4-(N-Tert-butoxycarbonylamino)tetrafluorophenylazide

Base Information

• Chemical Name: 4-(N-Tert-butoxycarbonylamino)tetrafluorophenylazide
• CAS No.: 294187-76-1
• Molecular Formula: C11H10F4N4O2
• Molecular Weight: 306.22
• DSSTox Substance ID: DTXSID10441561
• Nikkaji Number: J1.407.528C
• Wikidata: Q82258353
• Mol file: 294187-76-1.mol

Synonyms:294187-76-1;4-(N-TERT-BUTOXYCARBONYLAMINO)TETRAFLUOROPHENYLAZIDE;tert-butyl N-(4-azido-2,3,5,6-tetrafluorophenyl)carbamate;Carbamic acid, (4-azido-2,3,5,6-tetrafluorophenyl)-, 1,1-dimethylethyl ester (9CI);DTXSID10441561;QHWSSUUXMVEFHZ-UHFFFAOYSA-N;AKOS025295069;FT-0663963;J-017505;tert-Butyl (4-azido-2,3,5,6-tetrafluorophenyl)carbamate;(2,3,5,6-Tetrafluoro-4-azidophenyl)carbamic acid tert-butyl ester;2-Methyl-2-propanyl (4-azido-2,3,5,6-tetrafluorophenyl)carbamate;4-(N-tert-Butoxycarbonylamino)tetrafluorophenylazide, AldrichCPR

Chemical Property of 4-(N-Tert-butoxycarbonylamino)tetrafluorophenylazide

Chemical Property:

• Melting Point: 77-80°C
• PSA: 88.08000
• LogP: 4.05756
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 306.07398822
• Heavy Atom Count: 21
• Complexity: 422

Purity/Quality:

99% ^*data from raw suppliers

4-(N-tert-Butoxycarbonylamino)tetrafluorophenylazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=C(C(=C(C(=C1F)F)N=[N+]=[N-])F)F
• Uses: A protected photoaffinity reagent

Technology Process of 4-(N-Tert-butoxycarbonylamino)tetrafluorophenylazide

There total 5 articles about 4-(N-Tert-butoxycarbonylamino)tetrafluorophenylazide 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: 88.0%

4-azido-2,3,5,6-tetrafluoro-benzoyl azide (345976-51-4) + tert-butyl alcohol (75-65-0) → 4-(N-(tert-butoxycarbonyl)amino)tetrafluorophenyl azide (294187-76-1)

Guidance literature:

In benzene; at 70 ℃; for 7h;

DOI:10.1021/jo000402p

Reference yield:

methyl pentafluorobenzoate (36629-42-2) → 4-(N-(tert-butoxycarbonyl)amino)tetrafluorophenyl azide (294187-76-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / NaN₃ / acetone; H₂O / 16 h / Heating

2: 98 percent / aq. NaOH / methanol / 25 °C

3: 100 percent / PCl₅ / diethyl ether / 1 h / 20 °C

4: sodium azide / acetone; H₂O / 0.25 h / 0 °C

5: 88 percent / benzene / 7 h / 70 °C

With sodium hydroxide; sodium azide; phosphorus pentachloride; In methanol; diethyl ether; water; acetone; benzene; 1: Substitution / 2: Hydrolysis / 3: Substitution / 4: Substitution / 5: Rearrangement;

DOI:10.1021/jo000402p

Reference yield:

methyl 4-azidotetrafluorobenzoate (122590-75-4) → 4-(N-(tert-butoxycarbonyl)amino)tetrafluorophenyl azide (294187-76-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / aq. NaOH / methanol / 25 °C

2: 100 percent / PCl₅ / diethyl ether / 1 h / 20 °C

3: sodium azide / acetone; H₂O / 0.25 h / 0 °C

4: 88 percent / benzene / 7 h / 70 °C

With sodium hydroxide; sodium azide; phosphorus pentachloride; In methanol; diethyl ether; water; acetone; benzene; 1: Hydrolysis / 2: Substitution / 3: Substitution / 4: Rearrangement;

DOI:10.1021/jo000402p

upstream raw materials:

4-azido-2,3,5,6-tetrafluoro-benzoyl azide

tert-butyl alcohol

methyl pentafluorobenzoate

methyl 4-azidotetrafluorobenzoate

Downstream raw materials:

p-azidotetrafluoroaniline

4-(N-methyl-N-tert-butoxycarbonylamino)tetrafluorophenyl azide

N-methyl-4-azidotetrafluoroaniline

(E)-N-(6-chloro-4-methyl-4-hexenyl)-N-methyl-4-azidotetrafluoroaniline