Acridine

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]
179.4 kJ/mol[1]
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.

  1. ^ a b c d e f g h i Lide DR, ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  2. ^ a b c "MSDS of Acridine". www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-22.
  3. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 211, 214. doi:10.1039/9781849733069-FP001. 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).