1070-64-0

Basic information

• Product Name: Ethyl 6,8-dichlorooctanoate
• Synonyms: 6,8-dichloro-octanoicaciethylester;ETHYL-6,8-DICHLOROOCTANATE;ETHYL 6,8-DICHLOROOCTANOATE;6,8-DICHLOROETHYLCAPRYLATE;6,8-DICHLOROOCTANOATE;6,8-DICHLOROOCTANOIC ACID ETHYL ESTER(EDCO);6,8-DICHLOROETHYLOCTANOATE;6,8-Dichlorethylcaprylat
• CAS NO: 1070-64-0
• Molecular Formula: C₁₀H₁₈Cl₂O₂
• Molecular Weight: 241.15
• EINECS: 435-080-1
• Mol File: 1070-64-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 288.5 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.107 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00233mmHg at 25°C
• Refractive Index: n20/D 1.462(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Ethyl 6,8-dichlorooctanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 6,8-dichlorooctanoate(1070-64-0)
• EPA Substance Registry System: Ethyl 6,8-dichlorooctanoate(1070-64-0)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53-43
• Safety Statements: 26-36-61-37-24
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 1070-64-0(Hazardous Substances Data)

Usage

Chemical Properties

Colourless to Pale Yellow Oil

Uses

6,8-Dichlorooctanoic Acid Ethyl Ester is an industrial toxin as well as an intermediate product of lipoic acid synthesis.

Flammability and Explosibility

Notclassified

Synthesis

Dichloroethane in the organic solvent, 6-hydroxy -Chloro - octanoic acid ethyl ester with chlorinated reagent solid phosgene inN, N-dimethyl benzyl amine for the acid-binding agentEthyl 6-hydroxy-8-chlorooctanoate,Chlorination reagents,N, N-dimethylbenzylamine molar ratio1: 1.05: 0.12,The organic solvent was reacted with 6-hydroxy-8-The weight ratio of ethyl chlorocaprylate was1: 2.4 at a temperature ofN, N-dimethylbenzylamine was added dropwise at 10℃,Insulation temperature of 75 ,Insulation time 150min,In the reaction solution obtained,Water layer, water and 6 - hydroxy -8-chloro-ethyl octanoate weight ratio of 1:3, the upper organic phase.Vacuum distillation to collect vacuum 5mmHg,A temperature of 172-176℃,Ethyl 6,8-dichlorooctanoate,Product mol yield 95.68%, Purity 96.65%The bottom of the liquid base to adjust the pH value of 11,Layered,The upper layer was dewatered with sodium sulfateN, N-dimethylbenzylamine,The molar yield of the product was 96.69%Purity 99.71%.

InChI:InChI=1/C10H18Cl2O2/c1-2-14-10(13)6-4-3-5-9(12)7-8-11/h9H,2-8H2,1H3

Synthetic route

6-hydroxy-8-chlorooctanoic acid ethyl ester (1070-65-1) → 6,8-dichlorooctanoic acid ethyl ester (1070-64-0)

Conditions	Yield
With phosgene; N,N'-dimethylbenzylamine In 1,2-dichloro-ethane at 10 - 75℃; for 2.5h; Concentration; Solvent; Reagent/catalyst; Temperature;	96.69%
With pyridine; thionyl chloride; benzene
With thionyl chloride In toluene at 100℃; for 5h; Reagent/catalyst; Solvent; Cooling with ice; Large scale;	480 kg

C10H20O4 → 6,8-dichlorooctanoic acid ethyl ester (1070-64-0)

Conditions	Yield
With thionyl chloride at 80℃; for 4h; Reagent/catalyst; Temperature; Alkaline conditions;	87%

adipinic acid monoethyl ester (626-86-8) → 6,8-dichlorooctanoic acid ethyl ester (1070-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,1,2,2-tetrachloro-ethane; thionyl chloride / anschliessendes Behandeln mit Aethylen und Aluminiumchlorid und Behandeln der nach dem Versetzen mit wss.Salzsaeure erhaltenen nicht-waessrigen Phase des Reaktionsgemisches mit Natriumboranat in Aethanol 2: benzene; pyridine; thionyl chloride View Scheme

7-hydroxyheptanal (22054-13-3) → 6,8-dichlorooctanoic acid ethyl ester (1070-64-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: Pt/γ-Al2O3 / toluene / 100 °C 2: alumina / 350 °C 3: Amberlyst-15 / 10 h / 100 °C 4: Pd/γ-Al2O3; hydrogen / water / 100 °C / 37503.8 Torr / Sealed tube 5: thionyl chloride / 4 h / 80 °C / Alkaline conditions View Scheme

ethyl 7-hydroxyheptanoate (6149-48-0) → 6,8-dichlorooctanoic acid ethyl ester (1070-64-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: alumina / 350 °C 2: Amberlyst-15 / 10 h / 100 °C 3: Pd/γ-Al2O3; hydrogen / water / 100 °C / 37503.8 Torr / Sealed tube 4: thionyl chloride / 4 h / 80 °C / Alkaline conditions View Scheme

ethyl 6-heptenoate (25118-23-4) → 6,8-dichlorooctanoic acid ethyl ester (1070-64-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: Amberlyst-15 / 10 h / 100 °C 2: Pd/γ-Al2O3; hydrogen / water / 100 °C / 37503.8 Torr / Sealed tube 3: thionyl chloride / 4 h / 80 °C / Alkaline conditions View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → (R)-1,2-dithiolane-3-pentanoic acid (1200-22-2)

Conditions	Yield
With ammonium hydrogen sulfite; sodium sulfide nonahydrate; sulfur In propan-1-ol; water; isopropyl alcohol at 70℃; for 3.5h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Darkness;	30.6%

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 6,8-dichloro-octan-1-ol (98997-92-3)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 5,7-dichloro-heptanoic acid (100911-03-3)

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 8-bromo-1,3-dichloro-octane (120089-31-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: tetrachloromethane; phosphorus (III)-bromide View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 7,9-dichloro-nonanenitrile (99062-11-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium alanate; diethyl ether 2: tetrachloromethane; phosphorus (III)-bromide 3: aqueous ethanol View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 5,7-dichloro-heptanoic acid ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 2: benzene; sulfuric acid View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 7,9-dichloro-nonanoic acid ethyl ester (100402-37-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: lithium alanate; diethyl ether 2: tetrachloromethane; phosphorus (III)-bromide 3: aqueous ethanol 4: ethanol; hydrogen chloride 5: water View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 7,9-dichloro-nonaneimidic acid ethyl ester; hydrochloride (110358-77-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: lithium alanate; diethyl ether 2: tetrachloromethane; phosphorus (III)-bromide 3: aqueous ethanol 4: ethanol; hydrogen chloride View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → (+)-6,8-dichloro-octanoic acid (41443-60-1)

Conditions	Yield
Alkaline aqueous solution;

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 1,2-dithiolan-3-yl pentanoic acid ethyl ester (46353-61-1)

Conditions	Yield
With sodium sulfide; tetrabutylammomium bromide; sulfur In toluene for 5h; Reflux;
With sodium sulfide; tetrabutylammomium bromide; sulfur In water at 85℃; for 3h; Temperature; Reagent/catalyst;
With sodium sulfide; sulfur In water at 50 - 84℃; for 3h;

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → sodium 6,8-dichlorooctanoate (1451075-56-1)

Conditions	Yield
With sodium hydroxide In ethanol; water at 50℃; for 1.5h;
With water; sodium hydroxide In ethanol at 50℃; for 1.5h; Green chemistry;
With sodium hydroxide In water at 65℃; for 3h;
With water; sodium hydroxide In ethanol at 50℃; for 2h; Temperature; Solvent;

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(4-chlorobenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-63-9)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / 20 °C View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(furan-2-ylmethylene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-64-0)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / 20 °C View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(2-chlorobenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-65-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / 20 °C View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(2-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-66-2)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / Reflux View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(4-methylbenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-67-3)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / Reflux View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(3-methoxy-4-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-68-4)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / Reflux View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(3-hydroxy-4-methoxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-69-5)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / Reflux View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(4-(dimethylamino)benzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-70-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / Reflux View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(4-methoxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-71-9)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / Reflux View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(4-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-72-0)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / Reflux View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → C8H13O2Se2(1-)*Na(1+) (1451075-57-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2: disodium diselenide / ethanol; water / 2 h / 65 °C View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → N'-(3,4-dihydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-73-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate 5.1: ethanol / Reflux View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 5-(1,2-diselenolan-3-yl)pentanoic acid (6708-13-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → ethyl 5-(1,2-diselenolan-3-yl)pentanoate (1456816-57-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C View Scheme

6,8-dichlorooctanoic acid ethyl ester (1070-64-0) → 5-(1,2-diselenolan-3-yl)pentanehydrazide (1456816-58-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide / ethanol; water / 1.5 h / 50 °C 2.1: disodium diselenide / ethanol; water / 2 h / 65 °C 2.2: 0 °C / pH 1 3.1: acetyl chloride / 2 h / 20 °C 3.2: 20 °C 4.1: hydrazine hydrate View Scheme

Upstream product

• 626-86-8 adipinic acid monoethyl ester 
• 25118-23-4 ethyl 6-heptenoate 
• 6149-48-0 ethyl 7-hydroxyheptanoate 
• 22054-13-3 7-hydroxyheptanal 
• 1070-65-1 6-hydroxy-8-chlorooctanoic acid ethyl ester 

Downstream Products

• 1456816-63-9 N'-(4-chlorobenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-65-1 N'-(2-chlorobenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-66-2 N'-(2-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-67-3 N'-(4-methylbenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-68-4 N'-(3-methoxy-4-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-69-5 N'-(3-hydroxy-4-methoxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-70-8 N'-(4-(dimethylamino)benzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-71-9 N'-(4-methoxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-72-0 N'-(4-hydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-73-1 N'-(3,4-dihydroxybenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 6708-13-0 5-(1,2-diselenolan-3-yl)pentanoic acid 
• 1456816-59-3 N'-benzylidene-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-60-6 N'-(4-nitrobenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 
• 1456816-61-7 N'-(2,4-chlorobenzylidene)-5-(1,2-diselenolan-3-yl)pentanehydrazide 

Relevant articles and documents

Method for preparing 6,8-dichloroethyl caprylate

The invention provides a method for preparing 6,8-dichloroethyl caprylate. As shown in the following reaction formula, the method comprises the following reaction: performing oxidative esterificationon a compound 1 to obtain a compound 2, dehydrating to generate a compound 3, performing a Prins condensation reaction to obtain a compound 4, performing hydrolysis hydrogenation to obtain a compound5, and finally performing chlorination to obtain the 6,8-dichloroethyl caprylate. The method has the characteristics of easily available raw materials, simple process, high efficiency and environmental protection.

Preparation method of ethyl 6,8-dichlorocaprylate

The invention relates to a preparation method of ethyl 6,8-dichlorocaprylate, belonging to the technical field of preparation of organic compound intermediates. The preparation method comprises the steps of reacting ethyl 6-hydroxy-8-chlorocaprylate with a chlorination agent in an organic solvent by taking N,N-dimethylbenzylamine as an acid-binding agent, controlling the reaction temperature, maintaining the temperature after the reaction is finished, and controlling the temperature maintaining temperature and the temperature maintaining time to obtain reaction liquid, adding water for layering to obtain an organic phase at an upper layer, carrying out reduced pressure rectification to obtain ethyl 6,8-dichlorocaprylate, adding alkali to a lower layer to regulate pH for layering, and carrying out dehydration on the upper layer by virtue of anhydrous sodium sulphate so as to obtain N,N-dimethylbenzylamine, and recycling. By virtue of the preparation method, the chlorination capacity is improved, the yield reaches about 95%, the cycle use is realized, the discharging of wastewater is reduced, the process route is advanced, the process conditions are reasonable, the operation is simple and safe, the reaction yield is high, the production cost is relatively low, and three wastes are little.