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

Name
3,6-Dioxa-1,8-octanedithiol
EINECS 239-044-2
CAS No. 14970-87-7
Article Data13
CAS DataBase
Density 1.082 g/cm³
Solubility 11.4g/L at 19.8℃
Melting Point
Formula C₆H₁₄O₂S₂
Boiling Point 257.004 °C at 760 mmHg
Molecular Weight 182.308
Flash Point 109.233 °C
Transport Information UN 2810
Appearance
Safety 26-45
Risk Codes 22-23-36/37/38
Molecular Structure
Hazard Symbols T
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;
PSA 96.06000
LogP 0.87920

Synthetic route

: 19249-03-7
triethylene glycol di-(p-toluenesulfonate)

: 14970-87-7
3,6-dioxa-1,8-octandithiol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide; thiourea In ethanol	64.3%

: 112-27-6
2,2'-[1,2-ethanediylbis(oxy)]bisethanol

: 14970-87-7
3,6-dioxa-1,8-octandithiol

Conditions

Conditions	Yield
With hydrogenchloride; thiourea	55%
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 2089-30-7
(E)-1-(4-(allyloxy)phenyl)ethan-1-one oxime

: C28H40N2O6S2

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 96-32-2
bromoacetic acid methyl ester

: dimethyl 6,9-dioxa-3,12-dithiatetradecanedioate

Conditions

Conditions	Yield
With triethylamine In acetone at 20℃; for 0.25h;	98%
With triethylamine In acetone

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 106-89-8
epichlorohydrin

: C12H22O4S2

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 20℃; for 0.75h; Sonication;	98%
With sodium hydroxide In water

: 3194-70-5
2-vinyl-4,6-diamino-S-triazine

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 2,4-diamino-6-(2-{2-[2-(2-mercaptoethoxy)ethoxy]ethylthio}ethyl)-1,3,5-triazine

Conditions

Conditions	Yield
In methanol at 65℃; for 1h;	95%

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 130-15-4
[1,4]naphthoquinone

: C26H22O6S2

Conditions

Conditions	Yield
In ethanol at 20℃; for 48h;	94%

: 1,3-dimethyl-trans-2-oxa-{3}-ferrocenephane

: 14970-87-7
3,6-dioxa-1,8-octandithiol

A: meso-1,12-dimethyl-2,11-dithia-5,8-dioxa[12](1,1')ferrocenophane

B: meso-1,12-dimethyl-2,11-dithia-5,8-dioxa<12>(1,1')ferrocenophane

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane; benzene 48 qqqqqqqqqqqqqqqwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwww; wwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwwww;	A 93% B n/a
With trifluoroacetic acid In dichloromethane; benzene simultaneous dropwise addn. of 1,1'-bis(α-hydroxyalkyl)ferrocene (soln. in 1:1 CH2Cl2-C6H6) and dithiol (soln. in CH2Cl2) by stirring, refluxing with few drops CF3COOH for ca 48 h, washing with aq. NH3, water,dried over MgSO4; evaporating, chromy. (column, then TLC), elem. anal.;	A 93% B n/a

...Expand

: 106-92-3
Allyl glycidyl ether

: 14970-87-7
3,6-dioxa-1,8-octandithiol

A: C20H38O6S2

B: C20H38O6S2

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 8h; Inert atmosphere; Overall yield = 92 %;	A 93% B 7%

...Expand

: 110-86-1
pyridine

: indium(III) nitrate hydrate

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: C11H17InN2O5S2

Conditions

Conditions	Yield
Stage #1: pyridine; indium(III) nitrate hydrate In methanol for 0.25h; Inert atmosphere; Stage #2: 3,6-dioxa-1,8-octandithiol In methanol at 23℃; Inert atmosphere;	93%

...Expand

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 38768-08-0
2-(tosyloxy)tropone

: 2,2'-ethylenebis(ethylenethio)ditropone

Conditions

Conditions	Yield
With sodium hydride In ethanol; toluene for 3h; Heating;	92%

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 103-71-9
phenyl isocyanate

: 3,6-dioxaoctylene-1,8-bis(N-phenylthiocarbamate)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	91%

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 920-46-7
Methacryloyl chloride

: 1,2-bis[(2-methacryloylthio)ethoxy]ethane

Conditions

Conditions	Yield
With potassium hydroxide; Aliquat 336; 4-methoxy-phenol In chloroform for 0.25h; Acylation;	89.3%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5 - 20℃; for 3h;	1.3 g
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5 - 20℃; for 3h;	1.3 g

: 106-92-3
Allyl glycidyl ether

: 124-38-9
carbon dioxide

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: C22H38O10S2

Conditions

Conditions	Yield
Stage #1: Allyl glycidyl ether; 3,6-dioxa-1,8-octandithiol With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 8h; Inert atmosphere; Stage #2: carbon dioxide With lithium bromide In N,N-dimethyl-formamide at 80℃; under 1500.15 Torr; for 16h;	89%

...Expand

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 818-08-6
di(n-butyl)tin oxide

: 2,2-dibutyl-2-stanna-1,3-dithia-6,9-dioxacycloundecane

Conditions

Conditions	Yield
In toluene at 110℃; for 29h; Dean-Stark;	89%

: 110-78-1
Propyl isocyanate

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 3,6-dioxaoctylene-1,8-bis(N-propylthiocarbamate)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	89%

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: N,N-bis(methoxymethyl)-N-(p-bromophenyl)amine

: N-(p-bromphenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

Conditions

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-(p-bromophenyl)amine With copper(l) chloride at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,6-dioxa-1,8-octandithiol at 20℃; for 5h; Inert atmosphere;	88%

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 558445-90-2
perallyloxycucrbit[6]uril

polymer, two-dimensional network: polymer, two-dimensional network

Conditions

Conditions	Yield
In methanol at 29℃; for 20h; UV-irradiation;	87%

: 50-00-0
formaldehyd

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 123-54-6
acetylacetone

: 1586034-38-9
3,16-diacetyl-8,11-dioxa-5,14-dithiaoctadecane-2,17-dione

Conditions

Conditions	Yield
Stage #1: formaldehyd; 3,6-dioxa-1,8-octandithiol In water at 0.2℃; for 0.5h; Inert atmosphere; Stage #2: acetylacetone In ethanol; chloroform; water at 0.2℃; for 6h; Reagent/catalyst; Inert atmosphere;	86%

...Expand

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: N,N-bis(methoxymethyl)-N-(m-fluorophenyl)amine

: N-(m-fluorophenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

Conditions

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-(m-fluorophenyl)amine With copper(l) chloride at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,6-dioxa-1,8-octandithiol at 20℃; for 5h; Inert atmosphere;	86%

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 119461-40-4
S-(+)-2-methyl-N-p-tosylaziridine

: N,N'-((2S,15S)-7,10-dioxa-4,13-dithiahexadecane-2,15-diyl)bis(4-methylbenzenesulfonamide)

Conditions

Conditions	Yield
Stage #1: 3,6-dioxa-1,8-octandithiol With triethylamine In methanol at 20℃; for 0.166667h; Inert atmosphere; Stage #2: S-(+)-2-methyl-N-p-tosylaziridine In methanol at 20 - 35℃; for 5h; Inert atmosphere; regioselective reaction;	86%

: 50-00-0
formaldehyd

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 1,6,9-trioxa-3,12-dithiacyclotridecane

Conditions

Conditions	Yield
In water at 20℃; for 3h;	86%
In water at 20℃; for 3h;	86%

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: N,N-bis(methoxymethyl)-N-(m-chlorophenyl)amine

: 6-(m-chlorophenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

Conditions

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-(m-chlorophenyl)amine With copper(l) chloride at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,6-dioxa-1,8-octandithiol at 20℃; for 5h; Inert atmosphere;	85%

: 51-80-9
bis-(dimethylamino)methane

: 5452-35-7
cycloheptanamine

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: 6-cycloheptyl-1,11-dioxa-4,8-dithia-6-azacyclotridecane

Conditions

Conditions	Yield
Stage #1: bis-(dimethylamino)methane; 3,6-dioxa-1,8-octandithiol With samarium(III) chloride hexahydrate In chloroform at 20℃; for 0.5h; Stage #2: cycloheptanamine In ethanol; chloroform at 20℃; for 3h;	85%

...Expand

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: N,N-bis(methoxymethyl)-N-(m-bromophenyl)amine

: N-(m-bromphenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

Conditions

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-(m-bromophenyl)amine With copper(l) chloride at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,6-dioxa-1,8-octandithiol at 20℃; for 5h; Inert atmosphere;	84%

: 1,1'-dihydroxymethylferrocene

: 14970-87-7
3,6-dioxa-1,8-octandithiol

A: 84526-10-3
2,11,24,33-tetrathia-5,8,27,30-tetraoxa<12,12>(1,1')ferrocenophane

B: 80973-97-3
2,11-dithia-5,8-dioxa{12}(1,1')ferrocenophane

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane; benzene simultaneous dropwise addn. of 1,1'-bis(α-hydroxyalkyl)ferrocene (soln. in 1:1 CH2Cl2-C6H6) and dithiol (soln. in CH2Cl2) by stirring, refluxing with few drops CF3COOH for ca 24 h, washing with aq. NH3, water,dried over MgSO4; evaporating, chromy. (column or preparative HPLC), elem. anal.;	A 7% B 83%

...Expand

: 14970-87-7
3,6-dioxa-1,8-octandithiol

: N,N-bis(methoxymethyl)-N-(p-fluorophenyl)amine

: N-(p-fluorophenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

Conditions

Conditions	Yield
Stage #1: N,N-bis(methoxymethyl)-N-(p-fluorophenyl)amine With copper(l) chloride at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,6-dioxa-1,8-octandithiol at 20℃; for 5h; Inert atmosphere;	82%

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

Product Name

3,6-Dioxa-1,8-octanedithiol

Synthetic route

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

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