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3,6-Dioxa-1,8-octanedithiol

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Name

3,6-Dioxa-1,8-octanedithiol

EINECS 239-044-2
CAS No. 14970-87-7 Density 1.082 g/cm3
PSA 96.06000 LogP 0.87920
Solubility 11.4g/L at 19.8℃ Melting Point N/A
Formula C6H14O2S2 Boiling Point 257.004 °C at 760 mmHg
Molecular Weight 182.308 Flash Point 109.233 °C
Transport Information UN 2810 Appearance N/A
Safety 26-45 Risk Codes 22-23-36/37/38
Molecular Structure Molecular Structure of 14970-87-7 (3,6-Dioxa-1,8-octanedithiol) Hazard Symbols ToxicT
Synonyms

Ethanethiol,2,2'-(ethylenedioxy)di- (6CI,8CI);Ethyleneglycol di-2-mercaptoethyl ether;NSC 94782;Triethylene glycol dimercaptan;Triethylene glycol dithiol;1,2-Bis(2-mercaptoethoxy)ethane;1,2-Bis(2'-mercaptoethoxy)ethane;1,8-Dimercapto-3,6-dioxaoctane;2,2'-(Ethylenedioxy)diethanethiol;3,6-Dioxaoctane-1,8-dithiol;

Article Data 13

3,6-Dioxa-1,8-octanedithiol Synthetic route

19249-03-7

triethylene glycol di-(p-toluenesulfonate)

14970-87-7

3,6-dioxa-1,8-octandithiol

Conditions
ConditionsYield
Stage #1: triethylene glycol di-(p-toluenesulfonate) With thiourea In ethanol
Stage #2: With sodium hydroxide Heating;
92%
Multi-step reaction with 2 steps
1: sodium iodide / acetone / 18 h / 60 °C
2: hydrogenchloride / methanol; water / 3 h / 120 °C / Inert atmosphere
View Scheme

S,S‘-(3,6-dioxaoctane-1,8-diyl)-bis(thioacetate)

14970-87-7

3,6-dioxa-1,8-octandithiol

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 120℃; for 3h; Inert atmosphere;73%
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

14970-87-7

3,6-dioxa-1,8-octandithiol

Conditions
ConditionsYield
With potassium hydroxide; thiourea In ethanol64.3%
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

14970-87-7

3,6-dioxa-1,8-octandithiol

Conditions
ConditionsYield
With hydrogenchloride; thiourea55%
Multi-step reaction with 2 steps
1.1: 71 percent / aq. NaOH / tetrahydrofuran / 4 h / 0 °C
2.1: thiourea / aq. ethanol
2.2: 92 percent / aq. NaOH / Heating
View Scheme
Multi-step reaction with 2 steps
1: 63 percent / PBr3; pyridine
2: 64.3 percent / thiourea; aq. KOH / ethanol
View Scheme
112-26-5

1,2-bis(2-chloroethoxy)ethane

14970-87-7

3,6-dioxa-1,8-octandithiol

Conditions
ConditionsYield
With potassium hydroxide; thiourea 1.) 90percent ethanol, reflux, 5 h, 2.) water, reflux, 3 h; Yield given. Multistep reaction;
Stage #1: 1,2-bis(2-chloroethoxy)ethane With thiourea In ethanol for 2h; Substitution; Heating;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran Reduction;
With hydrazine hydrate; thiourea In water; toluene
With sodium trithiocarbonate In water Inert atmosphere;
106-92-3

Allyl glycidyl ether

764-99-8

diethylene glycol divinyl ether

14970-87-7

3,6-dioxa-1,8-octandithiol

poly(allyl glycidyl ether-co-diethylene glycol divinyl ether-co-dimercaptodioxaoctane)

poly(allyl glycidyl ether-co-diethylene glycol divinyl ether-co-dimercaptodioxaoctane)

Conditions
ConditionsYield
Stage #1: diethylene glycol divinyl ether; 3,6-dioxa-1,8-octandithiol With azobis(2-cyanobutane) at 50 - 70℃; for 2h;
Stage #2: Allyl glycidyl ether With azobis(2-cyanobutane) at 70℃; for 37h;
100%
106-92-3

Allyl glycidyl ether

764-99-8

diethylene glycol divinyl ether

14970-87-7

3,6-dioxa-1,8-octandithiol

poly(allyl glycidyl ether-co-diethylene glycol divinyl ether-co-dimercaptodioxaoctane)

poly(allyl glycidyl ether-co-diethylene glycol divinyl ether-co-dimercaptodioxaoctane)

Conditions
ConditionsYield
Stage #1: diethylene glycol divinyl ether; 3,6-dioxa-1,8-octandithiol With azobis(2-cyanobutane) at 60 - 70℃; for 10.8333h;
Stage #2: Allyl glycidyl ether With azobis(2-cyanobutane) at 70℃; for 42h;
100%
14970-87-7

3,6-dioxa-1,8-octandithiol

2089-30-7

(E)-1-(4-(allyloxy)phenyl)ethan-1-one oxime

C28H40N2O6S2

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; UV-irradiation;100%
826-29-9

4-allyloxymethyl-1,3-dioxolan-2-one

14970-87-7

3,6-dioxa-1,8-octandithiol

C22H38O10S2

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 70℃; for 6h; Inert atmosphere;99%
2033-24-1

cycl-isopropylidene malonate

14970-87-7

3,6-dioxa-1,8-octandithiol

149-73-5

trimethyl orthoformate

C20H26O10S2

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate for 1h; Reflux;
Stage #2: 3,6-dioxa-1,8-octandithiol for 2h; Reflux;
99%

3,6-Dioxa-1,8-octanedithiol Specification

The CAS registry number of Ethanethiol,2,2'-[1,2-ethanediylbis(oxy)]bis- is 14970-87-7. This chemical is also named as 2,2'-[Ethane-1,2-diylbis(oxy)]diethanethiol. Its EINECS registry number is 239-044-2. In addition, its molecular formula is C6H14O2S2 and molecular weight is 182.3. Its IUPAC name is called 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol.

Physical properties about this chemical are: (1)ACD/LogP: 1.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.302; (4)ACD/LogD (pH 7.4): 1.297; (5)ACD/BCF (pH 5.5): 5.748; (6)ACD/BCF (pH 7.4): 5.684; (7)ACD/KOC (pH 5.5): 121.697; (8)ACD/KOC (pH 7.4): 120.34; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 9; (12)Index of Refraction: 1.495; (13)Molar Refractivity: 49.129 cm3; (14)Molar Volume: 168.397 cm3; (15)Surface Tension: 36.5 dyne/cm; (16)Density: 1.083 g/cm3; (17)Flash Point: 109.233 °C; (18)Enthalpy of Vaporization: 47.457 kJ/mol; (19)Boiling Point: 257.004 °C at 760 mmHg; (20)Vapour Pressure: 0.024 mmHg at 25°C.

Uses of Ethanethiol,2,2'-[1,2-ethanediylbis(oxy)]bis-: it can be used to produce 9-methylene-1,4-dioxa-7,11-dithia-cyclotridecane at temperature of 55 - 60 °C. It will need reagent Cs2CO3 and solvent dimethylformamide. The yield is about 72 %.

Ethanethiol,2,2'-[1,2-ethanediylbis(oxy)]bis- can be used to produce 9-methylene-1,4-dioxa-7,11-dithia-cyclotridecane

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic if swallowed or by inhalation.It is harmful if swallowed. It is irritating to eyes, respiratory system and skin.In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Finally, in case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: C(COCCS)OCCS
(2)InChI: InChI=1/C6H14O2S2/c9-5-3-7-1-2-8-4-6-10/h9-10H,1-6H2
(3)InChIKey: HCZMHWVFVZAHCR-UHFFFAOYAO

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