o-Anisidine

o-Anisidine
Names
	Preferred IUPAC name 2-Methoxyaniline[1]
	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[2]
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[3]
	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)[4]
	NIOSH (US health exposure limits):
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). 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.

Direct Blue 15 is an azo dye produced from o-anisidine

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, FL: CRC Press. p. C-98. ISBN 0-8493-0462-8.
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).

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[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, FL: 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".