{[7-(bromomethyl)-2,6-dimethyl-3,5-dioxo-3H,5H-[1,2]diazolo[1,2-a]pyrazol-1-yl]methyl}trimethylazanium bromide

• ChemBase ID: 92321
• Molecular Formular: C13H19Br2N3O2
• Molecular Mass: 409.11686
• Monoisotopic Mass: 406.98440086
• SMILES: Cc1c(n2c(c(c(=O)n2c1=O)C)CBr)C[N+](C)(C)C.[Br-]
• Canonical SMILES: BrCc1n2c(C[N+](C)(C)C)c(c(=O)n2c(=O)c1C)C.[Br-]
• InChI: InChI=1S/C13H19BrN3O2.BrH/c1-8-10(6-14)15-11(7-17(3,4)5)9(2)13(19)16(15)12(8)18;/h6-7H2,1-5H3;1H/q+1;/p-1
• InChIKey: FCRPMMVPBVOKQS-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: {[7-(bromomethyl)-2,6-dimethyl-3,5-dioxo-3H,5H-[1,2]diazolo[1,2-a]pyrazol-1-yl]methyl}trimethylazanium bromide
• IUPAC Traditional name: {[7-(bromomethyl)-2,6-dimethyl-3,5-dioxo-[1,2]diazolo[1,2-a]pyrazol-1-yl]methyl}trimethylazanium bromide
• Synonyms: (Trimethylammonio)monobromobimane; 5-(Bromomethyl)-N,N,N,2,6-pentamethyl-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3-methanaminium bromide; Brombimane q; Thiolye MQ; qBBr; Monobromo(trimethylammonio)bimane bromide; Bromobimane q; Thiolyte MQ; Bromotrimethylammoniumbimane Bromide; Bromotrimethylammoniumbimame bromide

Database IDs

• CAS Number: 71418-45-6
• MDL Number: MFCD00036953; MFCD01322926
• Beilstein Number: 4630658
• PubChem SID: 24886141; 162079019
• PubChem CID: 474473

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -3.3919451
• LogD (pH = 7.4): -3.3919451
• Log P: -3.3919451
• Molar Refractivity: 90.9681 cm^3
• Polarizability: 29.399416 Å^3
• Polar Surface Area: 40.62 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble5 mg/mL; Methanol; Water
• Apperance: Yellow Solid
• Melting Point: 222-228°C (dec.); 222-237°C
• Fluorescence: λex 380 nm; λem 475 nm in 0.1 M phosphate pH 7.5

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥90.0% (HPLC)
• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C13H19Br2N3O2

DETAILS

Apollo Scientific Ltd - OR8851T

A charged fluorescent sulfhydryl active reagent.

Sigma Aldrich - 71028

Biochem/physiol Actions
Monobromobimanes are essentially nonfluorescent until conjugated and readily react with low molecular weight thiols. Unlike common monobromobimanes, this carries a positive charge, thus permitting separation of conjugates by electrophoresis or cation-exchange chromatography
Other Notes
Reagent for labeling thiols in biol. materials1,2

Toronto Research Chemicals - B688500

A charged fluoresent sulfhydryl active reagent. Bromotrimethylammoniumbimane is a derivative of monobromobimane containing a positive charge which permits separation of its conjugates by electrophoresis or cation-exchange chromatography. The membrane per

REFERENCES

• Meth. Enzymol., 143, 76 (1987)
• Proc. Natl. Acad. Sci. USA, 82, 1658 (1987)
• J. Leukocyte Biol., 45, 177 (1987)
• Arch. Biochem. Biophys., 282, 309 (1987)
• Zhu, Q-S., et al.: J.B.C., 278, 3112 (2003)