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Methyl thioglycolate

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Name

Methyl thioglycolate

EINECS 219-121-7
CAS No. 2365-48-2 Density 1.187
PSA 65.10000 LogP 0.08920
Solubility 40 g/L (20 ºC) in water Melting Point -24 ºC
Formula C3H6 O2 S Boiling Point 42-43 ºC (10 mmHg)
Molecular Weight 106.145 Flash Point 56 ºC
Transport Information UN 1992 3/PG 3 Appearance colorless or palegreen liquid
Safety Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of SOx. See also MERCAPTANS and ESTERS. Risk Codes R10;R20/22;R25;R36/37/38   
Molecular Structure Molecular Structure of 2365-48-2 (Methyl thioglycolate) Hazard Symbols
Synonyms

Acetic acid,mercapto-, methyl ester (6CI,7CI,8CI,9CI);2-Mercaptoacetic acid methyl ester;Mercaptoacetic acid methyl ester;Methyl 2-mercaptoacetate;Methylmercaptoacetate;Methyl thioglycolate;Methyl a-mercaptoacetate;NSC 75117;Thioglycolic acid methylester;

Article Data 23

Methyl thioglycolate Synthetic route

67-56-1

methanol

68-11-1

mercaptoacetic acid

2365-48-2

Methyl thioglycolate

Conditions
ConditionsYield
With sulfuric acid for 4h; Reflux;95%
With sulfuric acid for 4h; Reflux;94%
at 40℃; for 3h; Temperature;88.74%
84495-75-0

(N-Phenyl-formimidoylsulfanyl)-acetic acid methyl ester

A

68-11-1

mercaptoacetic acid

B

2365-48-2

Methyl thioglycolate

Conditions
ConditionsYield
With hydrogenchloride In water Ambient temperature;A 3%
B 93%
1665-64-1

methyl bis(thioacetate)

2365-48-2

Methyl thioglycolate

Conditions
ConditionsYield
With magnesium In methanol for 2h; Ambient temperature;85%
67-56-1

methanol

16312-21-3

3-methyl-thiazolidine-2,4-dione

2365-48-2

Methyl thioglycolate

Conditions
ConditionsYield
at 25℃; Rate constant; different sodium methoxide concentration;
122801-33-6

C18H18NO5S(1-)

A

96746-56-4

(E)-β-Methoxy-α-nitrostilbene

B

2365-48-2

Methyl thioglycolate

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 20℃; Equilibrium constant; Rate constant; ionic strength 0.5 M KCl;

[(6-Hydroxy-2,2-dimethyl-4-oxo-4H-[1,3]dioxin-5-yl)-methoxy-phenyl-methylsulfanyl]-acetic acid methyl ester

A

2365-48-2

Methyl thioglycolate

B

212068-02-5

methoxybenzylidene Meldrum's acid

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 20℃; Rate constant; Equilibrium constant;

7-[(1R,2R)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-3-methoxycarbonylmethylsulfanyl-5-oxo-cyclopentyl]-heptanoic acid methyl ester

A

16887-11-9

prostaglandin A1 methyl ester

B

2365-48-2

Methyl thioglycolate

Conditions
ConditionsYield
With deuterio phosphate buffer In d(4)-methanol at 25℃; pH=7.4; Equilibrium constant; Elimination;

7-[(2R,3R)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-3-methoxycarbonylmethylsulfanyl-5-oxo-cyclopent-(E)-ylidene]-heptanoic acid methyl ester

A

2365-48-2

Methyl thioglycolate

B

92711-55-2

Δ7-prostaglandin A1 methyl ester

Conditions
ConditionsYield
With deuterio phosphate buffer In d(4)-methanol at 25℃; pH=7.4; Equilibrium constant; Elimination;

C16H17O6S(1-)

A

1214-54-6

5-benzylidene Meldrum's acid

B

2365-48-2

Methyl thioglycolate

C

[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-phenyl-methylsulfanyl]-acetic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride In water; dimethyl sulfoxide at 20℃; Kinetics; Further Variations:; pH-values; Elimination; protonation;
771490-16-5

3-(4-hydroxy-phenyl)-2-(2-mercapto-acetylamino)-N-methyl-propionamide

SuccN-EELRRRLEELRRRRGG-SCH2C(O)-OMe

SuccN-EELRRRLEELRRRRGG-SCH2C(O)-OMe

A

SuccN-EELRRRLEELRRRRGG-SCH2C(O)-YNHMe

SuccN-EELRRRLEELRRRRGG-SCH2C(O)-YNHMe

B

2365-48-2

Methyl thioglycolate

Conditions
ConditionsYield
In phosphate buffer for 3h; pH=7.0; Equilibrium constant;

Methyl thioglycolate Consensus Reports

Reported in EPA TSCA Inventory.

Methyl thioglycolate Specification

With the cas registry number 2365-48-2, methylmercaptoacetate is a kind of clear colourless liquid. Its IUPAC name is methyl 2-sulfanylacetate and the systematic name is methyl sulfanylacetate. This chemical is sensitive to air and is insoluble in water while soluble in carbinol, alcohol and benzene and other organic solvent. As to its usage, it is the raw material of phytocide Thifensulfuron Methyl and it could be often used as the pharmaceutic intermediate.

The physical properties of this chemical are as follows: (1)(1)ACD/LogP: 0.65; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.65; (4)ACD/LogD (pH 7.4): 0.59; (5)ACD/BCF (pH 5.5): 1.84; (6)ACD/BCF (pH 7.4): 1.6; (7)ACD/KOC (pH 5.5): 53.8; (8)ACD/KOC (pH 7.4): 46.86; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 51.6; (13)Index of Refraction: 1.448; (14)Molar Refractivity: 25.61 cm3; (15)Molar Volume: 95.5 cm3; (16)Polarizability: 10.15 ×10-24 cm3; (17)Surface Tension: 32.4 dyne/cm; (18)Density: 1.11 g/cm3; (19)Flash Point: 35 °C; (20)Enthalpy of Vaporization: 38.88 kJ/mol; (21)Boiling Point: 151.9 °C at 760 mmHg; (22)Vapour Pressure: 3.58 mmHg at 25°C; (23)Exact Mass: 106.00885; (24)MonoIsotopic Mass: 106.00885; (25)Topological Polar Surface Area: 27.3; (26)Heavy Atom Count: 6; (27)Formal Charge: 0; (28)Complexity: 52.8.

Use of this chemical: methylmercaptoacetate could react with formaldehyde to produce chloromethylsulfanyl-acetic acid methyl ester, with the following condition: reagent: hydrogen chloride; reaction temp.: 0 °C.

When you are dealing with this kind of chemical, you should be much more careful and then take some measures to protect yourself. For one thing, it is harmful which may cause damage to health. And it is irritating to eyes, respiratory system and skin. If by inhalation or swallowed, it will be very dangerous. For another thing, it is toxic which may at low levels cause damage to health. Therefore, you should firstly wear suitable protective clothing, gloves and eye/face protection. And then take some instructions while meeting with the following conditions. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice; If in case of accident or if you feel unwell, seek medical advice immediately (show label where possible); After contacting with skin, wash immediately with plenty of ... (to be specified by the manufacturer).

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: COC(=O)CS
(2)InChI: InChI=1S/C3H6O2S/c1-5-3(4)2-6/h6H,2H2,1H3
(3)InChIKey: MKIJJIMOAABWGF-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
rat LD50 intraperitoneal 252mg/kg (252mg/kg)   Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974.
 
rat LD50 oral 84mg/kg (84mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0570921

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