22715-57-7

Basic information

• Product Name: 1,1-dibromo-2,2,3,3-tetramethylcyclopropane
• CAS NO: 22715-57-7
• Molecular Formula: C₇H₁₂Br₂
• Molecular Weight: 255.9782
• Mol File: 22715-57-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 178.5°C at 760 mmHg
• Flash Point: 55.7°C
• Density: 1.628g/cm³
• Vapor Pressure: 1.33mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: 1,1-dibromo-2,2,3,3-tetramethylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-dibromo-2,2,3,3-tetramethylcyclopropane(22715-57-7)
• EPA Substance Registry System: 1,1-dibromo-2,2,3,3-tetramethylcyclopropane(22715-57-7)

Safety Data

• Hazardous Substances Data: 22715-57-7(Hazardous Substances Data)

Usage

Type of compound

Brominated derivative of tetramethylcyclopropane

Structure

Cycloalkane with four methyl groups attached to the cyclopropane ring

Presence of bromine atoms

High reactivity

Chirality

Chiral compound with a non-superimposable mirror image

Applications

Used in organic synthesis as a reagent to synthesize other organic compounds

Handling and storage

Requires careful handling and storage to prevent hazardous chemical reactions

Upstream product

• 563-79-1 2,3-Dimethyl-2-butene 
• 135226-15-2 dibromocarbene 
• 110426-98-7 (4aR,8aS)-9,9-Dibromo-1,4-dihydro-4a,8a-methano-naphthalene 
• 115-11-7 isobutene 
• 75-25-2 Bromoform 
• 563-78-0 2,3-Dimethyl-1-butene 
• 558-13-4 carbon tetrabromide 
• 74-95-3 1,1-dibromomethane 

Downstream Products

• 53081-83-7 2,2,3,3-Tetramethyl-4,4-diphenylcyclobutanon 
• 56799-07-6 α-<2,2,3,3-Tetramethyl-1-(methylthio)-cyclopropyl>-benzylalkohol 
• 4773-87-9 3-bromo-2,4-dimethylpenta-1,3-diene 
• 90660-91-6 2-(2-bromo-1,1,3-trimethyl-2-butenyl)furan 
• 53422-93-8 3-bromo-2,4-dimethyl-2-penten-4-ol 
• 100045-88-3 1,1-bis(phenylthio)-2,2,3,3-tetramethylcyclopropane 
• 100082-44-8 1-bromo-1-(phenylthio)-2,2,3,3-tetramethylcyclopropane 
• 1350704-13-0 (2S,3S)-2-acryloyl-3-methyl-3-(4-methyl-3-(prop-1-en-2-yl)pent-3-en-1-yl)cyclohexanone 
• 1350704-15-2 (S)-trimethyl((3-methyl-3-(4-methyl-3-(prop-1-en-2-yl)pent-3-en-1-yl)cyclohex-1-en-1-yl)oxy)silane 
• 1350704-19-6 (2R,3S)-2-acryloyl-3-methyl-3-(4-methyl-3-(prop-1-en-2-yl)pent-3-en-1-yl)cyclohexanone 

Relevant articles and documents

EXPERIMENTAL EVIDENCE FOR A CORRELATION BETWEEN ISOSELECTIVE AND ISOKINETIC TEMPERATURES

From isokinetic temperatures β (Figures I and II) and activation enthalpies (Table I) an isoselective temperature of 368 K is calculated for cycloaddition reactions of dihalocarbenes with alkenes.This is in excellent accord with the experimental value of 360 +/- 10 K.

A PHOTOCHEMICAL SOURCE OF DIBROMO- AND DICHLOROCARBENE A CAUTIONARY TALE REGARDING THE STEREOCHEMISTRY OF DIBROMOCARBENE ADDITION REACTIONS

Photolysis of triene 3a or 3b yields dibromo- and dichlorocarbene which can be transferred to olefins in good yield.A warning is offered regarding the data recently interpreted as being "only consistent" with the formation of an intermediate in the addition of dibromocarbene to trans-cyclooctene.

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Route optimization and synthesis of taxadienone

Early process development toward the scalable production of taxadienone on a decagram scale is described. A continuous flow reactor was employed to safely run a potentially hazardous cyclopropane ring opening. The route featured two copper-mediated additions, a Diels-Alder reaction and a palladium-catalyzed Negishi coupling, to construct the final structure.

Total synthesis of taxane terpenes: Cyclase phase Dedicated to Professor Melanie S. Sanford on the occasion of her receipt of the Tetrahedron Young Investigator Award

A full account of synthetic efforts toward a lowly oxidized taxane framework is presented. A non-natural taxane, dubbed 'taxadienone', was synthesized as our first entry into the taxane family of diterpenes. The final synthetic sequence illustrates a seven-step, gram-scale, and enantioselective route to this tricyclic compound in 18% overall yield. This product was then modified further to give (+)-taxadiene, the lowest oxidized member of the taxane family of natural products.