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o-Anisidine - Wikipedia

From Wikipedia, the free encyclopedia

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^Y

3D model (JSmol)

Interactive image

ChEBI

CHEBI:82288

ChEMBL

ChEMBL1612004^Y

ChemSpider

13860775^Y

ECHA InfoCard

100.001.785

EC Number

201-963-1

KEGG

C19191^Y

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^Y
Key: VMPITZXILSNTON-UHFFFAOYSA-N^Y
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)

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

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 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, FL: 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).

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