(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:

97% ^*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
• General Description: (BOC-AMINOOXY)ACETIC ACID is a chemical compound used in chemoselective ligation strategies, particularly for oxime bond formation in peptide and protein conjugation. It serves as a protected aminooxyacetic acid derivative, where the tert-butoxycarbonyl (BOC) group shields the aminooxy functionality, enabling controlled reactions with aldehyde-containing molecules. This reagent facilitates site-specific modifications, such as in the synthesis of template-assembled synthetic proteins (TASP) or antibody conjugates, where its stable oxime linkage improves in vivo stability and targeting efficiency. The BOC group can be deprotected to expose the reactive aminooxy group, allowing conjugation under mild aqueous conditions, making it valuable in bioconjugation and drug development applications. **Returned paragraph (conclusion):** (BOC-AMINOOXY)ACETIC ACID is a versatile reagent for chemoselective oxime ligation, enabling stable conjugations in peptide synthesis, antibody labeling, and bioconjugation. Its BOC-protected aminooxy group ensures controlled reactivity, facilitating site-specific modifications with aldehyde-functionalized molecules, which is critical for applications in targeted drug delivery and protein engineering.

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

tert-butyl 2-{[4-(biotinylaminomethyl)benzyl]amino}-2-oxoethoxycarbamate

[(2S,5S,8S,11S)-8-[4-(2-Aminooxy-acetylamino)-butyl]-5-benzyl-11-(3-guanidino-propyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaaza-cyclopentadec-2-yl]-acetic acid

2-(N-tert-butoxycarbonyl-aminooxy)-N-(3-benzoyl-phenyl)-acetamide