880-52-4

Basic information

• Product Name: N-(1-Adamantyl)acetamide
• Synonyms: 1-ACETAMIDOADAMANTANE;1-ACETYLAMINOADAMANTANE;1-ACETAMIDOTRICYCLO[3.3.1.1(3,7)]DECANE;1-ACETAMINO ADAMANTANE;N-ACETYL-1-ADAMANTANAMINE;N-ACETYL ADAMANTAMINE;N-(1-ADAMANTYL)ACETAMIDE;1-acetyladamantanamine
• CAS NO: 880-52-4
• Molecular Formula: C₁₂H₁₉NO
• Molecular Weight: 193.29
• EINECS: 212-914-9
• Product Categories: Adamantane derivatives;chiral;Adamantanes;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Nitrogen Compounds;Organic Building Blocks;Protected Amines;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 880-52-4.mol
• Article Data: 79

Chemical Properties

• Melting Point: 148-149 °C(lit.)
• Boiling Point: 329.52°C (rough estimate)
• Flash Point: 210.6 °C
• Appearance: White to yellow/Crystalline Powder
• Density: 0.9854 (rough estimate)
• Vapor Pressure: 3.45E-05mmHg at 25°C
• Refractive Index: 1.4596 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 16.16±0.20(Predicted)
• CAS DataBase Reference: N-(1-Adamantyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-Adamantyl)acetamide(880-52-4)
• EPA Substance Registry System: N-(1-Adamantyl)acetamide(880-52-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-24/25-26
• WGK Germany: 3
• RTECS: AB4308000
• TSCA: Yes
• Hazardous Substances Data: 880-52-4(Hazardous Substances Data)

Usage

Acute toxicity

Intraperitoneal-mouse LD50: 520 mg/kg

Storage

The warehouse is ventilated and dry at low temperature; it is stored separately from food raw materials.

Chemical Properties

white to light yellow crystal powde

Uses

A metabolite of Adamantamine

Purification Methods

Wash the amide well with H2O, dry and recrystallise it from cyclohexane. It is an irritant. [Stetter et al. Chem Ber 92 1629 1959.]

InChI:InChI=1/C12H19NO/c1-8(14)13-12-5-9-2-10(6-12)4-11(3-9)7-12/h9-11H,2-7H2,1H3,(H,13,14)

Upstream product

• 60-35-5 acetamide 
• 58652-54-3 1-adamantyl trifluoroacetate 
• 281-23-2 adamantane 
• 4411-26-1 1-adamantylisothiocyanate 
• 108-24-7 acetic anhydride 
• 768-95-6 1-adamanthanol 
• 75-05-8 acetonitrile 
• 768-94-5 1-Adamantanamine 
• 64-19-7 acetic acid 
• 588-46-5 N-(phenylmethyl)acetamide 
• 64741-22-6 1-(N-Chloroacetylamino)adamantane 
• 1707-40-0 1-((3r,5r,7r)-adamantan-1-yl)ethan-1-one oxime 
• 24569-89-9 1,3-dehydroadamantane 
• 768-93-4 1-iodoadamantane 

Downstream Products

• 5001-18-3 1,3-adamantandiol 
• 702-82-9 3-aminoadamantan-1-ol 
• 778-10-9 N-(3-hydroxyadamantan-1-yl)acetamide 
• 768-94-5 1-Adamantanamine 
• 665-66-7 amantadine hydrochloride 
• 768-95-6 1-adamanthanol 
• 139524-50-8 N-Adamantan-1-yl-N-phenylsulfanyl-acetamide 

Relevant articles and documents

1-Acetamidoadamantane

In the title compound, C12H19NO, the bond lengths and angles are closely similar to those of two cagesubstituted 1-acetamidoadamantanes. The molecules are linked into polymeric chains through a weak N-H...O hydrogen bond [H...O 2.04 (2), N...O 2.928 (2) A and N-H...O 168 (1)°].

Preparation method of amantadine

The invention discloses a preparation method of amantadine, which belongs to the technical field of organic chemical synthesis, and is characterized by comprising the following steps: taking a compound adamantane as an initial raw material, generating an intermediate 1-acetamido adamantane in the presence of acetonitrile, a polyion liquid PIL catalyst and sulfuric acid, and then hydrolyzing the intermediate into amantadine in a system of alcohol and alkali. The preparation method is environment-friendly, post-treatment is convenient, the use amount of sulfuric acid and acetonitrile is greatly reduced through the catalyst polyion liquid, and post-treatment is simple. The ionic liquid catalyst can be recycled, so that the cost is greatly saved, and the method is suitable for large-scale industrial production.

Method for continuously preparing N-acetyl amantadine

The invention relates to the technical field of synthesis of N-acetyl amantadine, in particular to a method for continuously preparing N-acetyl amantadine. The method for continuously preparing N-acetyl amantadine comprises the following steps: carrying out continuous reaction in a micro-channel reactor by using adamantane, acetonitrile and acid as raw materials and halogenated alkane as a solvent, wherein the injection speed of adamantane, acetonitrile and halogenated alkane is recorded as V1, the injection speed of the acid is recorded as V2, and (V1+V2)* residence time=liquid holdup is satisfied.