Tert-butyl 3-bromophenethylcarbamate

Base Information

• Chemical Name: Tert-butyl 3-bromophenethylcarbamate
• CAS No.: 153732-25-3
• Molecular Formula: C13H18BrNO2
• Molecular Weight: 300.195
• Hs Code.: 2924297099
• DSSTox Substance ID: DTXSID20592735
• Wikidata: Q82486999
• Mol file: 153732-25-3.mol

Synonyms:TERT-BUTYL 3-BROMOPHENETHYLCARBAMATE;153732-25-3;tert-butyl N-[2-(3-bromophenyl)ethyl]carbamate;tert-Butyl (3-bromophenethyl)carbamate;MFCD11042237;tert-butyl [2-(3-bromophenyl)ethyl]carbamate;SCHEMBL904075;AMY4904;DTXSID20592735;TVNPKEKBYKTLNN-UHFFFAOYSA-N;AKOS015958936;AB62837;AS-62794;SY123382;N-tert-butoxycarbonyl-3-bromophenethylamine;DB-321590;CS-0035910;W11305;EN300-4353971;A809461;1,1-dimethylethyl [2-(3-bromophenyl)ethyl]carbamate;Z1505692733

Chemical Property of Tert-butyl 3-bromophenethylcarbamate

Chemical Property:

• PSA: 41.82000
• LogP: 3.72070
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 299.05209
• Heavy Atom Count: 17
• Complexity: 250

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl3-bromophenethylcarbamate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCC1=CC(=CC=C1)Br

Technology Process of Tert-butyl 3-bromophenethylcarbamate

There total 7 articles about Tert-butyl 3-bromophenethylcarbamate 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-(3-bromophenyl)ethanamine (58971-11-2) → [2-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (153732-25-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

Reference yield: 24.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-(3-bromophenyl)propanoic acid (42287-90-1) → [2-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (153732-25-3)

Guidance literature:

di-tert-butyl dicarbonate; 3-(3-bromophenyl)propanoic acid; With sodium azide; tetrabutylammomium bromide; zinc dibromide; In tetrahydrofuran; at 40 ℃; for 48h;

With sodium nitrite; In tetrahydrofuran; water; ethyl acetate; at 20 ℃; for 0.333333h;

DOI:10.1039/c4ob01926a

Reference yield:

(3-bromophenyl)acetonitrile (31938-07-5) → [2-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (153732-25-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium aluminium tetrahydride; sulfuric acid / tetrahydrofuran / 2 h / -5 - 20 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 2 h / 0 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; sulfuric acid; triethylamine; In tetrahydrofuran;

DOI:10.1055/s-0037-1610285

upstream raw materials:

di-tert-butyl dicarbonate

2-(3-bromophenyl)ethanamine

3-(3-bromophenyl)propanoic acid

m-bromobenzoic aldehyde

Downstream raw materials:

2-amino-4'-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenone

trans-methyl 3-(3'-{2''-[3'''-(2''''-tert-butoxycarbonylaminoethyl)phenyl]vinyl}phenyl)-propionate

(E)-1-(3-(2-aminoethyl)phenyl)-2-(O-methyl hydrocinnam-3’-yl)-ethene

methyl trans-3-{3-[2-[3-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]phenyl]vinyl]phenyl}propionate

Refernces

• 1、 Barrus, Daniel,Decker, Ann M.,Finlay, David B.,Gamage, Thomas F.,Glass, Michelle,Kenakin, Terry P.,Langston, Tiffany L.,Li, Jun-Xu,Nguyen, Thuy,Zhang, Yanan. "Development of 3-(4-Chlorophenyl)-1-(phenethyl)urea Analogues as Allosteric Modulators of the Cannabinoid Type-1 Receptor: RTICBM-189 is Brain Penetrant and Attenuates Reinstatement of Cocaine-Seeking Behavior". . . Retrieved 2022/01/03.
• 2、 Greve, Eric,Porter, Jacob D.,Dockendorff, Chris. "DFT-Assisted Design and Evaluation of Bifunctional Amine/Pyridine-Oxazoline Metal Catalysts for Additions of Ketones to Unactivated Alkenes and Alkynes". . p. 450 - 462. Retrieved 2019/01/10.