(Boc-aminooxy)acetic acid

Base Information

• Chemical Name: (Boc-aminooxy)acetic acid
• CAS No.: 42989-85-5
• Molecular Formula: C7H13NO5
• Molecular Weight: 191.184
• Hs Code.: 2928 00 90
• European Community (EC) Number: 628-980-0
• DSSTox Substance ID: DTXSID10373171
• Nikkaji Number: J1.289.261F
• Wikidata: Q72448316
• Mol file: 42989-85-5.mol

Synonyms:(Boc-aminooxy)acetic acid;42989-85-5;Boc-Aoa-OH;2-(((tert-Butoxycarbonyl)amino)oxy)acetic acid;Boc-AOAc-OH;2-[(2-methylpropan-2-yl)oxycarbonylamino]oxyacetic Acid;N-Boc-(carboxymethoxy)amine;2-({[(tert-butoxy)carbonyl]amino}oxy)acetic acid;Boc-3-(aminooxy)acetic acid;MFCD01632027;Acetic acid, [[[(1,1-dimethylethoxy)carbonyl]amino]oxy]-;2-(tert-butoxycarbonylaminooxy)acetic acid;Boc-aminooxyacetic acid;2-(Boc-aminooxy)-acetic acid;N-Boc-(carboxymethoxy)-amine;Boc-(nhoac)-oh;(Boc)aminooxyacetic acid;[(tert-Butoxycarbonyl)aminooxy]acetic Acid;(Boc-aminoxy)acetic acid;2-(t-Butyloxycarbonyl-aminooxy)-acetic acid;t-Boc-aminooxyacetic Acid;SCHEMBL307685;DTXSID10373171;QBXODCKYUZNZCY-UHFFFAOYSA-N;tert-Butoxycarbonylaminooxyacetic acid;Boc-AOA Tert-Boc-aminooxyacetic acid;AKOS009156496;GS-6570;tert-butyloxycarbonylaminoxy acetic acid;N-tert-butoxycarbonyl aminooxyacetic acid;SY019091;(Boc-aminooxy)acetic acid, >=98.0% (T);2-(tert-Butyloxycarbonylaminooxy)acetic acid;2-[(tert-Butoxycarbonylamino)oxy]acetic acid;B3338;CS-0030574;FT-0662558;EN300-227480;H10114;[(1,1-Dimethylethoxy)carbonyl]aminooxyacetic acid;A850863;[(1,1-dimethylethoxy)carbonyl]aminooxy acetic acid;J-501795;J-650267

Chemical Property of (Boc-aminooxy)acetic acid

Chemical Property:

• Melting Point: ~115 °C (dec.)
• Refractive Index: 1.46
• PKA: 2.97±0.10(Predicted)
• PSA: 84.86000
• Density: 1.214 g/cm³
• LogP: 0.91820
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 191.07937252
• Heavy Atom Count: 13
• Complexity: 196

Purity/Quality:

98%,99%, ^*data from raw suppliers

t-Boc-aminooxyacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NOCC(=O)O
• Uses: (Boc-aminooxy)acetic acid was employed to introduce a hydroxylamine moiety into peptides; reaction with an aldehyde to an oxime. It was used in the preparation of Boc-aminooxy tetra(ethylene glycol). (Boc-aminooxy)acetic acid was used in the preparation of Boc-aminooxy tetra(ethylene glycol). A Boc-protected bifunctional linking reagent

Technology Process of (Boc-aminooxy)acetic acid

There total 7 articles about (Boc-aminooxy)acetic acid 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: 83.0%

di-tert-butyl dicarbonate (24424-99-5) + aminooxyacetic acid (645-88-5) → [({[(2-methyl-2-propanyl)oxy]carbonyl}amino)oxy]acetic acid (42989-85-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1.5h;

Reference yield: 81.0%

2-(aminooxy)acetic acid hemihydrochloride + di-tert-butyl dicarbonate (24424-99-5) → [({[(2-methyl-2-propanyl)oxy]carbonyl}amino)oxy]acetic acid (42989-85-5)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 24h;

DOI:10.1002/anie.201605992

Reference yield: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + (aminooxy)acetic acid hemihydrochloride (2921-14-4,7776-18-3,20295-82-3) → [({[(2-methyl-2-propanyl)oxy]carbonyl}amino)oxy]acetic acid (42989-85-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 2h;

DOI:10.1016/j.tetlet.2003.09.128

upstream raw materials:

di-tert-butyl dicarbonate

(aminooxy)acetic acid hemihydrochloride

tert-Butyl N-hydroxycarbamate

bromoacetic acid

Downstream raw materials:

C₁₄H₂₀N₂O₅

C₅₇H₉₀N₁₆O₂₁S₃

C₂₁H₃₃N₃O₈

N-succinimidyl [[(t-butyloxycarbonyl)amino]oxy]acetate

Refernces

• 1、 Deroo, Stéphanie,Defrancq, Eric,Moucheron, Cécile,Kirsch-De Mesmaeker, Andrée,Dumy, Pascal. "Synthesis of an oxyamino-containing phenanthroline derivative for the efficient preparation of phenanthroline oligonucleotide oxime conjugates". . p. 8379 - 8382. Retrieved 2003.
• 2、 Kurth, Mark,Pelegrin, Andre,Rose, Keith,Offord, Robin E.,Pochon, Sibylle,et al.. "Site-Specific Conjugation of a Radioiodinated Phenethylamine Derivative to a Monoclonal Antibody Results in Increased Radioactivity Localization in Tumor". . p. 1255 - 1261. Retrieved 1993.
• 3、 Lamping, Matthias,Grell, Yvonne,Geyer, Armin. "Synthesis and conformational analysis of an expanded cyclic ketoxime-hexapeptide". . p. 228 - 235. Retrieved 2016/04/19.