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CAS RN: 20353-93-9 | Product Number: G0393

Gold's Reagent

Purity: >97.0%(T)(HPLC)
  • [[[(Dimethylamino)methylene]amino]methylene]dimethylammonium Chloride
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Product Number G0393
Purity / Analysis Method >97.0%(T)(HPLC)
Molecular Formula / Molecular Weight C__6H__1__4ClN__3 = 163.65  
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Hygroscopic
CAS RN 20353-93-9
Reaxys Registry Number 4020194
PubChem Substance ID 253660184
MDL Number


Appearance Light orange to Yellow to Green powder to crystal
Purity(HPLC) min. 97.0 area%
Purity(Nonaqueous Titration) min. 97.0 %
Melting point 97.0 to 101.0 °C
Properties (reference)
Melting Point 99 °C
Solubility (soluble in) Methanol
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
Related Laws: / Compliance with laws, Regulations
Transport Information:
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.


Formylation Reaction Using Gold’s Reagent


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.


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


1)One Atom Lynch Pin Transformations of Gold's Reagent

J. T. Gupton, K. F. Correia, B. S. Foster, Synth. Commun. 1986, 16, 365.

2)New Synthesis of 1,5-Disubstituted Imidazoles

Kirchlechner, M. Casutt, U. Heywang, M. W. Schwarz, Synthesis 1994, 247.

PubMed Literature

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