40846-66-0

Basic information

• Product Name: METHYL 2-ISOCYANO-3-METHYLBUTYRATE
• Synonyms: METHYL 2-ISOCYANOISOVALERATE;METHYL 2-ISOCYANO-3-METHYLBUTYRATE;Methyl 2-isocyano-3-methylbutyrate,96%
• CAS NO: 40846-66-0
• Molecular Formula: C₇H₁₁NO₂
• Molecular Weight: 141.17
• Mol File: 40846-66-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 63 °C (6.0008 mmHg)
• Appearance: clear yellowish liquid
• Density: 0.87
• Refractive Index: 1.422-1.424
• Storage Temp.: Refrigerator (+4°C)
• CAS DataBase Reference: METHYL 2-ISOCYANO-3-METHYLBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-ISOCYANO-3-METHYLBUTYRATE(40846-66-0)
• EPA Substance Registry System: METHYL 2-ISOCYANO-3-METHYLBUTYRATE(40846-66-0)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26
• Hazardous Substances Data: 40846-66-0(Hazardous Substances Data)

Usage

Chemical Properties

clear yellowish liquid

Upstream product

• 3154-46-9 Formyl-DL-valyl-methylester 
• 3154-46-9 (S)-methyl 2-formamido-3-methylbutanoate 
• 5619-05-6 DL-valine methyl ester hydrochloride 
• 4070-48-8 L-valine methyl ester 

Downstream Products

• 54011-36-8 α-Benzoyl-valinmethylester 
• 125294-72-6 2-Isocyano-3-methyl-2-(3-trimethylsilanyloxy-cyclohex-2-enyl)-butyric acid methyl ester 

Relevant articles and documents

Pd-Catalyzed Domino Imidoylation/Heck/C(sp2)-H Cyclization: Isocyanide Relay Strategy toward Tricyclic-Fused Heterocycles Containing an All-Carbon Quaternary Center

A palladium-catalyzed domino process for the quick assembly of tricyclic-fused heterocycles starting from aryl iodides and functionalized isocyanides containing a disubstituted terminal alkene has been developed. The process is triggered by intermolecular isocyanide insertion, followed by Heck-type carbopalladation of the intramolecular alkene moiety and subsequent C(sp2)-H activation. Moreover, an asymmetric version of this reaction could also be realized in good yield with moderate enantioselectivity after preliminary exploration of chiral ligands.

Synthesis of isocyanides through dehydration of formamides using XtalFluor-E

The formation of isocyanides from formamides using XtalFluor-E, [Et2NSF2]BF4, is presented. A wide range of formamides can be used to produce the corresponding isocyanides in up to 99% yield. In a number of cases, the crude products showed good purity (generally >80% by NMR) allowing to be used directly in multi-component reactions.

A cation-directed two-component cascade approach to enantioenriched pyrroloindolines

A cascade approach to complex pyrroloindolines bearing all-carbon quaternary stereocentres has been developed. This two-component process uses a chiral ammonium salt to control diastereo- and enantioselectivity in the addition of isocyanides to functionalized alkenes to afford pyrroloindolines with up to three stereocentres. A mechanistic proposal involving intramolecular hydrogen bond activation of the isocyanide is described.