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Gold's Reagent
(CAS RN:20353-93-9 Product Number:G0393)

Structure

Gold's Reagent
Synonym [[[(Dimethylamino)methylene]amino]methylene]dimethylammonium Chloride

General Information

Product Number G0393

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Purity/Analysis Method >97.0%(HPLC)(T)
Storage Temperature
M.F. / M.W. C6H14ClN3=163.65
CAS RN 20353-93-9
Related CAS RN
MDL Number MFCD00011793
Packaging and Container
  • Product Details
  • Safety & Regulations
  • Reference & Application

Specification

Purity(HPLC) min. 97.0 area%
Purity(Nonaqueous Titration) min. 97.0 %
Melting point 97.0 to 101.0 deg-C

References

Reaxys-RN 4020194
PubChem SID 253660184

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :If on skin: Wash with plenty of soap and water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Application

Synthesis of 4-Hydroxyquinazolines Using Gold’s Reagent

G0393, A0262

A dry, three-necked, round-bottomed flask is equipped with a condenser, thermometer, magnetic stirrer and is placed under a nitrogen atmosphere. Into the flask is placed 100 mL of dry dioxane and 6.8 g (0.05 mol) of 2-aminobenzamide and 9.9 g (0.061 mol) of Gold’s reagent. The resulting mixture is refluxed overnight and subsequently cooled to room temperature. Anhydrous sodium acetate (4.1 g, 0.05 mol) and glacial acetic acid (2 mL) are added and the resulting mixture is refluxed for 3 hr, cooled to room temperature, and the solvent is removed in vacuo. The solid residue is collected by vacuum filtration with the aid of a small amount (15 mL) of water. The solid is vacuum dried to yield 4.9 g (67% yield) of 4-hydroxyquinazoline.

References

Formylation Reaction Using Gold’s Reagent

G0393

A round-bottomed flask is equipped with a magnetic stirrer, condenser and placed under a nitrogen atmosphere. The apparatus is flame dried and 8.3 g (0.05 mol) of Gold’s reagent is introduced along with 100 mL of dry THF. The mixture is cooled in an ice-water bath and 34 mL (0.054 mol) of a 1.6 M solution of n-octylmagnesium bromide in THF is added dropwise via syringe. The resulting mixture is refluxed for several hours and stirred overnight at room temperature. The reaction mixture is cooled in an ice-water bath and 70 mL of 10% aqueous hydrochloric acid is added. After stirring for 15 min, the mixture is neutralized with solid sodium bicarbonate and extracted with chloroform (3 x 80 mL). The combined chloroform extracts are dried over anhydrous sodium sulfate and concentrated to give 9.0 g of a brown oil. This material is distilled (Kugelrohr) to yield 5.6 g (79% yield) of a yellow oil.

References

Synthesis of 5-Membered Heterocyclic Rings Using Gold’s Reagent

G0393

References

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