156876-26-5

Basic information

• Product Name: (R,S)-1-(3,4-(METHYLENEDIOXY)-6-NITROPHENYL)ETHYL CHLOROFORMATE
• Synonyms: 1-(3,4-(METHYLENEDIOXY)-6-NITROPHENYL)ETHYL CHLOROFORMATE;MENPOC;MENPOC CHLORIDE;(R,S)-1-(3,4-(METHYLENEDIOXY)-6-NITROPHENYL)ETHYL CHLOROFORMATE;1-(6-nitro-1,3-benzodioxol-5-yl)ethyl carbonochloridate
• CAS NO: 156876-26-5
• Molecular Formula: C₁₀H₈ClNO₆
• Molecular Weight: 273.63
• Mol File: 156876-26-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 400.9 °C at 760 mmHg
• Flash Point: 196.2 °C
• Appearance: /
• Density: 1.542 g/cm³
• Vapor Pressure: 1.23E-06mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: (R,S)-1-(3,4-(METHYLENEDIOXY)-6-NITROPHENYL)ETHYL CHLOROFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-1-(3,4-(METHYLENEDIOXY)-6-NITROPHENYL)ETHYL CHLOROFORMATE(156876-26-5)
• EPA Substance Registry System: (R,S)-1-(3,4-(METHYLENEDIOXY)-6-NITROPHENYL)ETHYL CHLOROFORMATE(156876-26-5)

Safety Data

• Hazardous Substances Data: 156876-26-5(Hazardous Substances Data)

Usage

General Description

"(R,S)-1-(3,4-(METHYLENEDIOXY)-6-NITROPHENYL)ETHYL CHLOROFORMATE is a chemical compound with the formula C11H10ClNO6. It is a chloroformate derivative, which means it contains a chloroformate functional group (-OCOCl) attached to an aromatic ring. The compound also contains a nitro group and a methylenedioxy group, which are both electron-withdrawing groups. This chemical is used in organic synthesis as a reagent for the introduction of the chloroformate group in various chemical reactions. It is important to handle this compound with caution, as chloroformates are known to be toxic and irritating to the skin, eyes, and respiratory system."

InChI:InChI=1/C10H8ClNO6/c1-5(18-10(11)13)6-2-8-9(17-4-16-8)3-7(6)12(14)15/h2-3,5H,4H2,1H3/t5-/m1/s1

Upstream product

• 159873-64-0 (R,S)-1-[4',5'-(methylenedioxy)-2'-nitrophenyl]ethanol 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 56136-84-6 methyl 3,4-(methylenedioxy)-6-nitrophenyl ketone 
• 75-44-5 phosgene 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 

Downstream Products

• 159873-70-8 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 
• 190850-08-9 5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N²-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate 
• 159873-69-5 Carbonic acid (2R,3S,5R)-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester 
• 190850-00-1 Carbonic acid (2R,3S,5R)-5-[6-diphenylcarbamoyloxy-2-(2-phenoxy-acetylamino)-purin-9-yl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester 
• 190849-99-1 Carbonic acid (2R,3S,5R)-5-(6-diphenylcarbamoyloxy-2-isobutyrylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester 
• 156876-24-3 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 
• 156876-25-4 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 
• 190850-02-3 Carbonic acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester 
• 190849-98-0 Carbonic acid (2R,3S,5R)-5-(2-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester 

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New methods based on photolithography and surface fluorescence were used to determine photodeprotection rates and stepwise yields for light-directed oligonucleotide synthesis using photolabile 5'-(((α-methyl-2- nitropiperonyl)-oxy)carbonyl)(MeNPOC)-2'-deoxynucleoside phosphoramidites on planar glass substrates. Under near-UV illumination (primarily 365 nm) from a mercury light source, the rate of photoremoval of the MeNPOC protecting group was found to be independent of both the nucleotide and length of the growing oligomer (t( 1/4 ) = 12 s at 27.5 mW/cm2). A moderate dependence on solvent polarity was observed, with photolysis proceeding most rapidly in the presence of nonpolar solvents or in the absence of solvent (e.g., t( 1/4 ) = 10 - 13 s at 27.5 mW/cm2). In solution, the photolysis rate was linearly dependent on light intensity over the range 5-50 mW/cm2. Average stepwise yields for the synthesis of dodecamer oligonucleotides were in the range of 92-94%, using monomers based on N6-(phenoxyacetyl)-2'-deoxyadenosine, N2- isobutyryl-2'-deoxyguanosine, N4-isobutyryl-2'-deoxycytidine, and thymidine. By comparison, an efficiency of 98%/step was obtained using a conventional 5'-dimethoxytrityl monomer with acid deprotection on the same support. The lower yields associated with the photochemical process appears to be due to incomplete recovery of free 5'-hydroxyl groups after photolysis on the support, although high yields of 5'-OH nucleosides (≤96%) are consistently observed when 5'-MeNPOC monomers are photolyzed in solution.