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5-Bromo-4-chloro-3-indolyl phosphate

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BCIP
Skeletal formula of BCIP
Ball-and-stick model of the BCIP molecule
Names
Preferred IUPAC name 5-Bromo-4-chloro-1H-indol-3-yl dihydrogen phosphate
Other names BCIP
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H6BrClNO4P/c9-4-1-2-5-7(8(4)10)6(3-11-5)15-16(12,13)14/h1-3,11H,(H2,12,13,14)Key: QRXMUCSWCMTJGU-UHFFFAOYSA-N
  • InChI=1/C8H6BrClNO4P/c9-4-1-2-5-7(8(4)10)6(3-11-5)15-16(12,13)14/h1-3,11H,(H2,12,13,14)Key: QRXMUCSWCMTJGU-UHFFFAOYAN
SMILES
  • C1=CC(=C(C2=C1NC=C2OP(=O)(O)O)Cl)Br
Properties
Chemical formula C8H6BrClNO4P
Molar mass 326.47 g·mol
Appearance Colorless
Solubility in water soluble in water (sodium salt)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

5-Bromo-4-chloro-3-indolyl phosphate (BCIP, X-phosphate, XP) is an artificial chromogenic substrate used for the sensitive colorimetric detection of alkaline phosphatase activity. It is, for example, used in immunoblotting, in situ hybridization, and immunohistochemistry, often in combination with nitro blue tetrazolium chloride (NBT). 5-bromo-4-chloro-3-indoxyl is oxidized by atmospheric oxygen to form the blue dye 5,5′-dibromo-4,4′-dichloro-indigo. It is also oxidized by nitroblue tetrazolium (NBT), which forms an insoluble dark blue diformazan precipitate after reduction. Alkaline phosphatase is commonly conjugated to secondary antibodies.

References

  1. "5-Bromo-4-chloro-3-indolyl phosphate disodium salt". Millipore Sigma.
  2. Alkaline phosphatase hydrolyses BCIP to 5-bromo-4-chloro-3-indoxyl<JP Horwitz J. Med. Chem., 1966, 9 (3), pp 447–447 and inorganic phosphate
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