Product Name

  • Name

    2,2'-Thiodiethanol

  • EINECS 203-874-3
  • CAS No. 111-48-8
  • Article Data56
  • CAS DataBase
  • Density 1.18 g/cm3
  • Solubility
  • Melting Point -16 ºC(lit.)
  • Formula C4H10O2S
  • Boiling Point 282 ºC at 760 mmHg
  • Molecular Weight 122.188
  • Flash Point 139.5 ºC
  • Transport Information
  • Appearance colourless liquid with characteristic odour
  • Safety 23-26-36/37/39-45
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 111-48-8 (2,2'-Thiodiethanol)
  • Hazard Symbols IrritantXi
  • Synonyms Ethanol,2,2'-thiodi- (6CI,8CI);1,5-Dihydroxy-3-thiapentane;2,2'-Dihydroxydiethylsulfide;2,2'-Thiobisethanol;2,2'-Thiodiglycol;3-Thiapentane-1,5-diol;Bis(2-hydroxyethyl) sulfide;Bis(2-hydroxyethyl)thioether;Bis(b-hydroxyethyl)sulfide;Di(2-hydroxyethyl) sulfide;Diethanol sulfide;Kromfax Solvent;NSC6289;Tedegyl;Thiodiethylene glycol;Thiodiglycol;b,b'-Dihydroxydiethyl sulfide;b,b'-Dihydroxyethyl sulfide;b-Thiodiglycol;
  • PSA 65.76000
  • LogP -0.29580

Synthetic route

oxirane
75-21-8

oxirane

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
With hydrogen sulfide at 20℃; Temperature;99.5%
With hydrogen sulfide
2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol; water at 20℃; for 0.0833333h; Green chemistry;98%
With dihydrogen peroxide In ethanol at 20℃; for 0.5h; Green chemistry;97%
With dihydrogen peroxide In ethanol at 20℃; for 1h; Catalytic behavior; Reagent/catalyst; Green chemistry; chemoselective reaction;90%
With dihydrogen peroxide In neat (no solvent, solid phase) at 20℃; for 0.583333h; Catalytic behavior; Green chemistry;76%
With dihydrogen peroxide In water at 20℃; for 0.1h; Rate constant; Mechanism; Thermodynamic data; ΔH(excit.), ΔS(excit.), stoichiometry, various pH, various concentrations;
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
at 120 - 125℃;
With potassium carbonate In neat (no solvent) at 120℃; for 0.29h; Catalytic behavior; Temperature;
bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
With water; zinc(II) oxide
With water In ethanol Kinetics;
2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-chloro-ethanol
107-07-3

2-chloro-ethanol

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
With sodium carbonate
2-chloro-ethanol
107-07-3

2-chloro-ethanol

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
With potassium hydrosulfide at 0℃;
With sodium hydrogensulfide at 25℃;
With sodium sulfide; water Darstellung;
With potassium sulfide; water
With sodium sulfide; water
oxirane
75-21-8

oxirane

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
With triethylamine at 15℃; Rate constant; Mechanism; Thermodynamic data; other temperature, E(a);
mustard chlorohydrin
693-30-1

mustard chlorohydrin

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
With water In ethanol at 25℃; Rate constant; further solvents, var. water concentration; charge separation in the transition state;
With water
bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

bis-(2-hydroxy-ethyl)-[2-(2-hydroxy-ethylsulfanyl)-ethyl]-sulfonium
64036-92-6

bis-(2-hydroxy-ethyl)-[2-(2-hydroxy-ethylsulfanyl)-ethyl]-sulfonium

C

C12H28O4S3(2+)

C12H28O4S3(2+)

Conditions
ConditionsYield
In water Title compound not separated from byproducts;
bis-(2-hydroxy-ethyl)-[2-(2-hydroxy-ethylsulfanyl)-ethyl]-sulfonium
64036-92-6

bis-(2-hydroxy-ethyl)-[2-(2-hydroxy-ethylsulfanyl)-ethyl]-sulfonium

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

mustard chlorohydrin
693-30-1

mustard chlorohydrin

C

bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

Conditions
ConditionsYield
With hydrogenchloride In water Product distribution; Mechanism;A 25.3 % Chromat.
B 64.8 % Chromat.
C 3.8 % Chromat.
C12H28O4S3(2+)

C12H28O4S3(2+)

A

1,4-Dithiane
505-29-3

1,4-Dithiane

B

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

C

mustard chlorohydrin
693-30-1

mustard chlorohydrin

D

bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

Conditions
ConditionsYield
With hydrogenchloride In water Product distribution; Mechanism;A 11.6 % Chromat.
B 15.1 % Chromat.
C 49.3 % Chromat.
D 20.2 % Chromat.
1-(p-Cyanophenyl)-3-triazene
95239-71-7

1-(p-Cyanophenyl)-3-triazene

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

C

N-

N-

D

N-

N-

E

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With water at 37℃; Product distribution; Mechanism; pH 7.2, phosphate buffer; also with 1-(p-cyanophenyl)-3-triazene: deuterium distribution;
(S)-2-tert-Butoxycarbonylamino-3-{[2-(2-tert-butoxy-ethylsulfanyl)-ethoxy]-hydroxy-phosphoryloxy}-propionic acid tert-butyl ester
182503-68-0

(S)-2-tert-Butoxycarbonylamino-3-{[2-(2-tert-butoxy-ethylsulfanyl)-ethoxy]-hydroxy-phosphoryloxy}-propionic acid tert-butyl ester

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

C3H6NO6P(2-)

C3H6NO6P(2-)

Conditions
ConditionsYield
With trifluoroacetic acid for 2h;
(S)-3-{Benzyloxy-[2-(2-tert-butoxy-ethylsulfanyl)-ethoxy]-phosphoryloxy}-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

(S)-3-{Benzyloxy-[2-(2-tert-butoxy-ethylsulfanyl)-ethoxy]-phosphoryloxy}-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

C3H6NO6P(2-)

C3H6NO6P(2-)

Conditions
ConditionsYield
With trifluoroacetic acid for 2h;
oxirane
75-21-8

oxirane

water
7732-18-5

water

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
at 20℃; Kinetics; auch in Gegenwart von Bis-<2-hydroxy-aethyl>-sulfid, sowie in Bis-<2-hydroxy-aethyl-sulfid>;
1H-imidazole
288-32-4

1H-imidazole

bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

2-[(2-imidazolylethyl)thio]ethanol

2-[(2-imidazolylethyl)thio]ethanol

C

8-thia-2-aza-5-azonia-spiro<4.5>deca-1,3-diene chloride

8-thia-2-aza-5-azonia-spiro<4.5>deca-1,3-diene chloride

Conditions
ConditionsYield
wss. Loesung vom pH 8.5;
water
7732-18-5

water

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

water
7732-18-5

water

iron(III) chloride
7705-08-0

iron(III) chloride

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

water
7732-18-5

water

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

sodium hypobromite

sodium hypobromite

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

ethanol
64-17-5

ethanol

potassium hydrosulfide

potassium hydrosulfide

2-chloro-ethanol
107-07-3

2-chloro-ethanol

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

bis(2-hydroxyethyl) disulfide
1892-29-1

bis(2-hydroxyethyl) disulfide

C

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

D

diethylene disulfide

diethylene disulfide

Conditions
ConditionsYield
at 0℃;
bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

A

hydrogenchloride
7647-01-0

hydrogenchloride

B

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
With water Hydrolysis;
bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

water
7732-18-5

water

zinc oxide

zinc oxide

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

water
7732-18-5

water

A

hydrogenchloride
7647-01-0

hydrogenchloride

B

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Conditions
ConditionsYield
at 25℃;
ethanol
64-17-5

ethanol

bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

zinc

zinc

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

bis(2-ethoxyethyl)sulfide
41719-25-9

bis(2-ethoxyethyl)sulfide

C

2-(2-ethoxy-ethylsulfanyl)-ethanol
874529-11-0

2-(2-ethoxy-ethylsulfanyl)-ethanol

D

1,2-bis-(2-ethoxy-ethylsulfanyl)-ethane
14440-87-0

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

Conditions
ConditionsYield
anderen Produkte: Aethylendimercaptan; Diaethylendisulfid; Aethylen; Schwefelwasserstoff; Chlorwasserstoff; Diaethylsulfid; Aethylvinylsulfid;
bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

water(2.25 mol)

water(2.25 mol)

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

1-chloro-1-<2-hydroxy-ethyl>-<1,4>dithiane

1-chloro-1-<2-hydroxy-ethyl>-<1,4>dithiane

1H-imidazole
288-32-4

1H-imidazole

bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

2'-hydroxy-2--diethyl sulfide

2'-hydroxy-2--diethyl sulfide

C

8-thia-2-aza-5-azonia-spiro<4.5>deca-1,3-diene chloride

8-thia-2-aza-5-azonia-spiro<4.5>deca-1,3-diene chloride

Conditions
ConditionsYield
bei pH 8;
bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

bis(2-chloroethylthioethyl)ether
63918-89-8

bis(2-chloroethylthioethyl)ether

water
7732-18-5

water

A

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

B

bis-<2-hydroxy-ethyl>-<2-(2-hydroxy-ethylsulfanyl)-ethyl>-sulfonium chloride

bis-<2-hydroxy-ethyl>-<2-(2-hydroxy-ethylsulfanyl)-ethyl>-sulfonium chloride

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

2Al(3+)*2C5H7O2(1-)*4C3H7O(1-)=[Al(C5H7O2)(C3H7O)2]2

2Al(3+)*2C5H7O2(1-)*4C3H7O(1-)=[Al(C5H7O2)(C3H7O)2]2

[(C5H7O2)2Al(C3H7O)2AlO(CH2)2S(CH2)2O]2
172702-72-6

[(C5H7O2)2Al(C3H7O)2AlO(CH2)2S(CH2)2O]2

Conditions
ConditionsYield
In benzene reflux (3h, C3H7OH distd. off with benzene); solvent evapn.; elem. anal.;100%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate
6386-38-5

methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate

2-[2-[3-(4-hydroxy-3,5-di-tert-butyl-phenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(4-hydroxy-3,5-di-tert-butyl-phenyl)propanoate
41484-35-9

2-[2-[3-(4-hydroxy-3,5-di-tert-butyl-phenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(4-hydroxy-3,5-di-tert-butyl-phenyl)propanoate

Conditions
ConditionsYield
With alumina-supported potassium hydroxide at 120 - 160℃; for 0.5h; Catalytic behavior; Temperature; Inert atmosphere;99.3%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

1,4-Oxathiane
15980-15-1

1,4-Oxathiane

Conditions
ConditionsYield
With copper(ll) bromide at 175℃; for 4h; Inert atmosphere; Sealed tube;99%
With Trichlorbutylstannan for 0.16h;42%
With sulfuric acid at 180℃;
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

2Al(3+)*2C6H9O3(1-)*4C3H7O(1-)=[Al(C6H9O3)(C3H7O)2]2

2Al(3+)*2C6H9O3(1-)*4C3H7O(1-)=[Al(C6H9O3)(C3H7O)2]2

(C6H9O3)2Al(C3H7O)2AlO(CH2)2S(CH2)2O
172702-73-7

(C6H9O3)2Al(C3H7O)2AlO(CH2)2S(CH2)2O

Conditions
ConditionsYield
In benzene reflux (3h, C3H7OH distd. off with benzene); solvent evapn.; elem. anal.;99%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

germanium tetra-isopropoxide
1134503-88-0

germanium tetra-isopropoxide

C10H22GeO4S

C10H22GeO4S

Conditions
ConditionsYield
In benzene Reflux;99%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

antimony(III) isopropoxide

antimony(III) isopropoxide

{HO(CH2)2S(CH2)2O}Sb{O(CH2)2S(CH2)2O}

{HO(CH2)2S(CH2)2O}Sb{O(CH2)2S(CH2)2O}

Conditions
ConditionsYield
In benzene byproducts: isopropanol; anhydrous atmosphere; molar ratio 1 : 2, refluxing (7 h); solvent removal (reduced pressure, pptn.), recrystn. (DMSO/benzene); elem. anal.;98%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

tetraethoxygermanium
14165-55-0

tetraethoxygermanium

C8H18GeO4S

C8H18GeO4S

Conditions
ConditionsYield
In benzene for 6h; Reflux;98%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

bis(2-hydroxyethyl)sulfoxide
3085-45-8

bis(2-hydroxyethyl)sulfoxide

Conditions
ConditionsYield
With dihydrogen peroxide for 72h; Ambient temperature;97%
With dinitrogen tetraoxide; pyrographite In dichloromethane at 20℃; for 0.133333h;95%
With N-(tert-butyl)-N-chloro-cyanamide In water; acetonitrile at 25℃;92%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

tetraethoxygermanium
14165-55-0

tetraethoxygermanium

C8H16GeO4S2

C8H16GeO4S2

Conditions
ConditionsYield
In benzene Reflux;97%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

stearic acid
57-11-4

stearic acid

bis-(2-stearoyloxy-ethyl)-sulfide
4275-32-5

bis-(2-stearoyloxy-ethyl)-sulfide

Conditions
ConditionsYield
With immobilized p-TsOH on activated carbon In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; chemoselective reaction;96%
at 160 - 180℃;
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

methylvinyldimethoxysilane
16753-62-1

methylvinyldimethoxysilane

2-methyl-2-vinyl-1,3-dioxa-6-thia-2-silacyclooctane
116393-20-5

2-methyl-2-vinyl-1,3-dioxa-6-thia-2-silacyclooctane

Conditions
ConditionsYield
With sodium methylate In methanol; benzene for 8h; Heating;95%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

thiomorpholine-3-one
5512-70-9

thiomorpholine-3-one

Conditions
ConditionsYield
With pyridine; 4-AcNH-1-oxo-2,2,6,6-tetramethylpiperidinium tetrafluoroborate In dichloromethane at 20℃; for 3h;95%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

antimony(III) isopropoxide

antimony(III) isopropoxide

(i-Pr-O)Sb{O(CH2)2S(CH2)2O}
135876-85-6

(i-Pr-O)Sb{O(CH2)2S(CH2)2O}

Conditions
ConditionsYield
In benzene byproducts: isopropanol; anhydrous conditions; molar ratio 1:1, refluxing (4 h, distn. off of i-PrOH, crystn.); recrystn. (DMSO/benzene); elem. anal.;95%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C32H62O4S
68818-42-8

C32H62O4S

Conditions
ConditionsYield
With immobilized p-TsOH on activated carbon In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; chemoselective reaction;95%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

sulfonyldiethanol
2580-77-0

sulfonyldiethanol

Conditions
ConditionsYield
With 5,10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphyrin iron(III) chloride; dihydrogen peroxide In ethanol at 20℃; for 0.25h;94%
With water; ozone
With dihydrogen peroxide; acetone
With Perbenzoic acid; ethanol; chloroform
With dihydrogen peroxide; acetic acid
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

bis(2-trimethylsiloxyethyl)sulfide
20486-03-7

bis(2-trimethylsiloxyethyl)sulfide

Conditions
ConditionsYield
With urea at 20 - 25℃; for 6h;93%
76%
With triethylamine In toluene at 20℃; for 24h;
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

A

3-thiapentan-1,5-dithiol
3570-55-6

3-thiapentan-1,5-dithiol

B

bis-mercaptodiethylsulphide

bis-mercaptodiethylsulphide

Conditions
ConditionsYield
With hydrogenchloride; hydrazine hydrate; thiourea In 5,5-dimethyl-1,3-cyclohexadiene; waterA n/a
B 93%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

sodium tetrachloroaurate(III) dihydrate

sodium tetrachloroaurate(III) dihydrate

1,2-bis-(diphenylphosphino)ethane
1663-45-2

1,2-bis-(diphenylphosphino)ethane

1,2-bis(diphenylphosphino)ethane digold(I) dichloride
18024-34-5

1,2-bis(diphenylphosphino)ethane digold(I) dichloride

Conditions
ConditionsYield
In water; acetone Au-complex was reduced to Au(I) by thiodiglycol in aq. acetone, ligand in acetone was added dropwise over 5 min, stirred for 1 h; ppt. was filtered off, washed with H2O and acetone; elem. anal.;93%
lauric acid
143-07-7

lauric acid

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

bis-(2-lauroyloxy-ethyl)-sulfide
4275-31-4

bis-(2-lauroyloxy-ethyl)-sulfide

Conditions
ConditionsYield
With immobilized p-TsOH on activated carbon In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; Reagent/catalyst; Concentration; Solvent; chemoselective reaction;92%
at 180℃;
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

4-chloro-3-nitrobenzoate
96-99-1

4-chloro-3-nitrobenzoate

3-amino-4-chloro-benzoic acid
2840-28-0

3-amino-4-chloro-benzoic acid

Conditions
ConditionsYield
In methanol; water92%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

chloroauric acid

chloroauric acid

methyl N-phenyldithiocarbamate
701-73-5

methyl N-phenyldithiocarbamate

AuCl(C6H5NHC(S)SCH3)

AuCl(C6H5NHC(S)SCH3)

Conditions
ConditionsYield
In acetone dissolution of HAuCl4 in acetone, addn. of S(CH2CH2OH)2, reacting (30 min), addn. of soln. of dithio-compd. in acetone; crystn. (2 weeks, -33°C); elem. anal.;91.3%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

C36H70O4S
68818-43-9

C36H70O4S

Conditions
ConditionsYield
With immobilized p-TsOH on activated carbon In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; chemoselective reaction;91%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

tert-butylthiacalix[4]arene
182496-55-5

tert-butylthiacalix[4]arene

TIMEOUT: 5s
827618-86-0

TIMEOUT: 5s

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In toluene at 20℃; for 1h; Mitsunobu reaction;90%
potassium cyanide

potassium cyanide

2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

chloroauric acid

chloroauric acid

triphenylphosphine
603-35-0

triphenylphosphine

cyano(triphenylphosphine)gold(I)

cyano(triphenylphosphine)gold(I)

Conditions
ConditionsYield
In water byproducts: KCl; reduction of HAuCl4 with thiodiglycol at 0°C, followed by the phosphine addition; intermediate complex was washed several times with EtOH and then reacted with KCN; elem. anal.;90%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

Diethyl carbonate
105-58-8

Diethyl carbonate

bis-(2-ethylcarbonate)ethyl sulfide
500798-11-8

bis-(2-ethylcarbonate)ethyl sulfide

Conditions
ConditionsYield
for 17h; Reflux;90%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

sodium tetrachloroaurate(III)*0.5H2O

sodium tetrachloroaurate(III)*0.5H2O

cis-1,2-bis-(diphenylphosphino)ethene
983-80-2

cis-1,2-bis-(diphenylphosphino)ethene

{Au(cis-bis(diphenylphosphino)ethylene)2}Cl
102532-72-9

{Au(cis-bis(diphenylphosphino)ethylene)2}Cl

Conditions
ConditionsYield
In water; acetone addn. of thiodiglycol to NaAuCl4 in H2O/Me2CO, then addn. of phosphine in Me2CO (molar ratio Au : phosphine = 1 : 3); elem. anal.;88%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

dichlorobis(2,2'-thiodiethanol)cobalt(II)
35872-09-4, 74779-08-1

dichlorobis(2,2'-thiodiethanol)cobalt(II)

Conditions
ConditionsYield
In methanol under N2 atm. to soln. CoCl2*6H2O in MeOH soln. 2,2'-thiodiethanol in methanol was added, mixt. was stirred for 1 day; soln. was concd. in vacuo; Et2O vapor diffusion; elem. anal.;87%
2,2'-thiobis-ethanol
111-48-8

2,2'-thiobis-ethanol

A

sulfonyldiethanol
2580-77-0

sulfonyldiethanol

B

4,4-Dioxo-4λ6-[1,4]oxathian-2-one
87220-53-9

4,4-Dioxo-4λ6-[1,4]oxathian-2-one

Conditions
ConditionsYield
With sodium bromite In water; acetic acid for 10h; Ambient temperature;A 12%
B 86%

2,2'-Thiodiethanol Consensus Reports

Reported in EPA TSCA Inventory.

2,2'-Thiodiethanol Specification

The β-Thiodiglycol, with the CAS registry number 111-48-8, is also known as 2,2'-Sulfanediyldiethanol. It belongs to the product category of Organics. Its EINECS registry number is 203-874-3. This chemical's molecular formula is C4H10O2S and molecular weight is 122.19. What's more, its IUPAC name is called 2-(2-Hydroxyethylsulfanyl)ethanol. β-Thiodiglycol is a viscous, clear to pale-yellow liquid. It is used as a solvent in a variety of applications ranging from dyeing textiles to inks in some ballpoint pens. In chemical synthesis, the production is used as a building block for protection products, dispersants, fibers, plasticizers, rubber accelerators, pesticides, dyes, and various other organic chemicals. In the manufacture of polymers, this chemical is used as a chain transfer agent. As an antioxidant, it is used as an additive in lubricants.

Physical properties about β-Thiodiglycol are: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 9.75; (5)ACD/KOC (pH 7.4): 9.75; (6)#H bond acceptors: 2; (7)#H bond donors: 2; (8)#Freely Rotating Bonds: 6; (9)Polar Surface Area: 65.76 Å2; (10)Index of Refraction: 1.523; (11)Molar Refractivity: 31.64 cm3; (12)Molar Volume: 103.5 cm3; (13)Surface Tension: 50 dyne/cm; (14)Density: 1.18 g/cm3; (15)Flash Point: 139.5 °C; (16)Enthalpy of Vaporization: 60.45 kJ/mol; (17)Boiling Point: 282 °C at 760 mmHg; (18)Vapour Pressure: 0.000407 mmHg at 25 °C.

Preparation of β-Thiodiglycol: this chemical can be prepared by Chlorohydrin with Sodium sulfide. This reaction needs reagent sulfuric acid at temperature of 90-95 °C.

2CH2Cl-CH2OH + Na2S → (CH2CH2OH)2S + 2NaCl

Uses of β-Thiodiglycol: it is used to produce other chemicals. For example, it can react with Methanol to get Bis-(2-methoxy-ethyl)-sulfane. The reaction occurs with reagent p-Toluenesulfonic acid monohydrate at temperature of 150 °C. The reaction time is 10 hours. The yield is 66 %.

β-Thiodiglycol can react with Methanol to get Bis-(2-methoxy-ethyl)-sulfane.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And in case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: OCCSCCO
(2) InChI: InChI=1S/C4H10O2S/c5-1-3-7-4-2-6/h5-6H,1-4H2
(3) InChIKey: YODZTKMDCQEPHD-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 3960mg/kg (3960mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
mouse LD50 subcutaneous 4gm/kg (4000mg/kg) GASTROINTESTINAL: OTHER CHANGES

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

ENDOCRINE: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 1, 1948.
rabbit LD50 intravenous 3gm/kg (3000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 1, 1948.
rabbit LD50 skin 20mL/kg (20mL/kg)   Union Carbide Data Sheet. Vol. 11/3/1971,
rat LD50 oral 6610mg/kg (6610mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
rat LD50 subcutaneous 4gm/kg (4000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 1, 1948.

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