(+-)-Mercaptosuccinic acid (HCID 6268)

Overview

Thiomalic acid is a C4-dicarboxylic acid. It is functionally related to a succinic acid. It is a conjugate acid of a thiomalate(1-).

Names & identifiers

Preferred name: (+-)-Mercaptosuccinic acid
IUPAC: 2-sulfanylbutanedioic acid
English name: Mercaptosuccinic acid
Molecular formula: C4H6O4S
Molecular weight: 150.15

Names & synonyms

Mercaptosuccinic acidThiomalic acid70-49-52-Mercaptosuccinic acid2-Thiomalic acidMonomercaptosuccinic acidMercaptosuccinateNSC-730294239W5L4HCHEBI:38705DTXSID20861615(+-)-mercaptosuccinic acid

Show more names

mercapto-Butanedioicacidusafm-2USAF M-2hiomalicaciusafek-p-6297USAF ek-p-62972-thiomalicacid

RefChem:483750DTXCID50810515200-736-4211-423-72-sulfanylbutanedioic acidButanedioic acid, mercapto-DL-Mercaptosuccinic acidMalic acid, 2-thio-

Database identifiers

CAS: 70-49-5
PubChem CID: 6268
DTXSID: DTXSID20861615
ChEMBL: CHEMBL4303414
ChEBI: CHEBI:38705
UNII: 94239W5L4H
EC Number: 200-736-4
Nikkaji: J4.877A

Properties

Computed structural properties

XLogP: -0.4
Topological polar surface area: 75.6 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 3
Heavy atoms: 9
Formal charge: 0
Complexity: 133

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Sulfur Compounds

Physical DescriptionWhite solid with a sulfudic odor; [Merck Index] Light brown solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point: 155 · 155-157 °C(lit.)
Boiling point: 241.69 °C · 241.69°C (rough estimate)
Density: 1.352 · 1.352 (estimate)
refractive index: 1.55 · 1.5500 (estimate)
storage temp.: 30 °C · Store below +30°C.
solubility: 500 g/l · 500g/l
form: Crystalline Powder
pka: 4.68 · pKa 4.68±0.04(H2O t = 20.0±0.05 I = 0.15) (Uncertain)
color: White to almost white
Water Solubility: 150 g/L · 150 g/L (20 ºC)
Merck: 14 · 14,9343
BRN: 1099858 · 1099858
InChI: 1S/C4H6O4S/c5-3(6)1-2(9)4(7)8/h2,9H,1H2,(H,5,6)(H,7,8)
InChIKey: NJRXVEJTAYWCQJ-UHFFFAOYSA-N
SMILES: OC(=O)CC(S)C(O)=O
CAS DataBase Reference: 70 · 70-49-5(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 94239 W5L4H · 94239W5L4H
NIST Chemistry Reference: 2 · 2-Sulfanylsuccinic acid(70-49-5)
EPA Substance Registry System: Butanedioic acid, mercapto- (70-49-5)
UNSPSC Code: 12352106 · 12352106
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xn,C
Risk Statements: 22 · 22-36/37/38-34-20/21/22
Safety Statements: 26 · 26-36-36/37/39-45-27
RIDADR: 1759 · 1759
WGK Germany: 3 · 3
RTECS: 8225000 · WM8225000
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29309070 · 29309070
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 4.5% (6 of 132) of reports.

Warning

H302 (92.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 132 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Butanedioic acid, mercapto-

Mercaptosuccinic acid: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryIntraperitoneal LD50 (mouse) = 200 mg/kg; [RTECS] A skin and strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesAcute Tox. 4 (92.4%)

Safety data

wgk: 3
tsca: TSCA listed
rtecs: WM8225000
ridadr: 1759
hs_code: 29309070
risk_code: 22-36/37/38-34-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn,C
safety_code: 26-36-36/37/39-45-27
hazard_class: 8
Storage Class: 11 - Combustible Solids
packing_group: III
target organs: Respiratory system
Hazard statements: H302-H315-H319-H335
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P270-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationButanedioic acid, 2-mercapto-: ACTIVE

Applications · 4 items

UsesAntirheumatic.

UsesMercaptosuccinic acid is used in the preparation of mercaptosuccinic acid diethyl ester by reaction with ethanol. It is also used as a brightening agent in metal plating. Further, it serves as an intermediate for the synthesis of corrosion inhibitors, soil fumigants, active pharmaceutical ingredients and electroplating agents.

UsesMercaptosuccinic acid has been used as a dopant for the synthesis of carbon nanodots from citric acid. It can be used as a capping and reducing agent to synthesize monolayer-capped gold nanoparticles.

General DescriptionMercaptosuccinic acid(MSA) is a chiral multifunctional intermediate material used as a stabilizing and capping agent in the synthesis of biologically active sulfurs.

Upstream & downstream products

Upstream raw materials

Maleic acid Thioacetic acid

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Additional notes

DefinitionChEBI: Thiomalic acid is a C4-dicarboxylic acid. It is functionally related to a succinic acid. It is a conjugate acid of a thiomalate(1-).