Conditions | Yield |
---|---|
With hydrogen sulfide at 20℃; Temperature; | 99.5% |
With hydrogen sulfide |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
at 120 - 125℃; | |
With potassium carbonate In neat (no solvent) at 120℃; for 0.29h; Catalytic behavior; Temperature; |
Conditions | Yield |
---|---|
With water; zinc(II) oxide | |
With water In ethanol Kinetics; |
Conditions | Yield |
---|---|
With sodium carbonate |
Conditions | Yield |
---|---|
With potassium hydrosulfide at 0℃; | |
With sodium hydrogensulfide at 25℃; | |
With sodium sulfide; water Darstellung; | |
With potassium sulfide; water | |
With sodium sulfide; water |
Conditions | Yield |
---|---|
With triethylamine at 15℃; Rate constant; Mechanism; Thermodynamic data; other temperature, E(a); |
Conditions | Yield |
---|---|
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
A
2,2'-thiobis-ethanol
B
bis-(2-hydroxy-ethyl)-[2-(2-hydroxy-ethylsulfanyl)-ethyl]-sulfonium
Conditions | Yield |
---|---|
In water Title compound not separated from byproducts; |
bis-(2-hydroxy-ethyl)-[2-(2-hydroxy-ethylsulfanyl)-ethyl]-sulfonium
A
2,2'-thiobis-ethanol
B
mustard chlorohydrin
C
bis (2-chloroethyl) sulphide
Conditions | Yield |
---|---|
With hydrogenchloride In water Product distribution; Mechanism; | A 25.3 % Chromat. B 64.8 % Chromat. C 3.8 % Chromat. |
A
1,4-Dithiane
B
2,2'-thiobis-ethanol
C
mustard chlorohydrin
D
bis (2-chloroethyl) sulphide
Conditions | Yield |
---|---|
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
A
2,2'-thiobis-ethanol
B
bis (2-chloroethyl) sulphide
E
4-Aminobenzonitrile
Conditions | Yield |
---|---|
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
A
2,2'-thiobis-ethanol
Conditions | Yield |
---|---|
With trifluoroacetic acid for 2h; |
A
2,2'-thiobis-ethanol
Conditions | Yield |
---|---|
With trifluoroacetic acid for 2h; |
Conditions | Yield |
---|---|
at 20℃; Kinetics; auch in Gegenwart von Bis-<2-hydroxy-aethyl>-sulfid, sowie in Bis-<2-hydroxy-aethyl-sulfid>; |
Conditions | Yield |
---|---|
wss. Loesung vom pH 8.5; |
water
dihydrogen peroxide
2-hydroxyethanethiol
2,2'-thiobis-ethanol
water
iron(III) chloride
2-hydroxyethanethiol
2,2'-thiobis-ethanol
ethanol
2-chloro-ethanol
A
2,2'-thiobis-ethanol
B
bis(2-hydroxyethyl) disulfide
C
2-hydroxyethanethiol
Conditions | Yield |
---|---|
at 0℃; |
Conditions | Yield |
---|---|
With water Hydrolysis; |
bis (2-chloroethyl) sulphide
water
A
hydrogenchloride
B
2,2'-thiobis-ethanol
Conditions | Yield |
---|---|
at 25℃; |
ethanol
bis (2-chloroethyl) sulphide
A
2,2'-thiobis-ethanol
B
bis(2-ethoxyethyl)sulfide
C
2-(2-ethoxy-ethylsulfanyl)-ethanol
D
1,2-bis-(2-ethoxy-ethylsulfanyl)-ethane
Conditions | Yield |
---|---|
anderen Produkte: Aethylendimercaptan; Diaethylendisulfid; Aethylen; Schwefelwasserstoff; Chlorwasserstoff; Diaethylsulfid; Aethylvinylsulfid; |
Conditions | Yield |
---|---|
bei pH 8; |
bis (2-chloroethyl) sulphide
bis(2-chloroethylthioethyl)ether
water
A
2,2'-thiobis-ethanol
2,2'-thiobis-ethanol
[(C5H7O2)2Al(C3H7O)2AlO(CH2)2S(CH2)2O]2
Conditions | Yield |
---|---|
In benzene reflux (3h, C3H7OH distd. off with benzene); solvent evapn.; elem. anal.; | 100% |
2,2'-thiobis-ethanol
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
Conditions | Yield |
---|---|
With alumina-supported potassium hydroxide at 120 - 160℃; for 0.5h; Catalytic behavior; Temperature; Inert atmosphere; | 99.3% |
2,2'-thiobis-ethanol
1,4-Oxathiane
Conditions | Yield |
---|---|
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
(C6H9O3)2Al(C3H7O)2AlO(CH2)2S(CH2)2O
Conditions | Yield |
---|---|
In benzene reflux (3h, C3H7OH distd. off with benzene); solvent evapn.; elem. anal.; | 99% |
Conditions | Yield |
---|---|
In benzene Reflux; | 99% |
Conditions | Yield |
---|---|
In benzene byproducts: isopropanol; anhydrous atmosphere; molar ratio 1 : 2, refluxing (7 h); solvent removal (reduced pressure, pptn.), recrystn. (DMSO/benzene); elem. anal.; | 98% |
Conditions | Yield |
---|---|
In benzene for 6h; Reflux; | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In benzene Reflux; | 97% |
Conditions | Yield |
---|---|
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
methylvinyldimethoxysilane
2-methyl-2-vinyl-1,3-dioxa-6-thia-2-silacyclooctane
Conditions | Yield |
---|---|
With sodium methylate In methanol; benzene for 8h; Heating; | 95% |
Conditions | Yield |
---|---|
With pyridine; 4-AcNH-1-oxo-2,2,6,6-tetramethylpiperidinium tetrafluoroborate In dichloromethane at 20℃; for 3h; | 95% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With immobilized p-TsOH on activated carbon In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
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
2,2'-thiobis-ethanol
bis(2-trimethylsiloxyethyl)sulfide
Conditions | Yield |
---|---|
With urea at 20 - 25℃; for 6h; | 93% |
76% | |
With triethylamine In toluene at 20℃; for 24h; |
Conditions | Yield |
---|---|
With hydrogenchloride; hydrazine hydrate; thiourea In 5,5-dimethyl-1,3-cyclohexadiene; water | A n/a B 93% |
2,2'-thiobis-ethanol
1,2-bis-(diphenylphosphino)ethane
1,2-bis(diphenylphosphino)ethane digold(I) dichloride
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
4-chloro-3-nitrobenzoate
3-amino-4-chloro-benzoic acid
Conditions | Yield |
---|---|
In methanol; water | 92% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With immobilized p-TsOH on activated carbon In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; chemoselective reaction; | 91% |
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In toluene at 20℃; for 1h; Mitsunobu reaction; | 90% |
Conditions | Yield |
---|---|
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
Diethyl carbonate
bis-(2-ethylcarbonate)ethyl sulfide
Conditions | Yield |
---|---|
for 17h; Reflux; | 90% |
2,2'-thiobis-ethanol
cis-1,2-bis-(diphenylphosphino)ethene
{Au(cis-bis(diphenylphosphino)ethylene)2}Cl
Conditions | Yield |
---|---|
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
dichlorobis(2,2'-thiodiethanol)cobalt(II)
Conditions | Yield |
---|---|
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
A
sulfonyldiethanol
B
4,4-Dioxo-4λ6-[1,4]oxathian-2-one
Conditions | Yield |
---|---|
With sodium bromite In water; acetic acid for 10h; Ambient temperature; | A 12% B 86% |
Reported in EPA TSCA Inventory.
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 %.
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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