2163-00-0

Basic information

• Product Name: 1,6-Dichlorohexane
• Synonyms: HEXAMETHYLENE CHLORIDE;HEXAMETHYLENE DICHLORIDE;1,6-Dichlorohexane,97%;1,6-DICHLOROHEXANE 98+%;1,6-dichloro-n-hexane;1,6-Dichlorohexane, 98% 100GR;Hexamethylene Chloride Hexamethylene Dichloride;1,6-DICHLOROHEXANE FOR SYNTHESIS
• CAS NO: 2163-00-0
• Molecular Formula: C₆H₁₂Cl₂
• Molecular Weight: 155.07
• EINECS: 218-491-7
• Product Categories: Industrial/Fine Chemicals;alpha,omega-Bifunctional Alkanes;alpha,omega-Dichloroalkanes;Monofunctional & alpha,omega-Bifunctional Alkanes
• Mol File: 2163-00-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: -13 °C
• Boiling Point: 87-90 °C15 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: Clear colourless liquid
• Density: 1.068 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.385mmHg at 25°C
• Refractive Index: n20/D 1.457(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 57mg/l
• Explosive Limit: 5.3-10.5%(V)
• Water Solubility: sparingly soluble
• BRN: 773673
• CAS DataBase Reference: 1,6-Dichlorohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Dichlorohexane(2163-00-0)
• EPA Substance Registry System: 1,6-Dichlorohexane(2163-00-0)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-53-52/53-51/53
• Safety Statements: 26-36-61-37/39
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 2163-00-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless liquid

General Description

Colorless liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,6-Dichlorohexane is incompatible with strong oxidizing and reducing agents. Also incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. Irritating vapors and toxic gases, such as hydrogen chloride and carbon monoxide, may be formed when involved in fire [USCG, 1999].

Health Hazard

Exposure can cause irritation of eyes, nose and throat.

Fire Hazard

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as hydrogen chloride and carbon monoxide, may be formed when involved in fire.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H12Cl2/c7-5-3-1-2-4-6-8/h1-6H2

Synthetic route

1,6-hexanediol (629-11-8) → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
Stage #1: 1,6-hexanediol With N,N-dimethylthiourea In dichloromethane at 20℃; Stage #2: With N-chloro-succinimide In dichloromethane at 20℃; for 1h; Irradiation;	98%
With hydrogenchloride; ammonium chloride In water at 50 - 110℃; for 3h; Reagent/catalyst;	96%
With thionyl chloride; Triphenylphosphine oxide at 20 - 80℃; for 3h;	87%

1,6-bis-chlorocarbonyloxy-hexane (2916-20-3) → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With hexabutylguanidinium chloride at 120℃; for 4h;	93%

3-(phenylsulfonyl)propyl chloride (19432-96-3) → 1-Chloropropane (540-54-5) + (cyclopropylsulfonyl)benzene (17637-57-9) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With sodium amalgam In benzene for 6h; Heating;	A 17% B 53% C 13%

1,6-hexanediol (629-11-8) → 6-chloro-1-hexanol (2009-83-8) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With tetrachloromethane; triphenylphosphine In acetonitrile Product distribution; Mechanism;	A 48% B 39%
With hydrogenchloride at 92 - 96℃;
With hydrogenchloride

1,6-Hexanediamine (124-09-4) → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With nitrosylchloride

N,N'-dibenzoylhexane-1,6-diamine (5326-21-6) → benzonitrile (100-47-0) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With phosphorus pentachloride Destillieren der erhaeltlichen Verbindung;

phosgene (75-44-5) + Hexamethylene diisocyanate (822-06-0) → 1,6-dichlorohexane (2163-00-0)

1-Chlorohexane (544-10-5) → 1,5-dichloro-hexane (54305-90-7) + 1,3-dichlorohexane (56375-88-3) + 1,4-dichlorohexane (50635-35-3, 140238-71-7, 140238-72-8) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With chlorine Further byproducts given;
With sulfuryl dichloride; dibenzoyl peroxide at 90℃; Further byproducts given;
With sulfuryl dichloride; dibenzoyl peroxide Further byproducts given;

1-Chlorohexane (544-10-5) → 1,5-dichloro-hexane (54305-90-7) + 1,2-dichlorohexane (2162-92-7) + 1,3-dichlorohexane (56375-88-3) + 1,4-dichlorohexane (50635-35-3, 140238-71-7, 140238-72-8) + 1,1-dichloro-n-hexane (62017-16-7) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With N-chloropiperidine; 2,2'-azobis(isobutyronitrile) In trifluoroacetic acid at 30℃; Product distribution; Rate constant; Irradiation; relative rate constants, position selectivity, substrate selectivity;
With chlorine In benzene at -10.1℃; Product distribution; dependence of the selectivity of chlorination on the conc. of benzene;
With N-chloropiperidine; 2,2'-azobis(isobutyronitrile) In trifluoroacetic acid at 30℃; for 3h; Product distribution; Rate constant; Irradiation; other objects - relative reactivities and relative rate constants for the various positions of chlorination;

1,6-diacetoxyhexane (6222-17-9) → 6-chloro-1-hexyl acetate (40200-18-8) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With aluminium trichloride at 154℃; for 1h; Product distribution; Mechanism; var. temp.;	A 29 % Chromat. B 4 % Chromat.

N-benzoyl-1H-hexahydroazepine (3653-39-2) + phosphorus pentachloride (10026-13-8, 874483-75-7) → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
folgend Destillieren;

hexanediol-(1.6)-diphenyl ether → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With hydrogenchloride at 165 - 175℃;

N-benzoyl-hexamethyleneimine → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With phosphorus pentachloride

1,6-Hexanediamine (124-09-4) + diethyl ether (60-29-7) + nitrosyl chloride → 1,5-dichloro-hexane (54305-90-7) + 1,6-dichlorohexane (2163-00-0) + unsaturated chloro compounds C6H11Cl

hydrogenchloride (7647-01-0) + 1,6-hexanediol (629-11-8) + CuCl → 6-chloro-1-hexanol (2009-83-8) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
unter kontinuierlicher Extraktion mit Toluol;

hydrogenchloride (7647-01-0) + 1,6-hexanediol (629-11-8) → 6-chloro-1-hexanol (2009-83-8) + 1,13-dichloro-7-oxatridecane (91692-23-8) + 13-chloro-7-oxatridecane-1-ol (108291-44-7) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
at 92 - 96℃; weitere Produkte: 6.6'-Dihydroxy-dihexylaether und Hexamethylenglykol-bis-<6-hydroxy-hexyl>-aether;

hydrogenchloride (7647-01-0) + 1,6-diphenoxyhexane (10125-18-5) → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
at 165 - 175℃; im geschlossenen Rohr;

C7H12ClFO2 → 1,6-difluorohexane (373-29-5) + 1-chloro-6-fluorohexane (1550-09-0) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With HBGF at 120℃; for 1.5h; Title compound not separated from byproducts;	A n/a B 57 % Spectr. C n/a

octane-1,8-dioic acid (505-48-6) → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With lead(IV) acetate; ammonium chloride at 20℃; for 4h; mechanical activation;	0.92 mmol
With lead(IV) acetate; ammonium chloride at 20℃; for 6h; mechanical activation;	0.94 mmol

octane-1,8-dioic acid (505-48-6) → 7-chloroheptanoic acid (821-57-8) + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With lead(IV) acetate; ammonium chloride at 20℃; for 48h;	A 0.13 mmol B 0.60 mmol
With lead(IV) acetate; ammonium chloride at 20℃; for 96h;	A 0.11 mmol B 0.44 mmol

1,6-hexanediol (629-11-8) → bis(6-chlorohexyl) ether + 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With hydrogenchloride; 1-methylimidazolium chloride at 80 - 135℃; Conversion of starting material;

1-methylimidazolium chloride (35487-17-3) → 1,6-dichlorohexane (2163-00-0)

Conditions	Yield
With hydrogenchloride

(c-C6H11)2SbLi (1013-90-7) + 1,6-dichlorohexane (2163-00-0) → {(c-C6H11)2Sb}2(CH2)6 (1060-74-8)

Conditions	Yield
In tetrahydrofuran; diethyl ether drop by drop addn. of 1,6-dichlorohexane in THF over 30 min to a (c-C6H11)2SbLi soln. in ether at -45°C; mixt. treated with aq. NH4Cl, evapn. of the ether;	98.9%
In tetrahydrofuran; diethyl ether drop by drop addn. of 1,6-dichlorohexane in THF over 30 min to a (c-C6H11)2SbLi soln. in ether at -45°C; mixt. treated with aq. NH4Cl, evapn. of the ether;	98.9%

1-(4-vinylbenzyl)-1H-imidazole (78430-91-8) + 1,6-dichlorohexane (2163-00-0) → 3,3'-(hexane-1,6-diyl)bis(1-(4-vinylbenzyl)-1H-imidazol-3-ium) chloride

Conditions	Yield
In acetonitrile at 80℃; for 12h; Inert atmosphere; Schlenk technique;	98%

1-methyl-1H-imidazole (616-47-7) + 1,6-dichlorohexane (2163-00-0) → 1,6-bis(3-methylimidazolium-1-yl)hexane dichloride

Conditions	Yield
With calcium chloride In acetonitrile for 48h; Reflux;	97%
In acetonitrile at 20℃; for 24h; Reflux;	87%
at 70 - 100℃; for 0.025h; Microwave irradiation;	82%

sodium formate (141-53-7) + 1,6-dichlorohexane (2163-00-0) → hexane-1,6-diyl diformate (61836-77-9)

Conditions	Yield
tetrabutylammomium bromide at 115℃; for 1.5h;	96%

3-Mercaptopropyltriethoxysilane (14814-09-6) + 1,6-dichlorohexane (2163-00-0) → 1-chloro-6-thiopropyltriethoxysilylhexane + 1,6-bis(thiopropyltriethoxysilyl) hexane

Conditions	Yield
Stage #1: 3-Mercaptopropyltriethoxysilane With sodium ethanolate In ethanol at 20℃; for 3h; Reflux; Stage #2: 1,6-dichlorohexane In ethanol at 80℃; for 3.5h; Reflux;	A 95% B 5%

4-(Diethylamino)salicylaldehyde (17754-90-4) + 1,6-dichlorohexane (2163-00-0) → C17H26ClNO2

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide for 6h; Reflux;	93.4%

1,6-dichlorohexane (2163-00-0) → hexamethylene-1,6-bis(thiosulfate)disodium salt

Conditions	Yield
With sodium hydroxide; sodium thiosulfate In water for 9h; pH=7.1 - 7.3; Product distribution / selectivity; Heating / reflux;	93.3%
With sodium hydroxide; sodium thiosulfate In water for 9h; pH=7.2 - 10.0; Product distribution / selectivity; Heating / reflux;	93.3%
With sodium hydroxide; sodium thiosulfate In water for 9h; pH=4.9 - 5.1; Product distribution / selectivity; Heating / reflux;	91.4%

1-(2,6-diisopropylphenyl)-1H-imidazole (25364-47-0) + 1,6-dichlorohexane (2163-00-0) → 1,1'-di(2,6-diisopropropylphenyl)-3,3'-(1,6-hexanediyl)diimidazolium dichloride

Conditions	Yield
at 140℃; for 24h;	93%
at 140℃; for 6h; neat (no solvent);	72%

1,6-dichlorohexane (2163-00-0) + 8-hydroxy-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehyde (115662-09-4) → C23H34ClNO2

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide for 6h; Reflux;	93%
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide Reflux;	90%
With potassium carbonate In N,N-dimethyl-formamide for 12h; Reflux; Inert atmosphere;	83%

1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2) + 1,6-dichlorohexane (2163-00-0) → 1,1'-(hexane-1,6-diyl)bis(1,8-diazabicyclo[5.4.0]undec-7-enium) dichlorine

Conditions	Yield
In cyclohexane for 8h; Reflux; Inert atmosphere;	93%

indole (120-72-9) + 1,6-dichlorohexane (2163-00-0) → 1,1'-hexane-1,6-diylbis(1H-indole) (95133-96-3)

Conditions	Yield
Stage #1: indole With sodium hydroxide In dimethyl sulfoxide Stage #2: 1,6-dichlorohexane In dimethyl sulfoxide at 20℃; for 3h; Further stages.;	92%

1,6-dichlorohexane (2163-00-0) + 1,1'-(1,6-hexanediyl)bisimidazole (69506-88-3) → 2Br(1-)*C18H30N4(2+)

Conditions	Yield
In toluene for 24h; Reflux;	92%

sodium dibenzyldithiocarbamate (55310-46-8) + 1,6-dichlorohexane (2163-00-0) → 1,6-bis(N, N-dibenzylcarbamothioyl)hexane

Conditions	Yield
With potassium iodide for 4h; Reagent/catalyst; Reflux;	91.8%

sodium dibenzyldithiocarbamate (55310-46-8) + 1,6-dichlorohexane (2163-00-0) → 1,6-bis(N,N-dibenzylthiocarbamoyl disulfide)hexane

Conditions	Yield
Stage #1: 1,6-dichlorohexane With sodium hydroxide; sodium thiosulfate In water for 9h; pH=7.1 - 7.3; Heating / reflux; Stage #2: sodium dibenzyldithiocarbamate With formaldehyd; sodium hydrogencarbonate In water; toluene at 22 - 23℃; for 23h; Product distribution / selectivity;	91%

sodium dibenzyldithiocarbamate (55310-46-8) + sodium thiosulfate + 1,6-dichlorohexane (2163-00-0) → 1,6-bis(N,N-dibenzylthiocarbamoyl disulfide)hexane

Conditions	Yield
Stage #1: sodium thiosulfate; 1,6-dichlorohexane With sodium hydroxide In water for 9h; pH=7.2; Heating / reflux; Stage #2: sodium dibenzyldithiocarbamate With formaldehyd; sodium hydrogencarbonate In water; toluene at 20 - 23℃; for 23h; pH=~ 8.3 - ~ 10.7; Product distribution / selectivity;	91%

sodium diphenylphosphide (4376-01-6) + 1,6-dichlorohexane (2163-00-0) → (6-chlorohexyl)diphenylphosphane (100649-32-9)

Conditions	Yield
In tetrahydrofuran; toluene at -40℃; 5 hour's addition;	90.6%

2-benzylbenzimidazole (621-72-7) + 1,6-dichlorohexane (2163-00-0) → C20H23ClN2 (1039358-79-6)

Conditions	Yield
With sodium hydroxide Heating;	90%

2-(phenoxymethyl)-1H-benzimidazole (6637-29-2) + 1,6-dichlorohexane (2163-00-0) → C20H23ClN2O (1039358-72-9)

Conditions	Yield
With sodium hydroxide Heating;	90%

3-Mercaptopropyltriethoxysilane (14814-09-6) + 1,6-dichlorohexane (2163-00-0) → 1-chloro-6-thiopropyltriethoxysilylhexane

Conditions	Yield
Stage #1: 3-Mercaptopropyltriethoxysilane With sodium ethanolate In ethanol at 20℃; for 3h; Reflux; Stage #2: 1,6-dichlorohexane In ethanol at 80℃; for 3.5h; Reflux;	89%
Stage #1: 3-Mercaptopropyltriethoxysilane With sodium ethanolate In ethanol at 20℃; for 3h; Reflux; Stage #2: 1,6-dichlorohexane In ethanol at 80℃; for 3.5h; Reflux;	89%
Stage #1: 3-Mercaptopropyltriethoxysilane With sodium ethanolate In ethanol at 80℃; for 3h; Stage #2: 1,6-dichlorohexane In ethanol at 80℃; for 5h;

3-Mercaptopropyltriethoxysilane (14814-09-6) + 1,6-dichlorohexane (2163-00-0) → 1,6-bis(thiopropyltriethoxysilyl) hexane

Conditions	Yield
Stage #1: 3-Mercaptopropyltriethoxysilane With sodium ethanolate In ethanol at 35℃; for 2h; Reflux; Stage #2: 1,6-dichlorohexane In ethanol at 80℃; for 4.5h; Reflux;	88%
Stage #1: 3-Mercaptopropyltriethoxysilane With ethanol; sodium ethanolate for 2h; Reflux; Stage #2: 1,6-dichlorohexane at 80℃; for 4.5h; Reflux;	88%

S,S-dimethyl dithiocarbonate (868-84-8) + 1,6-dichlorohexane (2163-00-0) → 6-chloro-1-methylsulfanylhexane (98429-85-7)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In water for 0.5h; Reflux;	87%

1-Butylimidazole (4316-42-1) + 1,6-dichlorohexane (2163-00-0) → 1,6-bis(3-butylimidazolium-1-yl)hexane dichloride

Conditions	Yield
In isopropyl alcohol for 16h; Reflux;	87%

3,5-dimethyl-1H-pyrazole (67-51-6) + 1,6-dichlorohexane (2163-00-0) → 1,1'-(hexane-1,6-diyl)-bis(3,5-dimethyl-1H-pyrazole) (135585-65-8)

Conditions	Yield
Stage #1: 3,5-dimethyl-1H-pyrazole With potassium hydroxide In dimethyl sulfoxide at 20 - 22℃; for 0.333333h; Stage #2: 1,6-dichlorohexane In dimethyl sulfoxide at 20 - 30℃;	84%

1,6-dichlorohexane (2163-00-0) + phenol (108-95-2) → 1-chloro-6-phenoxyhexane (71933-93-2)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate for 16h; Heating;	82%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1,6-dichlorohexane (2163-00-0) → C18H36N4(2+)*2Cl(1-)

Conditions	Yield
In acetonitrile at 20℃; for 24h;	82%

1,6-dichlorohexane (2163-00-0) → C12H27ClN(1+)*Cl(1-)

Conditions	Yield
With nickel; triethylamine at 100℃; for 12h; Autoclave; Inert atmosphere;	82%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1,6-dichlorohexane (2163-00-0) → 1,6-bis(2,3-dimethylimidazolium-1-yl)hexane dichloride

Conditions	Yield
In isopropyl alcohol for 16h; Reflux;	81%

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 629-11-8 1,6-hexanediol 
• 544-10-5 1-Chlorohexane 
• 3653-39-2 N-benzoyl-1H-hexahydroazepine 
• 10026-13-8 phosphorus pentachloride 
• 60-29-7 diethyl ether 
• 7647-01-0 hydrogenchloride 
• 10125-18-5 1,6-diphenoxyhexane 
• 505-48-6 octane-1,8-dioic acid 
• 35487-17-3 1-methylimidazolium chloride 
• 2916-20-3 1,6-bis-chlorocarbonyloxy-hexane 
• 6222-17-9 1,6-diacetoxyhexane 
• 75-44-5 phosgene 
• 822-06-0 Hexamethylene diisocyanate 

Downstream Products

• 14799-66-7 1,6-bis(chlorodimethylsilyl)hexane 
• 10125-18-5 1,6-diphenoxyhexane 
• 102953-17-3 2,2-diphenyl-8-piperidino-octanenitrile 
• 102897-06-3 8-diethylamino-2,2-diphenyl-octanenitrile 
• 22819-91-6 7-chloroheptanenitrile 
• 70466-03-4 N-(6-chlorohexyl)phthalimide 
• 870-62-2 N,N,N,N',N',N'-hexamethylhexanediammonium iodide 
• 373-15-9 hex-5-enyl fluoride 
• 373-29-5 1,6-difluorohexane 
• 1550-09-0 1-chloro-6-fluorohexane 
• 34683-73-3 1-chloro-6-iodohexane 
• 3246-10-4 1-(6-Chlor-hexyloxy)-2-methoxy-benzol 
• 133546-87-9 octanebis(thiolic)acid S,S-diphenyl ester 
• 61836-77-9 hexane-1,6-diyl diformate 

Relevant articles and documents

Preparation method of dichloroalkane

The invention discloses a preparation method of dichloroalkane, which comprises the following steps: mixing diol, a catalyst and a solvent, stirring and heating the components, introducing HCl gas into the mixture, and carrying out reflux reaction for 3-5 hours; and after the reaction is finished, treating the reaction solution to obtain dichloroalkane. According to the preparation method providedby the invention, the catalyst ammonium chloride is added, so that the reaction speed is obviously increased, and side reactions are reduced. In the invention, a large amount of solvent water is added in the reaction process, so that on one hand, the formation of monochloro ether by-products can be effectively inhibited, a water phase can be directly and repeatedly used, and basically no sewage is discharged; besides, by using the oil-water separator, the dichloroalkane product can be effectively separated, the product purity is high, and the yield is high.

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