Acridine

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Acridine
Acridine chemical structure
Names
Preferred IUPAC name
Acridine[3]
Other names
Dibenzo[b,e]pyridine[1]
2,3-Benzoquinoline[2]
Identifiers
3D model (
JSmol
)
120200
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.005.429 Edit this at Wikidata
EC Number
  • 205-971-6
143403
RTECS number
  • AR7175000
UNII
UN number 2713
  • InChI=1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H checkY
    Key: DZBUGLKDJFMEHC-UHFFFAOYSA-N checkY
  • InChI=1/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
    Key: DZBUGLKDJFMEHC-UHFFFAOYAF
  • n1c3c(cc2c1cccc2)cccc3
  • c1ccc2c(c1)cc3ccccc3n2
Properties
C13H9N
Molar mass 179.222 g·mol−1
Appearance White powder
Odor Irritating
Density 1.005 g/cm3 (20 °C)[1]
Melting point 106–110 °C (223–230 °F; 379–383 K)
at
standard pressure[1]
Boiling point 344.86 °C (652.75 °F; 618.01 K)
at
standard pressure[1]
46.5 mg/L[1]
Solubility Soluble in CCl4, alcohols, (C2H5)2O, C6H6[1]
log P 3.4[1]
Vapor pressure 0.34 kPa (150 °C)
2.39 kPa (200 °C)
11.13 kPa (250 °C)[4]
Acidity (pKa) 5.58 (20 °C)[1]
UV-vis (λmax) 392 nm[5]
−123.3×10−6 cm3/mol
Thermochemistry
205.07 J/mol·K[4]
208.03 J/mol·K[4]
Std enthalpy of
formation
(ΔfH⦵298)
 179.4 kJ/mol[1]
Std enthalpy of
combustion
(ΔcH⦵298)
 6581.3 kJ/mol[4]
Hazards
GHS labelling:
GHS07: Exclamation mark[5]
Danger
H302, H312, H315, H319, H332, H335[5]
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Lethal dose or concentration (LD, LC):
500 mg/kg (mice, oral)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.2 mg/m3 (benzene-soluble fraction)[6]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecules pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.

Isolation and syntheses

precipitates acridine bichromate. The bichromate is decomposed using ammonia
.

Acridine and its derivatives can be prepared by many synthetic processes. In the

meso
carbon atom are generated.

The Bernthsen acridine synthesis
The Bernthsen acridine synthesis

Other older methods for the

Lehmstedt-Tanasescu reaction
.

In

enzymology, an acridone synthase (EC 2.3.1.159) is an enzyme that catalyzes the chemical reaction

3 malonyl-CoA + N-methylanthraniloyl-CoA ⇌ 4 CoA + 1,3-dihydroxy-N-methylacridone + 3 CO2

Thus, the two

substrates of this enzyme are malonyl-CoA and N-methylanthraniloyl-CoA, whereas its three products are CoA, 1,3-dihydroxy-N-methylacridone, and CO2.[9]

Reactions

Acridine displays the reactions expected of an unsaturated N-heterocycle. It undergoes N-alkylation with

alkyl iodides to form alkyl acridinium iodides, which are readily transformed by the action of alkaline potassium ferricyanide to N-alkyl acridones
.

Basicity

Acridine and its homologues are weakly basic. Acridine is a photobase which has a ground state

pKa of 5.1, similar to that of pyridine, and an excited state pKa of 10.6.[10] It also shares properties with quinoline
.

Reduction and oxidation

Acridines can be reduced to the 9,10-dihydroacridines, sometimes called leucoacridines. Reaction with

oxidized by peroxymonosulfuric acid to the acridine amine oxide. The carbon 9-position of acridine is activated for addition reactions.[11]

Applications

Several

stain
useful for cell cycle determination.

Dyes

At one time acridine dyes were commercially significant, but they are now uncommon because they are not lightfast. Acridine dyes are prepared by condensation of 1,3-diaminobenzene derivatives. Illustrative is the reaction of 2,4-diaminotoluene with acetaldehyde:[13]

Synthesis of C.I. Basic Yellow 9, an acridine dye.

9-Phenylacridine is the parent base of chrysaniline or 3,6-diamino-9-phenylacridine, which is the chief constituent of the dyestuff phosphine (not to be confused with

rosaniline. Chrysaniline forms red-coloured salts, which dye silk and wool
in a fine yellow; and the solutions of the salts are characterized by their fine yellowish-green fluorescence. Chrysaniline was synthesized by O. Fischer and G. Koerner by condensing o-nitrobenzaldehyde with aniline, the resulting o-nitro-p-diaminotriphenylmethane being reduced to the corresponding o-amino compound, which on oxidation yields chrysaniline.

Benzoflavin, an isomer of chrysaniline, is also a dyestuff, and has been prepared by K. Oehler from m-phenylenediamine and benzaldehyde. These substances condense to form tetraaminotriphenylmethane, which, on heating with acids, loses ammonia and yields 3,6-diamino-9,10-dihydrophenylacridine, from which benzoflavin is obtained by oxidation. It is a yellow powder, soluble in hot water.[8]

Molecular biology

Acridine is known to induce small insertions or deletions in nucleotide sequences, resulting in frameshift mutations.[14] This compound was useful to identify the triplet nature of the genetic codes.[14]

Structure

As established by

polymorphs. All feature very similar planar molecules with nearly identical bond lengths and bond distances.[15][16]

Safety

Acridine is a skin irritant. Its LD50 (rats, oral) is 2,000 mg/kg and 500 mg/kg (mice, oral).[2]

See also

  • Lucigenin, a chemiluminescent compound derived from acridine

References

  1. ^
    ISBN 978-1-4200-9084-0
    .
  2. ^ a b c d "MSDS of Acridine". www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-22.
  3. ISBN 978-0-85404-182-4
    .
  4. ^ a b c d Acridine in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-22)
  5. ^ a b c Sigma-Aldrich Co., Acridine. Retrieved on 2014-06-22.
  6. ^ NIOSH Pocket Guide to Chemical Hazards. "#0145". National Institute for Occupational Safety and Health (NIOSH).
  7. doi:10.1002/cber.18700030223
    .
  8. ^ a b c  One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm H, ed. (1911). "Acridine". Encyclopædia Britannica. Vol. 1 (11th ed.). Cambridge University Press. p. 155.
  9. doi:10.1016/S0031-9422(00)95155-0
    .
  10. ISBN 978-0387-31278-1
    . Chapter 7. page 260.
  11. doi:10.1002/14356007.a01_147
  12. PMID 12171548
    .
  13. ISBN 978-3527306732
    .
  14. ^
    ISBN 978-1-284-10449-3
    .
  15. S2CID 174807725
    .
  16. S2CID 198349955
    .

Literature

External links

Wikisource has original text related to this article:
  • Media related to Acridine at Wikimedia Commons
  • Synthesis of acridone in Organic Syntheses 19:6; Coll. Vol. 2:15 [1] from
    Goldberg reaction
    .
  • Synthesis of 9-aminoacridine in Organic Syntheses 22:5; Coll. Vol. 3:53. [2] from N-phenylanthranilic acid.
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