2-tert-butoxycarbonylamino-2-methylpropionic acid, CAS No. 30992-29-1

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30992-29-1

Catalog No. EBD5908

CAS 30992-29-1

Name 2-tert-butoxycarbonylamino-2-methylpropionic acid

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Basic Information

Synonyms: 2-tert-butoxycarbonylamino-2-methylpropionic acid N-t-butyloxycarbonyl-α-aminoisobutyricacid 2-tert-butoxycarbonylamino-2-methylpropionicacid N-[(1,1-dimethylethoxy)carbonyl]-2-methyl-alanine Alanine,N-[(1,1-dimethylethoxy)carbonyl]-2-methyl- N-(tert-Butoxycarbonyl)-2-methylalanine 2-[(tert-butoxycarbonyl)amino]-2-methylpropanoate Boc-2-aminoisobutyricacid Boc-Aib-OH N-Boc-2-aminoisobutyricacid N-tert-Butoxycarbonyl-2-aminoisobutyricacid BOC-alpha-Methylalanine alpha-(boc-amino)isobutyricacid tert-BOC-alpha-aminoisobutyricacid

Molecular Formula: C9H17NO4

Molecular Weight: 203.24

MDL Number: MFCD00042973

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

2-tert-butoxycarbonylamino-2-methylpropionic acid, also known as N-Boc-2-aminoisobutyric acid, is a protected derivative of the non-proteinogenic amino acid ▒-aminoisobutyric acid (Aib). Its structure features a sterically hindered geminal dimethyl group at the ▒-carbon, which induces a strong preference for helical conformations in peptides. The tert-butoxycarbonyl (Boc) group protects the amine functionality, allowing for selective deprotection under acidic conditions. This compound is primarily utilized as a key building block in medicinal chemistry and peptide synthesis. The Aib residue is frequently incorporated into bioactive peptides to enhance metabolic stability, restrict conformational flexibility, and improve receptor binding affinity. It is a common fragment in the design of peptidomimetics and therapeutic peptides, particularly those targeting GPCRs or ion channels. Additionally, it serves as a versatile synthetic intermediate for constructing more complex small molecule libraries. As a protected amino acid, it is also a standard reagent in organic synthesis, functioning as a chiral or achiral building block for the preparation of diverse nitrogen-n-containing compounds. Its high purity and defined stereochemistry make it suitable for both research-scale synthesis and pharmaceutical development.

Physical Properties

Melting Point: 118-122 °C

Boiling Point: 327.625 °C at 760 mmHg

Flash Point: 151.943 °C

Density: 1.104 g/cm3

Storage: 0-6°C

Analytical Data

Appearance: white crystalline powder