Thiodiglykol

Thiodiglycol

HCID 5447CAS 111-48-8

Grundinformationen

Standard-SMILES
OCCSCCO
InChIKey
YODZTKMDCQEPHD-UHFFFAOYSA-N
Summenformel
C4H10O2S
Durchschnittliche Molmasse
122,19 g/mol
Monoisotopische Masse
122,04015056

Überblick

This material has many uses, including as a precursor to the sulfur mustard family of chemical weapons. It is chemically similar to thioglycol and is expected to react in a similar way to this material. See the chemical datasheet for thioglycol for more information.

Namen und Bezeichner

Bevorzugter Name
Thiodiglycol
IUPAC
2-(2-hydroxyethylsulfanyl)ethanol
Lokaler Name
Thiodiglykol
Englischer Name
2,2'-Thiodiethanol
Summenformel
C4H10O2S
Molmasse
122.19

Namen und Synonyme

thiodiglycol2,2'-Thiodiethanol111-48-8Thiodiethylene glycolThiodiethanolTedegylKromfax solventBis(2-hydroxyethyl) sulfide2,2'-THIOBISETHANOLBis(2-hydroxyethyl)sulfideEthanol, 2,2'-thiobis-Glyecine A
Weitere Namen anzeigen
2-HYDROXYETHYL SULFIDE2-(2-hydroxy-ethylsulfanyl)-ethanolGlycine AglyecineaTHYODIGLYCOL
2,2'-Thiodiglycol2-(2-hydroxyethylsulfanyl)ethanolTiodiglicolDi(2-hydroxyethyl) sulfideBis(2-hydroxyethyl) thioetherbis(hydroxyethyl)sulfideThiodiglycolumTiodiglicolo

Datenbank-Bezeichner

CAS
111-48-8
PubChem CID
5447
DTXSID
DTXSID6026878
ChEMBL
CHEMBL444480
ChEBI
CHEBI:75184
UNII
9BW5T43J04
EC Number
203-874-3
Nikkaji
J1.988G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,6
Polarare Oberfläche (TPSA)
65,8 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
4
Schwere Atome
7

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Sulfur Compounds (Alcohols)
CosmeticsAntioxidant
SpringerMaterials PropertiesBoiling point
LogP · 4 Einträge

log Kow = -0.63

-0.63

-0.75

-0.63

Odor · 2 Einträge

Characteristic odor

Odor similar to hydrogen sulfide

Density · 4 Einträge

1.1793 g/cu cm at 25 °C

Bulk density: 9.85 lb/gal

Relative density (water = 1): 1.18

1.1847 @ 20°C

Physikochemische Eigenschaften

Schmelzpunkt
16 °C · −16 °C(lit.)
Siedepunkt
164 · 164-166 °C20 mm Hg(lit.)
Dichte
1.221 g/mL · 1.221 g/mL at 25 °C(lit.)
Dampfdruck
0.26 Pa · 0.26Pa at 20℃
Brechungsindex
20 · n20/D 1.5215(lit.)
Flammpunkt
230 °F · >230 °F

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Ethanol, 2,2'-thiobis-

Ethanol, 2,2'-thiobis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2,2'-thiobis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 03-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/11663

Thiodiglycol: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible.
Fire Potential · 2 Einträge

Combustible when exposed to heat or flame.

Combustible.

Hazards Summary · 1 Eintrag

A mild eye and respiratory tract irritant; [ICSC] Causes mild skin irritation and moderate eye irritation in experimental animals; Not sensitizing in guinea pig maximization test; No evidence of mutagenicity; Emergency treatment: Glycols; [HSDB] An eye irritant; [eChemPortal: ESIS] A mild skin and moderate eye irritant; Causes diffuse hepatitis and other GI and endocrine changes in subcutaneous lethal-dose study of mice; [RTECS] An eye irritant; [Alfa Aesar MSDS]

Reactive GroupAlcohols and Polyols
EC ClassificationSymbol: Xi; R: 36; S: (2)

Sicherheit und Schutzausrüstung

Fire FightingUse water spray, foam, alcohol-resistant foam, carbon dioxide.
First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting.

Safe StorageSee Chemical Dangers.
Firefighting Hazards · 2 Einträge

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.

Decomposes on heating. This produces toxic and corrosive fumes including acetic acid fumes, hydrogen sulfide and sulfur oxides.

Fire Fighting Procedures · 3 Einträge

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

To fight fire, use alcohol foam, carbon dioxide, dry chemical.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.

Toxikologische Informationen

Ecotoxicity Values · 3 Einträge

EC50; Species: Pseudomonas putida (bacterium); Concentration: >10,000 mg/L for 17 hr; Effects: cell multiplication inhibition test /Conditions of bioassay not specified in source examined/

EC50; Species: Scenedesmus subspicatus (algae); Concentration: >500 mg/L for 72 hr; Effects: cell multiplication inhibition test /Conditions of bioassay not specified in source examined/

LC50; Species: Leuciscu idus (cyprinoid fish); Conditions: static; Concentration: >10,000 mg/L for 96 hr

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Koc values of 0.12-13.70 indicate that thiodiglycol is expected to have very high mobility in soil(1). Volatilization of thiodiglycol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Thiodiglycol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.09X10-4 mm Hg at 25 °C(3). Thiodiglycol was biologically transformed to thiodiglycolic acid at zero-order rate coefficients of 9.41X10-7 to 6.26X10-6 mol/L hr in 3 soils, with lag periods of 2 to 3.75 days, biodegradation was noted in 2 other soils, but transformation rates were not reported(1). The optimum pH for the biodegradation of thiodiglycol in soil has been reported as 8.25(4).

AQUATIC FATE: Koc values of 0.12-13.70(1) indicate that thiodiglycol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 1.9X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Thiodiglycol did not undergo hydrolysis at pH 4, 7 or 11(1). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of -0.63(5) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low. Thiodiglycol did not undergo photolysis in aqueous solution after irradiation by sunlight for 14 days(1). Based on studies done in aerobic sludge with 19% biodegradation in 4 weeks(6), anaerobic sludge with 42% biodegradation in 185 days(7) and in soil where biodegradation was noted in 5 soils(1), biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiodiglycol, which has a vapor pressure of 5.09X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase thiodiglycol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 14 hours(SRC), calculated from its rate constant of 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Thiodiglycol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Toxicity Summary · 1 Eintrag

IDENTIFICATION AND USE: Thiodiglycol is a syrupy, colorless, liquid. It is used as chemical intermediate, additive for textile printing. It is also a Schedule 2B precursor (dual-use chemicals with low to moderate commercial use and high-risk precursors) to mustard gas, sesquimustard, HT, T, and Q. It is used to manufacture ball-point pen ink. HUMAN STUDIES: The hydrolysis products of mustard gas are reported to exhibit toxicity. However, thiodiglycol, the major breakdown product, exhibits low toxicity. Therefore, it is likely that the majority of the toxic effects attributed to the hydrolysis products are due to unreacted mustard and bis(chloroethyl)polysulfides present in the original material. ANIMAL STUDIES: Acute dermal irritation was tested on rabbits. A very slight erythema was noted in 1 out of 3 animals 1 hour after treatment until day 4. The effect was completely reversible within 5 days. No cutaneous reactions were observed in the other 2 animals. In a guinea pig maximization test the challenge resulted in no skin reaction in thiodiglycol treated animals. In the Rat Inhalation Hazard Test, no mortality was reported after 8 hr exposure to a saturated atmosphere at room temperature. Immediately after the start of exposure, the animals showed attempts to escape. Irritation of the mucous membranes was observed 1 hr after start of exposure. In a prenatal developmental toxicity study in rats a significant increase in dumbbell ossifications of thoracic vertebral bodies was noted (12% versus 5.2% in control). Other significant increases in skeletal variations, such as rudimentary cervical ribs were also observed (7.1% versus 1.2% in control) as well as a general increase in total variations (concerning affected fetuses/litter: 52.9% versus 38.6% in control). Thiodiglycol did not induce reverse gene mutations in Salmonella typhimurium strains TA98, TA100, TA1535, TA1537, and E. coli WP2uvrA at concentrations up to 5 mg/plate in the presence or absence of metabolic activation. Thiodiglycol was not mutagenic in mouse lymphoma, and in vivo mouse micronucleus assays, but it induced chromosomal aberrations in Chinese hamster ovarian (CHO) cells. The mechanism of vesication from sulfur mustard remains unknown in spite of 80 years of investigation. It was reported that sulfur mustard-related inhibition of one or more protein (serine/threonine) phosphatases in tissue cytosol in vitro, could be a mechanism common to other vesicants such as cantharidin and Lewisite. This inhibition was related to the concentration of thiodiglycol, the hydrolysis product of sulfur mustard, rather than to the concentration of mustard itself. ECOTOXICITY STUDIES: It was not toxic to bluegill sunfish at 1,000 mg/L.

Ecotoxicity Excerpts/AQUATIC SPECIES/ ... It was slowly biodegraded under anaerobic conditions. It was not toxic to bluegill sunfish at 1,000 mg/L and its metabolism and environmental and biochemical effects are summarized.
Signs and Symptoms · 3 Einträge

Cough. Nausea.

Redness. Pain.

Diarrhoea. Nausea. Vomiting.

Regulatorische Informationen

DHS Chemicals of Interest (COI) · 4 Einträge

Thiodiglycol

30

2.2000000000000002

Chemical Weapons/Chemical Weapons Precursors chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques.

Sicherheitsdaten

F
3-13-23
wgk
1
tsca
TSCA listed
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29309090
RTECS-Nr.
KM2975000

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

The mechanism of vesication from sulfur mustard remains unknown in spite of 80 years of investigation. /The authors/ recently reported sulfur mustard-related inhibition of one or more protein (serine/threonine) phosphatases in tissue cytosol in vitro, suggesting a mechanism common to other vesicants such as cantharidin and Lewisite. /Their/ investigation showed that this inhibition was related to the concentration of 2,2'-thiobis-ethanol (thiodiglycol), the hydrolysis product of sulfur mustard, rather than to the concentration of mustard itself. Related work showed an increase in the rate of NAD (but not NADP) reduction upon the addition of thiodiglycol to mouse liver cytosol. This result provided evidence that metabolism beyond thiodiglycol may be contributing to protein phosphatase inhibition. This observation indicated that metabolism involving one or more dehydrogenases may be necessary to produce the ultimate inhibitor of the protein phosphatases. /The authors/ report here that thiodiglycol is a substrate for horse liver alcohol dehydrogenase (Km = 3.68+/-0.45 mM and Vmax = 0.22 +/-0.01 umol/ min/ mg protein) and for pyridine nucleotide-linked enzymes in mouse liver and human skin cytosol. The alcohol dehydrogenase-specific inhibitor 4-methylpyrazole inhibited the oxidation of thiodiglycol by the pure horse liver enzyme as well as by the enzymes in human skin and mouse liver cytosol, indicating that the activity in the tissue preparations is also alcohol dehydrogenase.

Biological Half-LifeThe apparent half-life of thiodiglycol in the urine of rats after cutaneous application of sulfur mustard is 2.4 days
Metabolism/Metabolites · 5 Einträge

Thiodiglycol is oxidized to four metabolites. In three of the four metabolites sulfur undergoes oxidation and in two of them acetic acid is formed. No information of toxic effects of the metabolites is recorded ... In rodents thiodiglycol can conjugate with glucuronic acid and sulfate or it can be converted to thiodiglycolic acid which can conjugate with glycine and glucuronic acid ... The major metabolite was thiodiglycol sulfoxide, minor metabolites were thiodiglycol sulfone, S-(2-hydroxyethylsulfinyl)acetic acid and S-(2-hydroxyethylthio)acetic acid. Only around 0.5 to 1% of thiodiglycol was excreted unchanged.

Skin blisters /from mustard gas exposure/ may be aspirated and the fluid obtained analyzed for thiodiglycol. The same estimation may be performed in blood and urine in order to differentiate blistering produced by ... other agents such as Lewisite ...

Metabolic studies with radioactively labelled mustard gas were performed in rodents ... The following metabolic pathways were proposed: hydrolyses to thiodiglycol and S-oxidation to sulfoxide and sulfone, followed by conjugation. Urinary metabolites in rats consisted of thiodiglycol and conjugates (15%), glutathione-bis-beta-chloroethylsulfide conjugates (45%), glutathione-bis-beta chloroethylsulfone (7%), bis-beta-chloroethylsulfone and conjugates (8%), and small amounts of cysteine conjugates. Urinary metabolites formed from intraperitoneal injection in rats were bis-cysteinylethylsulfone and thiodiglycol.

Urine, from human volunteers with no known exposure to sulfur mustard, contained detectable but very low concentrations (<0.2ng/mL) of thiodiglycol, consistent with previous observations using different methodologies. Combined concentrations of thiodiglycol and thiodiglycol sulfoxide were determined after reduction of the latter with titanium trichloride. In this case higher background levels (up to 3ng/mL) were observed, consistent with the sulfoxide being the major excretion product of the two metabolites. The method was applied to urine samples, stored frozen for 13 years, from two casualties of accidental mustard poisoning. Levels of thiodiglycol were 1 and 3 ng/mL, which increased to 78 and 104 ng/mL after treatment of the urine with titanium trichloride.

For more Metabolism/Metabolites (Complete) data for Thiodiglycol (7 total), please visit the HSDB record page.

MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Absorption, Distribution and Excretion · 5 Einträge

The procedure was applied to urine samples obtained from Iranian patients who were the alleged victims of an attack by chemical warfare agents (probably mustard gas). A number of control samples were investigated as well. Thiodiglycol was found in the urine of the Iranian patients in concentrations varying between 3 and 140 ng/mL. However, the detection of thiodiglycol in concentrations up to 55 ng/mL in control samples excluded the unambiguous verification of the use of mustard gas against the Iranian patients.

The modified procedure was applied to urine samples of several Iranian patients who were victims of an alleged attack with mustard gas and who were treated in European hospitals in 1986. With the exception of one relatively high value (330 ng/mL), the thiodiglycol concentrations were in the same range (10 to 100 ng/mL) as those found during an investigation in 1984. The urine of 20 male controls contained thiodiglycol amounts not above 20 ng/mL. The combined data obtained in 1984 and 1986 (25 Iranian patients and 25 controls) show statistically significant differences. Approximately 80% of the Iranian patients had levels above the 95% confidence limit calculated from the control group.

The purpose of this study was to develop an assay to study the flux of sulfur mustard (HD) through the skin and determine if metabolites are formed due to the epidermal metabolism of HD after topical exposure of the isolated perfused porcine skin flap (IPPSF) to 14C-HD. Four IPPSFs were topically dosed with 2.85 mg of 14C-HD in ethanol. Venous perfusate samples were collected and added to a 34% solution of NaCl and snap-frozen to inhibit the metabolism of HD until time for assay. Perfusate samples were extracted using a solid-phase extraction cartridge with ethyl acetate and then assayed using gas chromatography. Two of the 4 IPPSFs showed detectable levels of HD in the venous perfusate 15 min after dosing, with 1 of these 2 IPPSFs showing detectable levels of HD in the perfusate 2 hours after dosing. All 4 IPPSFS had no more than 3 metabolites of HD appearing in the perfusate throughout the 2 hr experiment, with one of the these metabolites identified as thiodiglycol. These experiments showed that little, if any, HD appears in the venous perfusate intact after percutaneous absorption and that epidermal metabolism of HD does occur to a significant degree in the IPPSF.

90% of an intraperitoneal dose of thiodiglycol in rats was excreted in the urine within 24 hr and by 8 days virtually all of the dose had been excreted. There was no significant excretion in the feces ... Only around 0.5 to 1% of thiodiglycol was excreted unchanged.

Background levels of thiodiglycol in human urine are normally <1 ng/mL ... Others have reported background levels of thiodiglycol to be from 1 to 55 ng/mL ... The source of these background levels is unknown.

Verwendung und Herstellung

Uses · 6 Einträge

A hydrolysis product of sulfur mustard (chemical weapon); Used as an intermediate for elastomers and antioxidants, a solvent for dyes in textile printing, to make ink for ball-point pens, and a precursor to mustard gas; Also used in the paint, lacquer, and varnish industry; in the polymers industry; and as a fixing agent, process regulator, and stabilizer; [HSDB] Used to make pulp, paper products, furniture, paints, pigments, dyestuffs, varnishes, coatings, and inks; Also used as a solvent for coloring paper, a softener for special rubbers, and possibly as an antioxidant in cosmetics; [OECD SIDS: Thiodiglycol - 2004]

Manufacture and export strictly controlled under the International Chemical Weapons Convention (can be used to make sulfur mustard); [OECD SIDS: Thiodiglycol - 2004]

Pulp and Paper Processing [Category: Industry]

Intermediate for elastomers and antioxidants; solvent for dyes in textile printing.

Thiodiglycol is used as a precursor for sulfur mustard ... It is also an important primary metabolite of sulfur mustard formed by simple hydrolysis.

/SRP: Chemical Weapons Convention/ schedule 2B precursor to mustard gas, sesquimustard, HT, T, and Q.

U.S. Production · 5 Einträge

2023: 75,000 - <500,000 lb

In 2004, participating countries declared 50.96 metric tons of thiodiglycol and reported that 50.96 metric tons of this Schedule 2 B chemical were destroyed.

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7137]

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Ethanol, 2,2'-thiobis-:

Industry UsesStabilizing agent
Methods of Manufacturing · 2 Einträge

Prepared from ethylene oxide and hydrogen sulfide.

Hydrolysis of dichloroethyl sulfide, interaction of ethylene chlorohydrin and sodium sulfide.

Household ProductsInformation on 13 consumer products that contain Thiodiglycol in the following categories is provided:
Use ClassificationCosmetics -> Antioxidant

Anwendungen

Verwendenantineoplastic, alkylating agent

Ergänzende Hinweise

DefinitionChEBI: A diol that is pentane-1,5-diol in which the methylene group at position 3 is replaced by a sulfur atom

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