''o''-Anisidine

o-Anisidine
Skeletal formula of o-anisidine
Ball-and-stick model of the o-anisidine molecule
Names
Preferred IUPAC name
2-Methoxyaniline
Other names
o-Anisidine (no longer recommended[1])
2-Anisidine
ortho-Aminoanisole
o-Methoxyaniline
2-Methoxy-1-aminobenzene
2-Methoxyphenylamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.785
EC Number 201-963-1
KEGG
UN number 2431
Properties[2]
C7H9NO
Molar mass 123.16 g·mol−1
Appearance Yellow liquid, turns brown upon exposure to air
Density 1.0923 g/cm3
Melting point 6.2 °C (43.2 °F; 279.3 K)
Boiling point 224 °C (435 °F; 497 K)
1.5 g/100 ml
Solubility soluble in ethanol, diethyl ether, acetone, benzene
-80.44·10−6 cm3/mol
Hazards
Main hazards potential occupational carcinogen[3]
Toxic (T)
Carc. Cat. 2
Muta. Cat. 3
R-phrases (outdated) R45, R23/24/25, R68
S-phrases (outdated) S53, S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Flash point 118 °C (244 °F; 391 K) (open cup)
415 °C (779 °F; 688 K)
Lethal dose or concentration (LD, LC):
2000 mg/kg (rat, oral)
1400 mg/kg (mouse, oral)
870 mg/kg (rabbit, oral)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 0.5 mg/m3 [skin][3]
REL (Recommended)
  : Ca TWA 0.5 mg/m3 [skin][3]
IDLH (Immediate danger)
 50 mg/m3[3]
Related compounds
Related compounds
 m-Anisidine
p-Anisidine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

o-Anisidine (2-anisidine) is a yellow liquid with a melting point of −1 to 5 °C and a density of 1.09 g/cm3. The vapor pressure is 0.05 mbar at 20 °C but increases greatly with temperature. It has an aromatic smell and is well absorbed by inhalation, oral ingestion and skin contact. o-Anisidine is a very toxic agent that causes blood, enzyme and nerve damage with cyanosis and the danger of suffocation.[3] The agent is an experimental carcinogen and is strongly suspected to be a human carcinogen also. o-Anisidine has dangerous pollutant properties for water. Non-wastewaters from the production of dyes containing o-Anisidine are listed as RCRA hazardous waste, with the code K181.[5] o-Anisidine is used in the manufacture of dyes. Workers in the dye industry may be occupationally exposed to it. Acute (short-term) exposure to o-anisidine results in skin irritation in humans. Workers exposed to o-anisidine by inhalation for 6 months developed headaches, vertigo, and effects on the blood. Animal studies have reported effects on the blood from chronic (long-term) dermal exposure to o-anisidine. No information is available on the reproductive, developmental, or carcinogenic effects of o-anisidine in humans. Animal studies have reported tumors of the urinary bladder from oral exposure to o-anisidine. EPA has not classified o-anisidine for carcinogenicity. The International Agency for Research on Cancer (IARC) has classified o-anisidine as a Group 2B, possible human carcinogen.[6]

References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 669. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001. The names ‘toluidine’, ‘anisidine’, and ‘phenetidine’ for which o-, m-, and p- have been used to distinguish isomers, and ‘xylidine’ for which numerical locants, such as 2,3-, have been used, are no longer recommended, nor are the corresponding prefixes ‘toluidine’, ‘anisidino’, ‘phenetidine’, and ‘xylidino’.
  2. ↑ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-98. ISBN 0-8493-0462-8..
  3. 1 2 3 4 5 "NIOSH Pocket Guide to Chemical Hazards #0034". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ "o-Anisidine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  5. ↑ http://www.epa.gov/osw/hazard/wastetypes/wasteid/dyes/index.htm
  6. ↑ https://pubchem.ncbi.nlm.nih.gov/compound/o-anisidine#section=Top
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