3-sulfanylpropanoic acid

• ChemBase ID: 108129
• Molecular Formular: C3H6O2S
• Molecular Mass: 106.14354
• Monoisotopic Mass: 106.00885043
• SMILES: OC(=O)CCS
• Canonical SMILES: OC(=O)CCS
• InChI: InChI=1S/C3H6O2S/c4-3(5)1-2-6/h6H,1-2H2,(H,4,5)
• InChIKey: DKIDEFUBRARXTE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-sulfanylpropanoic acid
• IUPAC Traditional name: 3-mercaptopropionic acid
• Synonyms: 3-Thiopropionic Acid; 2-Mercaptoethanecarboxylic Acid; Mercaptopropionic Acid; β-Mercaptopropanoic Acid; β-Mercaptopropionic Acid; β-Thiopropionic Acid; NSC 437; NSC 45157; 3-Mercaptopropionic Acid; 3-Mercaptopropionic acid; 3-mercaptopropanoic acid; β-MERCAPTOPROPIONIC ACID; 3-巯基丙酸

Database IDs

• CAS Number: 107-96-0
• EC Number: 203-537-0
• MDL Number: MFCD00004897
• Beilstein Number: 773807
• PubChem SID: 162088817; 24897049; 24882883
• PubChem CID: 6514

CALCULATED PROPERTIES

• Acid pKa: 4.565065
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.5337776
• LogD (pH = 7.4): -2.3084743
• Log P: 0.44778836
• Molar Refractivity: 25.0739 cm^3
• Polarizability: 9.887079 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 15-18 °C(lit.); 17-19°C; 18°C
• Boiling Point: 110-111 °C/15 mmHg(lit.); 110-111°C/15mm
• Flash Point: 199.4 °F; 93 °C; 93°C(199°F)
• Auto Ignition Point: 662 °F
• Density: 1.218 g/ml; 1.218 g/mL at 25 °C(lit.); 1.220
• Refractive Index: 1.4920; n20/D 1.492(lit.); n20/D 1.493
• Vapor Pressure: 0.04 mmHg ( 20 °C)

Safety Information

• Storage Warning: Air Sensitive & Hygroscopic
• RTECS: UF5270000
• European Hazard Symbols: Toxic (T)
• UN Number: 2922; UN2922
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 20-25-35; 25-34; R:25
• Safety Statements: 23-26-36/37/39-45; 7-26-36/37/39-45; S:28-29-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H331-H314-H318; H301-H314
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P301 + P310-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2

Product Information

• Purity: ≥98.0% (HPLC); ≥99%; ≥99.0% (HPLC); 99%
• Grade: puriss.; purum
• abs.: absorption/270 nm cut-off
• Linear Formula: HSCH2CH2CO2H

DETAILS

Sigma Aldrich - 63768

Application
suitable for amino acid analysis by means of OPA
Other Notes
High-speed RP-HPLC/FC analysis of amino acids1

Sigma Aldrich - M5801

Application
This compound is used to produce hydrophilic SAMs. The resulting monolayers which are terminated with carboxylic acids can be further functionalized1 to introduce more complex end groups such as enzymes for biosensor applications.2
Packaging
5, 100, 500 g in glass bottle

REFERENCES

• For a brief review of the reagent, see: Synlett, 1368 (2002).
• In the presence of a free-radical initiator, acts as a chain transfer reagent in the telomerization of short oligomers for biotechnological applications: J. Polym. Sci. A, 37, 2977 (1999).
• Can behave as a sulfide ion equivalent, e.g. the Cu-catalyzed reaction with aryl iodides leads to the diaryl sulfide, with loss of acrylic acid (reverse Michael): Synthesis, 523 (1989):