3386-33-2

Usage

Uses

Used in Environmental Analysis:
1-Chlorooctadecane is used as an internal standard for the determination of endocrine disrupters in water samples. This application is particularly important in environmental monitoring and assessment, as endocrine disrupters can have significant negative impacts on ecosystems and human health.
In the specific method mentioned, the Stir Bar Sorptive Extraction (SBSE) technique is employed to analyze water samples for the presence of endocrine disrupters. 1-Chlorooctadecane serves as a reliable internal standard, helping to ensure accurate and consistent results by providing a reference point for the quantification of target compounds. This allows researchers and analysts to more effectively identify and measure the levels of endocrine disrupters, contributing to a better understanding of their distribution and potential risks in aquatic environments.

InChI:InChI=1/C18H37Cl/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h2-18H2,1H3

Synthetic route

1-octadecanol (112-92-5) → 1-chlorooctadecane (3386-33-2)

Conditions	Yield
With hydrogenchloride; N-n-octylalkylpyridinium chlorides; mixture of at 150℃; for 8h; Product distribution / selectivity;	99.8%
With Amberlite IRA 93 (PCl5 form) In benzene for 5h; Heating;	96%
With hydrogenchloride; trimethyloctadecylammonium chloride for 10h; Irradiation;	77%

2-(octadecylthio)benzonitrile → 1,2-benzisothiazolin-3-one (2634-33-5) + 1-chlorooctadecane (3386-33-2)

Conditions	Yield
With water; chlorine In chlorobenzene at 20 - 65℃; for 3h;	A 93.5% B 210 g
With water; chlorine In chlorobenzene at 20 - 65℃; for 3h;

2-(octadecylthio)benzonitrile → 1,2-benzisothiazolin-3-one (2634-33-5) + 2-Chlorobenzonitrile (873-32-5) + 1-chlorooctadecane (3386-33-2)

Conditions	Yield
Stage #1: 2-(octadecylthio)benzonitrile With water; chlorine In chlorobenzene at 20 - 65℃; for 3h; Stage #2: With sodium hydroxide In water at 60 - 65℃; pH=9 - 10; Stage #3: With hydrogenchloride In water at 20 - 30℃; pH=3 - 4;	A 102 g B 93.5% C 210 g

stearic acid (57-11-4) → 1-chlorooctadecane (3386-33-2)

Conditions	Yield
With phosgene; 4-(dimethylamino)pyridine hydrochloride at 150℃;	91%

stearyl chloroformate (51637-93-5) → 1-chlorooctadecane (3386-33-2)

Conditions	Yield
With hexabutylguanidinium chloride at 120℃; for 4h;	90%

Octadecanethiol (2885-00-9) → 1-chlorooctadecane (3386-33-2)

Conditions	Yield
With tetrachloromethane; cross-linked polymer (containing 2.50 mmol of phosphine/g) for 3h; Heating;	78%
Multi-step reaction with 2 steps 1.1: tetrabutylammomium bromide; sodium hydroxide / chlorobenzene; water / 4 h / 65 - 70 °C / Inert atmosphere 2.1: chlorine; water / chlorobenzene / 3 h / 20 - 65 °C 2.2: 60 - 65 °C / pH 9 - 10 2.3: 20 - 30 °C / pH 3 - 4 View Scheme

ethene (74-85-1) → 1-chlorooctadecane (3386-33-2)

Conditions	Yield
With hydrogenchloride; dibenzoyl peroxide at 100℃; under 294203 - 367754 Torr;
With hydrogenchloride; dibenzoyl peroxide at 100℃; under 294203 - 367754 Torr;

thiocarbonic acid O-(4-chloro-phenyl) ester O-octadecyl ester (62008-64-4) → 1-chlorooctadecane (3386-33-2)

Conditions	Yield
With pyridine; benzenesulfenyl chloride

chlorosulfurous acid octadecyl ester → 1-chlorooctadecane (3386-33-2) + SO2

Conditions	Yield
at 97℃;

pyridine (110-86-1) + chlorosulfurous acid octadecyl ester → 1-chlorooctadecane (3386-33-2) + SO2

Conditions	Yield
at 54℃;

1-octadecanesulfonyl chloride (10147-41-8) → 1-chlorooctadecane (3386-33-2) + sulfur dioxide

Conditions	Yield
at 125℃; Rate constant; Pyrolysis;
at 150℃; Rate constant; Pyrolysis;
at 175℃; Rate constant; Pyrolysis;

octadecane (593-45-3) → 1-chlorooctadecane (3386-33-2) + 1-chlorooctadecane (71662-61-8)

Conditions	Yield
With tetrachloromethane; manganese(III) acetylacetonate; acetonitrile at 200℃; for 8h; Time; Sealed tube;

1-chlorooctadecane (3386-33-2) + (1R,2R)-2-aminocyclohexanol (931-15-7, 931-16-8, 6850-38-0, 6982-39-4, 33092-82-9, 38898-70-3, 74111-21-0, 108267-20-5) → (1R,2R)-2-(Stearoylamino)cyclohexanol

Conditions	Yield
	100%
	100%

1-chlorooctadecane (3386-33-2) + 2-hydroxymethylpyrrolidine (498-63-5) → (S)-1-Stearoyl-2-pyrrolidinemethanol

Conditions	Yield
	100%

1-chlorooctadecane (3386-33-2) + 7-ethyl-10-hydroxycamptothecin (86639-52-3, 110714-48-2, 130144-34-2) → 7-ethyl-10-hydroxycamptothecin-10-stearate

Conditions	Yield
Stage #1: 7-ethyl-10-hydroxycamptothecin With pyridine In dichloromethane for 0.333333h; Cooling with ice; Stage #2: 1-chlorooctadecane In dichloromethane at 20℃; for 12h; Reagent/catalyst; Solvent; Cooling with ice;	98.75%

1-chlorooctadecane (3386-33-2) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → N-nonadecyl nitrile (28623-46-3)

Conditions	Yield
Stage #1: 2-hydroxy-2-methylpropanenitrile With lithium hydroxide monohydrate In tetrahydrofuran at 50℃; for 1h; Stage #2: 1-chlorooctadecane In tetrahydrofuran	95.1%

1-chlorooctadecane (3386-33-2) + combrestatin A4 (117048-62-1, 117048-59-6) → (Z)-2-methoxy-5-(3,4, 5-trimethoxystyryl)phenyl stearate

Conditions	Yield
Stage #1: combrestatin A4 With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.333333h; Stage #2: 1-chlorooctadecane In dichloromethane at 0 - 20℃; for 2.25h;	94.32%

1-chlorooctadecane (3386-33-2) → octadecyltrichlorosilane (112-04-9)

Conditions	Yield
With trichlorosilane; tetra-n-butylphosphonium chloride at 170℃; for 6h;	93%

1-chlorooctadecane (3386-33-2) + N,N,N,N,-tetramethylethylenediamine (110-18-9) → C24H53N2(1+)*Cl(1-)

Conditions	Yield
In methanol at 50℃; for 28h; Inert atmosphere;	91.5%

1H-imidazole (288-32-4) + 1-chlorooctadecane (3386-33-2) → 1-octadecyl-1H-imidazole (5709-33-1)

Conditions	Yield
With sodium hydroxide; tetraethylammonium bromide In benzene for 72h; Heating;	90%

1-chlorooctadecane (3386-33-2) + sodium thiomethoxide (5188-07-8) → methyl n-octadecyl sulfide (40289-98-3)

Conditions	Yield
In ethanol Substitution; Heating;	88%

1-chlorooctadecane (3386-33-2) + N-Boc-1,3-diaminopropane (75178-96-0) → N-Boc-N’-stearoyl-1,3-diamine

Conditions	Yield
With triethylamine In dichloromethane Inert atmosphere;	87.7%

1-chlorooctadecane (3386-33-2) + 5-nitroindole (6146-52-7) → 5-nitro-1-octadecyl-1H-indole

Conditions	Yield
Stage #1: 5-nitroindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.666667h; Stage #2: 1-chlorooctadecane With sodium iodide In N,N-dimethyl-formamide; mineral oil	84.5%

(2-hydroxyethyl)(methyl)amine (109-83-1) + 1-chlorooctadecane (3386-33-2) → N-Octadecyl-N-methyl-β-hydroxyethylamine (32582-64-2)

Conditions	Yield
In acetone for 20h; Heating;	83%

2-bromo-pyridine (109-04-6) + 1-chlorooctadecane (3386-33-2) → 2-(octadec-1-ylthio)pyridine (1558056-00-0)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; Sodium thiosulfate pentahydrate; caesium carbonate In ethylene glycol; dimethyl sulfoxide at 120℃; Schlenk technique; Inert atmosphere; Green chemistry;	82%
With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; Sodium thiosulfate pentahydrate; caesium carbonate In ethylene glycol; dimethyl sulfoxide at 120℃; Inert atmosphere;	82%

1-chlorooctadecane (3386-33-2) + trans-2-phenyl-1,3-dioxan-5-ol (1708-40-3, 4141-19-9, 4141-20-2) → trans-5-(1-octadecyloxy)-2-phenyl-1,3-dioxan (87515-26-2)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 60℃; for 15h;	81%

1-chlorooctadecane (3386-33-2) + methylamine (74-89-5) → N-methyldioctadecylamine (4088-22-6)

Conditions	Yield
With sodium hydroxide; potassium iodide In water at 120℃; for 144h;	80%

1-chlorooctadecane (3386-33-2) + N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid (59-05-2) → (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid dioctadecyl ester (86669-32-1)

Conditions	Yield
With caesium carbonate In water; dimethyl sulfoxide for 45h; Ambient temperature;	76%

(4-(6,7-dihydroxy-4-thiaheptanoylamino)benzoyl)glutamic acid di-t-butyl ester + 1-chlorooctadecane (3386-33-2) → (4-(6,7-bis(stearyloxy)-4-thiaheptanoylamino)benzoyl)glutamic acid di-t-butyl ester

Conditions	Yield
With 2-(Dimethylamino)pyridine; sodium bicarbonate; triethylamine; citric acid In chloroform; water	76%

1-chlorooctadecane (3386-33-2) + 1-(4-ferrocenylphenyl)-3-(4-chlorobenzoyl)thiourea monohydrate → 4-ferrocenyl-N-((4-chlorobenzoyl)carbamothioyl)-N-octadecylbenzenium chloride

Conditions	Yield
In ethanol at 80℃; for 24h;	75%

1-chlorooctadecane (3386-33-2) + cis-5-hydroxyl-2-phenyl-1,3-dioxane (1708-40-3, 4141-19-9, 4141-20-2) → cis-5-(1-octadecyloxy)-2-phenyl-1,3-dioxan (82521-21-9)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 60℃;	67%
	67%

carbon disulfide (75-15-0) + 1-chlorooctadecane (3386-33-2) + 1-((3R,5aS,6R,8aS,9R,10R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)piperazine → C38H68N2O4S2

Conditions	Yield
Stage #1: carbon disulfide; 1-((3R,5aS,6R,8aS,9R,10R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)piperazine With triethylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: 1-chlorooctadecane In acetonitrile at 20 - 60℃; for 0.0833333h;	49.3%

1-chlorooctadecane (3386-33-2) + rac-3-(benzylsulfanyl)propane-1,2-diol (5149-49-5) → 1-Benzylsulfanyl-3-octadecyloxy-propan-2-ol

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 48h; Ambient temperature;	35%

1-chlorooctadecane (3386-33-2) + trans-atovaquone → 2-octadecanoxy-3-(E-4-(para-chlorophenyl)-cyclohexyl)-1,4-naphthoquinone

Conditions	Yield
Stage #1: trans-atovaquone With potassium carbonate In butanone for 0.5h; Reflux; Stage #2: 1-chlorooctadecane In butanone for 14h; Reflux;	26%

Upstream product

• 112-92-5 1-octadecanol 
• 74-85-1 ethene 
• 2885-00-9 Octadecanethiol 
• 110-86-1 pyridine 
• 10147-41-8 1-octadecanesulfonyl chloride 
• 593-45-3 octadecane 
• 57-11-4 stearic acid 
• 112-88-9 octadec-1-ene 
• 51637-93-5 stearyl chloroformate 
• 62008-64-4 thiocarbonic acid O-(4-chloro-phenyl) ester O-octadecyl ester 

Downstream Products

• 3165-81-9 1-octadecyl-pyridinium; chloride 
• 102-88-5 trioctadecylamine 
• 4445-06-1 octadecylcyclohexane 
• 123974-61-8 1-nitro-4-(n-octadecyloxy)benzene 
• 36588-29-1 octadecyl phenyl ether 
• 10564-74-6 1,2-dioctadecyldiselane 
• 593-45-3 octadecane 
• 112-99-2 Dioctadecylamine 
• 124-30-1 1-aminooctadecane 
• 10213-78-2 N,N-diethanolstearylamine 
• 3230-10-2 1,4-bis-octadecyloxy-benzene 
• 2439-55-6 N-methyl-1-octadecylamine 
• 3906-22-7 N-octadecylacetamide 
• 6297-03-6 19-oxaheptatriacontane 

Relevant academic research and scientific papers

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SYNTHETIC METHOD FOR THE PREPARATION OF 1, 2-BENZISOTHIAZOLIN-3-ONE

The present invention relates to a method for producing a 1,2-benzisothiazolin-3-one compound (I) by reacting a 2-halobenzonitrile compound (II) with a thiol compound (III) to form an intermediate (IV) and subsequently reacting the intermediate (IV) with a halogenation agent in the presence of water to form a reaction mixture (RM), comprising the 1,2-benzisothiazolin-3-one compound (I) and a halide compound (V).

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