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Chemical Structure| 58-27-5 Chemical Structure| 58-27-5
Chemical Structure| 58-27-5

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CAS No.: 58-27-5

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Menadione, a synthetic naphthoquinone, can be converted to active vitamin K2 in vivo.

Synonyms: Vitamin K3; NSC 4170; Menadione bisulfite

4.5 *For Research Use Only !

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Product Details of Menadione

CAS No. :58-27-5
Formula : C11H8O2
M.W : 172.18
SMILES Code : O=C(C1=C2C=CC=C1)C=C(C)C2=O
Synonyms :
Vitamin K3; NSC 4170; Menadione bisulfite
MDL No. :MFCD00001681
InChI Key :MJVAVZPDRWSRRC-UHFFFAOYSA-N
Pubchem ID :4055

Safety of Menadione

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Menadione

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 58-27-5 ]

[ 58-27-5 ] Synthesis Path-Downstream   1~4

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YieldReaction ConditionsOperation in experiment
69% With hydrogenchloride; sodium azide; In methanol; at 50℃; for 5.0h;pH 4.0;Inert atmosphere; 2-amino-3-methyl-l,4-naphthoquinone (le). Dissolved 2-methyl-l,4-naphthoquinone (560 mg, 3.3 mmol) in methanol (30 mL) and placed under inert atmosphere. Dissolved 1.37 g NaN3 in 10 mL water and acidified to pH 4 (83 drops of 12 M HC1). Added sodium azide solution to reaction flask and slowly heated reaction to 50C and then stirred for 5 hrs. Reaction was quenched with water and extracted with ethyl acetate (2x) The organic layers were combined and washed with saturated NaCl solution, dried with Mg2S04, and concentrated in vacuo. The reaction was purified on silica gel eluting with ethyl acetate and hexane (3 :7) to yield 423 mg orange powder le (69% yield). MS m/z calcd (M+) 188.07, found 188.04. 1H NMR (400 MHz, DMSO-d6) Shift 7.96 - 8.03 (m, 2H), 7.83 (dt, J = 1.25, 7.53 Hz, 1H), 7.71 - 7.78 (m, 1H), 6.86 (s, 2H), 1.97 (s, 3H). C13-HSQC (400 MHz, DMSO-d6) Shift 0.53, 28.28, 9.45, 39.58, 132.22, 125.73, 134.80, 125.94, 125.93, 134.81.
35% With trimethylsilylazide; at 20℃; for 216.0h; So a suspension of 2- methylnaphthalene- 1 ,4-dione (173 mg, l.O mmol) was added azidotrimethylsilane (134 1.0 mmol) and the mixture was stirred at room temperature for 9 days, after which time 0.2 M aq. citric acid (10 mL) was added and stirred 30 min. The insoluble material was collected via vacuum filtration and the solids washed with water and dried in vacuo and purified via MPLC (silica, 0-6% MeOH/CH2Cl2). Yield: 66 mg, 35%. lR NMR (400 MHz, DMSO-i δ 7.93 (dd, J = 7.6, 1.4 Hz, 2H), 7.77 (td, J= 7.6, 1.3 Hz, 1H), 7.68 (td, J= 7.5, 1.4 Hz, 1H), 6.78 (s, 2H), 1.92(s, 3H); C NMR (126 MHz, DMSO) δ 181.30, 146.91, 134.39, 132.97, 132.03, 130.20, 125.39, 110.38, 9.62; HRMS (ESI-TOF) m/z: [M + H]+ Calcd for CnH10NO2 188.0706; Found 188.0695
With hydrogenchloride; sodium azide; In ethanol; water; for 36.0h;pH 4.0;Reflux; General procedure: To a previously stirred solution of 2 g of 1 in 100 mL of ethanol was added 4.74 g of sodiumazide in 34 mL of distilled water, then adjusted to pH 4 with HCl and allowed to stir for 15 h at refluxtemperature. After completion of the reaction time, extraction was performed with ethyl acetate (3 x 100 mL). The organic extracts were washed with saline solution, dried over anhydrous Na2SO4 andconcentrated. The residue was crystallized from a mixture of diethyl ether/hexane to afford an orangepowder; 90% yield
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  • 2-((4-bromophenoxy)methyl)-3-methylnaphthalene-1,4-dione [ No CAS ]
 

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