187960-74-3

Basic information

• Product Name: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID
• Synonyms: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID
• CAS NO: 187960-74-3
• Molecular Formula: C₂₁H₃₂N₂O₈
• Molecular Weight: 440.49
• Mol File: 187960-74-3.mol

Chemical Properties

• Melting Point: 125-127 °C
• Boiling Point: 632.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.181±0.06 g/cm3(Predicted)
• PKA: 3.87±0.10(Predicted)
• CAS DataBase Reference: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID(187960-74-3)
• EPA Substance Registry System: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID(187960-74-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 187960-74-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Synthetic route

3,5-bis-(2-tert-butyloxycarbonylamino-ethoxy) methyl benzoate (184916-28-7) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
With sodium hydroxide	100%
With sodium hydroxide In 1,4-dioxane; methanol; water for 5h;	96%
With water; sodium hydroxide In 1,4-dioxane; methanol for 5h;	96%

di-tert-butyl dicarbonate (24424-99-5) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: NEt3 / CH2Cl2 / 27 h / 0 °C 2: 64 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 3: 95 percent / Tesser's base / 4.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 0 °C 2: potassium carbonate; N,N-dimethyl-formamide / 16 h / 50 °C 3: sodium hydroxide / water; methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 0 °C 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 3: sodium hydroxide; water / methanol; 1,4-dioxane / 5 h View Scheme

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 2: 95 percent / Tesser's base / 4.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide 2: NaOH View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 2: sodium hydroxide; water / methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 2 steps 1.1: potassium iodide; potassium carbonate / acetone / 16 h / 65 °C / Inert atmosphere 2.1: sodium hydroxide / water; methanol / 2 h / 70 °C / Inert atmosphere 2.2: pH 3 / Inert atmosphere View Scheme

3,5-Dihydroxybenzoic acid (99-10-5) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / H2SO4 / Heating 2: 64 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 3: 95 percent / Tesser's base / 4.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / Reflux 2: potassium carbonate; N,N-dimethyl-formamide / 16 h / 50 °C 3: sodium hydroxide / water; methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 3: sodium hydroxide; water / methanol; 1,4-dioxane / 5 h View Scheme

2-(tert-butoxycarbonylamino)ethyl bromide (39684-80-5) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 2: 95 percent / Tesser's base / 4.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide 2: NaOH View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; N,N-dimethyl-formamide / 16 h / 50 °C 2: sodium hydroxide / water; methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 2: sodium hydroxide; water / methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 2 steps 1.1: potassium iodide; potassium carbonate / acetone / 16 h / 65 °C / Inert atmosphere 2.1: sodium hydroxide / water; methanol / 2 h / 70 °C / Inert atmosphere 2.2: pH 3 / Inert atmosphere View Scheme

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) + 3,5-Bis-(2-amino-ethoxy)-benzoic acid methyl ester; hydrochloride → 3,5-Bis-{2-[3,5-bis-(2-tert-butoxycarbonylamino-ethoxy)-benzoylamino]-ethoxy}-benzoic acid methyl ester (187960-76-5)

Conditions	Yield
With BOP-peptide	100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate	100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.5h;	95%

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → 3,5-(di-aminoethoxy)-benzoic acid dihydrochloride

Conditions	Yield
With hydrogenchloride In diethyl ether; dichloromethane for 2h;	100%
With hydrogenchloride In diethyl ether; dichloromethane; water for 2h;	100%

O-benzylhydoxylamine hydrochloride (2687-43-6) + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → N-(benzyloxy)-3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzamide (1228435-28-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	86%

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) + N-Fmoc-L-Ser(t-But)-OEt → N-Boc-L-Phe-L-Ser(t-But)-OEt

Conditions	Yield
With potassium fluoride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 5h; Substitution;	84%

C18H33NO7P2 + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → C39H63N3O14P2

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	65%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;	65%

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → 3,5-Bis-{2-[3,5-bis-(2-tert-butoxycarbonylamino-ethoxy)-benzoylamino]-ethoxy}-benzoic acid (352426-84-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / BOP; N,N-diisopropylethylamine (DiPEA) / CH2Cl2 / 1.5 h / 20 °C 2: 94 percent / Tesser's base / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 100 percent / BOP 2: NaOH View Scheme
Multi-step reaction with 2 steps 1: 100 percent / BOP-peptide 2: NaOH View Scheme

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → 3,5-bis(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethoxy)benzoic acid (1185295-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; diethyl ether / 2 h 2: sodium carbonate / water; acetone / 18 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; water; diethyl ether / 2 h 2: sodium carbonate / water; acetone / 18 h / 20 °C View Scheme

C18H33NO7P2 + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → C29H47N3O10P2*2C2HF3O2

Conditions	Yield
Multi-step reaction with 2 steps 1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere 2: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere View Scheme

C10H9N3O + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → C31H39N5O8

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃;	466 mg

C21H23N5O4 + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → C63H83N9O18

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃;	70 mg

Upstream product

• 184916-28-7 3,5-bis-(2-tert-butyloxycarbonylamino-ethoxy) methyl benzoate 
• 39684-80-5 2-(tert-butoxycarbonylamino)ethyl bromide 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1185295-67-3 3,5-bis(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethoxy)benzoic acid 
• 1228435-28-6 N-(benzyloxy)-3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzamide 
• 352426-84-7 3,5-Bis-{2-[3,5-bis-(2-tert-butoxycarbonylamino-ethoxy)-benzoylamino]-ethoxy}-benzoic acid 
• 187960-76-5 3,5-Bis-{2-[3,5-bis-(2-tert-butoxycarbonylamino-ethoxy)-benzoylamino]-ethoxy}-benzoic acid methyl ester 

Relevant articles and documents

Sizing of amino acid based dendrimers in Langmuir monolayers

The size and monolayer morphology of synthesised amphiphilic amino acid based dendrimers is studied in a Langmuir trough using Brewster Angle microscopy.

DENDRONIZED METALLIC OXIDE NANOPARTICLES, A PROCESS FOR PREPARING THE SAME AND THEIR USES

The present invention relates to dendronized metallic oxide nanoparticles, a process for preparing the same and their uses.

OPTICAL IMAGING PROBES

The present invention relates to methods of visualising cells especially although not exclusively in vivo using a dye, such as a dendrimer-dye molecule or polybranched-dye molecule which is internalised by the cells and thus permits subsequent visualisation by confocal fluorescence endomicroscopy or other optical detectors. There is also provided internally quenched probes for use in visualising cells especially although not exclusively in vivo by confocal fluorescence endomicroscopy and the use of internally quenched probes in combination with confocal fluorescence endomicroscopy, for visualising cells by virtue of internalisation and dequenching of a probe by the cells. In a particular embodiment the cells are activated neutrophils, such as within the lung of a subject.

Efficient synthesis of small-sized phosphonated dendrons: Potential organic coatings of iron oxide nanoparticles

We report herein the synthesis of biocompatible small-sized phosphonated monomers and dendrons used as functional coatings of metal oxide nanoparticles, more specifically superparamagnetic iron oxides (SPIOs) for magnetic resonance imaging (MRI) and therapy through hyperthermia. The molecules were engineered to modulate their size, their hydrophilic and/or biocompatible character (poly(amido)amine versus oligoethyleneglycol), the number of anchoring phosphonate groups (monophosphonate versus phosphonic tweezers) and the number of peripheral functional groups for further grafting of dyes or specific vectors. Such a library of hydrophilic phosphonic acids opens new possibilities for the investigation of dendronized nanohybrids as theranostics.

Highly specific, multi-branched fluorescent reporters for analysis of human neutrophil elastase

Human neutrophil elastase (HNE) is a serine protease implicated in the pathogenesis of acute and chronic inflammatory disease. Here a series of, internally quenched, single fluorophore fluorescent reporters were synthesised that allowed the rapid, highly specific and sensitive analysis of HNE activity over closely related proteases. The Royal Society of Chemistry 2013.

Synthesis of bifunctional hydroxamic acids as novel ligands for the hydrophilic stabilization of iron oxide nanoparticles

A general method for synthesizing bifunctional hydroxamic acids containing carboxylic acid or amino functionalities is reported. Various products from simple alkyl to complex dendrimer-like structures are described. Such molecules have recently been used in ligand-exchange reactions for the hydrophilic stabilization of originally oleic acid protected iron oxide nanoparticles. Georg Thieme Verlag Stuttgart · New York.

Convergent synthesis and diversity of amino acid based dendrimers

The synthesis of amino acid based dendrimers 25 (fifth generation, 32 endgroups), 30 (fourth generation, 81 endgroups), chiral dendrimer 23 (third generation, 8 endgroups) as well as core-modified dendrimers 34 and 38 by the convergent method is described. The amino acid building blocks are derived from hydroxybenzoic acid derivatives and amino alcohol derivatives, and access to a considerable molecular diversity of these novel dendrimers can be achieved, The synthesis can be carried out on a relatively large scale, and this easy access of the dendrimers may lead to many potential applications.

Synthesis of a novel amino acid based dendrimer

An easy accessible dendrimer monomer 3,5-bis(2-tert-butyloxycarbonyl aminoethoxy) benzoic acid methyl ester 1 was designed. The monomer was converted to both the 'surface' and 'braching' monomer in a versatile synthesis of a novel amino acid based dendrimer by the covergent method, using the well established and high-yielding BOP-peptide coupling method.