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304-55-2

Basic Information
CAS No.: 304-55-2
Name: Butanedioic acid,2,3-dimercapto-, (2R,3S)-rel-
Article Data: 3
Cas Database
Molecular Structure:
Molecular Structure of 304-55-2 (Butanedioic acid,2,3-dimercapto-, (2R,3S)-rel-)
Formula: C4H6O4S2
Molecular Weight: 182.221
Synonyms: Butanedioicacid, 2,3-dimercapto-, (R*,S*)-;Succinic acid, 2,3-dimercapto-, meso- (8CI);Chemet;DIM-SA;DMSA;Ro 1-7977;meso-2,3-Dimercaptosuccinicacid;meso-Dimercaptosuccinic acid;
EINECS: 206-155-2
Density: 1.617 g/cm3
Melting Point: 196-198 °C (dec.)(lit.)
Boiling Point: 267.6 °C at 760 mmHg
Flash Point: 115.6 °C
Solubility: Soluble in water, and ethanol (25 mg/ml, results in colorless to light yellow, clear).
Appearance: white or off-white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-26-36
Transport Information: N/A
PSA: 152.20000
LogP: -0.24760
Synthetic route
53318-26-6

meso-2,3-bis(acetylthio)succinic acid

304-55-2

succimer

Conditions
ConditionsYield
With sodium hydroxide
With water; hydrazine hydrate at 0℃;
304-55-2

succimer

1066-45-1

trimethyltin(IV)chloride

[(meso-2,3-dimercaptosuccinate)tetrakis(trimethyltin(IV))]

Conditions
ConditionsYield
With sodium ethoxide In methanol; toluene N2, acid:ethoxide:Sn=1:4:1 molar ratio, acid and base stirred for 0.5 h,Sn compd. added, stirred at 40°C for 12 h; filtered, solvent removed (vac.), recrystd. (ethanol); elem. anal.;88%
304-55-2

succimer

2273-45-2

dimethyltin oxide

[(meso-2,3-dimercaptosuccinate)bis(dimethyltin(IV))]

Conditions
ConditionsYield
In methanol; toluene N2, stoich., refluxed in a Dean-Stark trap for 10 h; cooled to room temp., filtered, solvent removed (vac.); elem. anal.;88%
60-29-7

diethyl ether

304-55-2

succimer

2273-51-0

diphenyltin(IV) oxide

[(meso-2,3-dimercaptosuccinate)bis(diphenylaquatin(IV))]-diethyl ether-water (1/1/1)

Conditions
ConditionsYield
In methanol; toluene N2, stoich., refluxed in a Dean-Stark trap for 10 h; cooled to room temp., filtered, solvent removed (vac.), recrystd. (diethyl ether); elem. anal.;86%
67-56-1

methanol

304-55-2

succimer

1461-22-9

tributyltin chloride

[di(meso-2,3-dimercaptosuccinate)tris(di-n-butyltin(IV))di(n-butyl)(methanol)tin(IV)]

Conditions
ConditionsYield
With KOH In methanol; water High Pressure; N2, stoich., heated at 150°C for 3 d; cooled to room temp., crysts. filtered, washed (hexane); elem. anal., TGA;85%
With KOH In methanol; water High Pressure; mixt. of meso-2,3-dimercaptosuccinic acid (0.5 mmol), KOH (2 mmol), tri-n-butyltin chloride (2 mmol), CH3OH (10 ml) and H2O (5 ml) heated in Teflon-lined autoclave at 150°C for 3 d; cooled to room temp. for 24 h; crystals collected; washed with hexane; elem. anal.;85%
304-55-2

succimer

1461-22-9

tributyltin chloride

[(meso-2,3-dimercaptosuccinate)tetrakis(tri-n-butyltin(IV))]

Conditions
ConditionsYield
With sodium ethoxide In methanol; toluene N2, acid:ethoxide:Sn=1:4:1 molar ratio, acid and base stirred for 0.5 h,Sn compd. added, stirred at 40°C for 12 h; filtered, solvent removed (vac.); elem. anal.;85%
304-55-2

succimer

3151-41-5

tribenzyltin(IV) chloride

[(meso-2,3-dimercaptosuccinate)tetrakis(tribenzyltin(IV))]

Conditions
ConditionsYield
With sodium ethoxide In methanol; toluene N2, acid:ethoxide:Sn=1:4:1 molar ratio, acid and base stirred for 0.5 h,Sn compd. added, stirred at 40°C for 12 h; filtered, solvent removed (vac.); elem. anal.;85%
304-55-2

succimer

dibenzyltin oxide

943909-25-9

[(meso-2,3-dimercaptosuccinate)bis(dibenzyltin(IV))]

Conditions
ConditionsYield
In methanol; toluene N2, stoich., refluxed in a Dean-Stark trap for 10 h; cooled to room temp., filtered, solvent removed (vac.); elem. anal.;83%
304-55-2

succimer

ammonium pertechnetate

144-55-8

sodium hydrogencarbonate

Na5[99TcO(meso-dimercaptosuccinic acid)2]

Conditions
ConditionsYield
With tin(II) chloride dihdyrate In water at 20℃; for 0.5h;83%
304-55-2

succimer

639-58-7

triphenyltin chloride

[(meso-2,3-dimercaptosuccinate)tetrakis(triphenyltin)]

Conditions
ConditionsYield
With sodium ethoxide In methanol; toluene N2, acid:ethoxide:Sn=1:4:1 molar ratio, acid and base stirred for 0.5 h,Sn compd. added, stirred at 40°C for 12 h; filtered, solvent removed (vac.), recrystd. (CH2Cl2); elem. anal.;82%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The meso-2,3-Dimercaptosuccinic acid, with its CAS registry number 304-55-2, has the IUPAC name of 2,3-bis(sulfanyl)butanedioic acid. For being a kind of white crystalline powder, it is easily soluble in aqueous alkali, slightly soluble in carbinol while insoluble in water. Besides, it is stable chemically while incompatible with strong oxidizing agents. What's more, its product categories are including Organic acids; Analytical Chemistry; Ligands for Pharmaceutical Research; Radiopharmaceutical Chemistry (Chelating Reagents).

The physical properties of this chemical are as below: (1)ACD/LogP: 1.05; (2)# of Rule of 5 Violations: 0 ; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 152.2; (11)Index of Refraction: 1.617; (12)Molar Refractivity: 39.42 cm3; (13)Molar Volume: 112.663 cm3; (14)Polarizability: 15.627×10-24 cm3; (15)Surface Tension: 76.657 dyne/cm; (16)Density: 1.617 g/cm3; (17)Flash Point: 115.622 °C; (18)Enthalpy of Vaporization: 55.654 kJ/mol; (19)Boiling Point: 267.57 °C at 760 mmHg; (20)Vapour Pressure: 0.002 mmHg at 25°C; (21)Exact Mass: 181.97075; (22)MonoIsotopic Mass: 181.97075; (23)Topological Polar Surface Area: 76.6; (24)Heavy Atom Count: 10; (25)Complexity: 139.

When you are dealing with this kind of chemical, you should be cautious. This is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable protective clothing and then avoid contacting with skin and eyes. And if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Additionally, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C(C(C(=O)O)S)(C(=O)O)S
(2)InChI: InChI=1S/C4H6O4S2/c5-3(6)1(9)2(10)4(7)8/h1-2,9-10H,(H,5,6)(H,7,8)
(3)InChIKey: ACTRVOBWPAIOHC-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral > 5011mg/kg (5011mg/kg)   CRC Critical Reviews in Toxicology. Vol. 20, Pg. 83, 1989.
 
mouse LD50 subcutaneous 1725mg/kg (1725mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 131, Pg. 283, 1961.
 
rabbit LDLo intravenous 2700mg/kg (2700mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 131, Pg. 283, 1961.