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| CAS No.: | 68-11-1 |
|---|---|
| Name: | Mercaptoacetic acid |
| Molecular Structure: | |
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|
|
| Formula: | C2H4O2S |
| Molecular Weight: | 92.1186 |
| Synonyms: | Aceticacid, mercapto- (8CI,9CI);2-Mercaptoacetic acid;2-Mercaptoethanoic acid;2-Thioglycolic acid;Glycolic acid, 2-thio-;NSC 1894;Sulfhydrylacetic acid;Thioglycolic acid;Thiovanic acid;a-Mercaptoacetic acid; |
| EINECS: | 200-677-4 |
| Density: | 1.312 g/cm3 |
| Melting Point: | -16 °C(lit.) |
| Boiling Point: | 225.481 °C at 760 mmHg |
| Flash Point: | 99.841 °C |
| Solubility: | soluble in water |
| Appearance: | Clear liquid |
| Hazard Symbols: |
 T,  T+
|
| Risk Codes: | 23/24/25-34-26-24/25 |
| Safety: | 25-27-28-45-36/37-28C-23 |
| Transport Information: | UN 1940 8/PG 2 |
| PSA: | 76.10000 |
| LogP: | 0.00080 |
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| Conditions | Yield |
|---|---|
| With sulfuric acid at 40 - 43℃; Electrochemical reaction; | 96.7% |
| With Phenylalanine; pyrographite at 38℃; | |
| With sulfuric acid; cadmium Reduktion mit elektrolytisch gefaelltem Cadmiumpulver; |
- 79-14-1
glycolic Acid
- 79-08-3
bromoacetic acid
A
- 705924-36-3
2,2'-thiodiglycolic acid
B
- 68-11-1
mercaptoacetic acid
| Conditions | Yield |
|---|---|
| With hydrogen sulfide; hydrogen bromide In water | A n/a B 95% |
- 84495-75-0
(N-Phenyl-formimidoylsulfanyl)-acetic acid methyl ester
A
- 68-11-1
mercaptoacetic acid
B
- 2365-48-2
Methyl thioglycolate
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water Ambient temperature; | A 3% B 93% |
- 20069-27-6
2-(N-Phenyl-N-methyl-thiocarbamoylthio)acetic Acid
A
- 21076-11-9
4-methyl-4-phenyl-3-thiosemicarbazide
B
- 68-11-1
mercaptoacetic acid
| Conditions | Yield |
|---|---|
| With hydrazine hydrate In water at 85℃; for 0.416667h; | A 81% B n/a |
| Conditions | Yield |
|---|---|
| With hydrogenchloride at 130℃; |
- 16312-19-9
2-methylamino-Δ2-thiazolin-4-one
- 68-11-1
mercaptoacetic acid
- 68-11-1
mercaptoacetic acid
- 39130-96-6
thiazolidine-2,4-dione-2-semicarbazone
- 68-11-1
mercaptoacetic acid
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Consensus Reports
Standards and Recommendations
ACGIH TLV: TWA 1 ppm (skin)
DOT Classification: 8; Label: Corrosive
Specification
The Thioglycolic acid, with the 68-11-1, has the IUPAC name of 2-sulfanylacetic acid. This chemical is a kind of colorless liquid with an unpleasant odor which is sensitive to air and is soluble in water, ethanol and ethyl ether. And it is incompatible with diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agentscould. Besides, it could react readily with other oxidizing agents, generating heat, toxic and flammable gases
The physical properties of this chemical are as follows: (1)ACD/LogP: 0.09; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2; (4)ACD/LogD (pH 7.4): -3.47; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 51.6; (13)Index of Refraction: 1.503; (14)Molar Refractivity: 20.77 cm3; (15)Molar Volume: 70.2 cm3; (16)Polarizability: 8.23 ×10-24 cm3; (17)Surface Tension: 48.5 dyne/cm; (18)Density: 1.311 g/cm3; (19)Flash Point: 99.8 °C; (20)Enthalpy of Vaporization: 50.9 kJ/mol; (21)Boiling Point: 225.5 °C at 760 mmHg; (22)Vapour Pressure: 0.0314 mmHg at 25°C; (23)Exact Mass: 91.9932; (24)MonoIsotopic Mass: 91.9932; (25)Topological Polar Surface Area: 38.3; (26)Heavy Atom Count: 5; (27)Formal Charge: 0; (28)Complexity: 42.9.
Production method of this chemical: (N-phenyl-formimidoylsulfanyl)-acetic acid methyl ester could react to produce Thioglycolic acid and mercaptoacetic acid methyl ester, with the following condition: reagent: HCl; solvent: H2O; yield: 93%; other condition: ambient temperature.
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Use of this chemical: Thioglycolic acid could react with (E,E)-diisobutylidene-hydrazine to produce 2,2'-diisopropyl-[3,3']bithiazolidinyl-4,4'-dione, with the following condition: solvent: benzene; other condition: heating; yield: 24%.
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As to its usage, it is widely applied in many ways. It could be used as the material of blanket finishing agent and also as the chemical reagent; It could also used as the setting lotion, depilatory, PVC stabilizing agent, initiator of polymerization, accelerator and chain transfer agent, and metal surface treatment chemicals; Then it is often used as the pharmaceutic intermediate to produce the following chemical substance, such as biotin, zinc sulfate, and is also the important raw material of composing cysteine, industrial disinfectant.
When you are dealing with this kind of chemical, you should be much more careful and then take some measures to protect yourself. This is a kind of toxic chemical which may at very low levels cause damage to health, so if by inhalation, in contact with skin and if swallowed, it will be very dangerous. And it could cause burns. Therefore, you should wear suitable protective clothing and gloves and try to avoid contact with eyes. If contact with skin, take off immediately all contaminated clothing, and wash immediately with plenty of ... (to be specified by the manufacturer). And if in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). Besides, you should not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). Lastly, you should handle and open container with care.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C(C(=O)O)S
(2)InChI: InChI=1S/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)
(3)InChIKey: CWERGRDVMFNCDR-UHFFFAOYSA-N
Below are the toxicity information of this chemical:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LD50 | intraperitoneal | 157mg/kg (157mg/kg) | Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974. | |
| guinea pig | LD50 | oral | 126mg/kg (126mg/kg) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 586, 1969. | |
| mammal (species unspecified) | LD50 | oral | 250mg/kg (250mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974. | |
| mouse | LCLo | inhalation | 7mg/m3/2H (7mg/m3) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 111, 1982. | |
| mouse | LD50 | intraperitoneal | 138mg/kg (138mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 1713, 1981. | |
| mouse | LD50 | intravenous | 145mg/kg (145mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 60, Pg. 278, 1964. | |
| mouse | LD50 | oral | 242mg/kg (242mg/kg) | Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974. | |
| mouse | LD50 | skin | 47mg/kg (47mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989. |
| rabbit | LD50 | intravenous | 100mg/kg (100mg/kg) | Biochemical Journal. Vol. 41, Pg. 325, 1947. | |
| rabbit | LD50 | oral | 119mg/kg (119mg/kg) | Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974. | |
| rabbit | LDLo | skin | 300mg/kg (300mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 13(1), Pg. 48, 1969. |
| rat | LC50 | inhalation | 210mg/m3/4H (210mg/m3) | BEHAVIORAL: FOOD INTAKE (ANIMAL) LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: CHANGES IN LUNG WEIGHT | National Technical Information Service. Vol. OTS0554077, |
| rat | LD50 | intraperitoneal | 70mg/kg (70mg/kg) | Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974. | |
| rat | LD50 | oral | 114mg/kg (114mg/kg) | Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974. |