Tert-butyl 4-cyano-3-fluorobenzylcarbamate

Base Information

• Chemical Name: Tert-butyl 4-cyano-3-fluorobenzylcarbamate
• CAS No.: 229623-55-6
• Molecular Formula: C13H15 F N2 O2
• Molecular Weight: 250.273
• DSSTox Substance ID: DTXSID20448142
• ChEMBL ID: CHEMBL4927308
• Mol file: 229623-55-6.mol

Synonyms:229623-55-6;TERT-BUTYL 4-CYANO-3-FLUOROBENZYLCARBAMATE;tert-butyl N-[(4-cyano-3-fluorophenyl)methyl]carbamate;Carbamic acid,[(4-cyano-3-fluorophenyl)methyl]-, 1,1-dimethylethyl ester (9CI);SCHEMBL6928939;CHEMBL4927308;Tert-butyl N-[(4-cyano-3-fluoro-phenyl)methyl]carbamate;DTXSID20448142;N-[(4-cyano-3-fluorophenyl)methyl]carbamic acid tert-butyl ester;MFCD09037868;AKOS027327523;EN300-246971;A816447;Z1505698808;Carbamic acid,[(4-cyano-3-fluorophenyl)methyl]-,1,1-dimethylethyl ester(9ci)

Chemical Property of Tert-butyl 4-cyano-3-fluorobenzylcarbamate

Chemical Property:

• PSA: 62.12000
• LogP: 3.11298
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 250.11175589
• Heavy Atom Count: 18
• Complexity: 343

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl4-cyano-3-fluorobenzylcarbamate 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)NCC1=CC(=C(C=C1)C#N)F

Technology Process of Tert-butyl 4-cyano-3-fluorobenzylcarbamate

There total 5 articles about Tert-butyl 4-cyano-3-fluorobenzylcarbamate 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: 73.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-(aminomethyl)-2-fluorobenzonitrile (368426-73-7) → 4-(tert-butoxycarbonylaminomethyl)-2-fluorobenzonitrile (229623-55-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 16h; Inert atmosphere;

Reference yield:

2-fluoro-4-methylbenzonitrile (85070-67-3) → 4-(tert-butoxycarbonylaminomethyl)-2-fluorobenzonitrile (229623-55-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 54 percent / NBS; AIBN / CCl₄ / 4.5 h / Heating

2: 91 percent / Cs₂CO₃ / dimethylformamide / 0.5 h / 20 °C

3: NH₂NH₂ / butan-1-ol / 0.08 h / Heating

4: CH₂Cl₂ / 1 h / 20 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); caesium carbonate; hydrazine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1016/S0960-894X(02)00585-1

Reference yield:

4-cyano-3-fluorobenzylbromide (222978-03-2) → 4-(tert-butoxycarbonylaminomethyl)-2-fluorobenzonitrile (229623-55-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / Cs₂CO₃ / dimethylformamide / 0.5 h / 20 °C

2: NH₂NH₂ / butan-1-ol / 0.08 h / Heating

3: CH₂Cl₂ / 1 h / 20 °C

With caesium carbonate; hydrazine; In dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1016/S0960-894X(02)00585-1

upstream raw materials:

di-tert-butyl dicarbonate

4-(aminomethyl)-2-fluorobenzonitrile

4-bromo-3-fluorotoluene

2-fluoro-4-methylbenzonitrile

Downstream raw materials:

C₁₃H₁₈FN₃O₃

6-aminomethyl-benzo[d]isoxazol-3-ylamine

C₂₄H₂₄ClN₇O₃

tert-butyl ((3-aminobenzo[d]isoxazol-6-yl)methyl)carbamate

Refernces

• 1、 Le, Thuy G.,Kundu, Abhijit,Ghoshal, Atanu,Nguyen, Nghi H.,Preston, Sarah,Jiao, Yaqing,Ruan, Banfeng,Xue, Lian,Huang, Fei,Keiser, Jennifer,Hofmann, Andreas,Chang, Bill C. H.,Garcia-Bustos, Jose,Jabbar, Abdul,Wells, Timothy N. C.,Palmer, Michael J.,Gasser, Robin B.,Baell, Jonathan B.. "Optimization of Novel 1-Methyl-1 H-Pyrazole-5-carboxamides Leads to High Potency Larval Development Inhibitors of the Barber's Pole Worm". . p. 10875 - 10894. Retrieved 2019/01/04.
• 2、 Cui, Jingrong Jean,Araldi, Gian-Luca,Reiner, John E.,Reddy, Komandla Malla,Kemp, Scott J.,Ho, Jonathan Z.,Siev, Daniel V.,Mamedova, Lala,Gibson, Tony S.,Gaudette, John A.,Minami, Nathaniel K.,Anderson, Susanne M.,Bradbury, Annette E.,Nolan, Thomas G.,Semple. "Non-covalent thrombin inhibitors featuring P3-heterocycles with P1-bicyclic arginine surrogates". . p. 2925 - 2930. Retrieved 2007/10/03.