14970-87-7

Basic information

• Product Name: 3,6-DIOXA-1,8-OCTANEDITHIOL
• Synonyms: Triglycoldimercaptan;ETHYLENE GLYCOL BIS(2-MERCAPTOETHYL) ETHER;1,8-DIMERCAPTO-3,6-DIOXAOCTANE;1,2-BIS(2-MERCAPTOETHOXY)ETHANE;3,6-DIOXA-1,8-OCTANEDITHIOL;Triethyleneglycol dimrcaptan;Ethanethiol, 2,2-1,2-ethanediylbis(oxy)bis-;2,2′-[1,2-Ethandiylbis(oxy)]bis(ethanthiol)
• CAS NO: 14970-87-7
• Molecular Formula: C₆H₁₄O₂S₂
• Molecular Weight: 182.3
• EINECS: 239-044-2
• Mol File: 14970-87-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 225 °C(lit.)
• Flash Point: 132 °C
• Appearance: /
• Density: 1.12 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.39Pa at 20℃
• Refractive Index: n20/D 1.509(lit.)
• Solubility: Slightly soluble in water
• PKA: 9.34±0.10(Predicted)
• Water Solubility: 11.4g/L at 19.8℃
• BRN: 1901671
• CAS DataBase Reference: 3,6-DIOXA-1,8-OCTANEDITHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-DIOXA-1,8-OCTANEDITHIOL(14970-87-7)
• EPA Substance Registry System: 3,6-DIOXA-1,8-OCTANEDITHIOL(14970-87-7)

Safety Data

• Hazard Codes: T,N,Xn
• Statements: 22-23-36/37/38-51/53-20/22
• Safety Statements: 26-45-61
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 2
• Hazardous Substances Data: 14970-87-7(Hazardous Substances Data)

Usage

Uses

3,6-dioxa-1,8-octanedithiol (DODT) was used for cleaving peptides in the study to develop synthetic peptide serology to treat chronic chagas disease. DODT may be used to develop non-malodorous scavenger in Fmoc-based peptide synthesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 33, p. 1275, 1968 DOI: 10.1021/jo01267a089Triglycol dimercaptan

General Description

3,6-dioxa-1,8-octanedithiol is non volatile in nature.

Synthetic route

triethylene glycol di-(p-toluenesulfonate) (19249-03-7) → 3,6-dioxa-1,8-octandithiol (14970-87-7)

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) → 3,6-dioxa-1,8-octandithiol (14970-87-7)

Conditions	Yield
With hydrogenchloride In methanol; water at 120℃; for 3h; Inert atmosphere;	73%

1,2-bis-(2-bromo-ethoxy)-ethane (31255-10-4) → 3,6-dioxa-1,8-octandithiol (14970-87-7)

Conditions	Yield
With potassium hydroxide; thiourea In ethanol	64.3%

2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 3,6-dioxa-1,8-octandithiol (14970-87-7)

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

1,2-bis(2-chloroethoxy)ethane (112-26-5) → 3,6-dioxa-1,8-octandithiol (14970-87-7)

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;

Allyl glycidyl ether (106-92-3) + diethylene glycol divinyl ether (764-99-8) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → poly(allyl glycidyl ether-co-diethylene glycol divinyl ether-co-dimercaptodioxaoctane)

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%

Allyl glycidyl ether (106-92-3) + diethylene glycol divinyl ether (764-99-8) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → poly(allyl glycidyl ether-co-diethylene glycol divinyl ether-co-dimercaptodioxaoctane)

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%

3,6-dioxa-1,8-octandithiol (14970-87-7) + (E)-1-(4-(allyloxy)phenyl)ethan-1-one oxime (2089-30-7) → C28H40N2O6S2

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

4-allyloxymethyl-1,3-dioxolan-2-one (826-29-9) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → C22H38O10S2

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

cycl-isopropylidene malonate (2033-24-1) + 3,6-dioxa-1,8-octandithiol (14970-87-7) + trimethyl orthoformate (149-73-5) → C20H26O10S2

Conditions	Yield
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-octandithiol (14970-87-7) + bromoacetic acid methyl ester (96-32-2) → dimethyl 6,9-dioxa-3,12-dithiatetradecanedioate

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

3,6-dioxa-1,8-octandithiol (14970-87-7) + epichlorohydrin (106-89-8) → C12H22O4S2

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

2-vinyl-4,6-diamino-S-triazine (3194-70-5) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → 2,4-diamino-6-(2-{2-[2-(2-mercaptoethoxy)ethoxy]ethylthio}ethyl)-1,3,5-triazine

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

3,6-dioxa-1,8-octandithiol (14970-87-7) + [1,4]naphthoquinone (130-15-4) → C26H22O6S2

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

1,3-dimethyl-trans-2-oxa-{3}-ferrocenephane + 3,6-dioxa-1,8-octandithiol (14970-87-7) → meso-1,12-dimethyl-2,11-dithia-5,8-dioxa[12](1,1')ferrocenophane + meso-1,12-dimethyl-2,11-dithia-5,8-dioxa<12>(1,1')ferrocenophane

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

Allyl glycidyl ether (106-92-3) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → C20H38O6S2 + C20H38O6S2

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%

pyridine (110-86-1) + indium(III) nitrate hydrate + 3,6-dioxa-1,8-octandithiol (14970-87-7) → C11H17InN2O5S2

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%

3,6-dioxa-1,8-octandithiol (14970-87-7) + 2-(tosyloxy)tropone (38768-08-0) → 2,2'-ethylenebis(ethylenethio)ditropone

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

3,6-dioxa-1,8-octandithiol (14970-87-7) + phenyl isocyanate (103-71-9) → 3,6-dioxaoctylene-1,8-bis(N-phenylthiocarbamate)

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

3,6-dioxa-1,8-octandithiol (14970-87-7) + Methacryloyl chloride (920-46-7) → 1,2-bis[(2-methacryloylthio)ethoxy]ethane

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

Allyl glycidyl ether (106-92-3) + carbon dioxide (124-38-9) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → C22H38O10S2

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%

3,6-dioxa-1,8-octandithiol (14970-87-7) + di(n-butyl)tin oxide (818-08-6) → 2,2-dibutyl-2-stanna-1,3-dithia-6,9-dioxacycloundecane

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

Propyl isocyanate (110-78-1) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → 3,6-dioxaoctylene-1,8-bis(N-propylthiocarbamate)

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

3,6-dioxa-1,8-octandithiol (14970-87-7) + N,N-bis(methoxymethyl)-N-(p-bromophenyl)amine → N-(p-bromphenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

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%

3,6-dioxa-1,8-octandithiol (14970-87-7) + perallyloxycucrbit[6]uril (558445-90-2) → polymer, two-dimensional network

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

formaldehyd (50-00-0) + 3,6-dioxa-1,8-octandithiol (14970-87-7) + acetylacetone (123-54-6) → 3,16-diacetyl-8,11-dioxa-5,14-dithiaoctadecane-2,17-dione (1586034-38-9)

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%

3,6-dioxa-1,8-octandithiol (14970-87-7) + N,N-bis(methoxymethyl)-N-(m-fluorophenyl)amine → N-(m-fluorophenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

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%

3,6-dioxa-1,8-octandithiol (14970-87-7) + S-(+)-2-methyl-N-p-tosylaziridine (119461-40-4) → N,N'-((2S,15S)-7,10-dioxa-4,13-dithiahexadecane-2,15-diyl)bis(4-methylbenzenesulfonamide)

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%

formaldehyd (50-00-0) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → 1,6,9-trioxa-3,12-dithiacyclotridecane

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

3,6-dioxa-1,8-octandithiol (14970-87-7) + N,N-bis(methoxymethyl)-N-(m-chlorophenyl)amine → 6-(m-chlorophenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

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%

bis-(dimethylamino)methane (51-80-9) + cycloheptanamine (5452-35-7) + 3,6-dioxa-1,8-octandithiol (14970-87-7) → 6-cycloheptyl-1,11-dioxa-4,8-dithia-6-azacyclotridecane

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%

3,6-dioxa-1,8-octandithiol (14970-87-7) + N,N-bis(methoxymethyl)-N-(m-bromophenyl)amine → N-(m-bromphenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

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 + 3,6-dioxa-1,8-octandithiol (14970-87-7) → 2,11,24,33-tetrathia-5,8,27,30-tetraoxa<12,12>(1,1')ferrocenophane (84526-10-3) + 2,11-dithia-5,8-dioxa{12}(1,1')ferrocenophane (80973-97-3)

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%

3,6-dioxa-1,8-octandithiol (14970-87-7) + N,N-bis(methoxymethyl)-N-(p-fluorophenyl)amine → N-(p-fluorophenyl)-1,11-dioxa-4,8-dithia-6-azacyclotridecane

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%

Upstream product

• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 31255-10-4 1,2-bis-(2-bromo-ethoxy)-ethane 
• 112-26-5 1,2-bis(2-chloroethoxy)ethane 
• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 

Downstream Products

• 668491-08-5 [(mu.-PhS)Fe2(CO)6]2[μ-SCH2(CH2OCH2)2CH2S-μ] 
• 1309112-49-9 1,4-dioxa-7,13-dithia-10-(3-methoxyphenyl)-10-azacyclopentadecane 
• 240797-82-4 4-(1,4-dioxa-7,13-dithia-10-azacyclopentadecan-10-yl) benzaldehyde 
• 240797-81-3 10-phenyl-1,4-dioxa-7,13-dithia-10-aza-cyclopentadecane 
• 84323-78-4 3-Phenyl-1,7-dithia-15-crown-5 

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