Home Cart 0 Sign in  

[ CAS No. 23911-26-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 23911-26-4
Chemical Structure| 23911-26-4
Structure of 23911-26-4 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 23911-26-4 ]

Related Doc. of [ 23911-26-4 ]

Alternatived Products of [ 23911-26-4 ]
Product Citations

Product Details of [ 23911-26-4 ]

CAS No. :23911-26-4 MDL No. :MFCD00010697
Formula : C14H19N3O8 Boiling Point : -
Linear Structure Formula :HO2CCH2N(C2H4N(CH2CO)2O)2 InChI Key :RAZLJUXJEOEYAM-UHFFFAOYSA-N
M.W : 357.32 Pubchem ID :100825
Synonyms :
Chemical Name :Diethylenetriaminepentaacetic dianhydride

Safety of [ 23911-26-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23911-26-4 ]

* 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 [ 23911-26-4 ]

[ 23911-26-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 23911-26-4 ]
  • [ 3119-15-1 ]
  • [ 913816-97-4 ]
YieldReaction ConditionsOperation in experiment
80% In N,N-dimethyl-formamide; at 60℃; for 5.0h; Then, 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.515 g (1 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60C for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 80%. 1H NMR (D2O+NaOD, ppm) 2.36 (m, 8H, CH2CH2), 2.80~2.90 (d, 10H, CH2CO), 7.95 (s, 1H, Ar-H); 13C NMR (D2O+NaOD, ppm) 37.03, 52.05, 52.18, 58.89, 59.32, 74.93, 77.83, 80.44, 147.58, 153.27, 171.43, 180.04, 180.18; IR (cm-1) 3433, 1730, 1634, 1517, 1243.
80% In N,N-dimethyl-formamide; at 60℃; for 5.0h; 10.0 g (25 mmol) of DTPA was dispersed in 20 ml of pyridine. 18 g (0.18 mol) of acetic anhydride was added to the dispersion, and a reaction was allowed to take place at 65 for 24 hrs with stirring. After the reaction was completed, the reaction mixture was filtered to recover generated material. The recovered compound was washed with acetic anhydride and diethyl ether several times, and dried under pressure for 24 hrs, thereby obtaining a DTPA anhydride at a yield of 78%. IR(cm-1) 2979, 1820, 1774, 1641. Then, 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.515 g (1 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60 for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 80%. 1H NMR (D2O+NaOD, ppm) 2.36 (m, 8H, CH2CH2), 2.802.90 (d, 10H, CH2CO), 7.95 (s, 1H, Ar-H); 13C NMR (D2O+NaOD, ppm) 37.03, 52.05, 52.18, 58.89, 59.32, 74.93, 77.83, 80.44, 147.58, 153.27, 171.43, 180.04, 180.18; IR (cm-1) 3433, 1730, 1634, 1517, 1243.
  • 2
  • [ 23911-26-4 ]
  • [ 3119-15-1 ]
  • DTPA-bis(3-amido-2,4,6-triiodobenzoic acid) [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In N,N-dimethyl-formamide; at 60℃; for 5.0h; 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.13 g (2 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60C for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 75%. 1H NMR (D2O+NaOD, ppm) 2.34 m, 8H, CH2CH2), 2.78~2.86 (d, 10H, CH2CO), 7.92 (s, 2H, Ar-H).
75% In N,N-dimethyl-formamide; at 60℃; for 5.0h; 0.357 g (1 mmol) of the DTPA anhydride was added to 30 ml of anhydrous dimethylformamide (DMF), and mixed with stirring. This solution was supplemented with 0.13 g (2 mmol) of <strong>[3119-15-1]3-amino-2,4,6-triiodobenzoic acid</strong>, and allowed to react at 60 for 5 hrs with stirring. After the reaction was completed, the solvent was removed under pressure using an evaporator, and the remaining material was washed with ethanol and dried, thereby obtaining the desired product at a yield of 75%.
  • 3
  • [ 23911-26-4 ]
  • [ 7089-68-1 ]
  • [ 24424-99-5 ]
  • [ 14235-81-5 ]
  • [ 1609542-53-1 ]
  • C39H43N7O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
[2-[(4?-Aminophenylen)ethynylen]-l ,1 0-phenanthrolin-5/6-yl]amine 5 (1 eq.), DTPAdianhydride and triethylamine (5 eq.) were stirred in DMF under argon for 2 h at 80°C. The solvents were removed under reduced pressure. The residue was purified by RP-HPLC(water/MeCN).A potential problem regards the coupling of the antenna (compound 5) with the chelator (DTPA-anhydride) as the used DTPA- anhydride has two activated acid groups, but only the monosubstituted product is desired. The formation of a disubstituted product was reduced by applying the suitable excess of DTPA as described above and by a reaction design thatkeeps the concentration of compound 5 as small as possible.
Example 1: Syntheis of the amino-reactive phosphorescent dye of the invention Nitration of <strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> 150 ml concentrated sulphuric acid was placed in a 500 ml three-necked flask and <strong>[7089-68-1]2-Chloro-1,10-phenanthroline</strong> 1 (CAS-Nr. 7089-68-1)(30g) was added while cooled with ice and stirred. The solution was heated in an oil bath to 180 °C. At 80 °C, the solution boiled and a strong smoke emission could be observed. At 160 °C, nitric acid (65 percent, 80 ml) was added dropwise while maintaining a temperature of 170 °C. The bath temperature was increased to 215 °C, and the adding was performed in such a way that the temperature was below or equal to 160 °C. After complete addition of the nitric acid, the solution was heated under reflux for 1 h to 165 to 170 °C. Following this, the reaction mixture was cooled in a ice bath, added to approximately 1 kg ice and diluted with 1 l water. A sodium hydroxide solution (50 percent w/v) was added dropwise until the pH value of the reaction mixture was in a neutral/weak alkaline range. This was accompanied by formation of a slightly yellow precipitate. The precipitate was separated and washed with water. The crude product of the reaction was dried over night at 110 °C, extracted with chloroform via Soxleth extraction and reduced to a dry powder in rotary evaporator. Reduction of 2-chloro-5/6-nitro-1,10-phenanthroline 2-Chloro-5/6-nitro-1,10-phenanthroline 2 (1 eq.) was dissolved in methanol and hydrogenated under stirring in the presence of the catalyst (palladium/coal 10percent, 10molpercent) in a hydrogenation plant until no further hydrogen consumption could be observed. The catalyst was filtered off and the filtrate was reduced to dryness under reduced pressure (complete conversion). Introduction of a Boc group to 5/6-amino-<strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> Alternatively, the amine group of <strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> 3 may be protected with a Boc group. To do this, 5/6-amino-<strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> (1 eq.) was dissolved in dry DMF and triethylamine (5 eq.). Then, DMAP (1.1 eq.) and di-t-butyldicarbonate (2 eq.) were added The solution was stirred at room temperature for 20 h. Then, water was added and the aqueous phase was extracted three times with diethylether. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product was purified with silica gel (CH2Cl2). (63percent yield). Coupling of the Boc-protected 2-chloro-5/6-amino-1,10-phenanthroline and 4-ethinylaniline Triphenylphosphine (30 molpercent), [Pd(PPh3)2]Cl2 (3molpercent), the protected 2-chloro-5/6-amino-1,10-phenanthroline 4 (1 eq.) and copper(I)iodide (2molpercent) were placed in a three-necked flask and suspended in 30 ml methanol. The 4-ethinylaniline (1.2 eq.) was added dissolved in 20 ml methanol. The reaction mixture was refluxed for 10 h. The mixture was extracted three times with dichloromethan, respectively. The combined organic phases were washed with water and brine before being concentrated to dryness. Purification by flash-chromatography yielded compound 5 as a brown solid. Coupling of the 19 Boc-protected [2-[(4'-aminophenylen)ethynylen]-1,10-phenanthrolin-5/6-yl]amine and DTPA-anhydride [2-[(4'-Aminophenylen)ethynylen]-1,10-phenanthrolin-5/6-yl]amine 5 (1 eq.), DTPA-dianhydride and triethylamine (5 eq.) were stirred in DMF under argon for 2 h at 80°C. The sovents were removed under reduced pressure. The residue was purified by RP-HPLC (water/MeCN).
Recommend Products
Same Skeleton Products

Technical Information

Historical Records
; ;