38584-37-1

Basic information

• Product Name: 3-(Hydroxymethyl)-1-adamantol
• Synonyms: 3-(HYDROXYMETHYL)-1-ADAMANTANOL, 97%;1-Hydroxy-3-adamantylmethanol, 3-Hydroxytricyclo[3.3.1.13,7]decane-1-methanol;3-(Hydroxymethyl)-1-adamantol;1-Hydroxy-3-adamantylmethanol;3-Hydroxytricyclo[3.3.1.13,7]decane-1-methanol;3-Hydroxy-1-Adamantanemethanol;3-Hydroxy-1-hydroxyMethyladMantane;3-hydroxy-1-hydroxyMethyladaMantane
• CAS NO: 38584-37-1
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.26
• EINECS: 1312995-182-4
• Mol File: 38584-37-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 158-162 °C
• Boiling Point: 322.6 °C at 760 mmHg
• Flash Point: 156.5 °C
• Appearance: White to pale brown/Powder
• Density: 1.261 g/cm³
• Vapor Pressure: 2.2E-05mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.04±0.10(Predicted)
• CAS DataBase Reference: 3-(Hydroxymethyl)-1-adamantol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Hydroxymethyl)-1-adamantol(38584-37-1)
• EPA Substance Registry System: 3-(Hydroxymethyl)-1-adamantol(38584-37-1)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 38584-37-1(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C11H18O2/c12-7-10-2-8-1-9(3-10)5-11(13,4-8)6-10/h8-9,12-13H,1-7H2

Upstream product

• 14504-80-4 3-Hydroxyhomoadamantan 
• 93942-70-2 ethylene-methyl methacrylate 
• 770-71-8 1-adamantanemethanol 
• 828-51-3 1-Adamantanecarboxylic acid 
• 50-00-0 formaldehyd 
• 42711-75-1 3-hydroxyadamantane-1-carboxylic acid 
• 770-14-9 3,7-dimethylenebicyclo[3.3.1]nonane 
• 157774-19-1 3,6-dinitroxyhomoadamantane 
• 157774-23-7 3-(nitroxymethyl)adamantan-1-yl nitrate 
• 281-46-9 homoadamantane 
• 157774-22-6 3-nitroxymethyl-1-adamantanol 
• 84868-20-2 p-Toluolsulfonsaeure-(3-hydroxymethyl-1-adamantyl)ester 
• 36964-33-7 (3-bromotricyclo[3.3.1.1^3,7]dec-1-yl)methanol 

Downstream Products

• 1373399-49-5 2-(3-acetoxymethyl-1-adamantyl)-4-bromoanisole 
• 1373399-48-4 2-(3-acetoxymethyl-1-adamantyl)-4-methylphenol 
• 1373399-47-3 2-(3-acetoxymethyl-1-adamantyl)-4-bromophenol 
• 420120-31-6 3-hydroxytricyclo[3.3.1.1³'⁷]decane-1-carbaldehyde 
• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 361442-01-5 tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate 
• 709031-43-6 3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester 
• 1233844-88-6 C₁₃H₁₇F₂O₆S^(1-)*C₂₁H₂₁S⁽¹⁺⁾ 
• 1375457-72-9 C₁₃H₁₇F₂O₆S^(1-)*C₂₀H₂₆I⁽¹⁺⁾ 

Relevant articles and documents

Synthesis of (3-Hydroxyadamantan-1-yl)methanols

A convenient procedure has been developed for the synthesis of (3-hydroxyadamantan-1-yl)-methanols on the basis of nitroxylation of adamantan-1-ylmethanols with fuming nitring acid and subsequent reduction of intermediate nitric acid esters with hydrazine hydrate. The title diols have also been obtained by the reduction of 1-nitroxy-3-(nitroxymethyl)adamantanes. The nitroxylation process is accompanied by oxidation with the formation of substituted adamantane-1-carboxylic acids.

Radical addition of alkyl halides to formaldehyde in the presence of cyanoborohydride as a radical mediator. A new protocol for hydroxymethylation reaction

Hydroxymethylation of alkyl halides was achieved using paraformaldehyde as a radical C1 synthon in the presence of tetrabutylammonium cyanoborohydride as a hydrogen source. The reaction proceeds via a radical chain mechanism involving an alkyl radical addition to formaldehyde to form an alkoxy radical, which abstracts hydrogen from a hydroborate anion.

POLYMERIZABLE ADAMANTANE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME

A compound shown by the following formula: ???wherein each of R1a, R2a, R3aand R4arepresents a substituent selected from a non-reactive atom, a non-reactive group, a hydroxyl group and an amino group, and at least two members selected from R1a, R2a, R3aand R4aare a hydroxyl group, a carboxyl group or an amino group; is subjected to an esterification reaction or an amidation reaction with a polymerizable unsaturated compound (e.g., an alcohol, a carboxylic acid, an amine) in the presence of a catalyst comprising an element selected from the Group 3 elements, such as a samarium compound, to obtain a polymerizable adamantane derivative having at least one polymerizable unsaturated group in high yield.