123-04-6

Basic information

• Product Name: 3-(Chloromethyl)heptane
• Synonyms: 3-(chloromethyl)-heptan;3-chloromethyl-heptan;Chloro-iso-octane;Heptane, 3-(chloromethyl)-;hexane,1-chloro-2-ethyl-;TIMTEC-BB SBB005809;2-ETHYLHEXYL CHLORIDE;1-CHLORO-2-ETHYLHEXANE
• CAS NO: 123-04-6
• Molecular Formula: C₈H₁₇Cl
• Molecular Weight: 148.67
• EINECS: 204-594-4
• Mol File: 123-04-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: -70 °C
• Boiling Point: 166-168 °C
• Flash Point: 60 °C
• Appearance: Clear yellow/Liquid
• Density: 0.882
• Vapor Pressure: 1.69mmHg at 25°C
• Refractive Index: 1.432-1.436
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 0.0503 g/L (20 ºC)
• CAS DataBase Reference: 3-(Chloromethyl)heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Chloromethyl)heptane(123-04-6)
• EPA Substance Registry System: 3-(Chloromethyl)heptane(123-04-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-R36/37/38
• Safety Statements: 37/39-26-S37/39-S26
• RIDADR: 1993
• RTECS: MI8760000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 123-04-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid.Insoluble in water. Combustible.

Uses

Barchlor(R) 8I is used as chemical intermediate.

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

• 13281-06-6 N-(2-ethyl-hexyl)-propanediyldiamine 
• 956619-81-1 N-(2-ethylhexyl)ethylenediamine 
• 883903-22-8 1-bromo-4-(2'-ethylhexyl)benzene 
• 119630-26-1 4-(2-ethylhexyl)benzenamine 
• 949-13-3 2-octylphenol 
• 204583-39-1 2-(2-hydroxy-4-(2-ethylhexyl)oxy)phenyl-4,6-bis(4-phenyl)phenyl-1,3,5-triazine 
• 187393-00-6 tinosorb S 
• 14272-47-0 3-ethylheptanoic acid 
• 96582-33-1 Sn{CH₂CH(C₂H₅)C₄H₉}4 
• 589-81-1 3-methylheptane 
• 13067-81-7 (2-ethylhexyl)lithium 
• 1733-57-9 ethydiphenylphosphine oxide 
• 1653-16-3 3-(iodomethyl)heptane 
• 99867-99-9 2-<2-Aethyl-hexylmercapto>-aethanol 

Relevant articles and documents

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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.

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.