41443-60-1

Basic information

• Product Name: Ethyl 6,8-dichloro caprylate
• Synonyms: ETHYL 6,8-DICHLORO CAPRYLATE;ETHYL-6,8-DICHLOROOCTANATE;6,8-DICHLOROETHYLCAPRYLATE;6,8-DICHLOROCAPRYLATE;6,8-Dichloro-octanoic acid ethyl ester;6-HYDROXY-8-CHLOROOCTANOIC ACID ETHYL ESTER ,97+%;Octanoic acid,6,8-dichloro-
• CAS NO: 41443-60-1
• Molecular Formula: C₈H₁₄Cl₂O₂
• Molecular Weight: 241.15
• EINECS: 1308068-626-2
• Product Categories: Organic acids;Ester series
• Mol File: 41443-60-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 288.5ºC at 760 mmHg
• Flash Point: >230 °F
• Appearance: Colorless to yellowish transparent liquid
• Density: 1.107 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00233mmHg at 25°C
• Refractive Index: n20/D 1.462(lit.)
• PKA: 4.73±0.10(Predicted)
• CAS DataBase Reference: Ethyl 6,8-dichloro caprylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 6,8-dichloro caprylate(41443-60-1)
• EPA Substance Registry System: Ethyl 6,8-dichloro caprylate(41443-60-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 41443-60-1(Hazardous Substances Data)

Usage

Description

Ethyl 6,8-dichloro caprylate, also known as 6,8-dichloro-octanoic acid or 6,8-dichloro-octanoate, is a colorless to pale yellow liquid with chemical properties that make it a valuable intermediate in the synthesis of α-Lipoic acid (L468750) and its derivatives.

Uses

Used in Pharmaceutical Industry:
Ethyl 6,8-dichloro caprylate is used as an intermediate in the synthesis of α-Lipoic acid (L468750) for its role in the production of various pharmaceutical compounds. This acid serves as a crucial building block in the development of medications that can potentially treat a range of health conditions.
Used in Chemical Synthesis:
Ethyl 6,8-dichloro caprylate is used as a chemical intermediate for the creation of α-Lipoic acid derivatives, which can be further utilized in various applications across different industries, such as pharmaceuticals, nutraceuticals, and cosmetics. Its unique chemical structure allows for the development of novel compounds with potential therapeutic and functional benefits.

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

Synthetic route

(+)-8-chloro-6-hydroxy-octanoic acid (90435-60-2) → (+)-6,8-dichloro-octanoic acid (41443-60-1)

Conditions	Yield
With pyridine; sodium hydroxide; thionyl chloride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; toluene	80%

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

Conditions	Yield
With hydrogenchloride

(-)-6,8-dichlorooctanoic acid → (+)-6,8-dichloro-octanoic acid (41443-60-1)

Conditions	Yield
Stage #1: (-)-6,8-dichlorooctanoic acid With sodium hydroxide In 2-methoxy-ethanol; water at 60℃; for 5h; Stage #2: With sulfuric acid In 2-methoxy-ethanol; water pH=1 - 2;

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

Conditions	Yield
Alkaline aqueous solution;

(+)-6,8-dichloro-octanoic acid (41443-60-1) + (S)-1-phenyl-ethylamine (2627-86-3) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (R)-(+)-6,8-dichlorooctanoic acid S(-)α-methylbenzylamine salt + (S)-(-)-6,8-dichlorooctanoic acid R(+)α-methylbenzylamine salt

Conditions	Yield
Stage #1: (+)-6,8-dichloro-octanoic acid; (S)-1-phenyl-ethylamine In ethyl acetate at 0 - 20℃; Resolution of racemate; Stage #2: (R)-1-phenyl-ethyl-amine In ethyl acetate at 0 - 20℃; Resolution of racemate;	A 45% B n/a

(+)-6,8-dichloro-octanoic acid (41443-60-1) → 6,8-dichloro-octanoic acid (41443-60-1, 98441-83-9)

Conditions	Yield
With ephedrine dextrorotatory form;
With ephedrine levorotatory form;

(+)-6,8-dichloro-octanoic acid (41443-60-1) → (-)-Dihydrolipoic acid (462-20-4, 7516-48-5, 98441-85-1, 119365-69-4)

Conditions	Yield
Multistep reaction;

(+)-6,8-dichloro-octanoic acid (41443-60-1) + (S)-1-phenyl-ethylamine (2627-86-3) → (+)-6,8-dichlorooctanoic acid-(S)-(-)-α-methylbenzylamine

Conditions	Yield
In ethyl acetate at 0 - 10℃;
Stage #1: (+)-6,8-dichloro-octanoic acid; (S)-1-phenyl-ethylamine In ethyl acetate at 18 - 20℃; Stage #2: In ethyl acetate at 0 - 5℃;

(+)-6,8-dichloro-octanoic acid (41443-60-1) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (-)-6,8-dichlorooctanoic acid-(R)-(+)-methylbenzylamine

(+)-6,8-dichloro-octanoic acid (41443-60-1) → C8H14O8S4(2-)*2Na(1+)

Conditions	Yield
With sodium thiosulfate In ethanol; water at 60 - 70℃; for 6h;

Upstream product

• 1070-64-0 6,8-dichlorooctanoic acid ethyl ester 
• 90435-60-2 (+)-8-chloro-6-hydroxy-octanoic acid 

Downstream Products

• 41443-60-1 6,8-dichloro-octanoic acid 
• 462-20-4 (-)-Dihydrolipoic acid 

Relevant articles and documents

Method of preparing R-(+)-alpha-lipoic acid and its salt

The present invention discloses a method for preparing R-(+)-LA as well as its metal salts including sodium salt, potassium salt, calcium salt, magnesium salt, zinc salt, ferric salt, cooper salt , lithium salt and its organic salt, wherein a racemic Ethyl 6, 8-Dichlorooctanoic acid is employed as starting agents, followed by a hydrolysis and resolution processes to obtain (+)DCA, and then through sulfuration and cyclization process to obtain R-(+)-LA as well as its varied salts. A method for converting the (?)DCA to (+)DCA is also introduced.