82-66-6 Usage
Originator
Dipaxin,Upjohn,US,1955
Production Methods
Diphacinone is produced by condensation of 1,1-diphenyl
acetone with dimethyl phthalate in the presence of sodium
methoxide (30).
Manufacturing Process
A solution of sodium methoxide was prepared by adding 2.76 grams (0.12mol) of sodium to 50 ml of absolute methanol and gently warming the
mixture to effect complete solution of the sodium. To this was added 300
milliliters of dry benzene with vigorous stirring, whereafter excess methanol
was removed by concentrating the mixture to a volume of about 100 ml. To
the resulting sodium methoxide suspension was added a solution of 19.4
grams (0.1 mol) of dimethyl phthalate in 200 ml of dry benzene. The mixture
was heated to boiling and a solution of 21 grams (0.1 mol) of diphenylacetone
in 200 ml of dry benzene was added dropwise thereto. During addition
approximately 200 ml of liquid, which consisted of benzene together with
methanol formed during the course of the reaction, was distilled from the
reaction mixture. After addition of the diphenylacetone, the mixture was
heated under reflux for about 6 hours, cooled and stirred vigorously with 200
ml of 5% sodium hydroxide solution. The light yellow solid which separated was collected by filtration; the filtrate
was reserved for treatment as described below. Suspension in water of the
solid, which weighed 12 grams, and acidification of the mixture with dilute
hydrochloric acid produced a gum which soon crystallized. Recrystallization of
this solid from ethanol gave 10.2 grams (30%) of 2-diphenylacetyl-1,3-
indandione as a light yellow crystalline solid, which melted at 146-147°C.The filtrate mentioned above consisted of 3 layers. An oily layer which was
present between the aqueous and benzene layers was separated, acidified and
extracted with ether. The aqueous layer was likewise separated, acidified and
extracted with ether. The extracts were combined, dried and evaporated to
yield a heavy gum which was crystallized from ethanol to give an additional
2.5 grams of product which melted at 146-147°C. The total yield of 2-
diphenylacetyl-1,3-indandione was 12.7 grams (37%).
Therapeutic Function
Anticoagulant
Air & Water Reactions
Practically insoluble in water (17mg/L). Hydrolyzed by strong acid.
Reactivity Profile
DIPHACINONE is a ketone, and behaves as a weak acid. Forms water soluble alkali metal salts. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.
Health Hazard
DIPHACINONE is extremely toxic; probable oral lethal dose in humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful for a 150-lb. person. Many medical conditions will be aggravated by DIPHACINONE.
Fire Hazard
When heated to decomposition DIPHACINONE emits acrid smoke and fumes. Sensitive to light.
Trade name
DE-PESTER?[C]; DIDANDIN?;
DIPAXIN?; DITRAC?; GOLD CREST?; KILL-RO
RAT KILLER?; LIQUA-TOX?, diphacinone sodium
salt; ORAGULANT?; P. C. Q. ?; PID?; PROMAR?;
RAMIK?; RAT KILLER?; RODENT CAKE?[C];
SOLVAN?; TOMCAT?; U 1363?
Safety Profile
Poison by ingestion.
Inlxbits blood clotting, leading to
hemorrhages. Action similar to coumadin
(warfarin). A pesticide used in rodent
control. When heated to decomposition it
emits acrid smoke and irritating fumes
Metabolic pathway
Diphacinone is a member of the indandione class of anti-coagulants.
Its fate in rats and mice has been reported but no information on its
degradation in soil or plants has been published. It is metabolised by
hydroxylation and conjugation.
Degradation
Diphacinone is stable in solution at pH 6-9 for 14 days; it is hydrolysed in
less than 24 hours at pH 4 (PM). It is rapidly degraded under conditions of
aqueous photolysis (PM).
Check Digit Verification of cas no
The CAS Registry Mumber 82-66-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 2 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 82-66:
(4*8)+(3*2)+(2*6)+(1*6)=56
56 % 10 = 6
So 82-66-6 is a valid CAS Registry Number.
InChI:InChI=1/C23H16O3/c24-21-17-13-7-8-14-18(17)22(25)20(21)23(26)19(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14,19-20H
82-66-6Relevant articles and documents
A method for C2 acylation of 1,3-indandiones
Larsen, Brian J.,Rosano, Robert J.,Ford-Hutchinson, Thomas A.,Reitz, Allen B.,Wrobel, Jay E.
, p. 2762 - 2768 (2018/04/30)
The 1,3-indandione scaffold is an important structural motif used in the preparation of a large number of industrial chemical and pharmaceutical compounds. However, few approaches allow for the direct C2 acylation on these building blocks. A method was developed using DMAP and EDCI, which is mild in reactivity, covers a diverse range of carboxylic acid acylating agents, is compatible with electron releasing and withdrawing substituents on the 1,3-indandione partner, and performs well in a polar aprotic solvent (for solubility reasons) This method cleanly afforded twenty five different products in yields of 32–96%.
This product is a nationally controlled contraband or patented product, and the Lookchem platform doesn't provide relevant sales information.