Rhodamine B

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Rhodamine B
Names
Preferred IUPAC name
9-(2-Carboxyphenyl)-6-(diethylamino)-N,N-diethyl-3H-xanthen-3-iminium chloride
Other names
Rhodamine 610, C.I. Pigment Violet 1, Basic Violet 10, C.I. 45170
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.001.259 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C28H30N2O3.ClH/c1-5-29(6-2)19-13-15-23-25(17-19)33-26-18-20(30(7-3)8-4)14-16-24(26)27(23)21-11-9-10-12-22(21)28(31)32;/h9-18H,5-8H2,1-4H3;1H checkY
    Key: PYWVYCXTNDRMGF-UHFFFAOYSA-N checkY
  • CCN(CC)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](CC)CC)C=C3O2)C4=CC=CC=C4C(=O)O.[Cl-]
Properties
C28H31ClN2O3
Molar mass 479.02
Appearance red to violet powder
Melting point 210 to 211 °C (410 to 412 °F; 483 to 484 K) (Decomposes)
8 to 15 g/L (20 °C)[1][nt 1]
Hazards
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rhodamine B

tracer dye within water to determine the rate and direction of flow and transport. Rhodamine dyes fluoresce and can thus be detected easily and inexpensively with fluorometers
.

Rhodamine B is used in biology as a

acid-fast organisms, notably Mycobacterium. Rhodamine dyes are also used extensively in biotechnology applications such as fluorescence microscopy, flow cytometry, fluorescence correlation spectroscopy and ELISA.[citation needed
]

Other uses

Rhodamine B solution in water

Rhodamine B is often mixed with herbicides to show where they have been used.[2]

It is also being tested for use as a

teeth.[3] Rhodamine B is an important hydrophilic xanthene dye well known for its stability and is widely used in the textile industry, leather, paper printing, paint, coloured glass and plastic industries.[4]

Rhodamine B (BV10) is mixed with quinacridone magenta (PR122) to make the bright pink watercolor known as Opera Rose.[5]

Properties

A is the "open" form and B is the "closed" form
Rhodamine B closed form (A) and open form (B)

Rhodamine B can exist in equilibrium between two forms: an "open"/fluorescent form and a "closed"/nonfluorescent spirolactone form. The "open" form dominates in acidic condition while the "closed" form is colorless in basic condition.[6]

The fluorescence intensity of rhodamine B will decrease as temperature increases.[7]

The solubility of rhodamine B in water varies by manufacturer, and has been reported as 8 g/L and ~15 g/L,[1] while solubility in alcohol (presumably ethanol) has been reported as 15 g/L.[nt 1] Chlorinated tap water decomposes rhodamine B. Rhodamine B solutions adsorb to plastics and should be kept in glass.[8] Rhodamine B is tunable around 610 nm when used as a laser dye.[9] Its luminescence quantum yield is 0.65 in basic ethanol,[10] 0.49 in ethanol,[11] 1.0,[12] and 0.68 in 94% ethanol.[13] The fluorescence yield is temperature dependent;[14] the compound is fluxional in that its excitability is in thermal equilibrium at room temperature.[15]


Safety and health

In California, rhodamine B is suspected to be carcinogenic and thus products containing it must contain a warning on its label.

economically motivated adulteration, where it has been illegally used to impart a red color to chili powder, have come to the attention of food safety regulators.[17]

See also

References

  1. ^ a b "Safety data sheet" (PDF). Roth. 2013.
  2. doi:10.1080/03601239709373123
    .
  3. PMID 20027214
    .
  4. S2CID 252647552
    .
  5. ^ MacEvoy B. "Handprint: color making attributes". www.handprint.com.
  6. PMID 22180914
    .
  7. PMID 25844025
    .
  8. ISBN 90-5809-355-7
    .
  9. ^ Prahl S. "Rhodamine B". OMLC.
  10. doi:10.1016/0022-2313(82)90045-X
    .
  11. doi:10.1021/j100334a023
    .
  12. doi:10.1063/1.1725672
    .
  13. doi:10.1016/0047-2670(82)87023-8
    .
  14. doi:10.1021/j100451a030
    .
  15. PMID 31040423
    .(subscription required)
  16. ^ "Naval Jelly MSDS with Rhodamine B" (PDF). Locite Corporation. 20 October 1998. Archived from the original (PDF) on 2010-04-15.
  17. doi:10.1039/c5ay00028a
    . Retrieved 1 February 2018.

Notes

  1. ^ a b Ellis RC (November 16, 2015). "Reagent and Dye Solubility Chart". IHCWorld. Retrieved 9 February 2020. This is to be used as a guide only as solubility data varies between manufacturers for the same product, especially for dyes. Note that most sources simply indicate that the compound is water soluble without providing a g/L value.
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