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60239-18-1

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  • High quality 1,4,7,10-?Tetraazacyclododecane-?1,4,7,10-?Tetraacetic Acid supplier in China

    Cas No: 60239-18-1

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60239-18-1 Usage

Chemical Properties

Colourless crystals

Uses

Different sources of media describe the Uses of 60239-18-1 differently. You can refer to the following data:
1. Bifunctional DOTA aconjugates to peptides and has become an established strategy for constructing target-specific metal containing agents including targeted MRI contrast agents and diagnostic and ther apeutic radiopharmaceuticals.
2. 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) is a macrocyclic complexing agent.It has been used for radiolabeling of carbon nanotube bioconjugates by chelating 64Cu radioisotope.DOTA can be activated with N-hydroxysulfosuccinimidyl for conjugation with monoclonal antibodies in clinical radioimmunotherapy.It can form complexes with gadolinium for application as MRI contrast agents.Metal complexes of DOTA-peptide conjugates can be used as therapeutic radiopharmaceuticals.

Definition

ChEBI: An azamacrocyle in which four nitrogen atoms at positions 1, 4, 7 and 10 of a twelve-membered ring are each substituted with a carboxymethyl group.

Check Digit Verification of cas no

The CAS Registry Mumber 60239-18-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,0,2,3 and 9 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 60239-18:
(7*6)+(6*0)+(5*2)+(4*3)+(3*9)+(2*1)+(1*8)=101
101 % 10 = 1
So 60239-18-1 is a valid CAS Registry Number.
InChI:InChI=1/C16H28N4O8/c21-13(22)9-17-1-2-18(10-14(23)24)5-6-20(12-16(27)28)8-7-19(4-3-17)11-15(25)26/h1-12H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28)

60239-18-1 Well-known Company Product Price

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  • TCI America

  • (T1875)  1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic Acid  >97.0%(T)

  • 60239-18-1

  • 200mg

  • 1,350.00CNY

  • Detail
  • TCI America

  • (T1875)  1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic Acid  >97.0%(T)

  • 60239-18-1

  • 1g

  • 4,750.00CNY

  • Detail
  • Aldrich

  • (86734)  1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraaceticacid  ≥97.0% (CHN)

  • 60239-18-1

  • 86734-50MG

  • 1,214.46CNY

  • Detail
  • Aldrich

  • (86734)  1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraaceticacid  ≥97.0% (CHN)

  • 60239-18-1

  • 86734-250MG

  • 4,179.24CNY

  • Detail

60239-18-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name DOTA

1.2 Other means of identification

Product number -
Other names 2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:60239-18-1 SDS

60239-18-1Synthetic route

1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane-10-acetic acid
137076-54-1

1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane-10-acetic acid

A

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

B

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
With chlorotriisopropylsilane; water; trifluoroacetic acid for 3h; Time; Reagent/catalyst; Solvent;A 100%
B 100%
C43H58N4O8
1412494-57-5

C43H58N4O8

A

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

B

1-methyl-1-phenylethyl alcohol
617-94-7

1-methyl-1-phenylethyl alcohol

Conditions
ConditionsYield
With chlorotriisopropylsilane; water; trifluoroacetic acid for 0.833333h; Time; Reagent/catalyst; Solvent;A 100%
B 100%
2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid

2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 12h;89%
With trifluoroacetic acid In dichloromethane at 20℃; for 16h;85%
With trifluoroacetic acid In dichloromethane at 20℃;
chloroacetic acid
79-11-8

chloroacetic acid

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With sodium hydroxide In water at 70℃; for 30h; pH=9.5 - 10;88%
With (-)-cycleanine; sodium hydroxide In water at 80 - 85℃; pH=10 - 11; Large scale;82.7%
With sodium hydroxide In water at 80 - 85℃; pH=10 - 11; Industrial scale;82.7%
bromoacetic acid
79-08-3

bromoacetic acid

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h; Temperature; Reagent/catalyst;87.8%
tetraethyl 2,2',2'',2'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetraacetate

tetraethyl 2,2',2'',2'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetraacetate

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With water; sodium hydroxide In methanol at 55 - 60℃; for 12h;80.5%
Iodoacetic acid
64-69-7

Iodoacetic acid

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h;72%
chloroacetic acid lithium salt
19326-51-3

chloroacetic acid lithium salt

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h;43.8%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h;32.5%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h;24.8%
1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid mono(4-nitrophenyl) ester
474424-15-2

1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid mono(4-nitrophenyl) ester

A

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

B

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
In water for 1h; pH=7; Kinetics; Further Variations:; pH-values;
N,N',N'',N'''-tetrakis-(p-tolylsulphonyl)-triethylenetetramine
55442-07-4

N,N',N'',N'''-tetrakis-(p-tolylsulphonyl)-triethylenetetramine

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / K2CO3 / dimethylformamide / 30 h / 100 °C
2: 33 percent / conc. H2SO4 / 28 h / 115 °C
3: 88 percent / NaOH / H2O / 30 h / 70 °C / pH 9.5 - 10
View Scheme
cyclen tetratosylate
52667-88-6

cyclen tetratosylate

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 33 percent / conc. H2SO4 / 28 h / 115 °C
2: 88 percent / NaOH / H2O / 30 h / 70 °C / pH 9.5 - 10
View Scheme
triethylentetramine
112-24-3

triethylentetramine

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 97 percent / Et3N / acetonitrile / 5 h / 20 °C
2: 78 percent / K2CO3 / dimethylformamide / 30 h / 100 °C
3: 33 percent / conc. H2SO4 / 28 h / 115 °C
4: 88 percent / NaOH / H2O / 30 h / 70 °C / pH 9.5 - 10
View Scheme
2Na(1+)*Pb(2+)*(N(CH2COO)C2H4)4(4-)*2H2O=Na2Pb(N(CH2COO)C2H4)4*2H2O

2Na(1+)*Pb(2+)*(N(CH2COO)C2H4)4(4-)*2H2O=Na2Pb(N(CH2COO)C2H4)4*2H2O

A

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

B

lead(2+) cation

lead(2+) cation

Conditions
ConditionsYield
In perchloric acid Kinetics; decompn. of Pb compd. in aq. HClO4 depending from acid concn.;
C46H62N4O8
1412494-56-4

C46H62N4O8

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); 4-methyl-morpholine / dichloromethane / 3 h / 20 °C
2: chlorotriisopropylsilane; trifluoroacetic acid; water / 0.83 h
View Scheme
(1,4,7,10-tetraaza-cyclododec-1-yl)-acetic acid allyl ester
1023970-58-2

(1,4,7,10-tetraaza-cyclododec-1-yl)-acetic acid allyl ester

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / 16 h / 20 °C
2: tetrakis(triphenylphosphine) palladium(0); 4-methyl-morpholine / dichloromethane / 2 h / 20 °C
3: chlorotriisopropylsilane; trifluoroacetic acid; water / 3 h
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / 8 h / 20 °C
2: tetrakis(triphenylphosphine) palladium(0); 4-methyl-morpholine / dichloromethane / 3 h / 20 °C
3: chlorotriisopropylsilane; trifluoroacetic acid; water / 0.83 h
View Scheme
C31H56N4O8
1412494-55-3

C31H56N4O8

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); 4-methyl-morpholine / dichloromethane / 2 h / 20 °C
2: chlorotriisopropylsilane; trifluoroacetic acid; water / 3 h
View Scheme
1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / chloroform / 52 h / 20 °C
2: trifluoroacetic acid / dichloromethane / 12 h
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 40 h / Reflux
2: sodium hydroxide; water / methanol / 12 h / 55 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1: chloroform / 72 h / 20 °C
2: trifluoroacetic acid / dichloromethane / 20 °C
View Scheme
cyclen hydrochloride

cyclen hydrochloride

chloroacetic acid
79-11-8

chloroacetic acid

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 75℃; pH=10 - 10.5;
Stage #1: cyclen hydrochloride; chloroacetic acid With hydrogenchloride; sodium hydroxide In water at 0 - 75℃; pH=10 - 10.5;
Stage #2: In water pH=2.5 - 3;
With sodium hydroxide In water at 10 - 30℃; for 24h; Reagent/catalyst;
sodium monochloroacetic acid
3926-62-3

sodium monochloroacetic acid

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With sodium hydroxide In water for 5h; pH=11; Concentration; Large scale;
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h;
sodium 2-bromoacetate
1068-52-6

sodium 2-bromoacetate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h;
potassium iodoacetate
15973-59-8

potassium iodoacetate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h;
monosodium iodoacetate
305-53-3

monosodium iodoacetate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With lithium hydroxide monohydrate; water at 0 - 30℃; for 24h;
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

gadolinium(III) chloride hexahydrate

gadolinium(III) chloride hexahydrate

gadoteric acid
72573-82-1

gadoteric acid

Conditions
ConditionsYield
With potassium hydroxide In water at 60℃; for 24h; pH=5.5 - 7;100%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

manganese (II) sulfate monohydrate

manganese (II) sulfate monohydrate

Mn(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid(2-))*2H2O

Mn(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid(2-))*2H2O

Conditions
ConditionsYield
In water MnSO4*H2O dissolved in H2O, ligand added, stirred for 30 min; H2O evapd.; elem. anal.;99%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

scandium(III) acetate
3804-23-7

scandium(III) acetate

sodium hydroxide
1310-73-2

sodium hydroxide

3(Na[Sc(1,4,7,10-tetra-azacyclododecane-N,N',N'',N'''-tetraacetate)])*NaOH*18H2O

3(Na[Sc(1,4,7,10-tetra-azacyclododecane-N,N',N'',N'''-tetraacetate)])*NaOH*18H2O

Conditions
ConditionsYield
In water to aq. suspn. H4DOTA NaOH was added until pH 5, Sc(acetate)3 was added and heated at 60°C for 12 h at pH 4; soln. was concd., residue was dissolved in water, basified with NaOH at pH 7.0 and evapd. to dryness under reduced pressure;95%
lanthanum(III) oxide

lanthanum(III) oxide

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

sodium hydroxide
1310-73-2

sodium hydroxide

Na(1+)*2La(3+)*C8H16N4(CH2CO2)4(4-)*C8H16N4(CH2CO2)3CH2CO2H(3-)*10H2O=Na[La2(C8H16N4(CH2CO2)4)2H]*10H2O

Na(1+)*2La(3+)*C8H16N4(CH2CO2)4(4-)*C8H16N4(CH2CO2)3CH2CO2H(3-)*10H2O=Na[La2(C8H16N4(CH2CO2)4)2H]*10H2O

Conditions
ConditionsYield
In water stoich. amts., 85°C, stirring for several d; cooling to room temp., filtration, evapn. (reduced pressure);93%
gadolinium(III) oxide

gadolinium(III) oxide

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

1-deoxy-1-(methylamino)-D-glucitol
6284-40-8

1-deoxy-1-(methylamino)-D-glucitol

gadoterate meglumine

gadoterate meglumine

Conditions
ConditionsYield
Stage #1: 1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane; 1-deoxy-1-(methylamino)-D-glucitol In water for 0.05h; Green chemistry;
Stage #2: gadolinium(III) oxide In water for 0.283333h; Sonication; Green chemistry;
89%
morpholine
110-91-8

morpholine

gadolinium(III) oxide

gadolinium(III) oxide

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

gadoterate morpholine

gadoterate morpholine

Conditions
ConditionsYield
Stage #1: morpholine; 1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane In water for 0.05h; Sonication; Green chemistry;
Stage #2: gadolinium(III) oxide In water for 0.283333h; Sonication; Green chemistry;
85%
gadolinium(III) oxide

gadolinium(III) oxide

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Na(1+)*Gd(3+)*(CH2CH2N(CH2COO))4(4-)*H2O*4H2O=Na{Gd(CH2CH2N(CH2COO))4H2O}*4H2O

Na(1+)*Gd(3+)*(CH2CH2N(CH2COO))4(4-)*H2O*4H2O=Na{Gd(CH2CH2N(CH2COO))4H2O}*4H2O

Conditions
ConditionsYield
In water Gd2O3 and tetraazacyclododecanetetraacetic acid soln. was stirred at 368 K for 2 h, NaOH was slowly added at room temp. to pH 7 with stirring; after filtration mixt. was concd. in vac. and pptd. with acetone; recrystn. from hot H2O/acetone; elem. anal.;83%
gadolinium(III) oxide

gadolinium(III) oxide

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

1-deoxy-1-(methylamino)-D-glucitol
6284-40-8

1-deoxy-1-(methylamino)-D-glucitol

gadoteric dcid meglumine

gadoteric dcid meglumine

Conditions
ConditionsYield
In water at 40 - 50℃; for 3h; pH=7 - 9; Industrial scale;82%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

nickel(II)

nickel(II)

{(CH2CH2)NCH2COOH}2{(CH2CH2)NCH2COO}2Ni
107171-59-5

{(CH2CH2)NCH2COOH}2{(CH2CH2)NCH2COO}2Ni

Conditions
ConditionsYield
In water equimolar amounts of ligand and metal salt; pH 2.5;; crystallization after several days; elem. anal.;;80%
gadolinium(III) oxide

gadolinium(III) oxide

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

(2S,3S,4S,5R)-6-(methylamino)hexane-1,2,3,4,5-pentaol

(2S,3S,4S,5R)-6-(methylamino)hexane-1,2,3,4,5-pentaol

gadoteric dcid meglumine

gadoteric dcid meglumine

Conditions
ConditionsYield
In water at 40 - 50℃; for 3h; pH=7 - 9; Large scale;78.5%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

p-xylylidenediamine
539-48-0

p-xylylidenediamine

2,2',2''-(10-(2-(4-(aminomethyl)benzylamino)-2-oxoethyl)-1,4,7,10-tetraazacyclo-dodecane-1,4,7-triyl)triacetic acid
1314043-15-6

2,2',2''-(10-(2-(4-(aminomethyl)benzylamino)-2-oxoethyl)-1,4,7,10-tetraazacyclo-dodecane-1,4,7-triyl)triacetic acid

Conditions
ConditionsYield
With pyridine; diisopropyl-carbodiimide In water; acetonitrile75%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

zinc(II) cation

zinc(II) cation

(1,4,7,10-tetraazacyclododecane-N,N',N''-N'''-dihydrogentetraacetato)zinc
107171-57-3, 277333-19-4

(1,4,7,10-tetraazacyclododecane-N,N',N''-N'''-dihydrogentetraacetato)zinc

Conditions
ConditionsYield
In water equimolar amounts of ligand and metal salt; pH 2.5;; crystallization after several days; elem. anal.;;72%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

2-AMINOETHYL TRIMETHYLAMMONIUM CHLORIDE
10256-43-6

2-AMINOETHYL TRIMETHYLAMMONIUM CHLORIDE

10-<2-(trimethylammonio)ethylcarbamoylmetyhyl>-1,4,7,10-tetraazacyclododecane-1,4,7-tri(triacetic acid) chloride

10-<2-(trimethylammonio)ethylcarbamoylmetyhyl>-1,4,7,10-tetraazacyclododecane-1,4,7-tri(triacetic acid) chloride

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In pyridine; acetonitrile at 20℃; for 48h;71%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

copper(II) ion

copper(II) ion

{(CH2CH2)NCH2COOH}2{(CH2CH2)NCH2COO}2Cu
107171-58-4, 277333-30-9

{(CH2CH2)NCH2COOH}2{(CH2CH2)NCH2COO}2Cu

Conditions
ConditionsYield
In water equimolar amounts of ligand and metal salt; pH 2.5;; crystallization after several days; elem. anal.;;69%
gadolinium(III) oxide

gadolinium(III) oxide

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

gadolinium(III) 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid
72573-82-1

gadolinium(III) 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid

Conditions
ConditionsYield
In water for 3h;67.9%
In water addn. of gadolinium oxide to aq. soln. of tetraazacyclododecane deriv., mixt. heated at 90°C for 12 h; cooling to room temp., addn. of cation-exchange and anion-exchange resins, stirring for 60 min at room temp., filtration, filtrate freeze dried;61%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

NO2(C6H4)CH2CH(C(O)NHCH2CH2NH2)NHC(O)(C6H4)((C9BN2)(F)2(CH3)4(CH2CH3)2)

NO2(C6H4)CH2CH(C(O)NHCH2CH2NH2)NHC(O)(C6H4)((C9BN2)(F)2(CH3)4(CH2CH3)2)

NO2(C6H4)CH2CH(C(O)NHCH2CH2NHC(O)CH2(C8H16N4)(CH2C(O)OH)3)NHC(O)(C6H4)((C9BN2)(F)2(CH3)4(CH2CH3)2)

NO2(C6H4)CH2CH(C(O)NHCH2CH2NHC(O)CH2(C8H16N4)(CH2C(O)OH)3)NHC(O)(C6H4)((C9BN2)(F)2(CH3)4(CH2CH3)2)

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;65%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

3-bromopropyl biotin
1296869-99-2

3-bromopropyl biotin

C29H48N6O11S

C29H48N6O11S

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 82℃; for 18h;65%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

3-amino-deoxycombretastatin A4
162705-07-9

3-amino-deoxycombretastatin A4

C34H47N5O11

C34H47N5O11

Conditions
ConditionsYield
Stage #1: 1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane With thionyl chloride for 4h; Reflux;
Stage #2: 3-amino-deoxycombretastatin A4 With N-ethyl-N,N-diisopropylamine In dichloromethane at 30℃; for 3h; Cooling with ice;
65%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

N,N-bis(ethoxycarbonylmethyl)ethylenediamine

N,N-bis(ethoxycarbonylmethyl)ethylenediamine

(Ethoxycarbonylmethyl-{2-[2-(4,7,10-tris-{[2-(bis-ethoxycarbonylmethyl-amino)-ethylcarbamoyl]-methyl}-1,4,7,10-tetraaza-cyclododec-1-yl)-acetylamino]-ethyl}-amino)-acetic acid ethyl ester

(Ethoxycarbonylmethyl-{2-[2-(4,7,10-tris-{[2-(bis-ethoxycarbonylmethyl-amino)-ethylcarbamoyl]-methyl}-1,4,7,10-tetraaza-cyclododec-1-yl)-acetylamino]-ethyl}-amino)-acetic acid ethyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In chloroform; N,N-dimethyl-formamide at 20℃; for 30h;63%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

copper(ll) sulfate pentahydrate

copper(ll) sulfate pentahydrate

{(CH2CH2)NCH2COO}4(4-)*2Cu(2+)*5H2O={(CH2CH2)NCH2COO}4Cu2*5H2O

{(CH2CH2)NCH2COO}4(4-)*2Cu(2+)*5H2O={(CH2CH2)NCH2COO}4Cu2*5H2O

Conditions
ConditionsYield
In water pH=4; stochiometric amounts;; after 2-3 days crystallization; elem. anal.;;60%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

Met-OMe
10332-17-9

Met-OMe

C40H72N8O12S4

C40H72N8O12S4

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;55%
1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane
60239-18-1

1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane

gadolinium(III) trifluoromethanesulfonate

gadolinium(III) trifluoromethanesulfonate

gadolinium 2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododec-1-yl]acetic acid
783303-01-5, 83678-67-5, 881694-36-6, 881694-49-1

gadolinium 2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododec-1-yl]acetic acid

Conditions
ConditionsYield
With triethylamine In methanol at 45℃; for 48h;55%

60239-18-1Relevant articles and documents

Cherenkov Radiation-Mediated In Situ Excitation of Discrete Luminescent Lanthanide Complexes

Cosby, Alexia G.,Ahn, Shin Hye,Boros, Eszter

, p. 15496 - 15499 (2018)

Lanthanide luminescence, while ideal for in vivo applications owing to sharp emission bands within the optical window, requires high-intensity, short-wavelength excitation of small organic “antenna” chromophores in the vicinity of the lanthanide complex to access excited f-orbital states through intersystem crossing. Herein, we explored Cherenkov radiation of the radioisotopes 18F and 89Zr as an in situ source of antenna excitation. The effective inter- and intramolecular excitation of the terbium(III) complexes of a macrocylic polyaminocarboxylate ligand (hydration number (q)=0, quantum yield (φ)=47 %) as well as its analogue functionalized to append an intramolecular Cherenkov excitation source (q=0.07, φ=63 %) was achieved. Using conventional small-animal fluorescence imaging equipment, we have determined a detection limit of 2.5 nmol of Tb(III) complex in presence of 10 μCi of 18F or 89Zr. Our system is the first demonstration of the optical imaging of discrete luminescent lanthanide complexes without external short-wave excitation.

Method for preparing contrast agent

-

Paragraph 0005; 0058-0061, (2020/07/24)

The invention provides a method for preparing a contrast agent. Specifically, the preparation method comprises the following steps: enabling a complex liquid composition containing a macrocyclic chelate and lanthanide elements to sequentially pass through Relite CNS cationic resin and Relite 3As anionic resin to obtain a high-purity liquid solution, and then adjusting the pH value of the solution;and freeze-drying or low-temperature spray-drying to obtain a contrast agent solid, and further weighing a certain amount of the solid to prepare a contrast agent preparation for medical contrast.

Including and Declaring Structural Fluctuations in the Study of Lanthanide(III) Coordination Chemistry in Solution

Nielsen, Lea Gundorff,S?rensen, Thomas Just

, (2019/11/14)

The physicochemical properties of lanthanide(III) ions are directly linked to the structure of the surrounding ligands. Rapid ligand exchange prohibits direct structure-property relationships from being formed for simple complexes in solution because the property measured will be an average over several structures. For kinetically inert lanthanide(III) complexes, the simpler speciation may alleviate the problem, yet the archetypical complexes formed by ligands derived from cyclen are known to have at least four different forms in solution - each with a variation in the crystal field that gives rise to significantly different properties. Slow interchange between forms has been engineered, so that a single complex geometry can be studied, but fast or intermediate interchange between forms is much more commonly observed. The rapid structural fluctuation can report on the changing chemical environment and can be disregarded if a specific property of a lanthanide(III) complex is exploited in an application. However, if we are to understand the chemistry of the lanthanide(III) ions in solution, we must include the structural fluctuation that takes place even in kinetically inert lanthanide(III) complexes in our studies. Here, we have scrutinized the processes that determine the speciation of lanthanide(III) complexes of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetate (DOTA)-like ligands, in particular the processes that enable exchange between forms that have different physicochemical properties, exemplified by the exchange between the diastereomeric capped square-antiprismatic (cSAP) and capped twisted-square-antiprismatic (cTSAP) forms of DOTA-like lanthanide(III) complexes. In the characterization of a kinetically inert f-element complex, understanding the structural fluctuation in the system is critical because a single observed property can arise from a weighted average, from all forms present, or from a single form with a dominating contribution. Further, the experimental condition will influence both the distribution of lanthanide(III) species in solution and the rates of the processes that change the coordination sphere of the lanthanide(III) ions. This is highlighted using data from a series of cyclen-derived ligands with different pendant arms and different denticity. The data were obtained in experiments that take place on different time scales to show that the rate of the process that results in a structural change must be considered against the time of the experiment. We conclude that the structural fluctuations must be taken into account and that they cannot be predicted from the ligand structure. Thus, an estimate of the exchange rates between forms, the relative concentrations of the specific forms, and the effect of the specific structure of each form of the complex must be included in the description of the solution properties of f-element chelates.

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