Description

tert-Butyl (2-(hydroxymethyl)phenyl)carbamate (CAS No. 164226-32-8) is a high-purity carbamate derivative with the molecular formula C₁₂H₁₇NO₃. This compound features a tert-butyl carbamate group attached to a 2-(hydroxymethyl)phenyl moiety, making it a versatile intermediate in organic synthesis and pharmaceutical research. Its IUPAC name is tert-butyl N-[2-(hydroxymethyl)phenyl]carbamate, and it is also known by synonyms such as (2-Hydroxymethyl-phenyl)-carbamic acid tert-Butyl ester.

This product is supplied as a white to off-white crystalline powder with a purity of ≥95% (HPLC). It is soluble in common organic solvents like dichloromethane, dimethyl sulfoxide (DMSO), and methanol, but exhibits limited solubility in water. Proper storage conditions include keeping the compound in a cool, dry place (2-8°C) under inert atmosphere to ensure long-term stability.

Researchers and scientists utilize this compound as a key building block in the synthesis of complex molecules, particularly in medicinal chemistry and drug discovery. Its reactive hydroxymethyl and carbamate groups allow for further functionalization, enabling the development of novel pharmacophores and bioactive compounds.

Properties

• CAS Number: 164226-32-8
• Complexity: 235
• IUPAC Name: tert-butyl N-[2-(hydroxymethyl)phenyl]carbamate
• InChI: InChI=1S/C12H17NO3/c1-12(2,3)16-11(15)13-10-7-5-4-6-9(10)8-14/h4-7,14H,8H2,1-3H3,(H,13,15)
• InChI Key: QQAMZZFIHGASEX-UHFFFAOYSA-N
• Exact Mass: 223.12084340
• Molecular Formula: C12H17NO3
• Molecular Weight: 223.27
• SMILES: CC(C)(C)OC(=O)NC1=CC=CC=C1CO
• Topological: 58.6
• Monoisotopic Mass: 223.12084340
• Synonyms: 164226-32-8, tert-Butyl (2-(hydroxymethyl)phenyl)carbamate, tert-butyl N-[2-(hydroxymethyl)phenyl]carbamate, (2-Hydroxymethyl-phenyl)-carbamic acid tert-Butyl ester, TERT-BUTYL 2-(HYDROXYMETHYL)PHENYLCARBAMATE, Carbamic acid, N-[2-(hydroxymethyl)phenyl]-, 1,1-dimethylethyl ester, tert-Butyl [2-(hydroxymethyl)phenyl]carbamate, N-Boc-2-aminobenzyl alcohol, MFCD04974267, 2-(Boc-amino)benzyl alcohol, N-Boc-o-amino benzyl alcohol, SCHEMBL646870, SCHEMBL6595061, DTXSID90571072, QQAMZZFIHGASEX-UHFFFAOYSA-N, N-Boc-2-aminobenzyl alcohol, 97%, AKOS010758800, SB34115, 2-(t-butoxy)carbonylaminobenzyl alcohol, BS-21645, tert-butyl (2-hydroxymethylphenyl)carbamate, tert-Butyl(2-(hydroxymethyl)phenyl)carbamate, EN300-320848, N-(Tert-butoxycarbonyl)-2-(hydroxymethyl)aniline, (2-Hydroxymethylphenyl)-carbamic acid tert-butyl ester

Application

tert-Butyl (2-(hydroxymethyl)phenyl)carbamate serves as a valuable intermediate in the synthesis of pharmaceutical agents, particularly in the development of protease inhibitors and other therapeutic compounds. Its hydroxymethyl group can be further modified to introduce additional functional groups, enhancing its utility in medicinal chemistry. Researchers also employ this compound in the preparation of chiral auxiliaries and protecting groups for amine functionalities. Its stability and reactivity make it suitable for use in multi-step synthetic routes, including peptide coupling and heterocycle formation.

Safety and Hazards

GHS Hazard Statements

• H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
• H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Precautionary Statements

• P261, P264, P270, P272, P280, P301+P316, P302+P352, P321, P330, P333+P317, P362+P364, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (100%)
• Skin Sens. 1 (100%)

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