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58-27-5

Basic Information
CAS No.: 58-27-5
Name: Menadione
Article Data: 233
Cas Database
Molecular Structure:
Molecular Structure of 58-27-5 (Menadione)
Formula: C11H8O2
Molecular Weight: 172.183
Synonyms: 1,4-Naphthalenedione,2-methyl-;2-Methyl-1,4-naphthalenedione;Kipca;VK3;Karcon;Kayklot;Kanone;Kayquinone;Memodol;Menaquinone 0;Kappaxin;Aquakay;2-Methylnaphthoquinone;Menadionum;Klottone;Kappaxin (TN);3-Methyl-1,4-naphthoquinone;K-Thrombyl;2-Methyl-1,4-naphthochinon [German];Synkay;Methyl-1,4-naphthoquinone;Methyl-1,4-naphthalenedione;Usaf ek-5185;Kappaxan (VAN);Mitenone;2-Methyl-1,4-naftochinon [Czech];Prestwick_313;Menadion;2-Methyl-1,4-naphthochinon;Vitamin K3;1,4-Naphthoquinone, 2-methyl-;Juva-K;1,4-Naphthalenedione, 2-methyl-;Riboflavin (Vitamin B2);Kolklot;Vitamin K2 (0);Hemodal;1, 4-Naphthoquinone, 2-methyl-;Koaxin;Menaphthone;Kaykot;Menaphthon;MNQ;Kaergona;2-methyl-1,4-dihydronaphthalene-1,4-dione;
EINECS: 200-372-6
Density: 1.225 g/cm3
Melting Point: 105-107 °C(lit.)
Boiling Point: 304.5 °C at 760 mmHg
Flash Point: 113.8 °C
Solubility: insoluble in water
Appearance: bright yellow crystals
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38-43
Safety: 26-36-37/39-24
Transport Information: N/A
PSA: 34.14000
LogP: 2.01190
Synthetic route
481-85-6

2-methyl-1,4-naphthohydroquinone

58-27-5

menadione

Conditions
ConditionsYield
With iodate form of Amberlyst A26 In dichloromethane at 20℃; for 2h; further reagent;100%
With sulfuric acid; sodium bromide In dichloromethane; water at 15℃; for 2.98h; Electrolysis;99%
With carbon dioxide; oxygen In water at 35 - 60℃; under 57005.7 - 62256.2 Torr; for 0.0833333h; Autoclave;96%
7469-77-4

2-methylnaphthalen-1-ol

58-27-5

menadione

Conditions
ConditionsYield
With Co(salN-Medpt); oxygen In acetonitrile for 0.5h;100%
Stage #1: 2-methylnaphthalen-1-ol In acetonitrile at 74.84℃;
Stage #2: With dihydrogen peroxide In acetonitrile for 0.75h; Reflux; chemoselective reaction;
97.3%
With sulfuric acid; dihydrogen peroxide In water at 36 - 40℃; for 6h; Temperature; Solvent; Green chemistry;94.7%
91-57-6

2-Methylnaphthalene

58-27-5

menadione

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In water at 75℃; for 5h; Product distribution / selectivity;100%
With C69H63Cl6N3O9(3-)*1.5Cu(2+); acetic acid In water at 40 - 100℃; for 14h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration;93%
With dihydrogen peroxide; acetic acid In acetonitrile Catalytic behavior; Solvent; Reflux;93%

2-methyl-5,6,9,10-tetrahydro-1,4-naphthoquinone

58-27-5

menadione

Conditions
ConditionsYield
With palladium 10% on activated carbon In acetone for 24h; Reflux; Inert atmosphere;100%
With sodium dichromate; sulfuric acid; acetic acid a) 80-90 deg C, 1 h, b) RT, 12 h;93%
With manganese(II) bromide; copper(I) bromide In dimethyl sulfoxide at 85℃; under 600.06 Torr; for 26h; Temperature;91.3%
92071-59-5

C11H10O2

58-27-5

menadione

Conditions
ConditionsYield
With palladium 10% on activated carbon In acetone Reflux;100%
130-37-0

Hykinone

58-27-5

menadione

Conditions
ConditionsYield
With sodium hydroxide In chloroform; water at 20℃; Product distribution / selectivity;100%
With water; sodium carbonate at 25℃; for 120h; Time;
3090-46-8

2-methyl-5,8-dihydro-1,4-naphthalenediol

58-27-5

menadione

Conditions
ConditionsYield
With carbon dioxide; oxygen In water at 37 - 80℃; under 60756.1 - 69757 Torr; for 0.125h; Pressure; Temperature; Autoclave;98.4%
With lithium perchlorate In acetonitrile; tert-butyl alcohol at 16 - 18℃; for 8.6h; electrolysis on Pt electrodes;94%
With chromium(VI) oxide; acetic acid at 20℃;
16368-80-2

2-methyl-5,6,7,8-tetrahydronaphthalene-1,4-diol

58-27-5

menadione

Conditions
ConditionsYield
With carbon dioxide; oxygen In water at 37 - 80℃; under 58505.9 - 72007.2 Torr; for 0.111111h; Autoclave;95.7%
53772-19-3

1,4-dimethoxy-2-methylnaphthalene

58-27-5

menadione

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 0.166667h; Oxidation; Demethylation;94%
With bis-[(trifluoroacetoxy)iodo]benzene In methanol; water at 20℃; for 0.5h;92%
With tert.-butylhydroperoxide; poly(bis-1,2-phenylene) diselenide In tert-butyl alcohol at 80℃; for 12h;90%
With ammonium persulfate; silver nitrate In water; acetonitrile for 18h; Ambient temperature;56%
131-11-3

phthalic acid dimethyl ester

tert-butyl 3-cyanobutanoate

58-27-5

menadione

Conditions
ConditionsYield
Stage #1: phthalic acid dimethyl ester; tert-butyl 3-cyanobutanoate With potassium tert-butylate In toluene at 100 - 105℃; for 3h; Green chemistry;
Stage #2: With sodium hydroxide In water; toluene at 20 - 30℃; for 3h; Green chemistry;
Stage #3: With hydrogenchloride In water; toluene at 60℃; for 3h; pH=2 - 2.5; Green chemistry;
92.3%
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    CAS no:58-27-5 EINECS no:200-372-6 Synonym:Menadione (1.05793); Vitamin K2(0); Vitamin K3; menaphthone; Menadione; Vitamin K_3; 2-Methyl-1,4-dihydronaphthalene-1,4-dione MF:C11H8O2 MW:172.18 MP:105-108°C Appearance: White crystalline powd

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  • 2-METHYL-1,4-NAPHTHOQUINONE

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Chemistry

IUPAC Name: 2-methylnaphthalene-1,4-dione 
Empirical Formula: C11H8O2
Molecular Weight: 172.18g/mol
EINECS: 200-372-6
Structure of Menadione (CAS NO.58-27-5):

Index of Refraction: 1.592
Molar Refractivity: 47.6 cm3
Molar Volume: 140.5 cm3
Polarizability: 18.87×10-24cm3
Surface Tension: 46.4 dyne/cm
Density: 1.225 g/cm3
Flash Point: 113.8 °C
Enthalpy of Vaporization: 54.49 kJ/mol 
Melting Point: 105-107 °C(lit.)
Boiling Point: 304.5 °C at 760 mmHg
Vapour Pressure: 0.000871 mmHg at 25°C 
Solubility: oil: soluble
Form: crystalline
Color: yellow
Water Solubility: INSOLUBLE
Sensitive: Light Sensitive 
Stability: Stable. May be light sensitive. Incompatible with strong oxidizing agents. 
Product Categories: Biochemistry;Vitamins;Nutritional fortification substances;Vitamins and derivatives;Vitamin Ingredients;Miscellaneous Compounds 
Canonical SMILES: CC1=CC(=O)C2=CC=CC=C2C1=O
InChI: InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChIKey: MJVAVZPDRWSRRC-UHFFFAOYSA-N

Uses

 Menadione (CAS NO.58-27-5) is used as a source of vitamin K in the treatment of hypoprothrombinemia against vitamin K deficiency.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LDLo intraperitoneal 100mg/kg (100mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 43, Pg. 125, 1940.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral 500mg/kg (500mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 43, Pg. 125, 1940.
mouse LD50 subcutaneous 138mg/kg (138mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 111, 1942.
rabbit LDLo oral 230mg/kg (230mg/kg) VASCULAR: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 111, 1942.
rat LD50 intraperitoneal 75mg/kg (75mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-43
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R43:May cause sensitization by skin contact.
Safety Statements: 26-36-37/39-24
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection. 
S24:Avoid contact with skin.
WGK Germany: 3
RTECS: QL9100000
F: 8
Poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental teratogenic effects. Questionable carcinogen with experimental tumorigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Standards and Recommendations

IDENTIFICATION: Conforms
ASSAY: 98.5 - 101.5%
RESIDUE ON IGNITION: 0.1% max
LOSS ON DRYING: 0.5% max
HEAVY METALS: 20ppm max

Specification

  Menadione , its cas register number is 58-27-5. It also can be called 1,4-Naphthalenedione, 2-methyl- ; 2-Methyl-1,4-naphthochinon ; 2-Methylnaphthoquinone ; 3-Methyl-1,4-naphthoquinone ; Aquakay ; Aquinone ; Kayquinone ; Kipca ;
 Kipca-oil soluble ; Memodol ; Menaquinone ; Mitenon ; Mitenone ; Panosine ; Thyloquinone ; Vitamin K3 . Menadione (CAS NO.58-27-5) is a bright yellow crystals.