146432-41-9

Basic information

• Product Name: N,N-BIS(T-BUTYL-4-CARBOXYMETHYL)AMINOETHANOL
• Synonyms: N,N-BIS(T-BUTYL-4-CARBOXYMETHYL)AMINOETHANOL
• CAS NO: 146432-41-9
• Molecular Formula: C₁₄H₂₇NO₅
• Molecular Weight: 289.369
• Mol File: 146432-41-9.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N-BIS(T-BUTYL-4-CARBOXYMETHYL)AMINOETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-BIS(T-BUTYL-4-CARBOXYMETHYL)AMINOETHANOL(146432-41-9)
• EPA Substance Registry System: N,N-BIS(T-BUTYL-4-CARBOXYMETHYL)AMINOETHANOL(146432-41-9)

Safety Data

• Hazardous Substances Data: 146432-41-9(Hazardous Substances Data)

Upstream product

• 23147-58-2 glycolaldehyde dimer 
• 85916-13-8 tert-butyl iminodiacetate 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 141-43-5 ethanolamine 

Downstream Products

• 1566605-69-3 1,1-bis(benzyloxycarbonylmethyl)-4-methoxycarbonylmethyl-7,7-bis(tert-butoxycarbonylmethyl)-1,4,7-triazaheptane 
• 1566605-70-6 1-benzyl-1-methoxycarbonylmethyl-4,4-bis(tert-butoxycarbonylmethyl)-1,4-diazabutane 
• 1566605-88-6 C₆₆H₁₁₁N₉O₂₁ 
• 1566605-87-5 C₄₈H₈₃N₇O₁₇ 
• 1566605-86-4 C₄₇H₈₁N₇O₁₇ 
• 1566605-85-3 C₆₂H₉₅N₇O₁₇ 
• 1566605-79-5 C₄₄H₆₇N₅O₁₄ 
• 1566605-75-1 C₅₁H₈₉N₇O₁₈ 
• 1000991-94-5 C₃₄H₅₇N₃O₁₀ 
• 1000991-93-4 C₃₄H₅₅N₃O₁₂ 
• 1163255-14-8 4-benzyloxycarbonylmethyl-1,1,7,7-tetra(carboxymethyl)-1,4,7-triazaheptane 
• 178552-82-4 4-benzyloxycarbonylmethyl-1,1,7,7-tetra(tertbutyloxycarbonylmethyl)-1,4,7-triazaheptane 
• 174267-71-1 3,9-Bis(tert-butoxycarbonylmethyl)-6-carboxymethyl-3,6,9-triazaundecanedioic acid-di-tert-butyl ester 
• 1362022-22-7 C₃₈H₆₄N₄O₁₁ 

Relevant articles and documents

An unusual tandem cyclization-Stevens rearrangement mediated by Ph3P/DEAD or Bu3P/ADDP

Alcohols 1 and 10c when treated with Ph3P/DEAD or Bu3P/ADDP yield products resulting from intramolecular cyclization to form five- and six-membered, cyclic quaternary ammonium salts (respectively) which undergo a Stevens rearrangement in the same pot.

Evaluation of 99mTc(CO)3 complex of 2-methyl-5-nitroimidazole as an agent for targeting tumor hypoxia

An iminodiacetic acid (IDA) derivative of 2-methyl-5-nitroimidazole was synthesized as a carrier molecule for radiolabeling with the gamma emitting radioisotope, 99mTc, for imaging hypoxic regions of tumors. The ligand was synthesized in excellent yield and labeled using freshly prepared [99mTc(CO)3(H2O)3]+ intermediate. A complexation yield of over 95% could be achieved under mild conditions using a ligand concentration of 1 mg/mL [～3 × 10-3 M]. The complex was characterized by HPLC and its stability in human serum was studied. Biodistribution studies performed in Swiss mice bearing fibrosarcoma tumor showed maximum accumulation in the tumor to the extent of ～0.52 %ID/g at 30 min post-injection (pi). The major clearance of the complex was through the hepatobiliary route. The complex showed tumor/muscle ratio of 1.75 at 30 min pi, which significantly increased to 17 at 180 min pi. However, the tumor/blood ratio was below one throughout the period of study, which could be due to slow clearance of the complex from blood.

Selective protein purification by PEG-IDA-functionalized iron oxide nanoparticles

We developed a new heterobifunctional polyethylene glycol ligand for iron oxide nanoparticles with a group for covalent surface attachment and for chelating metal ions. After introduction of nickel ions, His-tagged fluorescent proteins were magnetically purified from a cell lysate. A high purity product and efficient magnetic separation were observed.

Discrete nanomolecular polyhedral borane scaffold supporting multiple gadolinium(III) complexes as a high performance MRI contrast agent

An icosahedral closo-B122- scaffold supports 12 copies of Gd3+-chelate held in close proximity with each other by suitable linkers which employ azide-alkyne click chemistry. This design is the first member of a new class of polyfunctional MRI contrast agents carrying a high payload of Gd3+-chelate in a sterically constrained configuration. The resulting contrast agent shows higher relaxivity values at high magnetic fields. MRI contrast agents currently in use are not as effective in this regard, presumably due to a lack of steric constraint of gadolinium centers and lower water exchange rates. In vivo MRI studies in mice show excellent contrast enhancement even at one-seventh of the safe clinical dose (0.04 mmol Gd/kg) for up to a 1 h exposure.

METAL CHELATORS FOR IMAGING, THERAPEUTICS, AND BIOANALYSIS

A variety of compounds are provided capable of chelating a metal, in particular a lanthanide such as Eu(III) and Tb(III). Luminescent complexes of the compound and a metal ion are also provided, in particular luminescent metal complexes are provided containing a lanthanide such as Eu(III) or Tb(III) and a compound described herein. In some aspects, the luminescent complexes are capable of exhibiting bright emissions with high quantum yields. Methods of making the compound are provided. Methods of using the compounds and luminescent complexes are also provided, for example for imaging and therapeutic applications.

Efficient route to pre-organized and linear polyaminopolycarboxylates: Cy-TTHA, Cy-DTPA and mono/di- reactive, tert-butyl protected TTHA/Cy-TTHA

Pre-organized polyaminopolycarboxylate chelators Cy-TTHA and Cy-DTPA were synthesized via modular five-step syntheses from commercially available starting materials in ～62% and 47% overall yields, respectively. Furthermore, strategies are reported for the efficient preparation of mono- and di-reactive, tert-butyl-protected TTHA/Cy-TTHA to selectively functionalize central chelators’ carboxylic acids.