(E)-tert-Butyl 4-methylbenzylidenecarbamate

Base Information

• Chemical Name: (E)-tert-Butyl 4-methylbenzylidenecarbamate
• CAS No.: 479423-39-7
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.283
• DSSTox Substance ID: DTXSID70459445
• Mol file: 479423-39-7.mol

Synonyms:479423-39-7;(E)-tert-Butyl 4-methylbenzylidenecarbamate;Tert-butyl (NE)-N-[(4-methylphenyl)methylidene]carbamate;(4-Methyl-BENZYLIDENE)-CARBAMIC ACID TERT-BUTYL ESTER;Carbamic acid, [(4-methylphenyl)methylene]-, 1,1-dimethylethyl ester (9CI);743430-45-7;DTXSID70459445;(E)-tert-Butyl4-methylbenzylidenecarbamate;tert-Butyl [(E)-(4-methylphenyl)methylidene]carbamate;2-Methyl-2-propanyl [(E)-(4-methylphenyl)methylene]carbamate

Chemical Property of (E)-tert-Butyl 4-methylbenzylidenecarbamate

Chemical Property:

• PSA: 38.66000
• LogP: 3.34900
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 219.125928785
• Heavy Atom Count: 16
• Complexity: 258

Purity/Quality:

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

(E)-tert-Butyl4-methylbenzylidenecarbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C=NC(=O)OC(C)(C)C
• Isomeric SMILES: CC1=CC=C(C=C1)/C=N/C(=O)OC(C)(C)C

Technology Process of (E)-tert-Butyl 4-methylbenzylidenecarbamate

There total 9 articles about (E)-tert-Butyl 4-methylbenzylidenecarbamate 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: 91.0%

tert-butyl (phenylsulfonyl(p-tolyl)methyl)carbamate (479423-27-3) → 4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine (479423-39-7)

Guidance literature:

With potassium carbonate; In dichloromethane; water; at 20 ℃; for 4h;

DOI:10.1039/c6cc00603e

Reference yield:

tert-butyl carbazate (4248-19-5) → 4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine (479423-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1: formic acid / methanol; H₂O / 72 h / 20 °C

2: anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating

With formic acid; potassium carbonate; In tetrahydrofuran; methanol; water;

DOI:10.1002/anie.200502674

Reference yield:

4-methyl-benzaldehyde (104-87-0) → 4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine (479423-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1: formic acid / methanol; water / 36 h / 20 °C

2: potassium carbonate; sodium sulfate / tetrahydrofuran / 18 h / Inert atmosphere; Reflux

With formic acid; potassium carbonate; sodium sulfate; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja203754p

upstream raw materials:

tert-butyl (p-tolyl(tosyl)methyl)carbamate

tert-butyl (phenylsulfonyl(p-tolyl)methyl)carbamate

tert-butyl carbazate

4-methyl-benzaldehyde

Downstream raw materials:

tert-butyl (1R,2S)-2-nitro-1-p-tolylpropylcarbamate

diethyl (1S)-1-[(R)-(tert-butoxycarbonylamino)(p-tolyl)methyl]-2-oxocyclopentanephosphonate

(S)-2-(((S)-tert-butoxycarbonylamino)(4-methylphenyl)methyl)-2-cyanocyclopentanone

C₁₇H₂₄N₂O₆

Refernces

• 1、 Gondo, Naruhiro,Tanigaki, Yusuke,Ueda, Yoshihiro,Kawabata, Takeo. "γ-Selective Vinylogous Aza-Morita-Baylis-Hillman Reaction with N -Carbamoylimines". . p. 398 - 402. Retrieved 2020/02/27.
• 2、 Kardile, Rahul Dadabhau,Liu, Rai-Shung. "Two Distinct Ag(I)- And Au(I)-Catalyzed Olefinations between α-Diazo Esters and N-Boc-Derived Imines". supporting information. p. 6452 - 6456. Retrieved 2019/09/06.