6588-68-7

Basic information

• Product Name: 3,5-DiMethyl-1-nitroadaMantane
• Synonyms: 3,5-DiMethyl-1-nitroadaMantane;AdaMantane-2 (1-Nitro-3,5-DiMethyladaMantane);1,3-Dimethyl-5-nitroadamantane
• CAS NO: 6588-68-7
• Molecular Formula: C₁₂H₁₉NO₂
• Molecular Weight: 209.28476
• Mol File: 6588-68-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 278.275 °C at 760 mmHg
• Flash Point: 109.707 °C
• Appearance: /
• Density: 1.134 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: 3,5-DiMethyl-1-nitroadaMantane(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DiMethyl-1-nitroadaMantane(6588-68-7)
• EPA Substance Registry System: 3,5-DiMethyl-1-nitroadaMantane(6588-68-7)

Safety Data

• Hazardous Substances Data: 6588-68-7(Hazardous Substances Data)

Usage

Uses

1,3-Dimethyl-5-nitroadamantane is a potential neuroprotective agent which may aid in the treatment of neurodegenerative disorders such as parkinsons.

Synthetic route

1,3-dimethyladamantane (702-79-4) → 1-nitro-3,5-dimethyl-adamantane (6588-68-7)

Conditions	Yield
With N-hydroxyphthalimide; air; Nitrogen dioxide In various solvent(s) at 70℃; under 760 Torr; for 14h;	70%
With nitric acid In neat (no solvent) at 200℃; for 1.5h;	39%
With nitric acid; N-hydroxyphthalimide In various solvent(s) at 60℃; for 15h;

N-hydroxyphthalimide (524-38-9) + 1,3-dimethyladamantane (702-79-4) + α,α,α-trifluorotoluene (98-08-8) → 1-nitro-3,5-dimethyl-adamantane (6588-68-7)

Conditions	Yield
With Nitrogen dioxide	60%

1,3-dimethyladamantane (702-79-4) → 1,3-dimethyl-5-adamantanol (707-37-9) + 1-nitro-3,5-dimethyl-adamantane (6588-68-7)

Conditions	Yield
With nitric acid; acetic acid; [H4PVMo11O40] at 82.85℃; under 760 Torr; Title compound not separated from byproducts;	A 10% B 41 % Chromat.
With nitric acid; acetic acid; [VO(H2O)5]H[PMo12O40] at 82.84℃; Title compound not separated from byproducts.;	A 38 % Chromat. B 56 % Chromat.

1-nitro-3,5-dimethyl-adamantane (6588-68-7) → 3,5-dimethyl-7-nitroadamantan-1-yl nitrate

Conditions	Yield
With nitric acid; acetic anhydride at 10℃; for 3h;	43%

1-nitro-3,5-dimethyl-adamantane (6588-68-7) → memantine hydrochloride (41100-52-1)

Conditions	Yield
Stage #1: 1-nitro-3,5-dimethyl-adamantane With iron; acetic acid at 20℃; for 4.5h; Stage #2: With hydrogenchloride In ethyl acetate for 0.5h;	449.2 g

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 702-79-4 1,3-dimethyladamantane 
• 98-08-8 α,α,α-trifluorotoluene 

Downstream Products

• 41100-52-1 memantine hydrochloride 

Relevant articles and documents

Selective Nitroxylation of Adamantane Derivatives in the System Nitric Acid–Acetic Anhydride

Abstract: A number of new nitroxyadamantanes have been synthesized by nitroxylation of the corresponding substrates with nitric acid in acetic anhydride. High electrophilicity and reduced acidity of the system HNO3–Ac2O increases the stability of nitrates and significantly decreases the probability of formation of alcohols. In some cases, nitrolysis and oxidation of functional groups in the substrate are observed.

[VO(H2O)5]H[PMo12O40]- catalyzed nitration of alkanes with nitric acid

[VO(H2O)5]H[PMo12O40], which contains vanadyl counter cations and PMo12O40 3-, can act as a catalyst for the nitration of various alkanes including alkylbenzenes using nitric acid as a nitrating agent in acetic acid at 356 K.

Efficient Catalytic Alkane Nitration with NO2 under Air Assisted by N-Hydroxyphthalimide

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