16104-50-0

Usage

Uses

Used in Organic Synthesis:
1,3-Dichloroadamantane is utilized as a building block in organic synthesis for the creation of various drug molecules. Its unique structure and reactivity contribute to the synthesis of complex organic compounds.
Used in Pharmaceutical Research:
In pharmaceutical research, 1,3-Dichloroadamantane serves as a key component in the development of new drug molecules. Its properties allow for the exploration of its potential in treating various medical conditions.
Used in Polymer and Resin Production:
1,3-Dichloroadamantane is employed in the production of polymers and resins, where its rigid structure and chemical properties enhance the performance and characteristics of these materials.
Used in Synthesis of Novel Compounds with Biological Activity:
1,3-Dichloroadamantane is recognized for its potential use as a precursor in the synthesis of novel compounds that exhibit interesting biological activity. This application opens up new avenues for the discovery of pharmaceuticals and other bioactive substances.

InChI:InChI=1/C10H14Cl2/c11-9-2-7-1-8(4-9)5-10(12,3-7)6-9/h7-8H,1-6H2

Upstream product

• 281-23-2 adamantane 
• 935-56-8 1-chloroadamantane 
• 127-65-1 chloroamine-T 
• 24375-05-1 N,N-dichloro-adamantan-1-amine 
• 772-26-9 1-chloro-3-hydroxyadamantane 
• 24569-89-9 1,3-dehydroadamantane 
• 67-56-1 methanol 
• 768-95-6 1-adamanthanol 
• 56-23-5 tetrachloromethane 
• 39917-36-7 3-bromo-1-adamantanecarbonyl chloride 
• 55982-64-4 1-chloroadamantanecarboxylic acid chloride 
• 78610-04-5 1-(N,N-Dichlorosulfonamido)-3-chloroadamantane 
• 4411-26-1 1-adamantylisothiocyanate 
• 17933-29-8 7-methylenebicyclo[3.3.1]nonan-3-one 

Downstream Products

• 281-23-2 adamantane 
• 94397-84-9 1-dimethylsilyladamantane 
• 66791-07-9 1-(trimethylsilyl)adamantane 
• 60509-83-3 (adamantan-1-yl)diphenylphosphine oxide 
• 163311-93-1 (1-adamantyl)diphenylphosphine 
• 869627-10-1 3-chloro-1-formyloxyadamantane 
• 869627-11-2 1,3-diformyloxyadamantane 
• 17933-29-8 7-methylenebicyclo[3.3.1]nonan-3-one 
• 53488-28-1 dinitrate of 1,3-adamantanediol 
• 40189-21-7 1,3-Diphenyladamantane 
• 5001-18-3 1,3-adamantandiol 
• 70402-92-5 1-adamantane 

Relevant academic research and scientific papers

ON THE MECHANISM OF LIQUID PHASE HALOGENATION OF ADAMANTANE DERIVATIVES

The novel mechanistic representation of adamantane derivatives halogenation process is introduced.

KOtBu as a single electron donor? Revisiting the halogenation of alkanes with CBr4 and CCl4

The search for reactions where KOtBu and other tert-alkoxides might behave as single electron donors led us to explore their reactions with tetrahalomethanes, CX4, in the presence of adamantane. We recently reported the halogenation of adamantane under these conditions. These reactions appeared to mirror the analogous known reaction of NaOH with CBr4 under phase-transfer conditions, where initiation features single electron transfer from a hydroxide ion to CBr4. We now report evidence from experimental and computational studies that KOtBu and other alkoxide reagents do not go through an analogous electron transfer. Rather, the alkoxides form hypohalites upon reacting with CBr4 or CCl4, and homolytic decomposition of appropriate hypohalites initiates the halogenation of adamantane.

PRODUCTION METHOD OF DICHLOROADAMANTANE

PROBLEM TO BE SOLVED: To provide a production method suitable for industrial production of dichloroadamantanes. SOLUTION: A method for producing dichloroadamantanes represented by formula (2) is provided, in which adamantanes represented by formula (1) are mixed with thionyl chloride by 4 to 10 times moles to 1 mole of the adamantanes in the presence of sulfuric acid to react. In formula (1), R1 to R3 each independently represent H, a halogen atom, an alkyl group or an aryl group, and when R1 to R3 represent Cl, the number of Cl is at most 1, and when no Cl is included, at least one of R1 to R3 is H. In formula (2), one of R4 to R6 is a chlorine atom. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT

METHOD FOR PRODUCING CHLOROADAMANTANES

PROBLEM TO BE SOLVED: To provide a production method suitable for industrial production of chloroadamantanes. SOLUTION: There is provided a method for producing chloroadamantanes represented by formula (2), in which bridgehead positions (1-, 3-, 5-, and 7-positions) of the adamantane are chlorinated, by mixing and reacting adamantanes (1) with thionyl chloride in the presence of sulfuric acid. (R1 to R3 each independently represent H or Ry; Ry represents a halogen atom, an alkyl group, or an aryl group; when there are a plurality of Ry's, respective Ry may be the same or different.) (When substituents R1, R2 and/or R3 are Ry's in the formula (1), substituents R4 to R6 at positions corresponding to the substituents R1 to R3 are the same as the substituents R1 to R3.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Chlorination of hydrocarbons with CCl4 catalyzed by complexes of Mn, Mo, V, Fe

Catalytic chlorination of alkanes, cycloalkanes, and adamantane utilizing tetrachloromethane as the source of chlorine and applying catalysts containing manganese, molybdenum, vanadium, and iron activated with nitrile ligands, alcohols, and water was fulfilled. The optimum ratios of catalysts and reagents and the best reaction conditions were found for selective synthesis of chlorine-substituted hydrocarbons derivatives. Pleiades Publishing, Ltd., 2013.

Cross-coupling of non-activated chloroalkanes with aryl grignard reagents in the presence of iron/N-heterocyclic carbene catalysts

An efficient and high-yielding cross-coupling reaction of various primary, secondary, and tertiary alkyl chlorides with aryl Grignard reagents was achieved by using catalytic amounts of N-heterocyclic carbene ligands and iron salts. This reaction is a simple and efficient arylation method having applicability to a wide range of industrially abundant chloroalkanes, including polychloroalkanes, which are challenging substrates under conventional cross-coupling conditions.

Chlorination of various substrates in subcritical carbon tetrachloride

Various aliphatic hydrocarbons and the side chains of aromatic hydrocarbons were chlorinated in subcritical carbon tetrachloride. Chlorination of aromatic compounds including 1,4-disubstituted benzenes was investigated. Ketones and sulfones were stable under the employed conditions. Sulfoxides were converted into sulfides in a low to modest yields. The coupling adducts between olefins and carbon tetrachloride were obtained from the reactions of olefins.

Chlorination of aliphatic hydrocarbons, aromatic compounds, and olefins in subcritical carbon tetrachloride

The reactions of various substrates including aliphatic hydrocarbons, aromatic compounds, and olefins were investigated in subcritical carbon tetrachloride. Ketones and sulfones were stable under the employed conditions. The coupling adducts between olefins and carbon tetrachloride were obtained from the reactions of olefins.

METHOD FOR REFINING HALOGENATED ADAMANTANES

PROBLEM TO BE SOLVED: To provide a method for refining halogenated adamantanes which is important as a raw material for highly functional materials such as heat-resistant polymer and electronic materials such as resist for semiconductors and having few oligomer content. SOLUTION: Halogenated adamantanes are refined by activated carbon in an alcohol solvent such as methanol, ethanol or 2-propyl alcohol and/or in a nitrile solvent such as acetonitrile or propionitrile. When the present method is applied to halogenated adamantanes produced from adamantanes and a halosulfonic acid and containing a higher molecular weight oligomer component than halogenated adamantanes difficult to remove in other method, the effect is remarkable.

METHOD FOR PRODUCING 1,3-ADAMANTANEDIOL

PROBLEM TO BE SOLVED: To provide a method for inexpensively producing 1,3-adamantanediol important as a raw material for a highly functional material such as a heat-resistant polymer, and an electronic material such as a resist for a semiconductor under a comparatively low pressure of ≤0.4 MPa, preferably ≤0.3 MPa. SOLUTION: The 1,3-adamantanediol is produced by using a 1,3-dihalogenated adamantane, for example, obtained by halogenating adamantane with chlorosulfonic acid as a raw material, and reacting the 1,3-dihalogenated adamantane with water in the presence of a water-soluble organic solvent such as N,N-dimethylformamide, and an alkali or alkaline earth metal salt of a carboxylic acid such as sodium acetate.