Phenacyl 4-(bromomethyl)phenylacetate

Base Information

• Chemical Name: Phenacyl 4-(bromomethyl)phenylacetate
• CAS No.: 66270-97-1
• Molecular Formula: C17H15BrO3
• Molecular Weight: 347.208
• Hs Code.: 29163990
• Mol file: 66270-97-1.mol

Synonyms:4-(Bromomethyl)phenylacetic acid phenacyl ester;2-Oxo-2-phenylethyl [4-(bromomethyl)phenyl]acetate;

Chemical Property of Phenacyl 4-(bromomethyl)phenylacetate

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 1.44E-08mmHg at 25°C
• Melting Point: 84-87 °C(lit.)
• Refractive Index: 1.597
• Boiling Point: 457.8 °C at 760 mmHg
• Flash Point: 230.7 °C
• PSA: 43.37000
• Density: 1.401 g/cm³
• LogP: 3.55010
• Storage Temp.: Store at RT.
• Solubility.: soluble in Toluene

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Oxo-2-phenylethyl2-(4-(bromomethyl)phenyl)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-28-36/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Phenacyl 4-(bromomethyl)phenylacetate is a building block for preparing amino acid PAM linker. The PAM ester is orthogonally stable to cleavage conditions of most protective groups used in FMOC-SPPS.

Technology Process of Phenacyl 4-(bromomethyl)phenylacetate

There total 4 articles about Phenacyl 4-(bromomethyl)phenylacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-bromophenylacetic acid (13737-36-5) + α-bromoacetophenone (70-11-1) → 4-(bromomethyl)-phenylacetic acid phenacyl ester (66270-97-1)

Guidance literature:

With triethylamine;

DOI:10.1021/jo00408a022

Reference yield:

4-tolylacetic acid (622-47-9) → 4-(bromomethyl)-phenylacetic acid phenacyl ester (66270-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / Br₂ / CCl₄ / 24 h / Ambient temperature; Irradiation

2: 1.) trifluoroacetic anhydride / 1.) benzene, room t., 1 h; 2.) benzene, room t., 3 h

With bromine; trifluoroacetic anhydride; In tetrachloromethane;

DOI:10.1246/bcsj.61.2467

Reference yield:

4-bromophenylacetic acid (13737-36-5) + 1-phenyl-2-hydroxyethanone (582-24-1) → 4-(bromomethyl)-phenylacetic acid phenacyl ester (66270-97-1)

Guidance literature:

With trifluoroacetic anhydride; Yield given. Multistep reaction; 1.) benzene, room t., 1 h; 2.) benzene, room t., 3 h;

DOI:10.1246/bcsj.61.2467

upstream raw materials:

4-bromophenylacetic acid

α-bromoacetophenone

1-phenyl-2-hydroxyethanone

4-tolylacetic acid

Downstream raw materials:

[4-(3-Hydroxy-4-methyl-5-oxo-2,5-dihydro-furan-2-ylmethyl)-phenyl]-acetic acid 2-oxo-2-phenyl-ethyl ester

hexane

(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 4-carboxymethyl-benzyl ester

4-(tert-butoxycarbonylaminoacetoxymethyl) phenylacetic acid

Refernces

• 1、 Takahashi, Sho,Hibino, Takeshi,Sawada, Seiji. "Synthesis of α-Helices Having a Positively Charged Random Coil-Block on Either N- or C-Terminal". . p. 2467 - 2472. Retrieved 2007/10/02.