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304-55-2

Basic Information
CAS No.: 304-55-2
Name: Butanedioic acid,2,3-dimercapto-, (2R,3S)-rel-
Molecular Structure:
Molecular Structure of 304-55-2 (Butanedioic acid,2,3-dimercapto-, (2R,3S)-rel-)
Formula: C4H6O4S2
Molecular Weight: 182.21
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:
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%
304-55-2

succimer

818-08-6

di(n-butyl)tin oxide

[(meso-2,3-dimercaptosuccinate)bis(di-n-butyltin(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.;80%
304-55-2

succimer

67-64-1

acetone

2,2-dimethyl-[1,3]dithiolane-4,5-dicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 9h;78%
With hydrogenchloride In water at 0 - 20℃;60%
67-56-1

methanol

304-55-2

succimer

27887-85-0

meso-dimercaptosuccinic acid dimethylester

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 8h; Cooling with ice;77.6%
With sulfuric acid Heating;

ammonium perrhenate

304-55-2

succimer

ammonium syn-endo-oxobis(SCH(COOH)CH(COOH)S)rhenate(V)

Conditions
ConditionsYield
With acetylhydrazine; HCl In acetonitrile Re compd. and acetylhydrazine (molar ratio 1:1) stirred in MeCN at room temp. for 10 min; concd. HCl added; stirred for 25 min; dimercaptosuccinic acid (2 equiv.) added; stirred for 3 h; filtered; solid washed with MeCN; dried under vac.; elem. anal.;75%
304-55-2

succimer

98-72-6

nitarsone

2-(4-nitrophenyl)-1,3,2-dithiaarsolane-4,5-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: nitarsone With ammonium 2-sulfanylacetate In ethanol; water; acetone at 55℃; for 1h;
Stage #2: succimer In acetone for 0.5h;
71%

ammonium perrhenate

304-55-2

succimer

144-55-8

sodium hydrogencarbonate

Na5[ReO(meso-dimercaptosuccinic acid)2]

Conditions
ConditionsYield
With tin(II) chloride dihdyrate In water at 20℃; for 0.5h;70%

{(C6H5)2AsCH2CH2P(C6H5)2PdCl2}*2CHCl3

304-55-2

succimer

{(C6H5)2AsCH2CH2P(C6H5)2Pd(SCH(COOH)CH(COOH)S)}*0.5C2H5OH

Conditions
ConditionsYield
With NaOH In ethanol; water add. of aq. soln. of 0.38 mmol NaOH to soln. of 0.20 mmol acid in ethanol/water (5:1); after 10 min addn. of mixture to suspension of 0.17 mmol palladium complex in ethanol; after 2 h concg. soln.;; pptn.; elem. anal.;;69%

{(C6H5)2PCH2CH2P(C6H5)2PtCl2}*2CHCl3

304-55-2

succimer

{(C6H5)2PCH2CH2P(C6H5)2Pt(SCH(COOH)CH(COOH)S)}

Conditions
ConditionsYield
With NaOH In ethanol; water add. of aq. soln. of 0.32 mmol NaOH to soln. of 0.35 mmol acid in ethanol/water (3:1); after 10 min addn. of mixture to suspension of 0.29 mmol platinum phosphine chloride in ethanol; after 1.5 h filtration; concg. filtrate;; pptn.; elem. anal.;;68%
98-50-0

p-aminophenylarsonic acid

304-55-2

succimer

2-(4-aminophenyl)-1,3,2-dithiaarsolane-4,5-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: p-aminophenylarsonic acid With ammonium 2-sulfanylacetate In ethanol at 55℃; for 1h;
Stage #2: succimer In ethanol for 0.5h;
68%

{(C6H5)2PCH2CH2P(C6H5)2PdCl2}*2CHCl3

304-55-2

succimer

{(C6H5)2PCH2CH2P(C6H5)2Pd(SCH(COOH)CH(COOH)S)}*C2H5OH

Conditions
ConditionsYield
With NaOH In ethanol; water add. of aq. soln. of 0.5 mmol NaOH to soln. of 0.478 mmol acid in ethanol/water (5:1); after 10 min addn. of mixture to suspension of 0.29 mmol palladium phosphine chloride in ethanol; after 2 h concg. soln.;; pptn.; elem. anal.;;64%

{(C6H5)2AsCH2CH2P(C6H5)2PtCl2}*2CHCl3

304-55-2

succimer

{(C6H5)2AsCH2CH2P(C6H5)2Pt(SCH(COOH)CH(COOH)S)}*C2H5OH

Conditions
ConditionsYield
With NaOH In ethanol; water add. of aq. soln. of 0.16 mmol NaOH to soln. of 0.16 mmol acid in ethanol/water (3:1); after 10 min addn. of mixture to suspension of 0.15 mmol platinum complex in ethanol; after 2 h filtration; concg. filtrate;; pptn.; elem. anal.;;62.5%
14647-21-3

cis-[NiBr2(1,2-bis(diphenylphosphino)ethane)]

304-55-2

succimer

{(C6H5)2PCH2CH2P(C6H5)2Ni(SCH(COOH)CH(COOH)S)}*2H2O

Conditions
ConditionsYield
In ethanol addn. of Ni complex to acid in ethanol; stirring for 2 h; filtration;; dissolving residue in aq. NaOH (pH = 10); addn. of dilute H2SO4; pptn.; elem. anal.;;54.2%
304-55-2

succimer

6269-93-8

4-ethoxyphenylarsonic acid

2-(4-ethoxyphenyl)-1,3,2-dithiaarsolane-4,5-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: 4-ethoxyphenylarsonic acid With ammonium 2-sulfanylacetate In ethanol at 55℃; for 1h;
Stage #2: succimer In ethanol for 0.5h;
32.8%
136733-06-7

(E)-1-(4-(phenyldiazenyl)phenyl)-1H-pyrrole-2,5-dione

304-55-2

succimer

2,3-bis[(2,5-dioxo-1-{4-[(E)-2-phenyldiazen-1-yl]phenyl}pyrrolidin-3-yl)sulfanyl] butanedioic acid

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 4h;24.8%
50-00-0

formaldehyd

304-55-2

succimer

28152-58-1

(4S,5R)-[1,3]Dithiolane-4,5-dicarboxylic acid

Conditions
ConditionsYield
With hydrogen cation
67-56-1

methanol

304-55-2

succimer

106-96-7

propargyl bromide

(2R,3S)-2,3-Bis-prop-2-ynylsulfanyl-succinic acid dimethyl ester

Conditions
ConditionsYield
With potassium hydroxide Alkylation; Heating;
123-51-3

i-Amyl alcohol

304-55-2

succimer

monoisoamyl meso 2,3-dimercaptosuccinic acid

304-55-2

succimer

cadmium(II) nitrate

2Cd(2+)*(SCHCOO)2(4-)*2H2O = (SCHCO2)2Cd2*2H2O

Conditions
ConditionsYield
With sodium hydroxide In not given soln. with ratio Cd(NO3)2:org. compd.:NaOH 3:1:4; filtration, washing (aq. EtOH), drying (room temp.); elem. anal.;
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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.