[ CAS No. 18653-98-0 ] {[proInfo.proName]}

Name: 18653-98-0|2,2'-((Ethane-1,2-diylbis(azanediyl))bis(methylene))diphenol|98%
Brand: Ambeed
SKU: A448921
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Quality Control of [ 18653-98-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 18653-98-0 ]

Product Details of [ 18653-98-0 ]

CAS No. :	18653-98-0	MDL No. :	MFCD00058922
Formula :	C₁₆H₂₀N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MLFXJCXPSODAIS-UHFFFAOYSA-N
M.W :	272.34	Pubchem ID :	199210
Synonyms :

Calculated chemistry of [ 18653-98-0 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.25
Num. rotatable bonds :	7
Num. H-bond acceptors :	4.0
Num. H-bond donors :	4.0
Molar Refractivity :	79.97
TPSA :	64.52 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.75
Log Po/w (XLOGP3) :	2.75
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	1.72
Log Po/w (SILICOS-IT) :	2.41
Consensus Log Po/w :	2.26

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.156 mg/ml ; 0.000571 mol/l
Class :	Soluble
Log S (Ali) :	-3.76
Solubility :	0.0473 mg/ml ; 0.000174 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.49
Solubility :	0.000887 mg/ml ; 0.00000326 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.58

Safety of [ 18653-98-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501	UN#:
Hazard Statements:	H303-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 18653-98-0 ]

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

Downstream synthetic route of [ 18653-98-0 ]

[ 18653-98-0 ] Synthesis Path-Downstream 1~88

1
[ 94-93-9 ]
[ 18653-98-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium tetrahydroborate; In methanol; at 30℃; for 0.5h;	General procedure: Sodium borohydride (2.0 equiv) was added to a stirring suspension of the imino-compound (1A-6A) (1.0 equiv) in methanol (20 mL) at room temperature. After 30 min the reaction mixture was poured on ice and the resulting suspension filtered. The obtained solid was washed with water and n-hexane to give the corresponding amino-derivate (1B-6B) in high yields. Some compounds have been already synthesized and characterized and our results (Supplementary data) are in complete agreement with those reported in the literature.
70%	With sodium tetrahydroborate; In N,N-dimethyl-formamide;	The ethylenediamine (0.003 mol), dissolved in 20 cm3 ofmethanol, was added dropwise to salysilaldehyde (1) (0.003 mol) in 150 cm3 of methanol. After the addition, the reaction mixture was stirred to room temperature, and 0.006 mol of sodium borohydride in 15 mL of dimethylformamide was added in portions with stirring. The yellow colour of the reaction mixture disappears with addition of all portion of sodium borohydride, indicated to completionof hydrogenation. When the reduction was completed,mixture was poured in cold distilled water. Formed white precipitate was washed with water and diethyl ether, andthen dried over anhydrous sodium sulphate.
	With methanol; sodium tetrahydroborate; for 0.25h;Reflux;	General procedure: General procedure for synthesis of BC-1209. 2-Hydroxybenzaldehyde (0.01 mol, 1.22 g) were added to a solution of ethylenediamine (0.005 mol, -350 ul) in anhydrous ethanol (20 ml). The resulting solution was heated and stirred for 10 min until the precipitation of the relevant Schiff base. The Schiff bases were filtered off, and washed with cold ethanol. The Schiff base was then added to 30 ml absolute methanol. A 10% solution of sodium borohydride (0.02 mol) was dissolved in absolute methanol and added to the Schiff base. When the dropwise addition of sodium borohydride was complete, the reaction solution was refluxed for an additional 15 min. Solvent was then removed through rotary evaporation and 40 ml cold water was added to liberate the secondary amine. The precipitation of BC-1209 were collected, washed with water and dried, followed by recrystallization from ethyl acetate.

	With sodium tetrahydroborate; In methanol; at 20℃; for 2h;	General procedure: Schiff base ligand can be easily converted to tetrahydro-Schiff base ligand by the hydrogenation ofCH=N to CH2-NH in presence of NaBH4 in MeOH.Tetrahydro-Schiff base ligands were prepared as follows:0.01 mol of SalenH2, SalhexenH2 or SalphenH2was dissolved in 60 mL of methanol, followed by theaddition of 0.011 mol of NaBH4 at ambient temperature.After stirring for 2 h, the solvent was removedunder reduced pressure. The solid product was furtherwashed with distilled water and recrystallized fromethanol, and the obtained materials were denoted as[H4]SalenH2, [H4]SalhexenH2 and [H4]SalphenH2,respectively. The 1H NMR spectra of [H4]SalenH2,[H4]SalhexenH2 and [H4]SalphenH2 are also shown inFig. 1. 1H NMR (CDCl3), δ, ppm: [H4]SalenH2 -7.25-6.78 (8H, m, Ar-H), 3.99 (4H, s, N-CH2CH2-N), 2.84 (4H, s, CH2-NH) (Fig. 1b);
	With hydrogenchloride; sodium tetrahydroborate; In methanol; water;	The di-Schiff base ligand from 1,3-propanediamine and salicylaldehydewas synthesized by a reported method [17]. 5 mmol of1,3-propanediamine (0.42 mL) was mixed with 10 mmol of the salicylaldehyde(1.04 mL) in methanol (30 mL). The resulting solutionwas refluxed for ca. 2 h and allowed to cool. Then 30 mL (5 mmol)of this prepared yellow methanolic ligand solution (H2L1) wascooled to 0 C, and solid sodium borohydride (570 mg, 15 mmol)was added to this methanol solution with stirring. After completionof addition, the resulting solution was acidified with concentratedHCl (12 mL) and then evaporated to dryness [18]. Thereduced Schiff base ligand H2L1R was extracted from the solid masswith methanol, and this colorless methanol solution (ca. 30 mL)was added to a methanolic solution (10 mL) of Cu(ClO4)26H2O(1.852 g, 5 mmol) to prepare the ‘‘metalloligand” [CuL1R]
	With hydrogen; In methanol; at 25℃; under 1520.1 Torr; for 24h;	First, 100 mL of methanol in which 3.5 × 10 -1 mmol of Compound II was dissolved was placed in a round bottom flask 101. Next, while supplying H 2 from the hydrogen cylinder of the hydrogen supply apparatus to the hydrogen supply module 1 at 2 atm, the mixture was stirred for 24 hours in an environment at an indoor temperature of 25 C.

Reference： [1]Organometallics,2013,vol. 32,p. 4391 - 4401
[2]ChemSusChem,2014,vol. 7,p. 2230 - 2239
[3]Letters in drug design and discovery,2010,vol. 7,p. 165 - 170
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6759 - 6763
[5]European Journal of Organic Chemistry,2003,p. 3913 - 3915
[6]European Journal of Medicinal Chemistry,2001,vol. 36,p. 651 - 658
[7]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2016,vol. 86,p. 19 - 25
[8]Bulletin de la Societe Chimique de France,1942,vol. <5>9,p. 806
[9]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 243 - 247
[10]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1984,vol. 23,p. 527 - 529
[11]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2002,vol. 41,p. 653 - 663
[12]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2008,vol. 47,p. 1726 - 1730
[13]Dalton Transactions,2009,p. 2337 - 2344
[14]Inorganica Chimica Acta,2013,vol. 406,p. 160 - 170
[15]Patent: WO2013/184202,2013,A1 .Location in patent: Page/Page column 53
[16]Journal of Fluorescence,2014,vol. 24,p. 675 - 681
[17]RSC Advances,2014,vol. 4,p. 28029 - 28035
[18]European Journal of Medicinal Chemistry,2014,vol. 87,p. 662 - 676
[19]RSC Advances,2014,vol. 4,p. 64717 - 64724
[20]Kinetics and Catalysis,2017,vol. 58,p. 290 - 299
Kinet. Katal.,2017,vol. 58,p. 304 - 314,11
[21]Polyhedron,2018,vol. 142,p. 16 - 24
[22]European Journal of Inorganic Chemistry,2018,vol. 2018,p. 1185 - 1191
[23]Patent: JP2018/145103,2018,A .Location in patent: Paragraph 0069; 0070

2
[ 50-00-0 ]
[ 18653-98-0 ]
[ 78358-41-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1-hexadecyl-1H-imidazol-3-ium oxalate; In water; at 90℃; for 0.166667h;	General procedure: To a 100 cm3 round-bottomed flask containing 15 cm3 ofwater were added 0.30 g of corresponding bis-secondaryamine (1.1 mmol), 0.13 g of paraformaldehyde (4.4 mmol,4 equivalent), and 2.5 mmol% of catalyst. The flask wasattached to a reflux condenser and heated under atmosphericconditions in an oil bath at 90 C for 10 min.Thereafter the flask was cooled in an ice bath and 15 cm3of cold water was added. The resulting solid product was collected by filtration and dried at room temperature.Recrystallization from an appropriate solvent gave pure 2e.

Reference： [1]Monatshefte fur Chemie,2017,vol. 148,p. 1085 - 1094
[2]Applied Organometallic Chemistry,2021,vol. 35
[3]Journal of Molecular Structure,2022,vol. 1262
[4]Journal of medicinal chemistry,1963,vol. 6,p. 701 - 705

3
[ 120-57-0 ]
[ 18653-98-0 ]
[ 97013-02-0 ]

Reference： [1]Journal of medicinal chemistry,1963,vol. 6,p. 701 - 705

4
[ 500-22-1 ]
[ 18653-98-0 ]
[ 20063-34-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 243 - 247

5
[ 50-00-0 ]
[ 74-90-8 ]
[ 18653-98-0 ]
[ 36053-27-7 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 449 - 456

6
[ 704-65-4 ]
[ 18653-98-0 ]
Acetic acid 2-[{2-[(2-acetoxy-benzyl)-(2-hydroxy-benzyl)-amino]-ethyl}-(2-hydroxy-benzyl)-amino]-methyl}-phenyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1992,p. 652 - 654

7
[ 18653-98-0 ]
[ 100-52-7 ]
[ 65953-58-4 ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1181 - 1184
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 243 - 247

8
N,N'-bis(2-hydroxybenzyl)ethylene diimine [ No CAS ]
[ 18653-98-0 ]

Reference： [1]Synthetic Communications,2000,vol. 30,p. 4387 - 4395

9
[ 18653-98-0 ]
[ 120-21-8 ]
[ 65953-59-5 ]

Reference： [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 651 - 658

10
[ 89-95-2 ]
[ 18653-98-0 ]
[ 95430-43-6 ]

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 3757 - 3768

11
[ 94-93-9 ]
[ 18653-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium tetrahydroborate; potassium hydroxide; In dichloromethane; at 0℃;	General procedure: The Schiff base (2.27 mmol) dissolved in dichloromethane (10 mL). Reaction mass cooled at 00C and 2-3 drops of conc. KOH solution added. The solution of NaBH4 (2.0 mmol) in methanol added dropwise. Reaction mass stirred for 4-5 h until the yellow colour disappeared. Reaction monitored on TLC. After completion of reaction solvent distilled and cold water (10 mL) added to dissolve residue. pH adjusted to 4-5 by addition of dilute HCl. The white solid filtered, washed with water dried. 2, 2?-[ethane-1, 2-diylbis(azanediyl methylene)]diphenol [RSB01]m.p.: 1180C; Colour: white; MS [M+2]: 273.99; FTIR(KBr cm-1): 3490, 3463, 3363, 3052, 2942, 2852, 2593, 1602, 1479, 1417, 1353, 1268, 1189, 1126, 1074, 960, 815, 757, 626; 1H NMR (300 MHz, DMSO-d6) delta: 2.481 (m, 4H), 3.770 (s, 4H), 5.031 (s, 2H), 6.658-6.686 (m, 4H), 7.01-7.06 (m, 4H), 13.335 (s, 2H); Elemental analysis [C16H20N2O2]: observed (Calculated): C 70.63% (70.56%), H 7.31% (7.40%), N 10.34% (10.29%).

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 3757 - 3768
[2]European Journal of Inorganic Chemistry,2005,p. 732 - 744
[3]Oriental Journal of Chemistry,2018,vol. 34,p. 2796 - 2805

12
[ 18653-98-0 ]
[ 100-10-7 ]
[ 97153-18-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2002,vol. 41,p. 653 - 663

13
[ 18653-98-0 ]
8,8-dichloro-18,19-dihydro-6λ⁵,8λ⁵,10λ⁵-6,10-nitrilo-16H,21H-[1,3,5,7,2,4,6]tetrazatriphosphonino[2,1-b:6,7-b']bis[1,3,2]benzoxazaphosphorine [ No CAS ]
3,3''-ethane-1,2-diylbis[4',4',6',6'-tetrachloro-3,4-dihydrospiro[1,3,2-benzoxazaphosphorine-2,2'λ⁵-[4λ⁵,6λ⁵][1,3,5,2,4,6]triazatriphosphorine]] [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 2088 - 2099

14
[ 93731-55-6 ]
[ 18653-98-0 ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 2479 - 2485

15
[ 18653-98-0 ]
[ 51-46-7 ]
1²,5²-dihydroxy-1(1,3),5(1,3)-dibenzene-3(1,3),7(1,3)-di-imidazolidincyclooctaphane [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 8335 - 8338

16
[ 89-95-2 ]
methylphosphite bound on the Wang resin A [ No CAS ]
[ 18653-98-0 ]

Reference： [1]European Journal of Inorganic Chemistry,2005,p. 732 - 744
[2]European Journal of Organic Chemistry,2003,p. 3913 - 3915
[3]Chemistry - A European Journal,2002,vol. 8,p. 3757 - 3768
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2002,vol. 41,p. 653 - 663

17
[ 18653-98-0 ]
2,2′-(((2-((2-hydroxybenzyl)amino)ethyl)azanediyl)bis(methylene))diphenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 3757 - 3768

18
[ 89-95-2 ]
Fmoc-L-proline Wang resin [ No CAS ]
[ 18653-98-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 651 - 658

19
[ 18653-98-0 ]
[ 35998-25-5 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 449 - 456

20
[ 18653-98-0 ]
[ 35998-29-9 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 449 - 456

21
[ 18653-98-0 ]
[ 103334-86-7 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 449 - 456

22
[ 90-02-8 ]
aqueous solution [ No CAS ]
[ 18653-98-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 243 - 247

23
[ 18653-98-0 ]
[ 69749-32-2 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1992,p. 652 - 654

24
[ 863393-98-0 ]
[ 18653-98-0 ]
N,N'-{N-ethyl-2-diethoxy}-2-methyl-imidazole-N,N'-bis(2-hydroxybenzyl)-ethylenediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.1%	With sodium tris(acetoxy)borohydride; In 1,1-dichloroethane; at 20℃; for 18h;	Placed N, N'-Bis (2-hydroxybenzyl) ethylenediamine (0.1 g,0..367 mmol) in a 100 ml round-bottom flask equipped with a stirrer under nitrogen. The solid was dissolved in 8 ml of dichloroethane, followed by addition of [N-{ethyl-2-diethoxy}-2- imidazolecarboxaldehyde] (0.165 g, 0.775 mmol) and sodium triacetoxyborohydride (0.178 g, 0.845 mmol). The solution was stirred at room temperature for 18 hours. The solution was then vacuumed down to residue. The residue was passed through a silca gel column using 0-20% methanol/methylene chloride as the solvents, yielding 0.049 g, 20. 1 % yield.lHNMR ((CDC13), 300 MHz): 1.10 (t, 12H), 2.10 (s, 8H), 2.77 (s, 2H), 3.34 (m, 4H), 3.58 (m, 4H), 3.77 (s, 2H), 3.84 (d, 2H), 4.45 (t, 2H), 6.72 (t, 2H), 6.85 (m, 8H), 6.96 (s, 2H), 7.13 (t, 2H). ES/MS = 666-668: expected 668.

Reference： [1]Patent: WO2005/79865,2005,A1 .Location in patent: Page/Page column 76

25
[ 18653-98-0 ]
[ 6147-53-1 ]
cobalt(II) ethylene-N,N'-di(salicylaldiminate) [ No CAS ]

Reference： [1]Russian Journal of Coordination Chemistry,2001,vol. 27,p. 486 - 492

26
tetrakis(acetato)diaquadicopper(II) [ No CAS ]
[ 18653-98-0 ]
(OC₆H₄CH₂NH(CH₂)2NHCH₂C₆H₄O)Cu [ No CAS ]

Reference： [1]Acta Chimica Hungarica,1991,vol. 128,p. 255 - 266

27
dipotassium oxopentachlororhenate⁽⁵⁺⁾ [ No CAS ]
[ 18653-98-0 ]
Re₂O₃((C₆H₄(O)CH₂NH(CH₂)2)2)2*2CHCl₃ [ No CAS ]

Reference： [1]Polyhedron,1994,vol. 13,p. 701 - 708

28
[ 18653-98-0 ]
[ 142-71-2 ]
[ 890933-43-4 ]

Reference： [1]Inorganica Chimica Acta,2006,vol. 359,p. 2455 - 2464

29
bis(acetylacetonato)dioxidomolybdenum(VI) [ No CAS ]
[ 18653-98-0 ]
[ 90858-42-7 ]

Reference： [1]Inorganic Chemistry,1984,vol. 23,p. 2564 - 2572

30
ammonium hexafluorophosphate [ No CAS ]
chromium chloride hexahydrate [ No CAS ]
[ 18653-98-0 ]
[ 79737-43-2 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1981,p. 1701 - 1707

31
[ 18653-98-0 ]
[ 6046-93-1 ]
[ 681484-82-2 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2006,vol. 249,p. 23 - 30

32
[ 139467-76-8 ]
[ 18653-98-0 ]
WO₂(C₁₆H₁₈N₂O₂) [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,1999,p. 313 - 321

33
[ 18653-98-0 ]
[ 14314-61-5 ]
((CH₃)2N)2Al((OC₆H₄CH₂NCH₂)2)Al((CH₃)2N)(Al(N(CH₃)2)2) [ No CAS ]

Reference： [1]Australian Journal of Chemistry,1996,vol. 49,p. 1333 - 1338

34
[ 18653-98-0 ]
[ 14314-61-5 ]
((OC₆H₄CH₂NCH₂)2)HAl(Al(N(CH₃)2)3)*CH₃C₆H₅ [ No CAS ]

Reference： [1]Australian Journal of Chemistry,1996,vol. 49,p. 1333 - 1338

35
cobalt(II) chloride hexahydrate [ No CAS ]
[ 18653-98-0 ]
[Co(HOC₆H₄CH₂NHCH₂CH₂NHCH₂C₆H₄OH)(H₂O)2]⁽²⁺⁾*2Cl^(1-)*3H₂O=[Co(C₁₆H₂₀N₂O₂)(H₂O)2]Cl₂*3H₂O [ No CAS ]

Reference： [1]Journal of Molecular Structure,2001,vol. 569,p. 121 - 128

36
copper(II) perchlorate hexahydrate [ No CAS ]
[ 18653-98-0 ]
Cu⁽²⁺⁾*Na⁽¹⁺⁾*(OC₆H₄CH₂NH)2C₂H₄^(2-)*ClO₄^(1-)=Cu(OC₆H₄CH₂NH)2C₂H₄NaClO₄ [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2003,p. 4010 - 4016

37
[ 67-56-1 ]
[ 18653-98-0 ]
sodium perchlorate [ No CAS ]
[ 6147-53-1 ]
Co⁽²⁺⁾*Na⁽¹⁺⁾*(OC₆H₄CH₂NH)2C₂H₄^(2-)*ClO₄^(1-)*CH₃OH=Co(OC₆H₄CH₂NH)2C₂H₄NaClO₄*CH₃OH [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2003,p. 4010 - 4016

38
[ 18653-98-0 ]
[ 1445-79-0 ]
((OC₆H₄CH₂NCH₂)2)Ga(CH₃)(Ga(CH₃)2)2 [ No CAS ]

Reference： [1]Organometallics,1995,vol. 14,p. 2880 - 2886

39
[ 18653-98-0 ]
[ 75-24-1 ]
[ 183280-81-1 ]

Reference： [1]Organometallics,1996,vol. 15,p. 4763 - 4769

40
[ 18653-98-0 ]
[ 75-24-1 ]
(CH₃)Al((CH₃)2Al)2((CH₂NCH₂C₆H₄O)2) [ No CAS ]

Reference： [1]Organometallics,1995,vol. 14,p. 1453 - 1460

41
zinc perchlorate [ No CAS ]
[ 18653-98-0 ]
Zn⁽²⁺⁾*Na⁽¹⁺⁾*(OC₆H₄CH₂NH)2C₂H₄^(2-)*ClO₄^(1-)*H₂O=Zn(OC₆H₄CH₂NH)2C₂H₄NaClO₄*H₂O [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2003,p. 4010 - 4016

42
[ 18653-98-0 ]
silver nitrate [ No CAS ]
[ 681429-53-8 ]

Reference： [1]European Journal of Inorganic Chemistry,2003,p. 4010 - 4016

43
[ 18653-98-0 ]
[ 97-93-8 ]
[ 183280-82-2 ]

Reference： [1]Organometallics,1996,vol. 15,p. 4763 - 4769

44
[ 18653-98-0 ]
[ 97-93-8 ]
[ 168097-15-2 ]

Reference： [1]Organometallics,1995,vol. 14,p. 3988 - 3995

45
[ 18653-98-0 ]
[ 818-08-6 ]
Sn(nBu)2(N,N'-bis(o-hydroxybenzyl)-1,2-diaminoethane^(2-)) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 664,p. 188 - 200

46
[ 18653-98-0 ]
[ 1115-99-7 ]
((OC₆H₄CH₂NCH₂)2)Ga(C₂H₅)(Ga(C₂H₅)2)2 [ No CAS ]

Reference： [1]Organometallics,1995,vol. 14,p. 2880 - 2886

47
[ 18653-98-0 ]
[ 100-99-2 ]
[ 183280-83-3 ]

Reference： [1]Organometallics,1996,vol. 15,p. 4763 - 4769

48
[ 18653-98-0 ]
[ 100-99-2 ]
[ 190523-31-0 ]

Reference： [1]Organometallics,1995,vol. 14,p. 3988 - 3995

49
[ 18653-98-0 ]
[ 2273-45-2 ]
SnMe₂(N,N'-bis(o-hydroxybenzyl)-1,2-diaminoethane^(2-)) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 664,p. 188 - 200

50
[ 18653-98-0 ]
[ 2273-51-0 ]
SnPh₂(N,N'-bis(o-hydroxybenzyl)-1,2-diaminoethane^(2-)) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 664,p. 188 - 200

51
vanadyl(IV) sulphate pentahydrate [ No CAS ]
[ 18653-98-0 ]
[VO(Rsal₂en)] [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2005,p. 732 - 744

52
[ 18653-98-0 ]
tin(ll) chloride [ No CAS ]
[ 172270-92-7 ]

Reference： [1]Journal of Organometallic Chemistry,1995,vol. 503,p. C4 - C7

53
[ 18653-98-0 ]
[ 532-55-8 ]
N,N'-bis(N-benzoyl-thiocarbamoyl)-N,N'-bis(2-hydroxybenzyl)ethane-1,2-diamine [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2008,vol. 47,p. 1726 - 1730

54
[ 18653-98-0 ]
C₁₆H₁₉B₃N₂O₆ [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2009,vol. 694,p. 3660 - 3666

55
[ 18653-98-0 ]
[ 11113-50-1 ]
[ 67-68-5 ]
[(N,N'-bis(o-hydroxybenzyl)-1,2-diaminoethane(-2H))B₃O₃(OH)]*DMSO [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2009,vol. 694,p. 3660 - 3666

56
[ 50-00-0 ]
[ 18653-98-0 ]
[ 121788-87-2 ]

Reference： [1]Dalton Transactions,2009,p. 2337 - 2344
[2]European Journal of Inorganic Chemistry,2018,vol. 2018,p. 1185 - 1191

57
[ 18653-98-0 ]
zirconium isopropoxide [ No CAS ]
[ 108-88-3 ]
[Ti(N,N'-bis(2-hydroxybenzyl)ethylenediamine^(2-))2]*2.5toluene [ No CAS ]

Reference： [1]Polyhedron,2010,vol. 29,p. 697 - 700

58
[ 546-68-9 ]
[ 75-09-2 ]
[ 18653-98-0 ]
[Ti(N,N'-bis(2-hydroxybenzyl)ethylenediamine^(2-))(isopropylate)2]*CH₂Cl₂ [ No CAS ]

Reference： [1]Polyhedron,2010,vol. 29,p. 697 - 700

59
[ 18653-98-0 ]
[ 66-77-3 ]
[ 843631-30-1 ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1181 - 1184

60
[ 18653-98-0 ]
[ 642-31-9 ]
[ 312946-45-5 ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1181 - 1184

61
[ 18653-98-0 ]
[ 708-06-5 ]
[ 312946-44-4 ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1181 - 1184

62
[ 90-02-8 ]
[ 107-15-3 ]
[ 18653-98-0 ]

Yield	Reaction Conditions	Operation in experiment
66%		To salicylaldehyde (1.22 g, 10 mmol) diluted by MeOH (50 mL), 1,2-diaminoethane (0.30 g, 5 mmol) diluted by MeOH (50 mL) was added with stirring. The reaction mixture was refluxed for 1 h and cooled by ice-water bath. Then, NaBH4 (1.0 g, 25 mmol) was added. The mixture was stirred for another 1 h and filtered. The solvent was removed by distillation. The residue was treated with the aqueous solution of 1 M NaOH (50 mL) and extracted by chloroform. The solution was treated with 3 M HCl and the acid phase was made basic by 1 M NaOH. The crude product was then extracted into chloroform. The chloroform extracts were combined and dried over anhydrous Na2SO4. The solvent was removed to give the colorless product. Yield 0.9 g (66%). IR data (ν, cm-1): 3337, 3212,3061, 2983, 2930, 2855, 1600, 1481, 1075. UV-Vis data(MeOH; λmax, nm): 260, 285. 1H NMR (300 MHz, CDCl3,ppm) δ 7.06 (q, 2H, ArH), 7.03 (d, 2H, ArH), 6.91 (q, 2H,ArH), 6.77 (d, 2H, ArH), 3.85 (s, 4H, CH2), 2.61 (t, 4H,CH2). Anal. Calcd. (%) for C16H20N2O2: C, 70.56; H, 7.40;N, 10.29. Found (%): C, 70.45; H, 7.47; N, 10.23.
	In ethanol;	All oxidants, solvents, ligands L1-4, aniline, and salicylaldehyde derivatives are commercially available and were used as received, except for MTO that was prepared following a standard literature procedure refPreviewPlaceHolder[8]. Ligand L5 was prepared by reaction of the corresponding ketone with hydroxylamine following a common procedure refPreviewPlaceHolder[9], and L6-13 were prepared through standard condensation reactions between an aldehyde and an amine derivative in ethanol and are well-known in the literature
		ethanediamine (2 ml, 29.9 mmol) was dissolve in methanol (25 ml) and kept under stirring at the temperature of 50 C, then salicylaldehyde (8 ml, 76.32 mmol) was added to the solution, a luminous-yellow precipitate was obtained; The precipitate was redissolved in methanol and reduced by excess of potassium borohydride, then adjust the pH value of the solution to 7.0. large amounts of water was added to the solution and a white precipitate was obtained. Washed with water and dried in the dryer. 1H-NMR (300 MHz, DMSO-d6): 7.10-6. 69 (2t, 8H, Ph), 3.80 (br s, 2H, Ph-CH), 2.55-2.50 (d, 2H, N-CH2). Anal. Cacld for C16H18N2O2: C, 71.09; H, 6.71; N, 10.36. Find: C, 71.23; H, 6.42; N, 10.35. IR: 3278, 2851, 2577, 1848, 1589, 1451, 1245, 1083, 974, 879, 749 cm-1.

Reference： [1]Acta Chimica Slovenica,2020,vol. 67,p. 159 - 166
[2]Inorganic Chemistry,2021,vol. 60,p. 12855 - 12869
[3]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1181 - 1184
[4]Journal of Catalysis,2011,vol. 283,p. 55 - 67
[5]Chemistry - A European Journal,2016,vol. 22,p. 9986 - 9995
[6]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 140,p. 437 - 443
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63
[ 18653-98-0 ]
Ni{Salen}*Zn(C₂H₅)2*toluene [ No CAS ]
Ni{Salen}*Zn(C₂H₅)2 [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1988,vol. 356,p. 249 - 258

64
[ 18653-98-0 ]
Ni{Salen}*Zn(C₂H₅)2*benzene [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1988,vol. 356,p. 249 - 258

65
[ 546-68-9 ]
[ 18653-98-0 ]
[(C₆H₄(O))CH₂NHCH₂CH₂NHCH₂(C₆H₄(O))]Ti(isopropoxide)2 [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 9802 - 9809

66
[ 75-15-0 ]
[ 18653-98-0 ]
potassium N,N'-bis(2-hydroxybenzyl)-1,2-ethanebis(dithiocarbamate) [ No CAS ]

Reference： [1]Applied Organometallic Chemistry,2011,vol. 25,p. 785 - 790

67
[ 18653-98-0 ]
[ 2950-45-0 ]
C₁₆H₁₆Cl₄N₆O₂P₄ [ No CAS ]
[ 1414869-06-9 ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 12841 - 12856

68
[ 18653-98-0 ]
[ 1414869-13-8 ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 12841 - 12856

69
[ 18653-98-0 ]
[ 1414869-15-0 ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 12841 - 12856

70
[ 18653-98-0 ]
C₂₄H₃₂Cl₂N₈O₂P₄ [ No CAS ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 12841 - 12856

71
[ 18653-98-0 ]
C₂₄H₃₂Cl₂N₈O₄P₄ [ No CAS ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 12841 - 12856

72
[ 90-02-8 ]
[ 18653-98-0 ]

Reference： [1]Organometallics,2013,vol. 32,p. 4391 - 4401
[2]Inorganica Chimica Acta,2013,vol. 406,p. 160 - 170
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6759 - 6763
[4]Patent: WO2013/184202,2013,A1
[5]Journal of Fluorescence,2014,vol. 24,p. 675 - 681
[6]RSC Advances,2014,vol. 4,p. 28029 - 28035
[7]RSC Advances,2014,vol. 4,p. 64717 - 64724
[8]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2016,vol. 86,p. 19 - 25
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Kinet. Katal.,2017,vol. 58,p. 304 - 314,11
[10]Oriental Journal of Chemistry,2018,vol. 34,p. 2796 - 2805

73
[ 18653-98-0 ]
[ 788094-30-4 ]

Reference： [1]Organometallics,2013,vol. 32,p. 4391 - 4401

74
[ 18653-98-0 ]
[ 7439-89-6 ]
[Fe₂2-((2-(2-hydroxybenzylamino)ethylamino)methyl)phenol₃]*0.38H₂O [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2013,vol. 406,p. 171 - 175

75
[ 18653-98-0 ]
cobalt(II) perchlorate hexahydrate [ No CAS ]
[ 1457998-32-1 ]

Reference： [1]Inorganica Chimica Acta,2013,vol. 406,p. 171 - 175

76
[ 19092-51-4 ]
[ 18653-98-0 ]

Reference： [1]Inorganica Chimica Acta,2013,vol. 406,p. 171 - 175

77
[ 18653-98-0 ]
meso-18,19-dihydro-8,8-dimorpholine-1-yl-6λ⁵,8λ⁵,10λ⁵-6,10-nitrilo-16H,21H[1,3,5,7,2,4,6]tetrazatriphosphecino[2,1-b:6,7-b']bis[1,3,2]benzoxazaphosphorine [ No CAS ]