tert-Butyl (4-hydroxy-2-methylbutan-2-yl)carbamate is a Boc-protected amino alcohol that provides steric control and adjustable polarity. The structure supports development of flexible linkers and modified residue analogs. Researchers apply it to explore hydrogen-bond behavior and conformational variability. Its protected amine enhances synthetic control.
CAT No: R2175
CAS No:167216-22-0
Synonyms/Alias:3-(Boc-amino)-3-methyl-1-butanol;167216-22-0;Carbamic acid, (3-hydroxy-1,1-dimethylpropyl)-, 1,1-dimethylethyl ester (9CI);MFCD19982636;TERT-BUTYL N-(4-HYDROXY-2-METHYLBUTAN-2-YL)CARBAMATE;tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate;DTXSID50573097;(3-Hydroxy-1,1-dimethylpropyl)-carbamic Acid 1,1-Dimethylethyl Ester; (3-Hydroxy-1,1-dimethylpropyl)carbamic Acid tert-Butyl Ester;;SCHEMBL1359163;DTXCID40523869;QHSUFODBDZQCHO-UHFFFAOYSA-N;SGA21622;AC2581;AKOS027399905;SB77938;3-(N-BOC-amino)-3-methyl-butan-1-ol;CS-12233;SY040943;DB-120322;CS-0162844;EN300-200825;3-(tert-butoxycarbonylamino)-3-methyl-1-butanol;3-hydroxy-1,1-dimethylpropylcarbamic acid tert-butyl ester;3-hydroxy-1,1dimethylpropylcarbamic acid tert-butyl ester;3hydroxy-1,1-dimethylpropylcarbamic acid tert-butyl ester;(3-Hydroxy-1,1-dimethyl-propyl)-carbamic acid tert-butyl ester;(3-Hydroxy-1,I-dimethyl-propyl)-carbamic acid tert-butyl ester;Carbamic acid,(3-hydroxy-1,1-dimethylpropyl)-,1,1-dimethylethyl ester(9ci);
tert-Butyl (4-hydroxy-2-methylbutan-2-yl)carbamate is a synthetic organic compound belonging to the carbamate family, characterized by the presence of both a tert-butyl carbamate group and a hydroxy-substituted alkyl chain. It serves as a valuable intermediate in organic synthesis, particularly for the protection and modification of amine functionalities. Its molecular architecture allows for selective reactivity, making it highly relevant in the development of complex molecules for biochemical research and industrial applications. Researchers and technical professionals utilize this compound for its stability under a range of reaction conditions and its compatibility with various synthetic methodologies.
Synthetic intermediate: As a protected amine derivative, tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate is frequently employed as a versatile building block in multistep organic synthesis. The carbamate moiety acts as a temporary protecting group for amines, enabling selective transformations on other functional groups without undesired side reactions. This property is particularly advantageous in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals, where stepwise construction of complex molecular architectures is required.
Protecting group strategy: In peptide chemistry and broader organic synthesis, the tert-butyl carbamate group (commonly referred to as Boc) is widely used for the protection of amine groups. The compound's structure allows for the introduction of a protected amino alcohol motif, which can be further manipulated and then deprotected under mild acidic conditions. This facilitates the sequential assembly of target molecules, providing chemists with precise control over reaction pathways and functional group compatibility.
Chiral auxiliary in asymmetric synthesis: The presence of both a hydroxy group and a sterically demanding tert-butyl carbamate moiety makes the compound suitable for use as a chiral auxiliary or precursor in asymmetric transformations. By introducing defined stereochemistry into reaction intermediates, it assists in the synthesis of enantiomerically enriched compounds. This capability is especially valuable in the production of optically active intermediates for research into biologically active molecules and advanced materials.
Analytical reference material: Due to its well-defined chemical structure, tert-butyl (4-hydroxy-2-methylbutan-2-yl)carbamate serves as a useful reference standard in analytical method development. It can be utilized for calibration and validation of chromatographic techniques such as HPLC or GC, supporting the accurate quantification and identification of related compounds in complex mixtures. This role underpins quality control processes in both research and industrial laboratory settings.
Functional group transformation studies: The compound is also employed in mechanistic studies exploring the reactivity of carbamates and hydroxyalkyl groups. Its dual functionality provides a model substrate for investigating selective deprotection, oxidation, or substitution reactions. Insights gained from such studies inform the design of novel synthetic methodologies and contribute to the advancement of organic and medicinal chemistry research.
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