164226-32-8

Basic information

• Product Name: BOC-2-AMINOBENZYLALCOHOL
• Synonyms: BOC-2-AMINOBENZYLALCOHOL;(2-HydroxyMethyl-phenyl)-carbaMic acid tert-butyl ester;tert-Butyl (2-(hydroxyMethyl)phenyl)carbaMate;2-(Boc-aMino)benzyl alcohol;Tert-butyl N-[2-(hydroxyMethyl)phenyl]carbaMate;N-Boc-2-aminobenzyl alcohol
• CAS NO: 164226-32-8
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.27
• Mol File: 164226-32-8.mol

Chemical Properties

• Flash Point: >230℃
• Appearance: /
• Density: 1.094 g/mL at 25 °C
• Refractive Index: n20/D1.527
• CAS DataBase Reference: BOC-2-AMINOBENZYLALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-2-AMINOBENZYLALCOHOL(164226-32-8)
• EPA Substance Registry System: BOC-2-AMINOBENZYLALCOHOL(164226-32-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• RIDADR: UN 2810 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 164226-32-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-2-Aminobenzylalcohol is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drug molecules. Its presence in the synthesis process is vital for creating a range of medications that address different health conditions.
Used in Organic Synthesis:
In the field of organic synthesis, BOC-2-Aminobenzylalcohol is employed as a fundamental building block, facilitating the creation of complex organic compounds. Its versatility in forming different chemical structures makes it an essential component in the synthesis of a wide array of organic molecules.
Used in Biologically Active Compounds:
BOC-2-Aminobenzylalcohol is used as a precursor in the synthesis of biologically active compounds, which are crucial for research in biochemistry and molecular biology. Its role in the formation of these compounds aids in the discovery of new therapeutic agents and the understanding of biological processes.

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 74965-31-4 N-(tert-butoxycarbonyl)-o-toluidine 
• 118-92-3 anthranilic acid 
• 552-89-6 2-nitro-benzaldehyde 
• 612-25-9 2-Nitrobenzyl alcohol 
• 24608-52-4 tert-butyl chloroformate 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 166329-43-7 N-tert-butoxycarbonyl-2-bromomethylaniline 
• 183145-75-7 [2-(Tetrahydro-pyran-2-yloxymethyl)-phenyl]-carbamic acid tert-butyl ester 
• 74965-38-1 tert-butyl (2-formylphenyl)carbamate 
• 263154-36-5 C₂₉H₂₉N₇O₇S₃ 
• 69395-24-0 (E)-2-amino-2'-nitrostilbene 
• 217300-86-2 N-<(2'-nitrostilben-2-yl)phenyl>-tert-butylcarbamate 
• 217300-92-0 N-<(2'-nitrostilben-2-yl)phenyl>-p-methoxyphenylcarbamate 
• 217088-74-9 N-(2'-(2,2,2-trichloroethylcarbamate)bibenzyl-2-yl)-p-methoxyphenylcarbamate 
• 217088-75-0 N-(2'-(p-nitrophenylcarbamate)bibenzyl-2-yl)-p-methoxyphenylcarbamate 
• 183145-78-0 [tert-Butoxycarbonyl-(2-formyl-phenyl)-amino]-acetic acid methyl ester 
• 183145-77-9 [tert-Butoxycarbonyl-(2-hydroxymethyl-phenyl)-amino]-acetic acid methyl ester 
• 183145-79-1 (E)-3-[2-(tert-Butoxycarbonyl-methoxycarbonylmethyl-amino)-phenyl]-acrylic acid 
• 183145-81-5 (E)-3-[2-(tert-Butoxycarbonyl-methoxycarbonylmethyl-amino)-phenyl]-acrylic acid methyl ester 
• 183145-76-8 {tert-Butoxycarbonyl-[2-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-amino}-acetic acid methyl ester 

Relevant articles and documents

A new approach to monoprotected 1,4-benzodiazepines via a one-pot N-deprotection/reductive cyclization procedure

A novel approach to 2,3,4,5-tetrahydro-1H-1,4-benzodiazepines starting from N-Boc-protected 2-aminobenzyl alcohols and N-nosyl-protected 2-aminoacetaldehyde dimethyl acetal is presented here. After connection of both building blocks under Mitsunobu condit

Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines

Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.

Designing and Accurately Developing a [6 + 2] Dipolar Cycloaddition for the Synthesis of Benzodiazocines

1,6-Dipolar cycloadditions represent a valuable strategy for the rapid construction of medium-sized rings. Herein, we describe the concept for the design of 1,6-dipoles that bypasses the regioselectivity. Through the introduction of an amino group into Morita-Baylis-Hillman (MBH) carbonates, unprecedented [6 + 2] dipolar cycloadditions were accurately developed with Cs2CO3, efficiently delivering a series of benzodiazocines in mild conditions. Computational studies bring a deeper understanding of this reaction.

DABCO catalyzed [4+2] annulations of Morita-Baylis-Hillman carbonates with isocyanates

A highly concise method for 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed [4+2] annulations ofo-amino-acylation of aryl MBH carbonates with isocyanates has been developed. For the first time, MBH carbonates served as 1,4-dipoles, providing functionalized 3,4-dihydroquinazolinones in mild conditions with good to excellent yields. The density functional theory calculations of the mechanism supports our hypothesis.

Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[ b]indolines

A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.

A Convenient Formal [4+2] Heterocylization Route to Bis(triflyl)tetrahydroquinolines

We report the sustainable and efficient synthesis of a new type of quinoline derivatives bearing one or two SO2CF3 groups. The protocol is metal-, catalyst- and irradiation-free, involves the use of readily available and stable precursors, and avoids the formation of side products. Also, the mild conditions of the process allow the tolerance of a wide range of functional groups.

Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst

An efficient approach for the Chemoselective N-tert-butoxycarbonylation of a variety of amines using diphenylglycoluril as organocatalyst has been described. For the first time, a plausible mechanism for the N-tert-butoxycarbonylation has been proposed using density functional theory (DFT) calculations supported by NMR studies. The reusability of the organocatalyst and observation of the desired N-Boc protected amines being formed without the formation of side products like urea, oxazolidinone, isocyanate, and N, N-di-Boc derivatives makes the present protocol desirable.

Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alcohol-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

SUBSTITUTED 1-HYDROXY-PYRIDIN-2(1H)-ONES, AND METHODS OF MAKING AND USING SAME

The present invention includes novel substituted 1-hydroxy-pyridin-2(1H)-ones, which can be used to treat or prevent hepatitis B virus (HBV) infections in a patient. In certain embodiments, the compounds and compositions of the invention inhibit HBV RNAse H activity.

Direct Access to 9-Chloro-1 H-benzo[ b]furo[3,4- e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade

An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.