[ CAS No. 185130-32-9 ] {[proInfo.proName]}

Name: 185130-32-9|1,4,7,10-Tetrakis(pyridin-2-ylmethyl)-1,4,7,10-tetraazacyclododecane|95%
Brand: Ambeed
SKU: A1512535
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Quality Control of [ 185130-32-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 185130-32-9 ]

Product Details of [ 185130-32-9 ]

CAS No. :	185130-32-9	MDL No. :	MFCD27965351
Formula :	C₃₂H₄₀N₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NVFSHTYUVXEYKP-UHFFFAOYSA-N
M.W :	536.71	Pubchem ID :	15377250
Synonyms :

Safety of [ 185130-32-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 185130-32-9 ]

* 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 [ 185130-32-9 ]

[ 185130-32-9 ] Synthesis Path-Downstream 1~52

1
[ 10045-25-7 ]
[ 6959-47-3 ]
[ 185130-32-9 ]

Yield	Reaction Conditions	Operation in experiment
20%	With sodium hydroxide at 20℃; for 96h;
20%	With sodium hydroxide In water at 20℃; for 96h;

Reference： [1]Wada, Atsushi; Watanabe, Masayuki; Yamanoi, Yoshinori; Nankawa, Takuya; Namiki, Kosuke; Yamasaki, Mikio; Murata, Masaki; Nishihara, Hiroshi [Bulletin of the Chemical Society of Japan, 2007, vol. 80, # 2, p. 335 - 345]
[2]Wada, Atsushi; Watanabe, Masayuki; Yamanoi, Yoshinori; Nishihara, Hiroshi [Chemical Communications, 2008, # 14, p. 1671 - 1673]

2
[ 185130-32-9 ]
cobalt(II) perchlorate hexahydrate [ No CAS ]
(Co(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane))(ClO₄)2*0.5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	In water; acetonitrile soln. of ligand in MeCN and aq. sol. of Co(ClO4)2*6H2O (molar ratio 1:1)mixed at room temp. for 0.5 h, filtered; elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Liu, He; Zhu, Hong-Ping; Liu, Qiu-Tian [Polyhedron, 2000, vol. 19, # 4, p. 431 - 435]

3
[ 185130-32-9 ]
[ 7791-07-3 ]
iron(II) chloride tetrahydrate [ No CAS ]
(Fe(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane))(ClO₄)2*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	In water; acetonitrile soln. of ligand in MeCN and aq. sol. of FeCl24H2O (molar ratio 1:1) mixed at room temp. for 0.5 h, filtered, filtrate treated with solid NaClO4H2O; elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Liu, He; Zhu, Hong-Ping; Liu, Qiu-Tian [Polyhedron, 2000, vol. 19, # 4, p. 431 - 435]

4
[ 185130-32-9 ]
manganese(II) perchlorate hexahydrate [ No CAS ]
manganese(II)(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(ClO₄)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In methanol; acetonitrile mixt. of the macrocycle and Mn salt (1:1 molar ratio) in CH3OH/CH3CN (1/1) at ca. 60°C under Ar for ca. 30 min; mixt. filtered, soln. evapd.; elem. anal.;

Reference： [1]Bu, Xian-He; Chen, Wei; Mu, Lin-Jing; Zhang, Zhi-Hui; Zhang, Ruo-Hua; Clifford, Thomas [Polyhedron, 2000, vol. 19, # 18-19, p. 2095 - 2100]

5
[ 185130-32-9 ]
hexaaquanickel(II) perchlorate [ No CAS ]
Ni(C₈H₁₆N₄(CH₂C₅H₄N)4)⁽²⁺⁾*2ClO₄^(1-)=[Ni(C₈H₁₆N₄(CH₂C₅H₄N)4)][ClO₄]2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	In ethanol refluxing (30 min); filtering, crystn. on slow evapn.; elem. anal.;

Reference： [1]Bu, Xian-He; Cao, Xi-Chuan; Chen, Wei; Zhang, Ruo-Hua; Thomas, Clifford [Polyhedron, 1998, vol. 17, # 2-3, p. 289 - 293]

6
[ 185130-32-9 ]
gadolinium nitrate hydrate [ No CAS ]
Gd₂(C₃₂H₄₀N₈)(NO₃)4⁽²⁺⁾*2NO₃^(1-) = [Gd₂(C₃₂H₄₀N₈)(NO₃)4](NO₃)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In ethanol stirring (60°C, 10 h); ppt, washing (EtOH, Et2O), drying (vac.); elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Wang, Hong-Mei [Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1998, vol. 28, # 7, p. 1127 - 1144]

7
[ 185130-32-9 ]
neodymium(III) nitrate hydrate [ No CAS ]
Nd₂(C₃₂H₄₀N₈)(NO₃)4⁽²⁺⁾*2NO₃^(1-) = [Nd₂(C₃₂H₄₀N₈)(NO₃)4](NO₃)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol stirring (60°C, 10 h); ppt, washing (EtOH, Et2O), drying (vac.); elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Wang, Hong-Mei [Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1998, vol. 28, # 7, p. 1127 - 1144]

8
[ 185130-32-9 ]
ytterbium(III) nitrate hydrate [ No CAS ]
Yb₂(C₃₂H₄₀N₈)(NO₃)4⁽²⁺⁾*2NO₃^(1-) = [Yb₂(C₃₂H₄₀N₈)(NO₃)4](NO₃)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	In ethanol stirring (60°C, 10 h); ppt, washing (EtOH, Et2O), drying (vac.); elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Wang, Hong-Mei [Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1998, vol. 28, # 7, p. 1127 - 1144]

9
[ 185130-32-9 ]
holmium(III) nitrate hydrate [ No CAS ]
Ho₂(C₃₂H₄₀N₈)(NO₃)4⁽²⁺⁾*2NO₃^(1-) = [Ho₂(C₃₂H₄₀N₈)(NO₃)4](NO₃)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	In ethanol stirring (60°C, 10 h); ppt, washing (EtOH, Et2O), drying (vac.); elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Wang, Hong-Mei [Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1998, vol. 28, # 7, p. 1127 - 1144]

10
[ 185130-32-9 ]
europium(III) nitrate hydrate [ No CAS ]
Eu₂(C₃₂H₄₀N₈)(NO₃)4⁽²⁺⁾*2NO₃^(1-) = [Eu₂(C₃₂H₄₀N₈)(NO₃)4](NO₃)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In ethanol stirring (60°C, 10 h); ppt, washing (EtOH, Et2O), drying (vac.); elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Wang, Hong-Mei [Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1998, vol. 28, # 7, p. 1127 - 1144]

11
[ 185130-32-9 ]
cerium(III) nitrate hydrate [ No CAS ]
Ce₂(C₃₂H₄₀N₈)(NO₃)4⁽²⁺⁾*2NO₃^(1-) = [Ce₂(C₃₂H₄₀N₈)(NO₃)4](NO₃)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	In ethanol stirring (60°C, 10 h); ppt, washing (EtOH, Et2O), drying (vac.); elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Wang, Hong-Mei [Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1998, vol. 28, # 7, p. 1127 - 1144]

12
[ 185130-32-9 ]
terbium(III) nitrate hydrate [ No CAS ]
Tb₂(C₃₂H₄₀N₈)(NO₃)4⁽²⁺⁾*2NO₃^(1-) = [Tb₂(C₃₂H₄₀N₈)(NO₃)4](NO₃)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In ethanol stirring (60°C, 10 h); ppt, washing (EtOH, Et2O), drying (vac.); elem. anal.;

Reference： [1]Bu, Xian-He; Lu, Shou-Liang; Zhang, Ruo-Hua; Wang, Hong-Mei [Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1998, vol. 28, # 7, p. 1127 - 1144]

13
[ 185130-32-9 ]
terbium(III) nitrate hexahydrate [ No CAS ]
[Tb(1,4,7,10-tetrakis(2'-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(nitrate)](nitrate)2*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	In acetonitrile under N2; soln. of terbium compd. and amine deriv. in acetonitrile refluxed for 3 d; filtration, evapn., drying under vac., recrystn. from methanol/ethyl acetate; elem. anal.;

14
[ 185130-32-9 ]
[ 7732-18-5 ]
[ 52093-25-1 ]
[Eu(1,4,7,10-tetrakis(2'-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(triflato)](triflate)2*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In acetonitrile under N2; soln. of europium compd. and amine deriv. in acetonitrile refluxed for 3 d; filtration, filtrate evapd. under vac., residue dried under vac., recrystn. from acetonitrile/ether; elem. anal.;

15
[ 185130-32-9 ]
europium(III) nitrate hexahydrate [ No CAS ]
[Eu(1,4,7,10-tetrakis(2'-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(nitrato)] dinitrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In acetonitrile under N2; soln. of europium compd. and azamacrocycle in acetonitrile refluxed for 3 d; filtration, evapn., drying under vac., recrystn. from methanol/ethyl acetate; elem. anal.;

16
[ 185130-32-9 ]
europium(III) chloride hexahydrate [ No CAS ]
[EuCl(1,4,7,10-tetrakis(2'-pyridylmethyl)-1,4,7,10-tetraazocyclododecane)]Cl₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol 1:1 mixt.;

Reference： [1]Wada, Atsushi; Watanabe, Masayuki; Yamanoi, Yoshinori; Nishihara, Hiroshi [Chemical Communications, 2008, # 14, p. 1671 - 1673]

17
[ 185130-32-9 ]
[ 67-56-1 ]
cobalt(II) nitrate hexahydrate [ No CAS ]
[(1,4,8,11-tetrakis(2-pyridylmethyl)-1,4,8,11-tetraazacyclotetradecane)bis(nitrato)dicobalt(II)] nitrate-methanol (1/1) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In methanol Co:cyclic compd.=3:1 molar ratio, a soln. of N compd. added to a soln. of Co salt at 40°C, vigorously stirred for 20 min; cooled to room temp.; elem. anal.;

Reference： [1]Narayanan, Jayanthi; Solano-Peralta, Alejandro; Ugalde-Saldivar, Víctor Manuel; Escudero, Roberto; Höpfl, Herbert; Sosa-Torres, Martha Elena [Inorganica Chimica Acta, 2008, vol. 361, # 9-10, p. 2747 - 2758]

18
[ 185130-32-9 ]
cobalt(II) chloride hexahydrate [ No CAS ]
[ 1044515-64-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	In ethanol Co:cyclic compd.=3:1 molar ratio, a soln. of N compd. added to a soln. of Co salt at 40°C, vigorously stirred for 20 min; cooled to room temp.; elem. anal.;

19
[ 185130-32-9 ]
[ 67-56-1 ]
bismuth (III) nitrate pentahydrate [ No CAS ]
[Bi(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)](NO₃)3*2CH₃OH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	In ethanol Bi(NO3)3*5H2O (0.41 mmol) added to soln. of org. ligand (0.37 mmol); stirred (4 h); filtered; evapd.; MeOH added; evapd. slowly; elem. anal.;

Reference： [1]Morfin, Jean-François; Tripier, Raphaël; Baccon, Michel Le; Handel, Henri [Inorganica Chimica Acta, 2009, vol. 362, # 6, p. 1781 - 1786]

20
[ 185130-32-9 ]
[ 75-09-2 ]
[ 7787-60-2 ]
[Bi(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)Cl₂]Cl*2CH₂Cl₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In dichloromethane BiCl3 (0.41 mmol) added to soln. of org. ligand (0.37 mmol) in dry CH2Cl2; refluxed; stirred (16 h); filtered; evapd.; CHCl3/CH2Cl2 added; evapd. slowly; elem. anal.;

Reference： [1]Morfin, Jean-François; Tripier, Raphaël; Baccon, Michel Le; Handel, Henri [Inorganica Chimica Acta, 2009, vol. 362, # 6, p. 1781 - 1786]

21
[ 6959-47-3 ]
[ 294-90-6 ]
[ 185130-32-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With caesium carbonate In acetonitrile for 24h; Inert atmosphere; Reflux;
73%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 2h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Natrajan, Louise S.; Khoabane, Ntai M.; Dadds, Benjamin L.; Muryn, Christopher A.; Pritchard, Robin G.; Heath, Sarah L.; Kenwright, Alan M.; Kuprov, Ilya; Faulkner, Stephen [Inorganic Chemistry, 2010, vol. 49, # 17, p. 7700 - 7709]
[2]Tsitovich, Pavel B.; Cox, Jordan M.; Benedict, Jason B.; Morrow, Janet R. [Inorganic Chemistry, 2016, vol. 55, # 2, p. 700 - 716]

22
[ 185130-32-9 ]
[ 52093-25-1 ]
Eu(CH₂CH₂)4(NCH₂C₅H₄N)4⁽³⁺⁾*3CF₃SO₃^(1-)=Eu(CH₂CH₂)4(NCH₂C₅H₄N)4(CF₃SO₃)3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With K₂CO₃ In dichloromethane

Reference： [1]Miller, Kyle J.; Saherwala, Ali A.; Webber, Benjamin C.; Wu, Yunkou; Sherry, A. Dean; Woods, Mark [Inorganic Chemistry, 2010, vol. 49, # 19, p. 8662 - 8664]

23
[ 185130-32-9 ]
terbium(III) trifluoromethanesulfonate [ No CAS ]
[Gd(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(MeCN)][OTf]3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac.;

Reference： [1]Natrajan, Louise S.; Khoabane, Ntai M.; Dadds, Benjamin L.; Muryn, Christopher A.; Pritchard, Robin G.; Heath, Sarah L.; Kenwright, Alan M.; Kuprov, Ilya; Faulkner, Stephen [Inorganic Chemistry, 2010, vol. 49, # 17, p. 7700 - 7709]

24
[ 185130-32-9 ]
neodymium(III) trifluoromethanesufonate [ No CAS ]
[Nd(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(OTf)][OTf]2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac.;

25
[ 185130-32-9 ]
gadolinium(III) trifluoromethanesulfonate [ No CAS ]
[Gd(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(OH₂)][OTf]3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac.;

26
[ 185130-32-9 ]
samarium(III) trifluoromethanesulfonate [ No CAS ]
[Sm(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)][OTf]3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac.;

27
[ 185130-32-9 ]
dysprosium(III) trifluoromethanesulfonate [ No CAS ]
[Dy(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)][OTf]3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac.;

28
[ 185130-32-9 ]
erbium(III) triflate [ No CAS ]
[Er(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(MeCN)][OTf]3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac.;

29
[ 185130-32-9 ]
[ 54761-04-5 ]
[Yb(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(OH₂)][OTf]3 [ No CAS ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 7700 - 7709

30
[ 185130-32-9 ]
lanthanum(lll) triflate [ No CAS ]
1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane lanthane tris(trifluoromethylsulfonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac., elem. anal.;

31
[ 185130-32-9 ]
[ 52093-25-1 ]
[Eu(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)(OTf)][OTf]2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac.;

32
[ 185130-32-9 ]
thulium(III) trifluoromethanesulfonate [ No CAS ]
[Tm(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane)][OTf]3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol soln. of cyclen in MeOH was added to methanolic soln. of lanthanide salt, warmed gently to 40°C for 24 h; evapd. in vac., crystd. from MeCN/Et2O, crystals were filtered, washed with Et2O, dried in vac.;

33
[ 185130-32-9 ]
lanthanum(lll) triflate [ No CAS ]
[La(1,4,7,10-tetrakis(pyridin-2-ylmethyl)-1,4,7,10-tetraazacyclododecane)(trifluoromethanesulfonate)](trifluoromethanesulfonate)₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In methanol at 40℃; for 3h;
74%	In methanol at 40℃; for 3h;	Synthesis of [LaL^py(OTf)](OTf)₂, (i.e. 1). Synthesis of [LaLpy(OTf)](OTf)2, (i.e. 1). A solution of Lpy (46 mg, 0.086 mmol) in 5 mL MeOH was added in a dropwise manner to a solution of La(OTf)3 (50. mg, 0.085 mmol) in 5 mL MeOH. The combined reagents were then heated at 40° C. for 3 h. The colorless solution was concentrated to dryness under vacuum at 40° C. to give a white oily residue. The residue was dissolved in 1 mL CH3CN. The slow vapor diffusion of Et2O at room temperature into this solution afforded needle-like colorless crystals of the desired compound. The crystals were washed with 3×1 mL Et2O and then dried in vacuo. Yield: 71 mg, 74%. IR (ATR, cm-1): 2867 w, 1607 m, 1571 m, 1483 m, 1444 m, 1380 w, 1313 m, 1254 s, 1209 s, 1153 s, 1076 m, 1024 vs, 974 m, 907 w, 839 w, 812 m, 780 m, 758 s, 731 w. Analysis calcd. for 1, C35H40N8F9LaO9S3: C, 37.44; H, 3.59; N, 9.98. Found: C, 37.11; H, 3.87; N, 9.80.

Reference： [1]Wilson, Justin J.; Birnbaum, Eva R.; Batista, Enrique R.; Martin, Richard L.; John, Kevin D. [Inorganic Chemistry, 2015, vol. 54, # 1, p. 97 - 109]
[2]Current Patent Assignee: TRIAD NATIONAL SECURITY LLC - US2015/344508, 2015, A1 Location in patent: Paragraph 0056

34
[ 185130-32-9 ]
copper(II) chloride hexahydrate [ No CAS ]
[Co(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetrazacyclododecane)]Cl₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide In water; acetonitrile for 0.666667h; Inert atmosphere;

Reference： [1]Tsitovich, Pavel B.; Cox, Jordan M.; Benedict, Jason B.; Morrow, Janet R. [Inorganic Chemistry, 2016, vol. 55, # 2, p. 700 - 716]

35
[ 185130-32-9 ]
iron(II) chloride tetrahydrate [ No CAS ]
[Fe(1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetrazacyclododecane)]Cl₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydroxide In water; acetonitrile for 0.666667h; Inert atmosphere;

Reference： [1]Tsitovich, Pavel B.; Cox, Jordan M.; Benedict, Jason B.; Morrow, Janet R. [Inorganic Chemistry, 2016, vol. 55, # 2, p. 700 - 716]

36
[ 4377-33-7 ]
[ 294-90-6 ]
[ 185130-32-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In acetonitrile Reflux;	Lpy (Scheme 1, far left) was synthesized by a known procedure involving reaction of slightly greater than four equivalents of 2-picolylchloride with cyclen in the presence of excess Cs2CO3 (20 equivalents) in refluxing CH3CN. Lpyd, Lpyr, and Lpz, were synthesized in moderate yields using the corresponding chloromethyl N-heterocycles shown in Scheme 1. The chloromethyl N-heterocycles were synthesized by reacting the corresponding methyl N-heterocycles with equiv of trichloroisocyanuric acid in refluxing chloroform (see: Schiess et al., Org. Lett. 2011, 13, 1436, incorporated by reference). The chloromethyl N-heterocycles were purified by column chromatography prior to reactions with cyclen.

Reference： [1]Current Patent Assignee: TRIAD NATIONAL SECURITY LLC - US2015/344508, 2015, A1 Location in patent: Paragraph 0033; 0034

37
[ 185130-32-9 ]
[ 54761-04-5 ]
C₃₂H₄₀N₈Yb⁽³⁺⁾*3CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 8929 - 8936

38
[ 185130-32-9 ]
[ 76089-77-5 ]
C₃₂H₄₀CeN₈⁽³⁺⁾*3CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 8929 - 8936

39
[ 185130-32-9 ]
[ 7732-18-5 ]
dysprosium(III) trifluoromethanesulfonate [ No CAS ]
C₃₂H₄₀DyFN₈⁽²⁺⁾*2CF₃O₃S^(1-)*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,4,8,11-tetrakis(2-pyridylmethyl)-1,4,8,11-tetraazacyclotetradecane; dysprosium(III) trifluoromethanesulfonate In methanol for 24h; Reflux; Stage #2: water In acetonitrile for 3h; Reflux;

Reference： [1]Canaj, Angelos B.; Singh, Mukesh Kumar; Regincós Marti, Emma; Damjanović, Marko; Wilson, Claire; Céspedes, Oscar; Wernsdorfer, Wolfgang; Rajaraman, Gopalan; Murrie, Mark [Chemical Communications, 2019, vol. 55, # 42, p. 5950 - 5953]

40
[ 185130-32-9 ]
[ 7732-18-5 ]
lanthanum(lll) triflate [ No CAS ]
C₃₂H₄₀FLaN₈⁽²⁺⁾*2CF₃O₃S^(1-)*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,4,8,11-tetrakis(2-pyridylmethyl)-1,4,8,11-tetraazacyclotetradecane; lanthanum(lll) triflate In methanol for 24h; Reflux; Stage #2: water In acetonitrile for 3h; Reflux;

41
[ 185130-32-9 ]
[ CAS Unavailable ]
[ 7732-18-5 ]
[ CAS Unavailable ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,4,7,10-tetrakis(2-pyridylmethyl)-1,4,7,10-tetraazacyclododecane; lanthanum trifluoromethanesulphonate; cerium trifluoromethanesulfonate In methanol Reflux; Stage #2: In acetonitrile for 2h; Reflux; Stage #3: amine hydrofluoride; lithium hydroxide monohydrate Further stages;