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54-36-4

Basic Information
CAS No.: 54-36-4
Name: METYRAPONE
Article Data: 8
Molecular Structure:
Molecular Structure of 54-36-4 (METYRAPONE)
Formula: C14H14 N2 O
Molecular Weight: 226.278
Synonyms: 1-Propanone,2-methyl-1,2-di-3-pyridyl- (6CI,8CI); 1,2-Bis(3-pyridyl)-2-methyl-1-propanone;2-Methyl-1,2-bis(3-pyridyl)-1-propanone; 2-Methyl-1,2-di(b-pyridyl)-1-propanone;2-Methyl-1,2-di-3-pyridyl-1-propanone; Mepyrapone; Methapyrapone;Methbipyranone; Methopirapone; Methopyrapone; Methopyrinine; Methopyrone;Metopiron; Metopirone; Metopyrone; Metroprione; Metyrapon; Metyrapone; NSC25265; Su 4885
EINECS: 200-206-2
Density: 1.12g/cm3
Melting Point: 52-55 °C(lit.)
Boiling Point: 384.4°Cat760mmHg
Flash Point: 189.3°C
Hazard Symbols: Xn
Risk Codes: 22-36/37/38
Safety: Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
PSA: 42.85000
LogP: 2.63710
Synthetic route

meso-2,3-di-(3-pyridyl)-2,3-butanediol

A

54-36-4

metyrapone

B

33977-49-0

3,3-di-pyridin-3-yl-butan-2-one

C

96953-46-7

3,3'-(1,2-bis-methylene-ethane-1,2-diyl)-bis-pyridine

D

(Z)-2,3-Di-pyridin-3-yl-4-sulfooxy-but-2-ene-1-sulfonic acid; compound with ammonia

Conditions
ConditionsYield
With sulfuric acid for 70h; Further byproducts given;A 22%
B 38%
C 13%
D 14%
4989-59-7

2,3-di-3-pyridyl-2,3-butanediol

A

54-36-4

metyrapone

B

33977-49-0

3,3-di-pyridin-3-yl-butan-2-one

Conditions
ConditionsYield
With sulfuric acid

meso-2,3-di-(3-pyridyl)-2,3-butanediol

A

54-36-4

metyrapone

B

33977-49-0

3,3-di-pyridin-3-yl-butan-2-one

Sulfuric acid mono-((1R,2S)-2-hydroxy-1-methyl-1,2-di-pyridin-3-yl-propyl) ester

D

Sulfuric acid mono-((1S,2R)-1-methyl-1,2-di-pyridin-3-yl-2-sulfooxy-propyl) ester

Conditions
ConditionsYield
With sulfuric acid at 23℃; Product distribution; Further Variations:; Reagents;

rac-2,3-di-(3-pyridyl)-2,3-butanediol

A

54-36-4

metyrapone

B

96953-46-7

3,3'-(1,2-bis-methylene-ethane-1,2-diyl)-bis-pyridine

Sulfuric acid mono-((1R,2R)-2-hydroxy-1-methyl-1,2-di-pyridin-3-yl-propyl) ester

Sulfuric acid mono-((1R,2R)-1-methyl-1,2-di-pyridin-3-yl-2-sulfooxy-propyl) ester

Conditions
ConditionsYield
With sulfuric acid at 23℃; Product distribution; Further Variations:; Reagents; Temperatures;
350-03-8

methyl-3-pyridylketone

54-36-4

metyrapone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: isopropyl alcohol; acetic acid / Einwirkung von UV-Licht
2: concentrated H2SO4
View Scheme
626-55-1

3-Bromopyridine

51227-29-3

2-methyl-1-(pyridin-3-yl)propan-1-one

54-36-4

metyrapone

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In tetrahydrofuran for 3.5h; Inert atmosphere; Reflux;

[Ru(2,2′-bipyridine)2(2-methyl-1,2-di-3-pyridil-1-propanone)2](PF6)2

75-05-8

acetonitrile

A

54-36-4

metyrapone

B

55124-54-4

bis(acetonitrile)bis(2,2'-bipyridine)ruthenium(II) hexafluorophosphate

Conditions
ConditionsYield
for 1h; Kinetics; Time; UV-irradiation;

[Ru(2,2′-bipyridine)2(2-methyl-1,2-di-3-pyridil-1-propanone)2](PF6)2

A

54-36-4

metyrapone

B

[Ru(2,2′-bipyridine)2(2-methyl-1,2-di-3-pyridil-1-propanone)(H2O)](PF6)2

Conditions
ConditionsYield
for 0.0166667h; Kinetics; Time; UV-irradiation;
Conditions
ConditionsYield
With sodium tetrahydroborate Reduction;100%
With sodium tetrahydroborate In methanol Reduction;
With human liver dihydrodiol dehydrogenase 4; NADPH In phosphate buffer at 25℃; pH=6.0; Enzyme kinetics; Further Variations:; Reagents;
54-36-4

metyrapone

1,3-dioxoisoindoline-2-yl-2-acetylamino-3-methylbutyrate

(S)-N-(2-methyl-1-(5-(2-methyl-2-(pyridin-3-yl)propanoyl)pyridin-2-yl)propyl)acetamide

Conditions
ConditionsYield
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In 1,4-dioxane for 14h; Minisci Aromatic Substitution; Irradiation; enantioselective reaction;70%
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Chemistry

Product Name: Metyrapone (CAS NO.54-36-4)


Molecular Formula: C14H14N2O
Molecular Weight: 226.27g/mol
Mol File: 54-36-4.mol
Einecs: 200-206-2
Melting Point: 52-55 °C(lit.)
Boiling point: 384.4 °C at 760 mmHg
Flash Point: 189.3 °C
Density: 1.12 g/cm3
Surface Tension: 45.4 dyne/cm
Enthalpy of Vaporization: 63.3 kJ/mol
Vapour Pressure: 4.11E-06 mmHg at 25°C
XLogP3-AA: 2
H-Bond Donor: 0
H-Bond Acceptor: 3
Structure Descriptors of Metyrapone (CAS NO.54-36-4):
  IUPAC Name: 2-methyl-1,2-dipyridin-3-ylpropan-1-one
  Canonical SMILES: CC(C)(C1=CN=CC=C1)C(=O)C2=CN=CC=C2
  InChI: InChI=1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,1-2H3 
  InChIKey: FJLBFSROUSIWMA-UHFFFAOYSA-N
Product Categories: Cytochrome P450 isozyme

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 subcutaneous 531mg/kg (531mg/kg)   Cesko-Slovenska Farmacie. Vol. 26, Pg. 140, 1977.
mouse LDLo intraperitoneal 300mg/kg (300mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 146, Pg. 395, 1964.
rat LD50 oral 521mg/kg (521mg/kg)   Drugs in Japan Vol. 6, Pg. 827, 1982.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Safety Information of Metyrapone (CAS NO.54-36-4):
Hazard Codes: XnHarmful
Risk Statements: 22-36/37/38
22:  Harmful if swallowed 
36:  Irritating to the eyes 
37:  Irritating to the respiratory system 
38:  Irritating to the skin 
Safety Statements: 26
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

Specification

 Metyrapone ,its CAS NO. is 54-36-4,the synonyms is 1,2-Di-3-pyridyl-2-methyl-1-propanone ; 1-Propanone, 1,2-di-3-pyridyl-2-methyl- ; 1-Propanone, 2-methyl-1,2-di-3-pyridinyl- ; 2-Methyl-1,2-bis(3-pyridyl)-1-propanone ; 2-Methyl-1,2-di-3-pyridyl-1-propanone ; EINECS 200-206-2 ; HSDB 2500 ; Methapyrapone ; Metyraponum ; NSC 25265 ; UNII-ZS9KD92H6V .