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57-41-0

Basic Information
CAS No.: 57-41-0
Name: 5,5-Diphenylhydantoin
Article Data: 79
Molecular Structure:
Molecular Structure of 57-41-0 (5,5-Diphenylhydantoin)
Formula: C15H12N2O2
Molecular Weight: 252.272
Synonyms: Hydantoin,5,5-diphenyl- (8CI);5,5-Diphenyl-1H-imidazolidine-2,4-dione;5,5-Diphenyl-2,4-imidazolidinedione;Aleviatin;DPH;Di-Lan;Dilabid;Dintoina;Diphantoin;Diphedan;Diphenat;Diphenylan;Ekko;Hidantal;Hydantol;Lehydan;NSC 8722;Phenytoin;Phenytoine;Sodanton;Zentropil;
EINECS: 200-328-6
Density: 1.258 g/cm3
Melting Point: 293-295 °C(lit.)
Boiling Point: 428.2°C at 760 mmHg
Flash Point: 11°C
Solubility: <0.01 g/100 mL at 19 °C in water
Appearance: white crystals or powder
Hazard Symbols: ToxicT, HarmfulXn, FlammableF
Risk Codes: 45-61-22-63-40-39/23/24/25-23/24/25-11-20/21/22
Safety: 53-45-36/37-16-7
Transport Information: UN 2811
PSA: 58.20000
LogP: 2.42720
Synthetic route
1097-57-0

ethyl 3-(5,5-diphenylhydantoin) formate

57-41-0

phenythoin

Conditions
ConditionsYield
With hydrazine hydrate In ethanol Heating;100%
21083-47-6

5,5-diphenyl-2-thioxoimidazolidin-4-one

57-41-0

phenythoin

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydrogencarbonate at 24℃; for 0.5h;100%
With tetrabromoglycoluril In ethanol at 40℃; for 0.166667h; Reagent/catalyst; Green chemistry;99%
With dihydrogen peroxide; acetic acid In water; N,N-dimethyl-formamide at 20℃; for 24h;92%
134-81-6

benzil

57-41-0

phenythoin

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃; for 0.05h; Sonication;98%
With chitosan decorated Fe3O4 magnetic nanoparticles In ethanol; water at 60℃; for 0.133333h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Green chemistry;98%
With dmap; potassium hydroxide In water; butan-1-ol at 119℃; for 0.666667h; Temperature;98.2%
134-81-6

benzil

A

5157-15-3

3a,6a-diphenylglycoluril

B

57-41-0

phenythoin

Conditions
ConditionsYield
With sodium hydroxide for 0.0333333h; Microwave irradiation; neat (no solvent);A 1.6%
B 98%
With potassium hydroxide In ethanol at 40℃; for 2h; Ultrasound irradiation;A 75%
B 14%
With potassium hydroxide In methanol at 64.84℃; for 24h;A n/a
B 61%

1-(Aminoacetyl)-5,5-diphenylimidazolidine-2,4-dione hydrochloride

57-41-0

phenythoin

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;93%
Multi-step reaction with 3 steps
1: 55 percent / 4 h / Heating
2: 71 percent / conc. aq. NH3 / ethanol / 24 h / Ambient temperature
3: 63 percent / 2percent aq. HCl / ethanol / 50 h / Heating
View Scheme
134-81-6

benzil

57-41-0

phenythoin

Conditions
ConditionsYield
With urea; sodium hydroxide In ethanol; water at 80℃; for 3h; Temperature; Large scale;91.4%
120-89-8

parabanic acid

71-43-2

benzene

57-41-0

phenythoin

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 100℃; for 2h;87%
1097-57-0

ethyl 3-(5,5-diphenylhydantoin) formate

A

1224-08-4

3-amino-5,5-diphenylimidazolidine-2,4-dione

B

57-41-0

phenythoin

Conditions
ConditionsYield
With hydrazine hydrate at 130 - 140℃; for 4h;A 9%
B 86%

potassium cyanide

119-61-9

benzophenone

506-87-6

ammonium carbonate

57-41-0

phenythoin

Conditions
ConditionsYield
In ethanol; water Heating;85%
With iron(III) oxide In neat (no solvent) at 70℃; for 0.9h; Bucherer-Bergs Reaction;85%
In ethanol; water for 0.166667h; Time; Bucherer-Bergs Reaction; Microwave irradiation;84%
In ethanol at 60℃; for 15h;
1118-02-1

trimethylsilyl isocyanate

93504-24-6

α,α-diphenylglycine methyl ester hydrochloride

57-41-0

phenythoin

Conditions
ConditionsYield
Stage #1: trimethylsilyl isocyanate; α,α-diphenylglycine methyl ester hydrochloride In water for 8h; Milling; Green chemistry;
Stage #2: With caesium carbonate In water Milling; Green chemistry;
84%
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Chemistry

MF: C15H12N2O2
MW: 252.27
EINECS: 200-328-6
DIHYDANTOIN,it's melting point is about  293-295 °C(lit.);Water Solubility  :less than 0.01 g/100 mL at 19 oC.
Following is the of DIHYDANTOIN:

Uses

DIHYDANTOIN can be used in antiepileptic and antiarrhythmic medicine.

Toxicity Data With Reference

1.   

dnd-esc 50 µmol/L

   MUREAV    Mutation Research. 89 (1981),95.
2.   

dni-hmn:lym 360 µmol/L

   TXAPA9    Toxicology and Applied Pharmacology. 33 (1975),38.
3.   

mnt-mus-ivn 500 µg/kg

   MUREAV    Mutation Research. 141 (1984),183.
4.   

orl-wmn TDLo:1620 mg/kg (female 1-39W post):CAR,TER

   JAMAAP    JAMA, Journal of the American Medical Association. 244 (1980),1464.
5.   

orl-wmn TDLo:730 mg/kg/1Y-C:CAR,BLD

   NKGZAE    Nippon Ketsueki Gakkai Zasshi. Journal of Japan Haematological Society. 46 (1983),1.
6.   

unr-wmn TDLo:1620 mg/kg (female 1-39W post):CAR,TER

   JAMAAP    JAMA, Journal of the American Medical Association. 244 (1980),1464.
7.   

unr-wmn TDLo:1620 mg/kg (female 1-39W post):CAR,TER

   LANCAO    Lancet. 2 (1980),481.
8.   

orl-wmn TD:730 mg/kg/1Y-C:CAR,BLD

   NKGZAE    Nippon Ketsueki Gakkai Zasshi. Journal of Japan Haematological Society. 43 (1980),711.
9.   

orl-chd TD:6023 mg/kg/1Y-C:NEO,BLD,SKN

   AJDEBP    Australasian Journal of Dermatology. 22 (1981),28.
10.   

orl-chd TDLo:3 mg/kg/3W:SKN

   CLPTAT &n

RTECS : MU1050000

Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 319.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 , 1977,p. 201.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 , 1977,p. 201.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

Safety Profile

Confirmed carcinogen producing lymphoma, Hodgkin's disease, tumors of the skin and appendages. Experimental carcinogenic and tumorigenic data. A human poison by ingestion. Poison experimentally by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by an unspecified route. Experimental teratogenic and reproductive effects. Human systemic effects by ingestion: dermatitis, change in motor activity (specific assay), ataxia (loss of muscle coordination), degenerative brain changes, encephalitis, hallucinations, distorted perceptions, irritability, and jaundice. Human teratogenic effects by ingestion: developmental abnormalities of the central nervous system, cardiovascular (circulatory) system, musculoskeletal system, craniofacial area, skin and skin appendages, eye, ear, other developmental abnormalities. Effects on newborn include abnormal growth statistics (e.g., reduced weight gain), physical abnormalities, other postnatal measures or effects, and delayed effects. Human mutation data reported. A drug for the treatment of grand mal and psychomotor seizures. When heated to decomposition it emits toxic fumes of NOx.

Hazard Codes  T,Xn,F
Risk Statements  45-61-63-40-39/23/24/25-11-20/21/22
Safety Statements  53-45-36/37-16-7