2425-54-9

Usage

Uses

1-Chlorotetradecane is used as a chemical intermediate for various applications across different industries. Its versatility as a synthetic intermediate makes it a valuable component in the production of various compounds and materials.
Used in Surfactant Production:
In the chemical industry, 1-Chlorotetradecane is used as a synthetic intermediate to prepare Dimethyldimyristyl ammonium chloride (D472560), a surfactant. Surfactants are essential in various applications, including the formulation of detergents, emulsifiers, and dispersants.
Used in Nonionic Microemulsion Preparation:
1-Chlorotetradecane is also utilized in the preparation of nonionic microemulsions, specifically in combination with pentaoxyethylene glycol dodecyl ether and water. These microemulsions have potential applications in the pharmaceutical, cosmetic, and food industries, where they can enhance the solubility and stability of active ingredients.
Used in Analytical Chemistry:
As an internal standard, 1-Chlorotetradecane is employed in the determination of 3-chloropropane-1,2-diol in hydrolyzed vegetable protein using capillary gas chromatography with electrolytic conductivity detection. This application highlights its importance in ensuring accurate and reliable analytical results in the field of chemistry.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 2295, 1984 DOI: 10.1016/S0040-4039(01)80237-9

InChI:InChI=1/C14H29Cl/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h2-14H2,1H3

Upstream product

• 74-85-1 ethene 
• 112-72-1 1-Tetradecanol 
• 629-73-2 1-Hexadecene 
• 6222-02-2 trifluoroacetic acid n-tetradecyl ester 
• 22521-90-0 1-methoxy-1-hydroperoxypentadecane 
• 1243-66-9 N-tetradecyl-p-toluenesulfonamide 
• 83485-97-6 C₂₀H₃₄Cl₂Te 
• 77953-88-9 1-Tetradecyl phenyl telluride 
• 6294-17-3 1-bromo-6-chlorohexane 
• 1070-00-4 trioctylaluminum 
• 111-66-0 oct-1-ene 
• 30089-00-0 9-octyl-9-bora-bicyclo[3.3.1]nonane 

Downstream Products

• 2785-54-8 tetradecylpyridinium chloride 
• 84860-63-9 N-tetradecylisoquinolinium chloride 
• 83763-20-6 myristic acid-(2-iodo-ethyl ester) 
• 71448-29-8 N-n-tetradecanoyl (L)-alanine 
• 17361-44-3 ditetradecylamine 
• 63906-11-6 3-carbamoyl-1-tetradecylpyridinium chloride 
• 30557-03-0 myristic acid-(3-chloro-2-hydroxy-propyl ester) 
• 14246-55-0 N-myristoylglycine 
• 2589-75-5 1-(4-hydroxy-phenyl)-tetradecan-1-one 
• 859947-01-6 1-(4-ethoxy-phenyl)-tetradecan-1-one 
• 29369-63-9 N-methyltetradecylamine 
• 54004-47-6 1-tetradecylimidazole 
• 629-59-4 tetradecane 
• 856-55-3 1-Tetradecyloxy-4-trimethylsilyl-benzol 

Relevant academic research and scientific papers

Iron-catalyzed AlkylAlkyl negishi coupling of organoaluminum reagents

The first iron-catalyzed cross-coupling reaction of alkyl halides with alkylaluminum reagents (alkylalkyl Negishi coupling) is developed using an iron/bisphosphine catalyst system. The reaction shows high functional group tolerance: various primary alkyl halides possessing a non-protected indole, carboxyl, or hydroxy group are coupled with primary alkylaluminum reagents in good yields. Potassium fluoride plays a key role to promote the reaction by generating an aluminate species, which facilitates the transmetalation between the organoaluminum and the iron catalyst.

Suzuki-miyaura cross-coupling reactions of unactivated alkyl halides catalyzed by a nickel pincer complex

A nickel(II) pincer complex, [(MeN2N)Ni-Cl], was used to catalyze alkyl-alkyl and alkyl-aryl Suzuki-Miyaura coupling reactions of unactivated alkyl halides. The coupling of 9-alkyl-9-borabicyclo[3.3.1]nonane and 9-phenyl-9-borabicyclo[3.3.1]nonane reagents with alkyl halides was achieved in modest to good yields. The reactions tolerated a variety of useful functional groups including ester, ether, furan, thioether, acetal, and Boc groups. Georg Thieme Verlag Stuttgart, New York.

Process for preparing alkyl chlorides

The invention relates to a process for preparing alkyl chlorides by reacting alcohols with gaseous hydrogen chloride in the presence of a catalyst, wherein the catalyst comprises at least one compound of the structure: wherein R1 is a linear alkyl group having from 1 to 20 carbon atoms, R2, R3, and R4 is selected from a hydrogen, an alkyl, an alkenyl, an aralkyl or an alkylaryl group from 1 to 20 carbon atoms, wherein the substituents of R2, R3, and R4 are all identical, are all different or two of the substituents of R2, R3, and R4 type are identical.

Covenient Halodeamination and Hydrodeamination of Primary Amines

Treatment of p-toluenesulfonamides of primary amines with 2 equiv of chloroamine at room temperature in the presence of base leads to reductive deamination.If excess chloroamine is present, the corresponding alkyl or aryl halides are obtained instead in good yields.Both reactions presumably proceed via tosylhydrazine and diazene intermediates; the course of the reaction is often governed by steric hindrance.Treatment of the isolated tosylhydrazine intermediate with base and chloroamine, bromine, or iodine also leads to the corresponding halides in very good yields.

REACTION OF ALKOXYHYDROPEROXIDES WITH METAL SALTS. ALKYL HALIDE PREPARATION

A synthesis is described of alkyl chlorides by reaction of methoxy hydroperoxides, prepared from 1-alkenes by ozonisation in methanol, with ferric chloride: RCH=CH2 --> RCH(OOH)OCH3 --> R. --> RCl.Yields of 1-chlorotetradecane were about 60percent; those of other halides from 38 to 57percent.

Organic Synthesis in Micellar Media. Oxidation of Alcohols and Their Conversion into Alkyl Chlorides

The use of micelles was investigated for various organic reactions: oxidation of alcohols with sodium hypochlorite in micelles, oxidation of alcohols with hexadecyltrimethylammonium chromate as micelle, and conversion of primary alcohols to 1-chloroalkanes by aqueous hydrogen chloride in the presence of micelles.In all cases, product isolation was simple and satisfactory yields were obtained.

A New and Efficient One-Pot Preparation of Alkyl Halides From Alcohols

Primary alkanols and 2-alkenols are converted into the corresponding halides in high yield by a one-pot, two-step reaction via transformation into intermediate trifluoroacetates followed by nucleophilic substitution with lithium halides.

REACTIONS OF HYDROXYL GROUPS WITH TOSYLCHLORIDE-DIMETHYLAMINOPYRIDINE SYSTEM. DIRECT SYNTHESIS OF CHLORIDES FROM HYDROXYCOMPOUNDS.

The reactions of various hydroxyl groups with tosylchloride-dimethylaminopyridine system were investigated and direct synthesis of allyl, alkyl and glycosyl chlorides are described.

PREPARATION OF ALKYL HALIDES VIA ORGANOTELLURIUMS

The conversion of phenyltelluroalkanes to haloalkanes was studied in connection with the homologation of alkyl halides.Similar reactions of 1,1-bis(phenyltelluro)alkanes provided a new synthetic method of aldehydes.

Ahmad-Strong synthesis of 8-, 9-, and 10-pentadecynoic acids.

Three pentadecynoic acids, with the triple bond in the 8-, 9-, and 10-positions, have been synthesized on a gram scale in over-all yield of 65% by refinements of the five-step Ahmad-Strong method; isolation of intermediates was shown to be unnecessary prior to purification of the acetylenic nitriles by column chromatography on silicic acid. The melting points of the pentadecynoic acids alternate regularly and widely with position of unsaturation, in marked contrast to behavior of the homologous octadecynoic acids described by Huber.