[ CAS No. 1070-64-0 ] {[proInfo.proName]}

Name: 1070-64-0|Ethyl 6,8-dichlorooctanoate|95%
Brand: Ambeed
SKU: A586355
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Quality Control of [ 1070-64-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1070-64-0 ]

SDS Specification

Alternatived Products of [ 1070-64-0 ]

Product Details of [ 1070-64-0 ]

CAS No. :	1070-64-0	MDL No. :	MFCD01711127
Formula :	C₁₀H₁₈Cl₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RFYDWSNYTVVKBR-UHFFFAOYSA-N
M.W :	241.15	Pubchem ID :	14053
Synonyms :

Calculated chemistry of [ 1070-64-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.9
Num. rotatable bonds :	9
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.06
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.17
Log Po/w (XLOGP3) :	3.09
Log Po/w (WLOGP) :	3.35
Log Po/w (MLOGP) :	3.15
Log Po/w (SILICOS-IT) :	3.77
Consensus Log Po/w :	3.31

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.69
Solubility :	0.495 mg/ml ; 0.00205 mol/l
Class :	Soluble
Log S (Ali) :	-3.31
Solubility :	0.118 mg/ml ; 0.00049 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.08
Solubility :	0.0202 mg/ml ; 0.0000838 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.71

Safety of [ 1070-64-0 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P273-P280-P302+P352+P312-P305+P351+P338+P310-P312-P362+P364-P391-P501	UN#:	3082
Hazard Statements:	H303-H312-H318-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1070-64-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1070-64-0 ]
Downstream synthetic route of [ 1070-64-0 ]

[ 1070-64-0 ] Synthesis Path-Upstream 1~2

1
[ 1070-65-1 ]
[ 1070-64-0 ]

Yield	Reaction Conditions	Operation in experiment
96.69%	With phosgene; N,N'-dimethylbenzylamine In 1,2-dichloro-ethane at 10 - 75℃; for 2.5 h;	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 ° C,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 ° C,Ethyl 6,8-dichlorooctanoate,Product mol yield 95.68percent, Purity 96.65percentThe 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 96.69percentPurity 99.71percent.
480 kg	With thionyl chloride In toluene at 100℃; for 5 h; Cooling with ice; Large scale	In the ice bath conditions,Will be 297KgThionyl chlorideAnd 1485Kg toluene into the 3000L reactor, Slowly drop 540Kg6-hydroxy-8-chlorooctanoate,While the continuous drying of dry air into the bubble, and control the air flow of 6.48L / min(That is, according to per kg 6-hydroxy-8-chloroctanoic acid ethyl ester air flow control in the 0.012L / min), 2 hours drop finished, after warming to 30 ~ 35 ,Insulation for 1 hour, and then heated to about 90 ~ 100 , to stop the bubble,After 2 hours of incubation, the reaction solution was neutralized with a 20percent aqueous solution of sodium carbonateTo neutral, layered, organic layer at atmospheric pressure to evaporate the solvent,A fraction of 170 to 180 ° C was collected under a vacuum of 5 mmHg,Get 480Kg6,8-dichloroctanoate, purity 98.3percent.

Reference： [1] Patent: CN105693510, 2016, A, . Location in patent: Paragraph 0047; 0048; 0049
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 416,418
[3] Patent: CN106966900, 2017, A, . Location in patent: Paragraph 0014; 0015; 0016; 0017; 0018; 0019; 0020; 0021

2
[ 626-86-8 ]
[ 1070-64-0 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 416,418

[ 1070-64-0 ] Synthesis Path-Downstream 1~55

1
[ 1070-64-0 ]
[ 98997-92-3 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 6151

2
[ 1070-64-0 ]
[ 100911-03-3 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 6151

3
[ 1070-65-1 ]
[ 1070-64-0 ]

Yield	Reaction Conditions	Operation in experiment
96.69%	With phosgene; N,N'-dimethylbenzylamine; In 1,2-dichloro-ethane; at 10 - 75℃; for 2.5h;	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 C,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 C,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%.
480 kg	With thionyl chloride; In toluene; at 100℃; for 5h;Cooling with ice; Large scale;	In the ice bath conditions,Will be 297KgThionyl chlorideAnd 1485Kg toluene into the 3000L reactor, Slowly drop 540Kg6-hydroxy-8-chlorooctanoate,While the continuous drying of dry air into the bubble, and control the air flow of 6.48L / min(That is, according to per kg 6-hydroxy-8-chloroctanoic acid ethyl ester air flow control in the 0.012L / min), 2 hours drop finished, after warming to 30 ~ 35 ,Insulation for 1 hour, and then heated to about 90 ~ 100 , to stop the bubble,After 2 hours of incubation, the reaction solution was neutralized with a 20% aqueous solution of sodium carbonateTo neutral, layered, organic layer at atmospheric pressure to evaporate the solvent,A fraction of 170 to 180 C was collected under a vacuum of 5 mmHg,Get 480Kg6,8-dichloroctanoate, purity 98.3%.

Reference： [1]Patent: CN105693510,2016,A .Location in patent: Paragraph 0047; 0048; 0049
[2]Journal of the American Chemical Society,1955,vol. 77,p. 416,418
[3]Patent: CN106966900,2017,A .Location in patent: Paragraph 0014; 0015; 0016; 0017; 0018; 0019; 0020; 0021

5
[ 626-86-8 ]
[ 1070-64-0 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 416,418

6
[ 1070-64-0 ]
[ 120089-31-8 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 6151

7
[ 1070-64-0 ]
[ 99062-11-0 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 6151

8
[ 1070-64-0 ]
5,7-dichloro-heptanoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 6151

9
[ 1070-64-0 ]
[ 100402-37-7 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 6151

10
[ 1070-64-0 ]
[ 110358-77-5 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 6151

11
[ 1070-64-0 ]
[ 41443-60-1 ]

Yield	Reaction Conditions	Operation in experiment
	Alkaline aqueous solution;	1, 100 g (0.4mol) racemic Ethyl 6, 8-Dichlorooctanoic acid (95% industrial grade) is prepared first, and then treated with an alkali hydrolysis process so as to obtain (+/-)-DCA 80 g, to be dissolved into 300 ml ethyl acetate, followed by 24 g (0.2 mol) S-(-)-alpha-phenethylamine, afterwards, gradually cooled down to a temperature range between 0-10 C., overnight, filtered, and ultimately obtain 30 g wet (+)DCA S-(-)-alpha-phenethylamine salt. Afterwards, a recrystallization process is followed, wherein the (+)DCA-S-(-)-alpha-phenethylamine salt is dissolved in the ethyl acetate, and acidified with diluted hydrochloric acid, and extracted by methylbenzene, and distilled at low temperature to remove solvent, finally obtain 18.8 g (+)-DCA, [alpha]D25+48-49.6 with a yield rate from 42% to 46%.

Reference： [1]Patent: US2007/15926,2007,A1 .Location in patent: Page/Page column 2

12
[ 1070-64-0 ]
[ 46353-61-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium sulfide; tetrabutylammomium bromide; sulfur; In water; at 85℃; for 3h;	Preparation of lipoic acid: (1): Weigh 20g of sodium sulfide dissolved in 80g of purified water, dissolved at 35 C, formulated into a sodium sulfide solution; (2): 20 g of 6,8-dichlorooctanoate and 5 g of sulfur are added to 100 g of water.2 g of tetrabutylammonium bromide was heated to 85 C, and the sodium sulfide solution obtained in the step (1) was slowly added to the aqueous solution. After adding sodium sulfide solution, The reaction was continued for 3 hours; after the reaction was completed, the temperature was lowered to 60 C. Resting for about 60 minutes, layering, to obtain ethyl lipoic acid; (3): adding ethyl lipoate to an aqueous solvent, Add 20g of sodium hydroxide and 1g of tetrabutylammonium bromide. Stir at 200r/min, raise the temperature to 60 C, and after the reaction is finished, filter while hot; (4): The filtrate obtained in the step (3) is cooled to 5 C, and then the pH is adjusted to 1 with hydrochloric acid, and filtered to obtain a crude lipoic acid; (5): The crude lipoic acid obtained in the step (4) is added to a mixed solvent (cyclohexane: ethyl acetate = 5:1 (w: w)), and stirred at 100 r/min. Heating to 40 C, holding for 30 minutes, so that the crude lipoic acid is completely dissolved,Then add purified water at 36 C and keep stirring for 10 minutes.The aqueous layer was removed after standing for 20 minutes, and the organic layer was heated to 40 C. After adding silica gel, stirring for 2 hours, suction filtration. Then cooled to 16 C,Stirring and crystallization for 1 hour, and suction filtration to obtain a fine product of lipoic acid wet. It was then dried at a temperature of 35 C for 12 hours.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3078 - 3083
[2]Patent: CN109925279,2019,A .Location in patent: Paragraph 0076-0081

13
[ 1070-64-0 ]
[ 1451075-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water; at 50℃; for 1.5h;	To a solution of <strong>[1070-64-0]ethyl 6,8-dichlorooctanoate</strong> (6.01 g, 25 mmol) in 95% ethanol (10mL)was added sodium hydroxide (2 g, 50 mmol) and water (38 mL). The mixture was heated to 50 C for 1.5 h and the aqueous disodium diselenide (prepared from 3.95 g selenium powder19) was then added dropwise at 65 C. After stirring for 2 h, the mixture was cooled to 40 C and activated carbon (8 g) was then added. After stirring for 0.5 h, the mixture was filtered, and the ethanol was distilled off under reduced pressure (caution: the temperatureof the filtrate must not exceed 50C). Water (400 mL) was added to the residue and the mixture was cooled to 0 C. A solution of 10% hydrochloric acid was then added dropwise till pH = 1, resulting in the formation of a solid product. The solid was filtered and washed thoroughly with water.
	With water; sodium hydroxide; In ethanol; at 50℃; for 1.5h;Green chemistry;	Sodium hydroxide (2 g, 50 mmol)and water (20 mL) were added to a solution of ethyl 6, 8-dichlorooctanoate(12 g, 50 mmol) in 95% ethanol (10 mL). The mixture washeated to 50 C for 1.5 h and selenium powder (5.9 g, 55 mmol) wasthen added. The mixture was heated to 80 C and a solution of sodiumsulfide nonahydrate (13.2 g, 55 mmol) in water (35 mL) and 95%ethanol (20 mL) was then added dropwise over a period of 1.5 h. 25%Aqueous sodium sulfite (46 mL) was added rapidly to the above mixtureand then the reaction temperature was kept at 60 C for 3h. Themixture was cooled to room temperature and filtered. To the filtratewas added water (300 mL) and activated carbon (4 g). After stirringfor 0.5 h at 50 C, the mixture was filtered, the filtrate was cooled to0 C and 10% aqueous hydrochloric acid was then added dropwise topH=1 resulting in formation of a solid product. The mixture was filtered,and the filter cake was washed thoroughly with water (20 mL),and dried to give a brown solid, which was recrystallised from ethylacetate to give (1): Brown solid, yield 85%, m.p. 73-75 C (lit.14 72-74 C). IR (cm-1) upsilon: 3026 (OH), 1697 (C=O), 729 (C-Se); 1H NMR(CDCl3): delta 3.90-3.95 (m, 1H, Se-CH-), 3.33 (t, 2H, J = 6.3 Hz,S-CH2-), 2.95-3.01 (m, 1H, S-CH2-CH-), 2.39 (t, 2H, J = 7.4 Hz,-CH2-CO-), 1.44-1.95 (m, 7H, -(CH2)3-CH2-CO-, S-CH2-CH-);APCI-MS: m/z (%): 255.0 ([M+H]+, 45). Anal. Calcd for C8H14O2SSe:C, 37.95; H, 5.57; O, 12.64. Found: C, 38.01; H, 5.59; O, 12.61%.

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2013,vol. 188,p. 1312 - 1319
[2]Journal of Chemical Research,2013,vol. 37,p. 311 - 314

14
[ 1070-64-0 ]
[ 1456816-63-9 ]