2,5-dioxopyrrolidin-1-yl 3-({3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropyl}disulfanyl)propanoate

• ChemBase ID: 107296
• Molecular Formular: C14H16N2O8S2
• Molecular Mass: 404.41544
• Monoisotopic Mass: 404.03480748
• SMILES: O=C(CCSSCCC(=O)ON1C(=O)CCC1=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCSSCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C14H16N2O8S2/c17-9-1-2-10(18)15(9)23-13(21)5-7-25-26-8-6-14(22)24-16-11(19)3-4-12(16)20/h1-8H2
• InChIKey: FXYPGCIGRDZWNR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-({3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropyl}disulfanyl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-({3-[(2,5-dioxopyrrolidin-1-yl)oxy]-3-oxopropyl}disulfanyl)propanoate
• Synonyms: DITHIOBIS(SUCCINIMIDYLPROPIONATE); Di(N-succinimidyl) 3,3′-dithiodipropionate; Dithiobis(succinimidyl propionate); Lomant’s reagent; 3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester); DTSP

Database IDs

• CAS Number: 57757-57-0
• EC Number: 260-931-5
• MDL Number: MFCD00042045
• Beilstein Number: 1518074
• PubChem SID: 24893777; 162094528
• PubChem CID: 93313

CALCULATED PROPERTIES

• Acid pKa: 17.407946
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.53222996
• LogD (pH = 7.4): -0.53222996
• Log P: -0.53222996
• Molar Refractivity: 89.7672 cm^3
• Polarizability: 35.692596 Å^3
• Polar Surface Area: 127.36 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble; chloroform: soluble50 mg/mL; DMF: soluble
• Apperance: powder
• Melting Point: 128-133 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C14H16N2O8S2

DETAILS

MP Biomedicals - 05203265

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D3669

Application
Homobifunctional cross-linking reagent containing a cleavable disulfide linkage. Typically coupled to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5).
Caution
Avoid use of reducing agents during coupling reactions.
Features and Benefits
The disulfide linkage is cleavable by mild reduction.

Sigma Aldrich - 43789

Other Notes
Cleavable cross-linking reagent 1,2,3