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

Chemical Properties

Colorless to pale yellow liquid

Uses

Different sources of media describe the Uses of 41443-60-1 differently. You can refer to the following data:
1. 6,8-Dichloro-octanoic Acid is an Intermediate in the synthesis of α-Lipoic acid (L468750) and its derivatives.
2. 6,8-Dichloro-octanoate is a Intermediate in the synthesis of α-Lipoic acid (L468750) and its derivatives.

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.