o-Anisidine

o-Anisidine
Names
	Preferred IUPAC name 2-Methoxyaniline
	Other names ortho-Anisidine; 2-Anisidine; ortho-Aminoanisole; o-Methoxyaniline; 2-Methoxy-1-aminobenzene; 2-Methoxyphenylamine
Identifiers
CAS Number	90-04-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82288;
ChEMBL	ChEMBL1612004 ;
ChemSpider	13860775 ;
ECHA InfoCard	100.001.785
EC Number	201-963-1;
KEGG	C19191 ;
PubChem CID	7000;
RTECS number	BZ5410000;
UNII	NUX042F201;
UN number	2431
CompTox Dashboard (EPA)	DTXSID5023877 ;
	InChI InChI=1S/C7H9NO/c1-9-7-5-3-2-4-6(7)8/h2-5H,8H2,1H3 Key: VMPITZXILSNTON-UHFFFAOYSA-N ; InChI=1/C7H9NO/c1-9-7-5-3-2-4-6(7)8/h2-5H,8H2,1H3;
	SMILES Nc1ccccc1OC;
Properties
Chemical formula	C7H9NO
Molar mass	123.155 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)
Solubility in water	1.5 g/100 ml
Solubility	soluble in ethanol, diethyl ether, acetone, benzene
Magnetic susceptibility (χ)	-80.44·10−6 cm3/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	potential occupational carcinogen
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331, H341, H350
Precautionary statements	P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 1 0
Flash point	118 °C (244 °F; 391 K) (open cup)
Autoignition; temperature	415 °C (779 °F; 688 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2000 mg/kg (rat, oral); 1400 mg/kg (mouse, oral); 870 mg/kg (rabbit, oral)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.5 mg/m3 [skin]
REL (Recommended)	: Ca TWA 0.5 mg/m3 [skin]
IDLH (Immediate danger)	50 mg/m3
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). verify (what is ?) Infobox references

o-Anisidine (2-anisidine) is an organic compound with the formula CH₃OC₆H₄NH₂. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

Production and use

It is prepared via methanolysis of 2-chloronitrobenzene:^[5]

NaOCH₃ + ClC₆H₄NO₂ → CH₃OC₆H₄NO₂ + NaCl

The resulting o-nitroanisole is reduced to o-anisidine.

o-Anisidine is used in the manufacture of dyes. It is nitrated to give 4-nitroanisidine. It is also a precursor to o-dianisidine.

One special use is as a heartwood indicator. An acid solution of o-anisidine is diazotized by adding a sodium nitrite solution. This mixture is applied to the wood and by reaction with polyphenols in the heartwood a reddish brown azo dye is formed.

Safety and environmental aspects

o-Anisidine is a dangerous pollutant from the production of dyes. It is listed as RCRA hazardous waste, with the code K181.^[6] The International Agency for Research on Cancer (IARC) has classified o-anisidine as a Group 2B, possible human carcinogen.^[7]

References

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 669. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4. 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'.
^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. p. C-98. ISBN 0-8493-0462-8.
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0034". National Institute for Occupational Safety and Health (NIOSH).
^ "o-Anisidine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
^ "Hazardous Waste". 2015-07-23.
^ "o-Anisidine".

External links

International Chemical Safety Card 0970
NIOSH Pocket Guide to Chemical Hazards. "#0034". National Institute for Occupational Safety and Health (NIOSH).

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 669. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4. 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, Florida: CRC Press. p. C-98. ISBN 0-8493-0462-8.

[NIOSH-3] NIOSH Pocket Guide to Chemical Hazards. "#0034". National Institute for Occupational Safety and Health (NIOSH).

[4] "o-Anisidine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Booth-5] Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.

[6] "Hazardous Waste". 2015-07-23.

[7] "o-Anisidine".

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