41003-94-5

Basic information

• Product Name: DIETHYL ISOCYANOMETHYLPHOSPHONATE
• Synonyms: DIETHYL ISOCYANOMETHYLPHOSPHONATE;ISOCYANOMETHYL-PHOSPHONIC ACID DIETHYL ESTER;ISOCYANOMETHYLPHOSPHONONIC ACID DIETHYL ESTER;[(Diethoxyphosphinyl)methyl] isocyanide;Diethoxyphosphinylmethyl isocyanide;Diethyl isocyanomethylphosphonate,97%;Diethyl isocyanomethylphosphonate 97%;Diethyl (isocyanomethyl)
• CAS NO: 41003-94-5
• Molecular Formula: C₆H₁₂NO₃P
• Molecular Weight: 177.14
• Mol File: 41003-94-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 84-87 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.105 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.433(lit.)
• Storage Temp.: 2-8°C
• BRN: 4674920
• CAS DataBase Reference: DIETHYL ISOCYANOMETHYLPHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL ISOCYANOMETHYLPHOSPHONATE(41003-94-5)
• EPA Substance Registry System: DIETHYL ISOCYANOMETHYLPHOSPHONATE(41003-94-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-9
• Hazardous Substances Data: 41003-94-5(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to yellow liquid

Uses

Reactant for:Copper-catalyzed cycloaddition reactionsPreparation of orally bioavailable diamide prodrugs that lower glucose in diabetic animals through inhibition of fructose-1,6-bisphosphataseSynthesis of sterol analogs as antifungal agents against plant pathogensAsymmetric synthesis of steroidal 2,5-diketopiperazines prepared via isocyanide chemistry based on stereoselective Ugi four component condensation and subsequent cyclocondensation reactionsThe Passerini reaction

InChI:InChI=1/C6H12NO3P/c1-4-9-11(8,6-7-3)10-5-2/h4-6H2,1-2H3

Upstream product

• 50917-72-1 aminomethylphosphonic acid diethyl ester 
• 33512-26-4 diethyl (phthalimidomethyl)phosphonate 
• 41003-95-6 N-Formylaminomethanphosphonsaeurediethylester 

Downstream Products

• 90476-40-7 [(2-{Benzyl-[2-(2,2,2-trifluoro-acetylamino)-acetyl]-amino}-2-phenyl-acetylamino)-methyl]-phosphonic acid diethyl ester 
• 41003-16-1 (Z)-1-(2-isocyanovinyl)-4-methoxybenzene 
• 41003-99-0 (E)-1-(2-isocyanovinyl)-4-methoxybenzene 
• 90476-37-2 ({2-[Benzyl-(2-formylamino-acetyl)-amino]-2-methyl-propionylamino}-methyl)-phosphonic acid diethyl ester 
• 90476-41-8 [(2-{Benzyl-[2-(2,2,2-trifluoro-acetylamino)-acetyl]-amino}-2-methyl-propionylamino)-methyl]-phosphonic acid diethyl ester 
• 90476-38-3 [(Benzyl-{1-[(diethoxy-phosphorylmethyl)-carbamoyl]-1-methyl-ethyl}-carbamoyl)-formylamino-methyl]-phosphonic acid diethyl ester 
• 144878-79-5 2-(Diethoxy-phosphoryl)-5-phenylsulfanyl-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester 
• 90476-46-3 (R,S)-N-(N-Tritylglycyl-N-benzylvalyl)-aminomethanphosphonsaeure-diethylester 
• 90476-47-4 [(2-{Benzyl-[2-(2-benzyloxycarbonylamino-acetylamino)-acetyl]-amino}-3-methyl-butyrylamino)-methyl]-phosphonic acid diethyl ester 
• 90476-39-4 [(2-{Benzyl-[2-(2,2,2-trifluoro-acetylamino)-acetyl]-amino}-3-methyl-butyrylamino)-methyl]-phosphonic acid diethyl ester 
• 90476-36-1 (R,S)-N-(N-Formylglycyl-N-benzylvalyl)-aminomethanphosphonsaeure-diethylester 
• 79370-09-5 (5-Phenyloxazol-4-yl)phosphonsaeure-diethylester 
• 125759-93-5 [(1S,2S)-1-(3,5-Dinitro-benzoylamino)-2-hydroxy-2-phenyl-ethyl]-phosphonic acid diethyl ester 
• 125759-93-5 [(1R,2R)-1-(3,5-Dinitro-benzoylamino)-2-hydroxy-2-phenyl-ethyl]-phosphonic acid diethyl ester 

Relevant articles and documents

Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme

Installation of olefins into molecules is a key transformation in organic synthesis. The recently discovered decarboxylation-assisted olefination in the biosynthesis of rhabduscin by a mononuclear non-heme iron enzyme (P.IsnB) represents a novel approach in olefin construction. This method is commonly employed in natural product biosynthesis. Herein, we demonstrate that a ferryl intermediate is used for C-H activation at the benzylic position of the substrate. We further establish that P.IsnB reactivity can be switched from olefination to hydroxylation using electron-withdrawing groups appended on the phenyl moiety of the analogues. These experimental observations imply that a pathway involving an initial C-H activation followed by a benzylic carbocation species or by electron transfer coupled β-scission is likely utilized to complete C=C bond formation.