3-ethyl-2-{[(4Z)-1-ethyl-1,4-dihydroquinolin-4-ylidene]methyl}-1,3-benzothiazol-3-ium iodide

• ChemBase ID: 156576
• Molecular Formular: C21H21IN2S
• Molecular Mass: 460.37431
• Monoisotopic Mass: 460.04701768
• SMILES: CC[n+]1c2ccccc2sc1/C=c\1/ccn(c2c1cccc2)CC.[I-]
• Canonical SMILES: CCn1cc/c(=C/c2sc3c([n+]2CC)cccc3)/c2c1cccc2.[I-]
• InChI: InChI=1S/C21H21N2S.HI/c1-3-22-14-13-16(17-9-5-6-10-18(17)22)15-21-23(4-2)19-11-7-8-12-20(19)24-21;/h5-15H,3-4H2,1-2H3;1H/q+1;/p-1
• InChIKey: OVIKCIXFYVKSDD-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-2-{[(4Z)-1-ethyl-1,4-dihydroquinolin-4-ylidene]methyl}-1,3-benzothiazol-3-ium iodide
• IUPAC Traditional name: 3-ethyl-2-{[(4Z)-1-ethylquinolin-4-ylidene]methyl}-1,3-benzothiazol-3-ium iodide
• Synonyms: 1,3′-Diethyl-4,2′-quinolylthiacyanine iodide

Database IDs

• CAS Number: 15941-82-9
• EC Number: 240-075-9
• MDL Number: MFCD00800282
• Beilstein Number: 3817591
• PubChem SID: 162250713; 24862889
• PubChem CID: 6440951

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.94945437
• LogD (pH = 7.4): 0.9494875
• Log P: 0.9494879
• Molar Refractivity: 114.5133 cm^3
• Polarizability: 40.28965 Å^3
• Polar Surface Area: 7.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble
• Melting Point: 272-274 °C(lit.)
• Fluorescence: λex 502 nm; λem 545 nm in TE buffer pH 8.0 (with DNA)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPCE)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C21H21IN2S

DETAILS

Sigma Aldrich - 36811

Other Notes
A "thiazole orange" analogue for nucleic acid staining. Application in the flow cytometric evaluation of reticulocytes1