent in the 1 position=--(CH2)3 COOEt) is dissolved in 100 ml of 10% NaOH. This solution is refluxed for 1/2 hour. It is cooled, neutralized with acetic acid to pH 5, and the precipitate formed is filtered off and dried. Yield: 9.2 g (60%) of crude xanthine (V) (substituent in the 1 position=--(CH2)3 COOH, R3 =butyl, R2 =H).

Reference： [1]Patent: US5338741,1994,A
[2]Patent: US5053433,1991,A

33
[ 28822-58-4 ]
soya lecithin [ No CAS ]
[ 69-89-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	This is done for example by the following procedure: 0.2 g of 3-isobutyl-1-methylxanthine (IBMX), 3.6 g of soya lecithin and 0.4 g of beta-sitosterol are dissolved in 25 ml of methylene chloride. This organic solution is evaporated in a rotating round-bottomed flask at 45 C. under reduced pressure to give a lipidic film deposited on the inner wall of the flask. The film obtained is taken up in 95.8 g of distilled water or buffer solution to give a suspension of lipidic vesicles.

Reference： [1]Patent: US5470579,1995,A

34
[ 69-89-6 ]
[ 10357-68-3 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In water; at 100℃; for 2h;	EXAMPLE 15 8-{4-[2-(Tnfluoromethyl')phenoxy]pphiendin-l-vU-3,9-dihvdro-lH-pu?ne-2,6-dione Step 1: 8-bromo-3,9-dihvdro-lH-purine-2,6-dione To a mixture of <strong>[69-89-6]xanthin</strong>e (100 mg, 0.66 mmol) in water (0.65 mL) was added bromine (0.05 mL, 0.99 mmol) m a 4-mL glass vial. The vial was capped and heated at 1000C. After 2 h, the mixture was cooled to room temperature, filtered and the solid washed with water and then Et2O. The product was dried under high vacuum to give the title product as a solid. leta NMR (500 MHz, DMSO-d6): delta 14.09 (1 H, s), 11.64 (1 H, s), 10.91 (1 H, s). MS (+ESI) m/z 232, 233 (MH+).

Reference： [1]Patent: WO2007/56846,2007,A1 .Location in patent: Page/Page column 45-46

Yield	Reaction Conditions	Operation in experiment
		Example 8 5-[8-(4-Acetylamino-benzyl)-1-benzyl-2,6-dioxo-1,2,6,7-tetrahydro-purin-3-ylmethyl]-furan-2-carboxylic acid; compound with trifluoro-acetic acid This compound was prepared by a method similar to that described in example 5 except that 5-chloromethyl-furan-2-carboxylic acid methyl ester was used in place of 3-bromomethylfuran. The methyl ester was hydrolyzed to the carboxylic acid during cyclization to form the xanthine. MS, m/z(M+)=513.1654.

36
hydrated cobalt(II) bromide [ No CAS ]
[ 69-89-6 ]
Co(xnH)2(xn)Br [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1989,vol. 161,p. 29 - 34

37
Co(II) chloride hydrate [ No CAS ]
[ 69-89-6 ]
Co(xnH)2(xn)Cl [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1989,vol. 161,p. 29 - 34

38
cobalt(II) iodide hydrate [ No CAS ]
[ 69-89-6 ]
Co(xnH)2(xn)I*H₂O [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1989,vol. 161,p. 29 - 34

39
[ 14701-21-4 ]
[ 69-89-6 ]
Ag⁽¹⁺⁾*C₅H₃N₄O₂^(1-)=AgC₅H₃N₄O₂ [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1946,vol. 65,p. 751 - 767

40
PdClC₁₈H₁₀N₂OCH₃ [ No CAS ]
silver nitrate [ No CAS ]
[ 69-89-6 ]
(PdC₁₈H₁₀N₂OCH₃)2(C₅H₃N₄O₂)⁽¹⁺⁾*NO₃^(1-)={(PdC₁₈H₁₀N₂OCH₃)2(C₅H₃N₄O₂)}NO₃ [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1993,p. 307 - 309

41
dihydrogen hexachloroplatinate [ No CAS ]
[ 69-89-6 ]
(xanthinium)2 hexachloroplatinate(IV) * 2 xanthinium chloride * 8 H₂O [ No CAS ]

Reference： [1]Thermochimica Acta,1985,vol. 93,p. 73 - 76

42
[ 13454-96-1 ]
[ 69-89-6 ]
(xanthinium)2 hexachloroplatinate(IV) * 2 xanthinium chloride * 8 H₂O [ No CAS ]

Reference： [1]Thermochimica Acta,1986,vol. 97,p. 67 - 76

43
[ 7646-85-7 ]
[ 69-89-6 ]
dixanthinium tetrachlorozincate [ No CAS ]

Reference： [1]Journal of Thermal Analysis,1983,vol. 28,p. 3 - 10
[2]Inorganica Chimica Acta,1992,vol. 197,p. 135 - 140

44
palladium dichloride [ No CAS ]
[ 69-89-6 ]
Pd(C₅H₄N₄O₂)2Cl₂*2H₂O [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1983,vol. 79,p. 250 - 251

45
palladium dichloride [ No CAS ]
[ 69-89-6 ]
2(C₅H₅N₄O₂)⁽¹⁺⁾*PdCl₄^(2-)*2H₂O = (C₅H₅N₄O₂)2PdCl₄(H₂O)2 [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1983,vol. 79,p. 250 - 251

46
copper(II) choride dihydrate [ No CAS ]
[ 69-89-6 ]
Cu⁽⁴⁺⁾*2C₅H₃N₄O₂^(1-)*2Cl^(1-)*2H₂O=Cu(C₅H₃N₄O₂)2Cl₂*2H₂O [ No CAS ]

Reference： [1]Polyhedron,1986,vol. 5,p. 1357 - 1362

47
[ 1184-57-2 ]
[ 69-89-6 ]
(CH₃Hg)3N₃(CO)2C₂NCH*2H₂O [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 2249 - 2259

48
[ 40661-97-0 ]
[ 1184-57-2 ]
[ 69-89-6 ]
(CH₃Hg)4N₃(CO)2C₂NCH⁽¹⁺⁾*ClO₄^(1-)*2H₂O=(CH₃Hg)4N₃(CO)2C₂NCHClO₄*2H₂O [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 2249 - 2259

49
[ 40661-97-0 ]
[ 1184-57-2 ]
[ 69-89-6 ]
(CH₃Hg)3N₃H(CO)2C₂NCH⁽¹⁺⁾*ClO₄^(1-)*H₂O=(CH₃Hg)3N₃H(CO)2C₂NCHClO₄*H₂O [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 2249 - 2259

50
[ 2374-27-8 ]
[ 1184-57-2 ]
[ 69-89-6 ]
(CH₃Hg)4N₃(CO)2C₂NCH⁽¹⁺⁾*NO₃^(1-)=(CH₃Hg)4N₃(CO)2C₂NCHNO₃ [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 2249 - 2259

51
[ 2374-27-8 ]
[ 1184-57-2 ]
[ 69-89-6 ]
(CH₃Hg)3N₃H(CO)2C₂NCH⁽¹⁺⁾*NO₃^(1-)*H₂O=(CH₃Hg)3N₃H(CO)2C₂NCHNO₃*H₂O [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 2249 - 2259

52
cobalt(II) perchlorate hydrate [ No CAS ]
[ 69-89-6 ]
Co⁽²⁺⁾*(NHCONHCCCONCHN)^(1-)*2(NHCONHCCCONHCHN)*ClO₄^(1-)*H₂O=[Co(NHCONHCCCONCHN)(NHCONHCCCONHCHN)2]ClO₄*H₂O [ No CAS ]