23074-42-2

Basic information

• Product Name: 1-Adamantanecarbonitrile
• Synonyms: IFLAB-BB F1928-0022;LABOTEST-BB LT00007841;1-ADAMANTYL CYANIDE;1-ADAMANTANECARBONITRILE;1-CYANOADAMANTANE;ADAMANTANE-1-CARBONITRILE;AKOS BC-0472;RARECHEM AQ TC 1003
• CAS NO: 23074-42-2
• Molecular Formula: C11H15N
• Molecular Weight: 161.24
• EINECS: 245-413-9
• Product Categories: Adamantane derivatives;Adamantanes
• Mol File: 23074-42-2.mol
• Article Data: 84

Chemical Properties

• Melting Point: 193-196 °C(lit.)
• Boiling Point: 277.57°C (rough estimate)
• Flash Point: 110.9 °C
• Appearance: white granular powder
• Density: 0.9100 (rough estimate)
• Vapor Pressure: 0.00538mmHg at 25°C
• Refractive Index: 1.4600 (estimate)
• Solubility: soluble in Benzene,Methanol,Ethanol
• CAS DataBase Reference: 1-Adamantanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Adamantanecarbonitrile(23074-42-2)
• EPA Substance Registry System: 1-Adamantanecarbonitrile(23074-42-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-20/21-36/37/38
• Safety Statements: 36-23-26
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 23074-42-2(Hazardous Substances Data)

Usage

Chemical Properties

white granular powder

Uses

1-Adamantanecarbonitrile was used as starting reagent for the synthesis of adamantyl-l,3,4-oxathiazol-2-one.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 5239, 1980 DOI: 10.1021/jo01314a003Synthesis, p. 1140, 1985 DOI: 10.1055/s-1985-31453

General Description

1-Adamantanecarbonitrile reacts with W2(OCMe3)6 to yield W(CAd)(OCMe3)3 (Ad=1-adamantyl).

InChI:InChI=1/C11H15N/c12-7-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-6H2

Upstream product

• 768-95-6 1-adamanthanol 
• 143-33-9 sodium cyanide 
• 24225-08-9 methanesulfonyl cyanide 
• 91233-19-1 1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione 
• 22110-53-8 1-adamantyl isocyanide 
• 828-51-3 1-Adamantanecarboxylic acid 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 82094-57-3 1-(Prop-2-ene-1-sulfonyl)-adamantane 
• 795-63-1 1-<(p-tolylsulfonyl)methoxy>adamantane 
• 2942-58-7 diethyl cyanophosphonate 
• 768-93-4 1-iodoadamantane 
• 281-23-2 adamantane 

Downstream Products

• 67886-57-1 1-Amino-1-(1-adamantyl)-2-phenylsulfonylethen 
• 712-74-3 1,2,4,5-benzenetetracarbonitrile radical anion 
• 828-51-3 1-Adamantanecarboxylic acid 
• 1660-04-4 1-acetyladamantane 
• 139026-44-1 1-(1-adamantyl)-1-phenylmethanamine 
• 60196-90-9 1-(1-adamantyl)propan-1-amine 
• 50543-85-6 adamantylthioamide 
• 770-71-8 1-adamantanemethanol 
• 62472-38-2 adamantane-1,3-dicarbonitrile 
• 100083-96-3 1-(1-adamantyl)-2,2-dimethyl-1-propanone triphenylphosphoranylidenehydrazone 
• 2094-74-8 1-Adamantanecarbaldehyde 
• 53658-91-6 1-adamantanecarboxamidoxime 
• 59223-70-0 3-hydroxy-1-adamantanecarbonitrile 
• 91120-86-4 3-fluoroadamantane-1-carbonitrile 

Relevant articles and documents

Reactions of 1,3-dehydroadamantane with inorganic oxygen-free acids

A convenient and efficient procedure has been developed for the synthesis of 1-azidoadamantane, 1-adamantyl isocyanate, and 1-adamantyl isothiocyanate by reaction of 1,3-dehydroadamantane with hydrazoic, isocyanic, and isothiocyanic acids, respectively, under mild conditions. The reaction of 1,3-dehydroadamantane with hydrogen cyanide under analogous conditions gives adamantane-1-carbonitrile in a poor yield which may be improved using hexane as solvent.

Lewis Acid-Catalyzed Preparation of Bridge-head Adamantanoid Nitriles from their Corresponding Halides and Trimethylsilyl Cyanide

Bridge-head adamantyl and diamantyl nitriles 2 have been prepared in good yields by refluxing the corresponding halides 1 with trimethylsilyl cyanide and tin(IV) chloride in dichloromethane.

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).