1-(6-Nitrobenzo[d][1,3]dioxol-5-yl)ethyl carbonochloridate

Base Information

• Chemical Name: 1-(6-Nitrobenzo[d][1,3]dioxol-5-yl)ethyl carbonochloridate
• CAS No.: 156876-26-5
• Molecular Formula: C10H8ClNO6
• Molecular Weight: 273.6266
• European Community (EC) Number: 811-365-8
• Mol file: 156876-26-5.mol

Synonyms:156876-26-5;1-(6-nitrobenzo[d][1,3]dioxol-5-yl)ethyl carbonochloridate;(r,s)-1-(3,4-(methylenedioxy)-6-nitrophenyl)ethyl chloroformate;1-(6-nitro-1,3-benzodioxol-5-yl)ethyl carbonochloridate;1-(4,5-methylenedioxy-2-nitrophenyl)ethyl chloroformate;LLQGXKKNTCFHEE-UHFFFAOYSA-N;starbld0018300;SCHEMBL3768323;AC4541;MFCD05864010;AKOS015958890;SY249541;FT-0719398;EN300-265843;1-(6-nitro-1,3-dioxaindan-5-yl)ethyl chloroformate;F9995-1203;1-(4,5- methylenedioxy-2-nitrophenyl)ethyl chloroformate;CARBONOCHLORIDIC ACID,1-(6-NITRO-1,3-BENZODIOXOL-5-YL)ETHYL ESTER

Chemical Property of 1-(6-Nitrobenzo[d][1,3]dioxol-5-yl)ethyl carbonochloridate

Chemical Property:

• Vapor Pressure: 1.23E-06mmHg at 25°C
• Refractive Index: 1.588
• Boiling Point: 400.9 °C at 760 mmHg
• Flash Point: 196.2 °C
• PSA: 90.58000
• Density: 1.542 g/cm³
• LogP: 3.28310
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 273.0040147
• Heavy Atom Count: 18
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Carbonochloridic acid 1-(6-nitro-1,3-benzodioxol-5-yl) ethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC2=C(C=C1[N+](=O)[O-])OCO2)OC(=O)Cl

Technology Process of 1-(6-Nitrobenzo[d][1,3]dioxol-5-yl)ethyl carbonochloridate

There total 5 articles about 1-(6-Nitrobenzo[d][1,3]dioxol-5-yl)ethyl carbonochloridate 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%

bis(trichloromethyl) carbonate (32315-10-9) + (R,S)-1-[4',5'-(methylenedioxy)-2'-nitrophenyl]ethanol (159873-64-0) → 5′-(α-methyl-2-nitropiperonyl)oxycarbonyl chloride (156876-26-5)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ja910688s

Reference yield: 80.0%

phosgene (75-44-5) + (R,S)-1-[4',5'-(methylenedioxy)-2'-nitrophenyl]ethanol (159873-64-0) → 5′-(α-methyl-2-nitropiperonyl)oxycarbonyl chloride (156876-26-5)

Guidance literature:

In tetrahydrofuran; toluene; for 30h;

DOI:10.1021/ja039565w

Reference yield: 52.0%

(R,S)-1-[4',5'-(methylenedioxy)-2'-nitrophenyl]ethanol (159873-64-0) + trichloromethyl chloroformate (503-38-8) → 5′-(α-methyl-2-nitropiperonyl)oxycarbonyl chloride (156876-26-5)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.chembiol.2019.08.006

upstream raw materials:

phosgene

(R,S)-1-[4',5'-(methylenedioxy)-2'-nitrophenyl]ethanol

1-(benzo[d][1,3]dioxol-6-yl)ethanone

methyl 3,4-(methylenedioxy)-6-nitrophenyl ketone

Downstream raw materials:

Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

Carbonic acid (2R,3S,5R)-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-5-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N²-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate

Refernces

• 1、 Gautier, Arnaud,Nguyen, Duy P.,Lusic, Hrvoje,An, Wenlin,Deiters, Alexander,Chin, Jason W.. "Genetically encoded photocontrol of protein localization in mammalian cells". . p. 4086 - 4088. Retrieved 2010.
• 2、 -. "GENETICALLY ENCODED PHOTO CONTROL". Page/Page column 9. . Retrieved 2013/02/28.