Dicoumarol

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Names

[ CAS No. ]:
66-76-2

[ Name ]:
Dicoumarol

[Synonym ]:
Acavyl
Antitrombosin
Coumarin, 3,3'-methylenebis[4-hydroxy-
Dufalone
Cumid
Trombosan
3,3'-Methylenebis[4-hydroxycoumarin]
4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
Baracoumin
Dicoumal
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
Temparin
Dicuman
3,3’-methylenebis(4-hydroxy-2H-1-benzopyran-2-one)
4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-
3,3’-methylenebis(4-hydroxycoumarin)
Dicumarol
Bishydroxycoumarin
3,3'-Methylene-bis(4-hydroxycoumarin)
EINECS 200-632-9
Dicoumarol
3,3’-methylenebis(4-hydroxy-2H-chromen-2-one)
Dicoumarin
3,3'-Methylenebis(4-hydroxy-2H-chromen-2-one)
3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one]
Acadyl
3,3’-methylenebis[4-hydroxy-2H-1-benzopyran-2-one]
Dicumarine
MFCD00006857
Kumoran
Melitoxin
3,3'-methylenebis(4-hydroxycoumarin)

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
620.7±55.0 °C at 760 mmHg

[ Melting Point ]:
290-292 °C(lit.)

[ Molecular Formula ]:
C₁₉H₁₂O₆

[ Molecular Weight ]:
336.295

[ Flash Point ]:
231.9±25.0 °C

[ Exact Mass ]:
336.063385

[ PSA ]:
100.88000

[ LogP ]:
3.55

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.731

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GN7875000

CHEMICAL NAME :: Coumarin, 3,3'-methylenebis(4-hydroxy-

CAS REGISTRY NUMBER :: 66-76-2

BEILSTEIN REFERENCE NO. :: 0335444

LAST UPDATED :: 199706

DATA ITEMS CITED :: 23

MOLECULAR FORMULA :: C19-H12-O6

MOLECULAR WEIGHT :: 336.31

WISWESSER LINE NOTATION :: T66 BOVJ EQ D1- DT66 BOVJ EQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SMWOAS Schweizerische Medizinische Wochenschrift. (Schwabe & Co., Steintorst 13, 4010 Basel, Switzerland) V.50- 1920- Volume(issue)/page/year: 83,471,1953

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 52 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - ulcerated nasal septum Gastrointestinal - ulceration or bleeding from large intestine

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 50,228,1942

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 233 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - ulcerated nasal septum Gastrointestinal - ulceration or bleeding from large intestine

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 50,228,1942

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 91 mg/kg

TOXIC EFFECTS :: Cardiac - other changes Vascular - pulse pressure increase

REFERENCE :: DIPHAH Dissertationes Pharmaceuticae. (Warsaw, Poland) V.1-17, 1949-65. For publisher information, see PJPPAA. Volume(issue)/page/year: 17,163,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(1),360,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 42 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 222,107,1954

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 27ZIAQ "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973 Volume(issue)/page/year: -,57,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 75 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 222,107,1954

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 22 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 222,107,1954

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 59 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - ulcerated nasal septum Gastrointestinal - ulceration or bleeding from large intestine

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 50,228,1942 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 112 mg/kg/30D-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - acute pulmonary edema Blood - hemorrhage Related to Chronic Data - death

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 50,228,1942

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 180 mg/kg/30D-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - acute pulmonary edema Blood - hemorrhage Related to Chronic Data - death

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 50,228,1942

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 127 mg/kg/7D-I

TOXIC EFFECTS :: Related to Chronic Data - death

REFERENCE :: DIPHAH Dissertationes Pharmaceuticae. (Warsaw, Poland) V.1-17, 1949-65. For publisher information, see PJPPAA. Volume(issue)/page/year: 17,163,1965

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 150 mg/kg/30D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - acute pulmonary edema Blood - hemorrhage Related to Chronic Data - death

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 50,228,1942

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 20 mg/kg/4D-I

TOXIC EFFECTS :: Related to Chronic Data - death

REFERENCE :: DIPHAH Dissertationes Pharmaceuticae. (Warsaw, Poland) V.1-17, 1949-65. For publisher information, see PJPPAA. Volume(issue)/page/year: 17,163,1965

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 4200 ug/kg/42D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - acute pulmonary edema Blood - hemorrhage Related to Chronic Data - death

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 50,228,1942 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 110 mg/kg

SEX/DURATION :: female 31-40 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - other neonatal measures or effects

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 57,965,1949

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 28 mg/kg

SEX/DURATION :: female 28-30 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 77,1135,1959 *** REVIEWS *** TOXICOLOGY REVIEW PLMJAP Pahlavi Medical Journal. (Shiraz, Iran) V.1-9, 1970-78. Volume(issue)/page/year: 6,160,1975 TOXICOLOGY REVIEW AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 77,1135,1959 TOXICOLOGY REVIEW NYSJAM New York State Journal of Medicine. (Medical Soc. of the State of New York, POB 5405, Lake Success, NY 11042) V.1- 1901- Volume(issue)/page/year: 64,493,1964 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83988 No. of Facilities: 33 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 297 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H372-H411

[ Precautionary Statements ]:
P260-P301 + P312 + P330

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T,N

[ Risk Phrases ]:
R22;R48/25;R51/53

[ Safety Phrases ]:
37-45-61

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
GN7875000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

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Ethylidene dicoumarol
Dicoumarol derivative,7
Dicoumarol derivative,2
1-(2-methoxyphenyl)dicoumarol
symmetric dicoumarol analogue,2
symmetric dicoumarol analogue,5
1-(1-(Benzo[d]oxazol-2-yl)pyrrolidine-2-carbonyl)-4-phenylpiperidine-4-carbonitrile
(1-(Benzo[d]oxazol-2-yl)pyrrolidin-2-yl)(4-(methylsulfonyl)piperazin-1-yl)methanone
5-((Phenylamino)methyl)picolinimidamide dihydrochloride
(1-(benzo[d]oxazol-2-yl)pyrrolidin-2-yl)(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone
N-(4-chlorophenethyl)-3-(pyridin-2-yloxy)benzamide
N-(2-oxo-2H-chromen-3-yl)-3-(pyridin-2-yloxy)benzamide
N-(isoxazol-3-yl)-3-(pyridin-2-yloxy)benzamide
N-(4,5-dihydrothiazol-2-yl)-3-(pyridin-2-yloxy)benzamide
N-(2-methoxyphenethyl)-3-(pyridin-2-yloxy)benzamide
Ethyl 4-amino-5-iodonicotinate

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