bromo({[(bromozincio)methyl]zincio}methyl)zinc; oxolane

• ChemBase ID: 128675
• Molecular Formular: C6H12Br2OZn3
• Molecular Mass: 456.10688
• Monoisotopic Mass: 449.712915
• SMILES: Br[Zn]C[Zn]C[Zn]Br.C1CCCO1
• Canonical SMILES: C1CCCO1.Br[Zn]C[Zn]C[Zn]Br
• InChI: InChI=1S/C4H8O.2CH2.2BrH.3Zn/c1-2-4-5-3-1;;;;;;;/h1-4H2;2*1H2;2*1H;;;/q;;;;;;2*+1/p-2
• InChIKey: CCTHTLJWXPUNGT-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: bromo({[(bromozincio)methyl]zincio}methyl)zinc; oxolane
• IUPAC Traditional name: bromo({[(bromozincio)methyl]zincio}methyl)zinc; tetrahydrofuran
• Synonyms: cyclo-Dibromodi-?-methylene[?-(tetrahydrofuran)]trizinc; Nysted reagent; cyclo-Dibromodi-μ-methylene[μ-(tetrahydrofuran)]trizinc; Nysted Reagent; 环-二溴二-μ-亚甲基[μ-(四氢呋喃)]三锌; Nysted 试剂

Database IDs

• CAS Number: 41114-59-4
• MDL Number: MFCD00134567
• Merck Index: 146737
• PubChem SID: 24863854
• Chemspider ID: 21171210
• Wikipedia Title: Nysted_reagent

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.6108
• LogD (pH = 7.4): 1.6108
• Log P: 1.6108
• Molar Refractivity: 26.423 cm^3
• Polarizability: 21.17705 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: -14.8 °F; -26 °C; -26.0°C; -26°C(-15°F)
• Density: 1.186; 1.186 g/mL at 25 °C(lit.)

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Flammable (F); X; Irritant (Xi)
• UN Number: 3399; UN3399
• German water hazard class: 3
• Hazard Class: 4.3
• Packing Group: 2; II
• Risk Statements: 11-14-19-22-36/37/38; 11-19-36/37
• Safety Statements: 16-26; 16-26-36; 8-16-26-30-33-36/37-60
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• Main Hazard: Flammable, may form explosive peroxides and reacts violently with water
• GHS Hazard statements: H225-H261-H351-H302-H315-H319-H335; H225-H318-H335
• GHS Precautionary statements: P210-P231+P232-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338
• RID/ADR: UN 3399 4.3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.

Product Information

• Purity: 20% w/w suspension in THF
• Concentration: 20 wt. % suspension in THF
• Empirical Formula (Hill Notation): C6H12Br2OZn3

DETAILS

Sigma Aldrich - 381985

Application
Useful reagent for the methylenation of ketones and α-ketols.
Reactant for:
• Synthesis of amphidinolide T3 using a ring-closing metathesis and asymmetric dihydroxylation strategy1
• Methylenation of carbonyl compounds2
• Olefination reactions3
Packaging
100 g in glass bottle