t-boc-N-amido-PEG2-bromide

Base Information

• Chemical Name: t-boc-N-amido-PEG2-bromide
• CAS No.: 164332-88-1
• Molecular Formula: C9H18BrNO3
• Molecular Weight: 268.151
• Mol file: 164332-88-1.mol

Synonyms:tert-butyl 2-(2-bromoethoxy)ethylcarbamate;tert-butyl (2-(2-bromo)ethoxy)ethylcarbamate;

Chemical Property of t-boc-N-amido-PEG2-bromide

Chemical Property:

• Boiling Point: 336.6±22.0 °C(Predicted)
• PKA: 12.19±0.46(Predicted)
• PSA: 47.56000
• Density: 1.283±0.06 g/cm3(Predicted)
• LogP: 2.31350
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Soluble in Water, DMSO, DCM, DMF

Purity/Quality:

99% ^*data from raw suppliers

BocNH-PEG1-CH2CH2Br min.97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: t-boc-N-amido-PEG2-bromide is a PEG derivative containing a bromide group and Boc-protected amino group. The hydrophilic PEG spacer increases solubility in aqueous media. The bromide (Br) is a very good leaving group for nucleophilic substitution reactions. The Boc group can be deprotected under mild acidic conditions to form the free amine.
• Uses: t-boc-N-amido-PEG2-bromide can be used in medical research, drug-release, nanotechnology and new materials research, cell culture. In the study of ligand, polypeptide synthesis support, a graft polymer compounds, new materials, and polyethylene glycol-modified functional coatings and other aspects of the active compound. tert-Butyl (2-(2-bromoethoxy)ethyl)carbamate is a cleavable ADC linker for the synthesis of antibody drug conjugates (ADCs).

Technology Process of t-boc-N-amido-PEG2-bromide

There total 3 articles about t-boc-N-amido-PEG2-bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-(2-tert-butyloxycarbonylaminoethoxy)ethanol (139115-91-6) → tert-butyl N-[2-(2-bromoethoxy)ethyl]carbamate (164332-88-1)

Guidance literature:

2-(2-tert-butyloxycarbonylaminoethoxy)ethanol; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;

With lithium bromide; In dichloromethane; acetone; at 20 ℃;

Reference yield: 82.0%

silicon dioxide hydrate (23382-09-4,10279-57-9,98759-73-0) + 2-(2-(bis(tert-butoxycarbonyl)amino)ethoxy)ethyl methanesulfonate (1181224-95-2) → tert-butyl N-[2-(2-bromoethoxy)ethyl]carbamate (164332-88-1)

Guidance literature:

With lithium bromide; In water; acetone;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl N-[2-(2-bromoethoxy)ethyl]carbamate (164332-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 18 h / 0 - 20 °C

2: carbon tetrabromide; triphenylphosphine / dichloromethane / 18 h / 0 - 20 °C

With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane;

upstream raw materials:

silicon dioxide hydrate

2-(2-(bis(tert-butoxycarbonyl)amino)ethoxy)ethyl methanesulfonate

di-tert-butyl dicarbonate

2-(2-tert-butyloxycarbonylaminoethoxy)ethanol

Downstream raw materials:

tert-butyl 2-(2-(2-chloro-5-nitrophenoxy)ethoxy)ethylcarbamate

Refernces

• 1、 Noguchi, Takao,Roy, Bappaditya,Yoshihara, Daisuke,Tsuchiya, Youichi,Yamamoto, Tatsuhiro,Shinkai, Seiji. "Translation of dicarboxylate structural information to fluorometric optical signals through self-assembly of guanidinium-tethered oligophenylenevinylene". . p. 13938 - 13944. Retrieved 2014.
• 2、 Wang, Siwen,Yang, Dazhou,Singh, Mandeep,Joo, Hyun,Rangel, Vanessa M.,Tran, Aaron,Phan, Erich,Xue, Liang. "Thiazole orange – Spermine conjugate: A potent human telomerase inhibitor comparable to BRACO-19". . p. 20 - 33. Retrieved 2019/05/06.