Name: Succimer
SKU: 304-55-2

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Basic Information

Molecular Structure:
CAS No.:	304-55-2
Name:	Succimer

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:	Xi
Risk Codes:	36/37/38
Safety:	24/25-26-36
PSA:	152.20000
LogP:	-0.24760

Synthetic route

: 53318-26-6
meso-2,3-bis(acetylthio)succinic acid

: 304-55-2
succimer

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 304-55-2
succimer

: 1461-22-9
tributyltin chloride

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With tin(II) chloride dihdyrate In water at 20℃; for 0.5h;	83%

...Expand

: 304-55-2
succimer

: 639-58-7
triphenyltin chloride

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

Conditions

Conditions	Yield
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.

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Consensus Reports

Specification