18022-46-3

Basic information

• Product Name: (2-Propenyloxy)methylcyclopropane
• Synonyms: (2-Propenyloxy)methylcyclopropane
• CAS NO: 18022-46-3
• Molecular Formula: C7H12O
• Molecular Weight: 112.17
• Mol File: 18022-46-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2-Propenyloxy)methylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: (2-Propenyloxy)methylcyclopropane(18022-46-3)
• EPA Substance Registry System: (2-Propenyloxy)methylcyclopropane(18022-46-3)

Safety Data

• Hazardous Substances Data: 18022-46-3(Hazardous Substances Data)

Usage

General Description

(2-Propenyloxy)methylcyclopropane, also known as isopropenylmethoxymethylcyclopropane or IMMCP, is a chemical compound with the molecular formula C7H12O. It is a colorless liquid with a faint odor, and is used as a flavoring agent and aroma compound in the food industry. It is also used in the production of fragrances and perfumes. IMMCP is considered to be a skin and eye irritant, and may have harmful effects if ingested or inhaled. It is important to handle this chemical with caution and follow safety guidelines when working with it.

Upstream product

• 186581-53-3 diazomethane 
• 557-40-4 Allyl ether 
• 2516-33-8 Cyclopropylmethanol 
• 106-95-6 allyl bromide 

Downstream Products

• 64340-98-3 ([1-propenyloxy]methyl)cyclopropane 

Relevant articles and documents

THE WITTIG REARRANGEMENT AS A PRACTICAL METHOD FOR ALDEHYDE SYNTHESIS

If the rearrangement of metalated allyl ethers 2 (or 4) is accomplished in the presence of potassium tert-butoxide, primary alkyl groups preferentially migrate to the unsubstituted allylic terminus (γ-position).Enolates 7 and 1-vinylalcoholates 6 (by alkyl migration to the α-position, adjacent to the oxygen atom) are produced in an approximate ratio of 9 : 1.Because of the endo-configuration of their organometallic precursors, the enolates exclusively emerge in the (Z)-configuration as shown by trapping with chlorotrimethylsilane and isolation of the resulting O-silyl (Z)-enethers.Hydrolysis of the latter affords the corresponding aldehydes with good yields. -The rearrangement is mechanistically still obscure.A concerted process as the main reaction mode is unlikely.The intermediacy of zwitterionic metallomers 18 and solvent caged radical pairs 17 is tentatively suggested.