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Glycol dimercaptoacetate

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Name

Glycol dimercaptoacetate

EINECS 204-653-4
CAS No. 123-81-9 Density 1.313
PSA 130.20000 LogP -0.06760
Solubility 20 g/L (20 ºC) Melting Point N/A
Formula C6H10 O4 S2 Boiling Point 317 ºC
Molecular Weight 210.275 Flash Point 167 ºC
Transport Information N/A Appearance Clear, colorless liquid. With a stench.
Safety Poison by ingestion. When heated to decomposition it emits toxic fumes of SOx. See also MERCAPTANS. Risk Codes R20/21/22;R36/38;R51/53   
Molecular Structure Molecular Structure of 123-81-9 (Glycol dimercaptoacetate) Hazard Symbols
Synonyms

Aceticacid, mercapto-, 1,2-ethanediyl ester (9CI); Acetic acid, mercapto-, ethyleneester (6CI,7CI,8CI); Ethylene glycol, bis(mercaptoacetate) (8CI); EGTG; EGTG(polythiol); Ethylene bis(mercaptoacetate); Ethylene glycolbis(2-mercaptoacetate); Ethylene glycol bis(thioglycolate); Ethylene glycolbis(thioglycolic ester); Ethylene mercaptoacetate; Ethylenebis(thioglycolate);Glycol bis(mercaptoacetate); Glycol dimercaptoacetate; Glycol(bisthioglycolate); NSC 30032; PETP

Article Data 3

Glycol dimercaptoacetate Synthetic route

107-21-1

ethylene glycol

68-11-1

mercaptoacetic acid

123-81-9

ethylene glycol dimercaptoacetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;70%
With sulfuric acid at 70 - 80℃; Reagent/catalyst; Temperature; Large scale;
107-21-1

ethylene glycol

68-11-1

mercaptoacetic acid

A

7380-58-7

mercapto-acetic acid-(2-hydroxy-ethyl ester)

B

123-81-9

ethylene glycol dimercaptoacetate

Conditions
ConditionsYield
toluene-4-sulfonic acid at 110 - 150℃; for 5h;
5356-85-4

methylbis(trimethylsilyloxy)vinylsilane

123-81-9

ethylene glycol dimercaptoacetate

1,14-bis(1,1,1,3,5,5,5-heptamethyltrisiloxy)-6,9-dioxa-3,12-dithiatetradecane-5,10-dione

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In benzene at 50 - 60℃; for 1h; Irradiation;96%
123-81-9

ethylene glycol dimercaptoacetate

107-02-8

acrolein

158199-70-3

Ethylen-bis(6-oxo-3-thiahexanoat)

Conditions
ConditionsYield
With triethylamine In chloroform for 12h; Ambient temperature;95%
99396-97-1

(AuCl)2(μ-trans-1,2-bis(diphenylphosphino)ethylene)

123-81-9

ethylene glycol dimercaptoacetate

2966-50-9

silver trifluoroacetate

[CH2OCOCH2SAu)2(μ-trans-Ph2PCHCHPPh2)]

Conditions
ConditionsYield
In methanol; dichloromethane byproducts: AgCl; (darkened flask); addn. of soln. of silver compd. in methanol to soln. of gold compd. in CH2Cl2, stirring for 30 min, filtration through Celite,addn. of dithiol deriv. in CH2Cl2, stirring for 3 h; addn. of pentane, filtration, washing with acetone and ether, elem. anal.;93%
123-81-9

ethylene glycol dimercaptoacetate

818-08-6

di(n-butyl)tin oxide

2,2-dibutyl-2-stanna-1,3-dithia-6,9-dioxacycloundecane-5,10-dione

Conditions
ConditionsYield
In toluene at 110℃; for 29h; Dean-Stark;93%
In toluene at 110℃; for 24h; Dean-Stark;89%
63640-04-0

1,4-bis(diphenylphosphino)butane digold(I) dichloride

123-81-9

ethylene glycol dimercaptoacetate

2966-50-9

silver trifluoroacetate

909123-30-4

[(CH2OCOCH2SAu)2)(μ-Ph2P(CH2)4PPh2)]

Conditions
ConditionsYield
In methanol; dichloromethane byproducts: AgCl; (darkened flask); addn. of soln. of silver compd. in methanol to soln. of gold compd. in CH2Cl2, stirring for 30 min, filtration through Celite,addn. of dithiol deriv. in CH2Cl2, stirring for 3 h; addn. of pentane, filtration, washing with acetone and ether, elem. anal.;87%
64659-16-1

Au2Cl2{μ-Ph2P(CH2)6PPh2}

123-81-9

ethylene glycol dimercaptoacetate

2966-50-9

silver trifluoroacetate

909123-32-6

[(CH2OCOCH2SAu)2)(μ-Ph2P(CH2)6PPh2)]

Conditions
ConditionsYield
In methanol; dichloromethane byproducts: AgCl; (darkened flask); addn. of soln. of silver compd. in methanol to soln. of gold compd. in CH2Cl2, stirring for 30 min, filtration through Celite,addn. of dithiol deriv. in CH2Cl2, stirring for 3 h; addn. of pentane, filtration, washing with acetone and ether, elem. anal.;85%
123-81-9

ethylene glycol dimercaptoacetate

74-99-7

prop-1-yne

A

8-methyl-1,4-dioxa-7,10-dithiacyclododecane-5,12-dione

B

8,20-Dimethyl-1,4,13,16-tetraoxa-7,10,19,22-tetrathia-cyclotetracosane-5,12,17,24-tetraone

Conditions
ConditionsYield
With tripropylborane In methanol; hexane; benzene at 20℃;A 48%
B 9%
156842-95-4

MoCl(CO)2(1,10-phenanthroline)(η(3)-CH2C(COCl)C=CH2)

75-09-2

dichloromethane

123-81-9

ethylene glycol dimercaptoacetate

(MoCl(CO)2(C12H8N2)CH2CCCH2COSCH2COOCH2)2*CH2Cl2

Conditions
ConditionsYield
With triethylamine In dichloromethane (N2); dropwise addn. of dithiol to a soln. of molybdenum complex and amine in CH2Cl2, stirring for 2 h; storage at low temp., filtration, recrystn. (CH2Cl2/petrol), drying in vac.; elem. anal.;47%

Glycol dimercaptoacetate Chemical Properties

IUPAC:   2-(2-Sulfanylacetyl)oxyethyl 2-sulfanylacetate
 Mercapto di-acetic acid, ethylene ester (123-81-9)  is also called for  AI3-26087 ; Acetic acid, mercapto-, 1,2-ethanediyl ester ; BRN 1948305 ; EINECS 204-653-4 ; Ethylene bis(mercaptoacetate) ; Ethylene bis(thioglycolate) ; Ethylene glycol bis(mercaptoacetate) ; Ethylene glycol bis(thioglycolate) ; Ethylene glycol bis(thioglycolic ester) ; Ethylene mercaptoacetate ; Ethylenebis(thioglycolate) ; GDMA ; Glycol bis(mercaptoacetate) ; Glycol dimercaptoacetate ; NSC 30032 ; Acetic acid, 2-mercapto-, 1,1'-(1,2-ethanediyl) ester ; Ethylene di(S-thioacetate) and so on.
Molecular Weight: 210.27
Molecular Formula: C6H10O4S2
EINECS: 204-653-4
LogP: ACD/LogP: 0.90
XLogP: 0.60
ALOGPS: 0.75 
ACD/LogD (pH 5.5): 0.89 
ACD/LogD (pH 7.4): 0.72 
ACD/BCF (pH 5.5): 2.8 
ACD/BCF (pH 7.4): 1.89 
ACD/KOC (pH 5.5): 72.7 
ACD/KOC (pH 7.4): 48.95 
H bond acceptors: 4 
H bond donors: 0 
Freely Rotating Bonds: 9   
Index of Refraction: 1.516 
Molar Refractivity: 49.18 cm
Molar Volume: 162.6 cm3   
Surface Tension: 46.2 dyne/cm 
Density: 1.292 g/cm
Flash Point: 242.1°C 
Enthalpy of Vaporization: 55.84 kJ/mol 
Boiling Point: 317.1°C at 760 mmHg 
Vapour Pressure: 0.000394 mmHg at 25°C
The appearance of  Mercapto di-acetic acid, ethylene ester (123-81-9) is clear liquid.
The molecular structure of  Mercapto di-acetic acid, ethylene ester (123-81-9):

Glycol dimercaptoacetate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo oral 50mg/kg (50mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0546402,
rat LD50 oral 330mg/kg (330mg/kg)   International Tin Research Institute Publication. Vol. 538, Pg. 17, 1978.

Glycol dimercaptoacetate Consensus Reports

Reported in EPA TSCA Inventory.

Glycol dimercaptoacetate Safety Profile

Poison by ingestion. When heated to decomposition it emits toxic fumes of SOx. See also MERCAPTANS.
Hazard Codes:  XnHarmful,N Dangerous
Risk Statements:  22-36/37/38-51/53-36/38-20/21/22 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R36/38:Irritating to eyes and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements:  26-36-57-36/37/39-29 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S57:Use appropriate container to avoid environmental contamination. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S29:Do not empty into drains.
RIDADR:  2810
WGK Germany:  2
RTECS:  AI6600000
HazardClass:  6.1(b)
PackingGroup:  III
HS Code:  29309070

Glycol dimercaptoacetate Specification

1.Treatment of  Mercapto di-acetic acid, ethylene ester (123-81-9) in Wastewater :
Total removal:1.85  percent
Total biodegradation:0.09  percent
Total sludge adsorption:1.76  percent
Total to air:0.00  percent
(using 10000 hr Bio P,A,S)
2. Handling and Storage
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation. 
Storage: Store in a cool, dry place. Store in a tightly closed container. 
3.Fire Fighting Measures
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. 
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 

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