123-04-6

Usage

Uses

Used in Chemical Synthesis:
3-(Chloromethyl)heptane is used as a chemical intermediate for the synthesis of various organic compounds. Its chloromethyl group allows for easy functionalization and subsequent reactions, making it a versatile building block in the chemical industry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(Chloromethyl)heptane is used as a key intermediate in the production of various drugs. Its ability to form covalent bonds with other molecules makes it a valuable component in the development of new pharmaceuticals.
Used in Agrochemical Industry:
3-(Chloromethyl)heptane is also utilized in the agrochemical industry for the synthesis of pesticides and other agrochemical products. Its reactivity and stability contribute to the development of effective and safe products for agricultural use.
Used in Polymer Industry:
In the polymer industry, 3-(Chloromethyl)heptane serves as a monomer or a building block for the synthesis of various polymers. Its chloromethyl group can be polymerized to form polymers with specific properties, such as increased reactivity or improved solubility.
Used in Dye and Pigment Industry:
3-(Chloromethyl)heptane is used as an intermediate in the production of dyes and pigments. Its ability to form covalent bonds with other molecules allows for the creation of a wide range of colors and properties in dyes and pigments.

Hazard

Moderate fire risk.

Flammability and Explosibility

Flammable

InChI:InChI=1/C8H17Cl/c1-3-5-6-8(4-2)7-9/h8H,3-7H2,1-2H3

Synthetic route

2-Ethylhexyl alcohol (104-76-7) → 3-(chloromethyl)heptane (123-04-6)

Conditions	Yield
With hydrogenchloride; N-n-butylalkylpyridinium chlorides; mixture of at 135℃; for 22h; Product distribution / selectivity;	99.3%
With chloro-trimethyl-silane; dimethyl sulfoxide for 0.166667h;	92%
With pyridine; thionyl chloride at 0 - 55℃;	89%

2-Ethylhexyl chloroformate (24468-13-1) → 3-(chloromethyl)heptane (123-04-6)

Conditions	Yield
With N,N-dimethyl-formamide In chloroform at 72℃;	86%
pyrographite

2-Ethylhexyl alcohol (104-76-7) + benzoyl chloride (98-88-4) → 3-(chloromethyl)heptane (123-04-6) + Velate 368 (5444-75-7)

Conditions	Yield
With 2,3-diethyl-2-cyclopropen-1-one In tert-butyl methyl ether at 60℃; for 24h; Catalytic behavior; Temperature;	A 81% B n/a
With 1-pyrrolidinecarboxaldehyde In 1,4-dioxane at 80℃; for 12h; Sealed tube; Green chemistry;	A 52 %Spectr. B 40 %Spectr.

2-Ethylhexyl alcohol (104-76-7) + 4-methoxy-benzoyl chloride (100-07-2) → 3-(chloromethyl)heptane (123-04-6) + 2-ethyl-1-hexyl 4-methoxybenzoate

Conditions	Yield
With 2,3-diethyl-2-cyclopropen-1-one In tert-butyl methyl ether at 40℃; for 20h; chemoselective reaction;	A 78% B n/a

2-Ethylhexyl alcohol (104-76-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-(chloromethyl)heptane (123-04-6) + (2-ethylhex-1-yl) formiate (5460-45-7)

Conditions	Yield
With benzoyl chloride at 100℃; for 2.25h;	A 65% B n/a

tris(2-ethylhexyl) phosphite (301-13-3) + 2-Chloro-N,N-diethylacetamide (2315-36-8) → 3-(chloromethyl)heptane (123-04-6) + bis(2-ethyl-1-hexyl) (N,N-diethylcarbamoylmethyl)phosphonate (66258-31-9)

Conditions	Yield
at 165 - 170℃; under 160 - 200 Torr;	A n/a B 62.1%

2,4-bis(biphenyl-4-yl)-6-((2,4-dihydroxy)phenyl)-1,3,5-triazine + 3-(chloromethyl)heptane (123-04-6) → 2-(2-hydroxy-4-(2-ethylhexyl)oxy)phenyl-4,6-bis(4-phenyl)phenyl-1,3,5-triazine (204583-39-1)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In n-heptane; water at 70 - 90℃; for 5h; Temperature;	95.08%

3-(chloromethyl)heptane (123-04-6) + bis-(2-ethyl-hexyl)-tin (2+); dichloride (25430-97-1) → Sn{CH2CH(C2H5)C4H9}4 (96582-33-1)

Conditions	Yield
With Na	93.6%
With sodium	93.6%

3-(chloromethyl)heptane (123-04-6) → (2-ethylhexyl)lithium (13067-81-7)

Conditions	Yield
With lithium In n-heptane at 20℃;	90%

3-(chloromethyl)heptane (123-04-6) + sodium thiomethoxide (5188-07-8) → methyl 2-ethylhexyl sulfone (1225278-92-1)

Conditions	Yield
Stage #1: 3-(chloromethyl)heptane; sodium thiomethoxide In water at 60℃; for 2h; Inert atmosphere; Stage #2: With dihydrogen peroxide In dichloromethane at 60℃; for 2h;	90%

3-(chloromethyl)heptane (123-04-6) + (4-aminophenyl)boronic acid (89415-43-0) → 4-(2-ethylhexyl)benzenamine (119630-26-1)

Conditions	Yield
With potassium phosphate; palladium diacetate; DavePhos In 1,4-dioxane for 4h; Reflux;	88.6%

3-(chloromethyl)heptane (123-04-6) + 4-Bromophenylboronic acid (5467-74-3) → 1-bromo-4-(2'-ethylhexyl)benzene

Conditions	Yield
With potassium phosphate; palladium diacetate; DavePhos In 1,4-dioxane for 4h; Reflux;	77.6%

3-(chloromethyl)heptane (123-04-6) + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 2-(2-ethylhexyl)-5,5-dimethyl-1,3,2-dioxaborinane

Conditions	Yield
With chlorotris(triphenylphosphine)cobalt(I); sodium ethanolate; 1,3-dicyclohexylimidazol-2-ylidene In tert-butyl methyl ether at 50℃; for 24h; Inert atmosphere;	70%
With iron(II) bis(trimethylsilyl)amide; sodium ethanolate In hexane; tert-butyl methyl ether at 80℃; for 22h; Inert atmosphere; Sealed tube;	70%

3-(chloromethyl)heptane (123-04-6) + carbon dioxide (124-38-9) → 3-ethylheptanoic acid (14272-47-0, 42330-40-5, 57403-75-5)

Conditions	Yield
With nickel(II) bromide dimethoxyethane; manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetrabutylammomium bromide In N,N-dimethyl-formamide at 60℃; under 760.051 Torr; Schlenk technique;	49%

3-(chloromethyl)heptane (123-04-6) + Trimethylenediamine (109-76-2) → N-(2-ethyl-hexyl)-propanediyldiamine (13281-06-6)

Conditions	Yield
In ethanol for 24h; Heating;	48%

3-(chloromethyl)heptane (123-04-6) + N,N-dimethylaminododecane (112-18-5) → (2-ethyl-hexyl)-dodecyl-dimethyl-ammonium; chloride

3-(chloromethyl)heptane (123-04-6) → 2-ethylhexane-1-thiol (7341-17-5)

Conditions	Yield
With sodium hydrogensulfide; hydrogen sulfide; ethylene glycol

3-(chloromethyl)heptane (123-04-6) → bis(2-ethylhexyl)sulfide (16679-04-2)

Conditions	Yield
With sodium sulfide; ethylene glycol at 135℃;

3-(chloromethyl)heptane (123-04-6) + 4-chloro-phenol (106-48-9) → 2-ethyl-1-hexene (1632-16-2) + 2-(1-ethyl-1-methyl-pentyl)-4-chloro-phenol

Conditions	Yield
at 160 - 170℃;

3-(chloromethyl)heptane (123-04-6) + 2-hydroxyethanethiol (60-24-2) → 2-(2-ethyl-hexylsulfanyl)-ethanol (99867-99-9)

Conditions	Yield
With sodium hydroxide

3-(chloromethyl)heptane (123-04-6) → 3-(iodomethyl)heptane (1653-16-3)

Conditions	Yield
With perhydrodibenzo-18-crown-6; potassium iodide In water Yield given;

diethyl ether (60-29-7) + 3-(chloromethyl)heptane (123-04-6) + chloro-diphenylphosphine (1079-66-9) → diphenyl-3-(3-methylheptyl)phosphine oxide + ethydiphenylphosphine oxide (1733-57-9)

Conditions	Yield
With hydrogenchloride; aluminium trichloride In benzene for 4h; Mechanism; Product distribution; Heating; followed by hydrolysis with H2O at 0 deg C; other alkyl halides investigated;

3-(chloromethyl)heptane (123-04-6) + chloro-diphenylphosphine (1079-66-9) → diphenyl-3-(3-methylheptyl)phosphine oxide + ethydiphenylphosphine oxide (1733-57-9)

Conditions	Yield
With hydrogenchloride; aluminium trichloride; water 1.) diethyl ether, benzene, reflux, 4h, 2.) 0 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

3-(chloromethyl)heptane (123-04-6) + lithium hydride → 3-methylheptane (589-81-1)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

N-(3-hydroxy-2-methylprop-1-yl)-2,6-dimethylmorpholine + 3-(chloromethyl)heptane (123-04-6) → N-[3-(2-ethylhexyloxy)-2-methylprop-1-yl]-2,6-dimethylmorpholine

Conditions	Yield
With sodium hydroxide; tetrabutyl-ammonium chloride In water

Upstream product

• 104-76-7 2-Ethylhexyl alcohol 
• 24468-13-1 2-Ethylhexyl chloroformate 
• 301-13-3 tris(2-ethylhexyl) phosphite 
• 2315-36-8 2-Chloro-N,N-diethylacetamide 
• 115-86-6 phosphoric acid triphenyl ester 
• 770-12-7 O-phenyl phosphorodichloridate 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 98-88-4 benzoyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 141-78-6 ethyl acetate 

Downstream Products

• 7341-17-5 2-ethylhexane-1-thiol 
• 16679-04-2 bis(2-ethylhexyl)sulfide 
• 1632-16-2 2-ethyl-1-hexene 
• 99867-99-9 2-<2-Aethyl-hexylmercapto>-aethanol 
• 1653-16-3 3-(iodomethyl)heptane 
• 1733-57-9 ethydiphenylphosphine oxide 
• 13067-81-7 (2-ethylhexyl)lithium 
• 589-81-1 3-methylheptane 
• 13281-06-6 N-(2-ethyl-hexyl)-propanediyldiamine 
• 956619-81-1 N-(2-ethylhexyl)ethylenediamine 
• 96582-33-1 Sn{CH₂CH(C₂H₅)C₄H₉}4 
• 187393-00-6 tinosorb S 
• 204583-39-1 2-(2-hydroxy-4-(2-ethylhexyl)oxy)phenyl-4,6-bis(4-phenyl)phenyl-1,3,5-triazine 
• 949-13-3 2-octylphenol 

Relevant academic research and scientific papers

(2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow

We report the on-demand generation of hexane-soluble (2-ethylhexyl)sodium (1) from 3-(chloromethyl)heptane (2) using a sodium-packed-bed reactor under continuous flow conditions. Thus, the resulting solution of 1 is free of elemental sodium and therefore suited for a range of synthetic applications. This new procedure avoids the storage of an alkylsodium and limits the handling of metallic sodium to a minimum. (2-Ethylhexyl)sodium (1) proved to be a very useful reagent and undergoes in-line Br/Na-exchanges as well as directed sodiations. The resulting arylsodium intermediates are subsequently trapped in batch with various electrophiles such as ketones, aldehydes, Weinreb-amides, imines, allyl bromides, disulfides and alkyl iodides. A reaction scale-up of the Br/Na-exchange using an in-line electrophile quench was also reported.

A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions

A general formamide-catalyzed protocol for the efficient transformation of alcohols into alkyl chlorides, which is promoted by substoichiometric amounts (down to 34 mol %) of inexpensive trichlorotriazine (TCT), is introduced. This is the first example of a TCT-mediated dihydroxychlorination of an OH-containing substrate (e.g., alcohols and carboxylic acids) in which all three chlorine atoms of TCT are transferred to the starting material. The consequently enhanced atom economy facilitates a significantly improved waste balance (E-factors down to 4), cost efficiency, and scalability (>50 g). Furthermore, the current procedure is distinguished by high levels of functional-group compatibility and stereoselectivity, as only weakly acidic cyanuric acid is released as exclusive byproduct. Finally, a one-pot protocol for the preparation of amines, azides, ethers, and sulfides enabled the synthesis of the drug rivastigmine with twofold SN2 inversion, which demonstrates the high practical value of the presented method.

Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency

A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive SN-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional groups.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Ni-Catalyzed Carboxylation of Unactivated Alkyl Chlorides with CO2

A catalytic carboxylation of unactivated primary, secondary, and tertiary alkyl chlorides with CO2 at atmospheric pressure is described. This protocol represents the first intermolecular cross-electrophile coupling of unactivated alkyl chlorides, thus leading to new knowledge in the cross-coupling arena.

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.

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.

Process to prepare alkyl phenyl phosphates

The present invention relates to a process to prepare dialkyl monophenyl phosphate, monoalkyl diphenyl phosphate or mixtures thereof wherein dichloromonophenyl phosphate and/or monochlorodiphenyl phosphate is reacted with an aliphatic alcohol in the presence of a Lewis acid catalyst and in the absence of solvent at a temperature of 40 to 200°C and a pressure of 0 to 1 bar. The present invention further relates to mixtures of monoalkyl diphenyl phosphates and dialkyl monophenyl phosphates obtainable from the above process and the use of such mixtures as a plasticiser and/or a flame retardant.