6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide; trifluoroacetic acid

• ChemBase ID: 172485
• Molecular Formular: C12H16F3N3O5
• Molecular Mass: 339.2677496
• Monoisotopic Mass: 339.10420529
• SMILES: C1=CC(=O)N(C1=O)CCCCCC(=O)NN.C(F)(F)(F)C(=O)O
• Canonical SMILES: OC(=O)C(F)(F)F.NNC(=O)CCCCCN1C(=O)C=CC1=O
• InChI: InChI=1S/C10H15N3O3.C2HF3O2/c11-12-8(14)4-2-1-3-7-13-9(15)5-6-10(13)16;3-2(4,5)1(6)7/h5-6H,1-4,7,11H2,(H,12,14);(H,6,7)
• InChIKey: DRURMGRBAVYWCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide; trifluoroacetic acid
• IUPAC Traditional name: 6-(2,5-dioxopyrrol-1-yl)hexanehydrazide; trifluoroacetic acid
• Synonyms: 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic Acid Hydrazide 2,2,2-Trifluoroacetate; EMCH-TFA; 6-Maleimidocaproic Acid Hydrazide, Trifluoroacetic Acid

Database IDs

• CAS Number: 151038-94-7
• PubChem SID: 164228395
• PubChem CID: 23509306

CALCULATED PROPERTIES

• Acid pKa: 12.707881
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.6254041
• LogD (pH = 7.4): -0.6228848
• Log P: -0.6228506
• Molar Refractivity: 59.2954 cm^3
• Polarizability: 22.167364 Å^3
• Polar Surface Area: 92.5 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 104-105°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M136800

A sulfhydryl and carbonyl reactive heterobifunctional crosslinking reagent. Useful for preparing immunoconjugates of doxorubicin.Spacer Arm: 11.8 Angstroms

REFERENCES

• Trail, P.A., et al.: Science, 261, 212 (1993)