5-(isocyanatomethyl)-2H-1,3-benzodioxole

Base Information

• Chemical Name: 5-(isocyanatomethyl)-2H-1,3-benzodioxole
• CAS No.: 71217-46-4
• Molecular Formula: C9H7 N O3
• Molecular Weight: 177.159
• Hs Code.: 2932990090
• DSSTox Substance ID: DTXSID80579769
• Mol file: 71217-46-4.mol

Synonyms:71217-46-4;5-(isocyanatomethyl)-2H-1,3-benzodioxole;5-(isocyanatomethyl)-1,3-benzodioxole;1,3-Benzodioxole,5-(isocyanatomethyl)-;5-(isocyanatomethyl)-1,3-dioxaindane;SCHEMBL20766560;DTXSID80579769;MFCD08435909;AKOS010079625;MS-22415;EN300-144777;G41884;5-(Isocyanatomethyl)-1,3-benzodioxole, AldrichCPR;F2163-0002

Chemical Property of 5-(isocyanatomethyl)-2H-1,3-benzodioxole

Chemical Property:

• Vapor Pressure: 0.00444mmHg at 25°C
• Boiling Point: 277.8°C at 760 mmHg
• Flash Point: 136.9°C
• PSA: 47.89000
• Density: 1.3g/cm³
• LogP: 1.25110
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 225

Purity/Quality:

98%min ^*data from raw suppliers

5-(Isocyanatomethyl)-1,3-benzodioxole 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)CN=C=O
• Uses: 5-(Isocyanatomethyl)-1,3-benzodioxole is used to develop novel nonhematotoxic naphthalimide derivative with potent antitumor activity

Technology Process of 5-(isocyanatomethyl)-2H-1,3-benzodioxole

There total 5 articles about 5-(isocyanatomethyl)-2H-1,3-benzodioxole 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: 46.8%

phosgene (75-44-5) + C11H17NO2Si → C9H7NO3 + 5-(isocyanatomethyl)-2H-1,3-benzodioxole (71217-46-4)

Guidance literature:

In toluene; at 0 ℃; Title compound not separated from byproducts.;

DOI:10.1134/S1070363206030182

Reference yield:

1,3-benzodioxol-5-ylmethyl amine (2620-50-0) + bis(trichloromethyl) carbonate (32315-10-9) → 5-(isocyanatomethyl)-2H-1,3-benzodioxole (71217-46-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere; Reflux;

DOI:10.1002/cmdc.201700307

Reference yield:

phosgene (75-44-5) + 1,3-benzodioxol-5-ylmethyl amine (2620-50-0) → 5-(isocyanatomethyl)-2H-1,3-benzodioxole (71217-46-4)

Guidance literature:

In ethyl acetate; at 60 - 100 ℃;

DOI:10.1021/jm00099a003

upstream raw materials:

phosgene

1,3-benzodioxol-5-ylmethyl amine

1,3-benzodioxole-5-acetic acid

bis(trichloromethyl) carbonate

Downstream raw materials:

4-{1-[(Benzo[1,3]dioxol-5-ylmethyl)-carbamoyl]-3,3-diethyl-4-oxo-azetidin-2-yloxy}-benzoic acid

Refernces

• 1、 Giacomini, Daria,Martelli, Giulia,Piccichè, Miriam,Calaresu, Enrico,Cocuzza, Clementina Elvezia,Musumeci, Rosario. "Design and Synthesis of 4-Alkylidene-β-lactams: Benzyl- and Phenethyl-carbamates as Key Fragments to Switch on Antibacterial Activity". . p. 1525 - 1533. Retrieved 2017/09/25.
• 2、 Aoyama, Yasunori,Uenaka, Masaaki,Konoike, Toshiro,Hayasaki-Kajiwara, Yoko,Naya, Noriyuki,Nakajima, Masatoshi. "Inhibition of serine proteases: Activity of 1,3-diazetidine-2,4-diones". . p. 1691 - 1694. Retrieved 2007/10/03.