40851-66-9

Basic information

• Product Name: 2-(Boc-aminomethyl)phenylacetic acid
• Synonyms: BOC-2-AMINOMETHYL-PHENYLACETIC ACID;[2-(TERT-BUTOXYCARBONYLAMINO-METHYL)-PHENYL]-ACETIC ACID;BOC-2-AMINOMETHYL-PHENYLACETIC ACID 98%;2-(Boc-aminomethyl)phenylacetic acid;2-(N-tert-Butoxycarbonylaminomethyl)phenylacetic acid;2-[(Boc-aMino)Methyl]benzeneacetic acid;2-(2-(((tert-Butoxycarbonyl)amino)methyl)phenyl)acetic acid
• CAS NO: 40851-66-9
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.3
• EINECS: 1806241-263-5
• Product Categories: Beta-Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 40851-66-9.mol

Chemical Properties

• Boiling Point: 435.2 °C at 760 mmHg
• Flash Point: 217 °C
• Appearance: /
• Density: 1.163 g/cm³
• Vapor Pressure: 2.4E-08mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.26±0.10(Predicted)
• BRN: 1080474
• CAS DataBase Reference: 2-(Boc-aminomethyl)phenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Boc-aminomethyl)phenylacetic acid(40851-66-9)
• EPA Substance Registry System: 2-(Boc-aminomethyl)phenylacetic acid(40851-66-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 40851-66-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-(Boc-aminomethyl)phenylacetic acid is used as a building block for the synthesis of various pharmaceutical compounds. Its Boc-protected amino group allows for selective reactions at the aminomethyl moiety, which can be deprotected under acidic conditions to reveal the free amine, facilitating further functionalization and the creation of diverse drug candidates.
Used in Molecular Modeling:
2-(Boc-aminomethyl)phenylacetic acid is used as a component in the study of molecular modeling on oligomers built from 2-aminomethylphenylacetic acid. 2-(Boc-aminomethyl)phenylacetic acid's structure provides insights into the conformation and interactions of oligomers, which can be crucial for understanding their biological activities and potential applications in drug design.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-(Boc-aminomethyl)phenylacetic acid serves as an intermediate for the production of various organic compounds, including those with potential applications in materials science, pharmaceuticals, and agrochemicals. Its versatility in reactions and the ease of protecting and deprotecting the amino group make it a valuable synthetic building block.

InChI:InChI=1/C14H19NO4/c1-14(2,3)19-13(18)15-9-11-7-5-4-6-10(11)8-12(16)17/h4-7H,8-9H2,1-3H3,(H,15,18)(H,16,17)

Upstream product

• 20921-96-4 methyl 2-(2-cyanophenyl)acetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 40851-65-8 2-Aminomethylphenylacetic acid 
• 749832-15-3 methyl 2-(2-(aminomethyl)phenyl)acetate 
• 57486-69-8 methyl 2-(2-bromophenyl)acetate 
• 18698-97-0 ortho-bromophenylacetic acid 
• 147410-31-9 methyl 2-(N-(tert-butoxycarbonyl)aminomethyl)phenylacetate 
• 124-38-9 carbon dioxide 
• 138350-83-1 N-(tert-butoxycarbonyl)-2-methylbenzylamine 

Downstream Products

• 24331-94-0 1,4-dihydro-3(2H)-isoquinolinone 
• 141044-63-5 o-(aminomethyl)phenylacetyl-Cys-D-Val 
• 40851-65-8 2-Aminomethylphenylacetic acid 
• 67638-10-2 2-[2-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]acetic acid 
• 1351949-15-9 C₁₈H₂₇N₅O₄ 
• 1351949-99-9 C₃₈H₄₉N₇O₆ 
• 1351949-95-5 C₂₆H₃₈N₆O₆ 
• 1351949-78-4 C₃₅H₄₂N₄O₅ 
• 1351949-66-0 C₂₃H₃₁N₃O₅ 
• 808753-00-6 2-(2-aminomethyl-phenyl)-N-methyl-N-(1-phenyl-2-pyrrolidin-1-yl-ethyl)-acetamide 

Relevant articles and documents

The comparison of protecting methods to the amino group in 2-Aminomethylphenylacetic acid

2-Aminomethylphenylacetic acid is an important intermediate of ceforanide, and this article compared two different protecting agents for protecting the amino group in 2-aminomethylphenylacetic acid by BOC (Di-tert butyl dicarbonate) or acetacetic ester, a

Arylacetamide κ opioid receptor agonists with reduced cytochrome P450 2D6 inhibitory activity

Some κ opioid receptor agonists of the arylacetamide class, for example, ICI 199441 (1), were found to strongly inhibit the activity of cytochrome P450 2D6 (CYP2D6) (1: CYP2D6 IC50 = 26 nM). Certain analogs bearing a substituted sulfonylamino group, for example, 13, were discovered to have significantly reduced CYP2D6 inhibitory activity (13: CYP2D6 IC50 > 10 μM) while displaying high affinity toward the cloned human κ opioid receptor, good κ/δ and κ/μ selectivity, and potent in vitro and in vivo agonist activity.

Sulfonylamino phenylacetamide derivatives and methods of their use

Sulfonylamino phenylacetamide derivatives of the general formula are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed. In certain embodiments, the compounds of the invention that, preferably: (1) bind with high affinity to κ opioid receptors; (2) display good opioid receptor selectivity of κ versus μ and κ versus δ; and (3) do not substantially inhibit cytochrome P450 enzymatic activity, in particular CYP2D6, CYP2C9 and CYP3A4.

PREPARATION OF TETRAHYDROISOQUINOLINES FROM N-(TERT-BUTOXYCARBONYL)-2-METHYLBENZYLAMINES

Dilithiation of N-(tert-butoxycarbonyl)-2-methylbenzylamine (1a) followed by treatment with N,N-dimethylformamide affords 2-(tert-butoxycarbonyl)-3-hydroxy-tetrahydroisoquinoline (3a).Dehydration and reduction of 3a afford BOC-tetrahydroisoquinoline (5a).The methodology is also applicable to synthesis of chloro and fluoro substituted tetrahydroisoquinolines (5b,c), 3 and 4-substituted derivatives (8,10), and the hexahydro-2H-benzoquinolizine ring system (13).