5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanehydrazide

• ChemBase ID: 134151
• Molecular Formular: C10H18N4O2S
• Molecular Mass: 258.34052
• Monoisotopic Mass: 258.11504684
• SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NN)NC(=O)N2
• Canonical SMILES: NNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C10H18N4O2S/c11-14-8(15)4-2-1-3-7-9-6(5-17-7)12-10(16)13-9/h6-7,9H,1-5,11H2,(H,14,15)(H2,12,13,16)/t6-,7-,9-/m0/s1
• InChIKey: KOZWHQPRAOJMBN-ZKWXMUAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanehydrazide
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanehydrazide
• Synonyms: (+)-Biotin hydrazide

Database IDs

• CAS Number: 66640-86-6
• MDL Number: MFCD00078532
• Beilstein Number: 28347
• PubChem SID: 162228428; 24848623; 24892012
• PubChem CID: 83872

CALCULATED PROPERTIES

• Acid pKa: 12.749984
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): -0.78654814
• LogD (pH = 7.4): -0.78402865
• Log P: -0.7839947
• Molar Refractivity: 66.3572 cm^3
• Polarizability: 25.801302 Å^3
• Polar Surface Area: 96.25 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≤20 mg/mL
• Apperance: powder
• Melting Point: 245-247 °C
• Optical Rotation: [α]20/D +68±3°, c = 0.5% in DMF

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (TLC); ≥98.0% (CHN)
• Empirical Formula (Hill Notation): C10H18N4O2S

DETAILS

Sigma Aldrich - B7639

Application
Reagent for labeling surface functional groups, biologically active molecules such as antibodies, lectins, sugars, nucleic acids or molecules with free carboxylic or keto groups. Typically used for coupling to glycoproteins through the carbohydrate by hydrazone formation.

Sigma Aldrich - 14403

Other Notes
The hydrazide functional group allows biotinylation of glycolipids and glycoproteins via the oligosaccharide moiety.; In affinity cytochemistry1; Biotinylation of DNA2; Immobilization of DNA3; For the synthesis of maleimidobiotins4