4860-03-1

Basic information

• Product Name: 1-Chlorohexadecane
• Synonyms: 1-Chlorhexadecan;1-Chlorohexadceane;1-chloro-hexadecan;1-Hexadecylchlorid;Hexadecane,1-chloro-;Palmityl chloride;N-HEXADECYL CHLORIDE;1-CHLOROHEXADECANE
• CAS NO: 4860-03-1
• Molecular Formula: C₁₆H₃₃Cl
• Molecular Weight: 260.89
• EINECS: 225-461-7
• Product Categories: Pharmaceutical Intermediates;Alkyl Chlorides;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Indolines ,Indoles ,Indazoles
• Mol File: 4860-03-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 8-14 °C(lit.)
• Boiling Point: 149 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Liquid
• Density: 0.865 g/mL at 25 °C(lit.)
• Vapor Pressure: 129 mm Hg ( 21 °C)
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: <0.02g/l
• Water Solubility: 0.02 g/L (20 ºC, Dec.)
• BRN: 1748498
• CAS DataBase Reference: 1-Chlorohexadecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chlorohexadecane(4860-03-1)
• EPA Substance Registry System: 1-Chlorohexadecane(4860-03-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4860-03-1(Hazardous Substances Data)

Usage

Chemical Properties

1-Chlorohexadecane is Liquid

Uses

Different sources of media describe the Uses of 4860-03-1 differently. You can refer to the following data:
1. 1-Chlorohexadecane is used as chemical intermediate.
2. 1-Chlorohexadecane is used as solvent , surfactants, pharmaceuticals, antibacterial spray.

Synthesis Reference(s)

Chemistry Letters, 7, p. 923, 1978Synthetic Communications, 6, p. 21, 1976 DOI: 10.1080/00397917608062128

General Description

The electron impact mass spectra of 1-chlorohexadecane was studied by sampling with supersonic molecular beams.

InChI:InChI=1/C16H33Cl/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h2-16H2,1H3

Synthetic route

2-dimethylamino-ethanesulfonic acid hexadecyl ester; hydrochloride (66143-55-3) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
In benzene at 81℃; for 0.5h;	100%
In benzene

1-Hexadecanol (36653-82-4) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With tetrachloromethane; cross-linked polymer (containing 2.50 mmol of phosphine/g) for 2h; Heating;	98%
With hydrogenchloride; hexadecylpyridinium bromide for 16h; Heating;	92%
With hydrogenchloride; zinc(II) chloride

1-chloro-7-hexadecyne (24471-13-4) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With sodium tetrahydroborate; hydrogen; nickel diacetate; zinc(II) oxide In ethanol at 35 - 55℃; for 40.5h;	97.7%

(3-hexadecyloxysulfonyl-propyl)-trimethyl-ammonium; chloride (66143-63-3) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
In toluene at 110℃; for 2h;	95%

dihexadecyl sulfide (3312-77-4) + 2-carboxybenzene diazonium chloride (4661-46-5) → 1-Chlorohexadecan (4860-03-1) + diphenyl sulfide (139-66-2) + hexadecyl-phenyl sulfide (37616-35-6)

Conditions	Yield
With methyloxirane In 1,2-dichloro-ethane for 0.75h; Heating;	A 86% B 93.5% C 6%

dihexadecyl sulfide (3312-77-4) → 1-Chlorohexadecan (4860-03-1) + diphenyl sulfide (139-66-2) + hexadecyl-phenyl sulfide (37616-35-6)

Conditions	Yield
With 2-carboxybenzene diazonium chloride; methyloxirane In 1,2-dichloro-ethane for 0.75h; Heating;	A 86% B 93.5% C 6%

hexadecyl-phenyl sulfide (37616-35-6) + 2-carboxybenzene diazonium chloride (4661-46-5) → 1-Chlorohexadecan (4860-03-1) + diphenyl sulfide (139-66-2)

Conditions	Yield
In 1,2-dichloro-ethane for 0.75h; Heating;	A 87.5% B 93.5%

hexadecyl-phenyl sulfide (37616-35-6) → 1-Chlorohexadecan (4860-03-1) + diphenyl sulfide (139-66-2)

Conditions	Yield
With 2-carboxybenzene diazonium chloride In 1,2-dichloro-ethane for 0.75h; Heating;	A 87.5% B 93.5%

2-carboxybenzene diazonium chloride (4661-46-5) → 1-Chlorohexadecan (4860-03-1) + diphenyl sulfide (139-66-2) + hexadecyl-phenyl sulfide (37616-35-6)

Conditions	Yield
With dihexadecyl sulfide; methyloxirane In 1,2-dichloro-ethane for 0.75h; Heating;	A 86% B 93.5% C 6%

cetyl chloroformate (26272-90-2) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With hexabutylguanidinium chloride at 120℃; for 4h;	92%

1-tosyl-1-hexadecylhydrazine (146404-40-2) → 1-Chlorohexadecan (4860-03-1) + p-toluenesulfonyl chloride (98-59-9)

Conditions	Yield
With N-chloro-succinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation;	A 88% B n/a
With N-chloro-succinimide In tetrahydrofuran for 16h; Product distribution; Mechanism; Ambient temperature; Irradiation; reactions of N-substituted-N-tosylhydrazines with NCS and NBS;	A 88% B n/a

hexadecyl <2>betylate fluorosulfate → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With sodium chloride In dichloromethane; water at 50℃; for 18h;	80%

1-Hexadecanol (36653-82-4) + pivaloyl chloride (3282-30-2) → 1-Chlorohexadecan (4860-03-1) + hexadecyl pivalate (32767-89-8)

Conditions	Yield
With N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;	A 75% B n/a

benzyl(hexadecyl)sulfane (100330-20-9) + 2-carboxybenzene diazonium chloride (4661-46-5) → 1-Chlorohexadecan (4860-03-1) + Benzyl phenyl sulfide (831-91-4) + hexadecyl-phenyl sulfide (37616-35-6) + benzyl chloride (100-44-7)

Conditions	Yield
With methyloxirane In 1,2-dichloro-ethane for 0.75h; Heating;	A 11% B 8% C 74% D 65%

benzyl(hexadecyl)sulfane (100330-20-9) → 1-Chlorohexadecan (4860-03-1) + Benzyl phenyl sulfide (831-91-4) + hexadecyl-phenyl sulfide (37616-35-6) + benzyl chloride (100-44-7)

Conditions	Yield
With 2-carboxybenzene diazonium chloride; methyloxirane In 1,2-dichloro-ethane for 0.75h; Heating;	A 11% B 8% C 74% D 65%

benzyl(hexadecyl)sulfane (100330-20-9) → 1-Chlorohexadecan (4860-03-1) + Benzyl phenyl sulfide (831-91-4) + 3,3,6-Trimethyl-4-phenylmercapto-heptadien-(1,5) (100339-90-0) + benzyl chloride (100-44-7)

Conditions	Yield
With 2-carboxybenzene diazonium chloride; methyloxirane In 1,2-dichloro-ethane for 0.75h; Heating;	A 11% B 8% C 74% D 65%

ethene (74-85-1) → 1-Chlorohexadecan (4860-03-1)

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

1-(2-tetrahydropyranyloxy)hexadecane (58587-19-2) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With sulfuryl dichloride In dichloromethane

1-penten (109-67-1) + 11-chloroundec-1-ene (872-17-3) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With potassium hydroxide; borane-THF 1) THF, 2) THF, Pt-anode, 30 mA/cm-2, 110 mF, 0 deg C; Yield given. Multistep reaction;

C22H38Cl2Te (83485-98-7) → 1-Chlorohexadecan (4860-03-1) + diphenyl ditelluride (32294-60-3)

Conditions	Yield
With sodium chloride In N,N-dimethyl-formamide at 100℃; for 1h; Yield given;

4-dimethylamino-butane-1-sulfonic acid hexadecyl ester; hydrochloride → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
In toluene at 110℃; for 8h;	90 % Spectr.

chloroacetic acid (79-11-8) + 1-hexadecylcarboxylic acid (57-10-3) + alkali → 1-Chlorohexadecan (4860-03-1) + n-triacontane (638-68-6)

Conditions	Yield
an Platinelektroden; bei einer Stromdichte von ca.0.8 Amp/cm2.Electrolysis;

thionyl chloride (7719-09-7) + 1-Hexadecanol (36653-82-4) → 1-Chlorohexadecan (4860-03-1)

hydrogenchloride (7647-01-0) + 1-Hexadecanol (36653-82-4) + sulfuric acid (7664-93-9) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
at 160℃; in Gegenwart von verschiedenen Metallchloriden und -sulfaten;

hydrogenchloride (7647-01-0) + hexadecyl stearate (1190-63-2) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
at 160℃;

cetyl acetate → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With hydrogenchloride; zinc(II) oxide at 180℃;

potassium chloroacetate (7748-25-6) + palmitynacidic potassium → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With ethanol at 70 - 75℃; Electrolysis;

stearic acid cetyl ester → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With hydrogenchloride; zinc(II) chloride at 160℃;

hydrogenchloride (7647-01-0) + 1-Hexadecanol (36653-82-4) + ZnCl2 → 1-Chlorohexadecan (4860-03-1)

1-Chlorohexadecan (4860-03-1) → hexadecanyl bromide (112-82-3)

Conditions	Yield
With sodium bromide; 1,1-dibromomethane In N,N-dimethyl-formamide at 100℃; for 6h; different amounts of NaBr; further temperatures;	99%

1-methyl-1H-imidazole (616-47-7) + 1-Chlorohexadecan (4860-03-1) → 1-hexadecyl-3-methylimidazolium chloride

Conditions	Yield
at 160℃; for 0.5h; Microwave irradiation; Neat (no solvent);	98%
for 0.0527778h; Microwave irradiation; neat (no solvent);	92%
In N,N-dimethyl-formamide at 90℃; for 70h; Inert atmosphere;	86%

1-Chlorohexadecan (4860-03-1) + 2-Phenylphenol (90-43-7) → biphenyl-2-yl-hexadecyl ether (52820-10-7)

Conditions	Yield
Stage #1: 2-Phenylphenol With potassium hydroxide In dimethyl sulfoxide at 100℃; for 2h; Inert atmosphere; Stage #2: 1-Chlorohexadecan In dimethyl sulfoxide at 70 - 80℃; for 7.5h;	96%

1-Chlorohexadecan (4860-03-1) + tris(2-phenylethyl)phosphine (95704-32-8) → C40H60P(1+)*Cl(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 160℃; for 8h; Inert atmosphere;	93.1%

2-(N,N-dimethylamino)ethanol (108-01-0) + 1-Chlorohexadecan (4860-03-1) → N,N-dimethyl-N-hexadecyl-N-(2-hydroxyethyl)ammonium chloride (24625-03-4)

Conditions	Yield
In ethanol Reflux;	92%
In methanol for 16h; Heating;	52%
In methanol for 24h; Reflux;	40%
at 60 - 70℃;

1-Chlorohexadecan (4860-03-1) → Hexadecane (544-76-3)

Conditions	Yield
With sodium tetrahydroborate; cetyltributylphosphonium bromide In water; toluene at 80℃; for 6h; Product distribution;	91%
With sodium tetrahydroborate; 1-{6-[dibutyl(chloro)stannyl]hexyl}-3-methyl-1H-imidazolium iodide In methanol; acetonitrile at 80℃; for 36h; Inert atmosphere;	81%
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene Heating;	68 % Chromat.
With hydrogen In n-heptane at 199.84℃; under 22502.3 Torr; Kinetics; Autoclave;

1-Chlorohexadecan (4860-03-1) + 2-(diphenylphosphinyl)-N-[3-(1H-imidazol-1-yl)propyl]-acetamide (1228996-38-0) → 1-[3-[[(diphenylphosphinyl)acetyl]amino]propyl]-3-hexadecyl-1H-imidazol-3-ium chloride (1228996-23-3)

Conditions	Yield
In acetonitrile Sealed tube; Reflux;	91%

1-Chlorohexadecan (4860-03-1) + potassium acetate (127-08-2) → hexadecyl acetate (629-70-9)

Conditions	Yield
With aluminum oxide at 275℃; for 0.0416667h; Irradiation;	90%

1-Chlorohexadecan (4860-03-1) + sodium thiomethoxide (5188-07-8) → methyl n-hexadecyl sulfide (27563-68-4)

Conditions	Yield
In ethanol Substitution; Heating;	87%

1H-imidazole (288-32-4) + 1-Chlorohexadecan (4860-03-1) → 1-hexadecyl-1H-imidazole (58175-55-6)

Conditions	Yield
With sodium hydroxide; tetraethylammonium bromide In benzene for 72h; Heating;	86%

picoline (108-89-4) + 1-Chlorohexadecan (4860-03-1) → 1-hexadecyl-4-methyl pyridinium chloride (13106-53-1)

Conditions	Yield
for 12h; Heating;	85%
at 135 - 145℃;	118 g

1-Chlorohexadecan (4860-03-1) + 3,5-dinitrobenzyl chloride (74367-78-5) → (3,5-dinitrobenzyl)(hexadecyl)sulfane (1618101-59-9)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.25h;	84%

1-Chlorohexadecan (4860-03-1) + N,N-bis(2-sulfonic acid ethyl)amine → N,N-bis(2-sulfoethyl)-1-hexadecanamine (78108-00-6)

Conditions	Yield
With sodium hydroxide In water; acetone at 50℃; for 1h; pH=9 - 10;	84%

1-Chlorohexadecan (4860-03-1) + carbon dioxide (124-38-9) + sodium 4-tert-butylphenolate (5787-50-8) → n-hexadecyl 5-tert-butyl-2-hydroxybenzoate

Conditions	Yield
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 15 - 75℃; under 5250.53 Torr; for 10h; Temperature; Reagent/catalyst;	82.3%

1-Chlorohexadecan (4860-03-1) + 2-amino-1,3-bis(1-ethoxyethoxy)-4-E-D-erythro-octadec-4-ene (97818-15-0) → 1,3-bis(1-ethoxyethoxy)-2-hexadecanamido-4-E-D-erythro-octadec-4-ene

Conditions	Yield
With dmap In pyridine at 20℃; for 1h;	81%

1-Chlorohexadecan (4860-03-1) + carbon dioxide (124-38-9) + sodium salt of 2,4-di-tertbutylphenol (75376-45-3) → 3,5-di-tert-butyl-2-hydroxybenzoic acid n-hexadecyl ester

Conditions	Yield
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 15 - 75℃; under 5250.53 Torr; for 10h; Temperature; Reagent/catalyst;	79.5%

poly(monoethanolamine vinyl ether), weight-average molecular weight 720; monomer(s) monoethanolamine vinyl ether + 1-Chlorohexadecan (4860-03-1) → poly-N-(2-vinyloxyethyl)-N-hexadecylammonium chloride

Conditions	Yield
In isopropyl alcohol for 16h; Heating;	78%

Upstream product

• 109-67-1 1-penten 
• 872-17-3 11-chloroundec-1-ene 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 79-11-8 chloroacetic acid 
• 57-10-3 1-hexadecylcarboxylic acid 
• 544-76-3 Hexadecane 
• 7782-50-5 chlorine 
• 143-27-1 hexadecylamine 
• 3312-77-4 dihexadecyl sulfide 
• 36653-82-4 1-Hexadecanol 
• 3282-30-2 pivaloyl chloride 
• 24471-13-4 1-chloro-7-hexadecyne 
• 81609-29-2 1-phenyltellurohexadecane 
• 83634-99-5 4-Dimethylamino-butane-1-sulfonic acid hexadecyl ester 

Downstream Products

• 18924-67-9 2,2'-(hexadecylazanediyl)diethanol 
• 112-02-7 cetyltrimethylammonium chloride 
• 7089-36-3 N-methyl-N-(β-hydroxyethyl)-n-hexadecylamine 
• 24625-03-4 N-hexadecyl-N,N-dimethyl-N-(2-hydroxyethyl)ammonium chloride 
• 41622-39-3 3-(hexadecylthio)propionic acid 
• 5693-28-7 4-n-hexadecyloxy-3-methoxybenzoic acid 
• 61546-01-8 1-hexadecyl-3-methylimidazolium chloride 
• 49636-58-0 1-hexadecylbenzotriazole 
• 41272-12-2 tributylhexadecylphosphonium chloride 
• 1812-53-9 N,N-dimethyl-N,N-dihexadecylammonium chloride 
• 60687-82-3 hexadecyl-bis-(2-hydroxy-ethyl)-methyl-ammonium; chloride 
• 255906-42-4 toluene-4-sulfonic acid 2-hexadecyloxy-3-[2-(2-hexadecyloxy-ethoxy)-ethoxy]-propyl ester 
• 7110-00-1 n-hexadecyl benzyl sulfoxide 
• 60273-43-0 3,4-bis(hexadecyloxy)-benzaldehyde 

Relevant articles and documents

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METHOD FOR PRODUCING REDUCED HALIDE COMPOUND HAVING UNDERGONE REDUCTION OF CARBON-CARBON UNSATURATED BOND

A halide compound having one or more carbon-carbon unsaturated bonds is catalytically reduced with substantially no dehalogenation to produce a reduced halide compound in which at least one of the one or more unsaturated bonds is reduced. Specifically provided is a method for producing a reduced halide compound including steps of: reacting a nickel compound, a zinc compound, and a borohydride compound in a solvent to obtain a reduction catalyst; and subjecting a halide compound having one or more carbon-carbon unsaturated bonds to catalytic reduction in the presence of the reduction catalyst to reduce at least one of the one or more carbon-carbon unsaturated bonds to thereby obtain a reduced halide compound.

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