| Identification | More | [Name]
o-Anisidine | [CAS]
90-04-0 | [Synonyms]
1-AMINO-2-METHOXYBENZENE
2-AMINOANISOLE
2-AMINOPHENYL METHYL ETHER
2-ANISIDINE
2-METHOXYANILINE
A-ESTER VINYL SULPHONE
AKOS BBS-00003674
O-AMINOANISOLE
O-AMINOPHENOL METHYL ETHER
O-ANISIDINE
O-METHOXYANILINE
ORTHO ANISIDINE
2-Methoxy-1-aminobenzene
2-methoxy-benzenamin
2-Methoxybenzenamine
2-methoxy-Benzenamine
2-methoxyphenylamine
2-Methoxy-phenylamine
ai3-08584
amino-1methoxy-2benzene | [EINECS(EC#)]
201-963-1 | [Molecular Formula]
C7H9NO | [MDL Number]
MFCD00007688 | [Molecular Weight]
123.15 | [MOL File]
90-04-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Anisidine exists as ortho-, meta-, and paraisomers.
They have characteristic amine (fishy) odors. | [Melting point ]
3-6 °C(lit.)
| [Boiling point ]
225 °C(lit.)
| [density ]
1.092 g/mL at 25 °C(lit.)
| [vapor pressure ]
<0.1 at 25 °C (NIOSH, 1994) | [refractive index ]
n20/D 1.574(lit.)
| [Fp ]
210 °F
| [storage temp. ]
Refrigerator | [solubility ]
14g/l | [form ]
Powder/Solid | [pka]
4.52(at 25℃) | [color ]
Off-white | [PH]
7.3 (1g/l, H2O, 20℃) | [Stability:]
Stable. Incompatible with strong oxidizing agents, acid anhydrides, chloroformates, acids, some plastics, rubber. Air sensitive. | [Water Solubility ]
13 g/L (20 ºC) | [Sensitive ]
Light Sensitive | [Detection Methods]
GC,NMR | [Merck ]
14,667 | [BRN ]
386210 | [Henry's Law Constant]
1.25 at 25 °C (approximate - calculated from water solubility and vapor pressure) | [Dielectric constant]
5.2300000000000004 | [Exposure limits]
Potential occupational carcinogen. NIOSH REL: TWA 0.5 mg/m3, IDLH 50
mg/m3; OSHA PEL: TWA 0.5 mg/m3; ACGIH TLV: TWA 0.1 ppm (adopted). | [InChIKey]
VMPITZXILSNTON-UHFFFAOYSA-N | [LogP]
1.180 | [Uses]
Intermediate for azo dyes and for guaiacol.
| [CAS DataBase Reference]
90-04-0(CAS DataBase Reference) | [IARC]
2A (Vol. Sup 7, 73, 127) | [NIST Chemistry Reference]
Benzenamine, 2-methoxy-(90-04-0) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
90-04-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi | [Risk Statements ]
R45:May cause cancer.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R68:Possible risk of irreversible effects. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2431 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
BZ5410000
| [F ]
8 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29222200 | [Safety Profile]
Confirmed carcinogen.
Moderately toxic by ingestion. Mutation data
reported. When heated to decomposition it
emits toxic fumes of NOx. | [Hazardous Substances Data]
90-04-0(Hazardous Substances Data) | [Toxicity]
Acute oral LD50 for rats 2,000 mg/kg, wild birds 422 mg/kg, mice 1,400 mg/kg, rabbits 870
mg/kg (quoted, RTECS, 1985). | [IDLA]
50 mg/m3 |
| Hazard Information | Back Directory | [General Description]
Clear, yellowish to reddish or brown liquid with an amine (fishy) odor. | [Reactivity Profile]
O-ANISIDINE(90-04-0) is sensitive to heat. O-ANISIDINE(90-04-0) is also sensitive to exposure to light. This chemical is incompatible with strong oxidizers. O-ANISIDINE(90-04-0) is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. O-ANISIDINE(90-04-0) will attack some forms of plastics, rubber and coatings. . | [Air & Water Reactions]
This chemical darkens on exposure to air. Insoluble in water. | [Hazard]
Strong irritant. Toxic when absorbed
through the skin. Possible carcinogen.
| [Potential Exposure]
Anisidines are used in the manufacture
of azo dyes; pharmaceuticals; textile-processing chemicals
Incompatibilities: Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Attacks some coatings
and some forms of plastic and rubber. | [Fire Hazard]
This chemical is combustible. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR
if heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical
attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
| [Shipping]
UN2431 Anisidines, Hazard Class: 6.1; Labels:
6.1-Poisonous materials | [Description]
o-Anisidine was produced commercially in the United States
from the 1920s until late 1950s. By 2009, worldwide only six
industries manufactured o-anisidine, but none produced
hydrochloride salt. o-Anisidine was available from 44 suppliers,
including 20 US suppliers, and the hydrochloride salt was
available from eight suppliers, including five US suppliers. US
imports of o-anisidine and its hydrochloride salt are reported in
the category ‘o-anisidines, p-anisidines, and p-phenetidine,’ and
US exports are reported in the category ‘a(chǎn)nisidines, dianisidines,
phenetidines, and their salts.’ From 1989 to 2008,
imports ranged from a high of over 4.6 million kg in 1996 to
zero in 2007 and 2008, and exports ranged from zero to
262 000 kg. Reports filed under the US Environmental
Protection Agency’s (EPA) Toxic Substances Control Act
Inventory Up Rule indicated that United States production plus
imports of o-anisidine totaled 500 000 lb–1 million lb in 1986,
1990, and 2006; 1 million–10 million lb in 1990 and 1998;
and 10 000–500 000 lb in 2002. | [Chemical Properties]
Anisidine exists as ortho-, meta-, and paraisomers. They have characteristic amine (fishy) odors.
o-Anisidine (or o-methoxyaniline) is an aromatic amine with a methoxyl group ortho to the amino group of aniline. It is a colorless to yellowish, pink, or reddish liquid.o-Anisidine is soluble in water and mineral oils, and miscible with alcohol, benzene, acetone, and diethylether. o-Anisidine hydrochloride, a salt of o-anisidine, is a grayish crystalline solid or powder at room temperature and is soluble in water (NTP, 2011).
| [Waste Disposal]
Dissolve in combustible solvent
(alcohols, benzene, etc.) and spray solution into furnace
equipped with afterburner and scrubber, or burn spill
residue on sand and soda ash absorbent in a furnace. | [Physical properties]
Colorless, yellow to reddish liquid with an amine-like odor. Becomes brown on exposure to air. | [Definition]
ChEBI: O-anisidine is a substituted aniline that is aniline in which the hydrogen ortho to the amino group has been replaced by a methoxy group. It is used as a chemical intermediate in the synthesis of azo pigments and dyes. It has a role as a reagent and a genotoxin. It is a monomethoxybenzene, a substituted aniline and a primary amino compound. | [Synthesis Reference(s)]
Tetrahedron Letters, 24, p. 4733, 1983 DOI: 10.1016/S0040-4039(00)86242-5 | [Health Hazard]
o-Anisidine was carcinogenic in
experimental animals. | [Carcinogenicity]
o-Anisidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity in experimental animals. | [Environmental Fate]
Biological. o-Anisidine should be biodegradable according to OECD guidelines (Brown and
Labouerer (1983).
Chemical/Physical. At influent concentrations (pH 3.0) of 10, 1.0, 0.1, and 0.01 mg/L, the GAC
adsorption capacities were 52, 20, 7.8, and 3.0 mg/g, respectively. At pHs 7 and 9, the GAC
adsorption capacities were 110, 50, 23, and 10 mg/g at influent concentrations of 10, 1.0, 0.1, and
0.01 mg/L, respectively (Dobbs and Cohen, 1980). | [Purification Methods]
It is separated from the m-and p-isomers by steam distillation. It is also separated from its usual synthetic precursor o-nitroanisole by dissolving it in dilute HCl (pH <2.0) extracting the nitro impurity with Et2O, adjusting the pH to ~8.0 with NaOH, extracting the amine into Et2O or steam distilling. Extract the distillate with Et2O, dry the extract (Na2SO4), filter, evaporate and fractionate the residual oil. Protect the almost colourless oil from light which turns it yellow in color. [Biggs & Robinson J Chem Soc 3881961, Nodzu et al. Yakugaku Zasshi (J Pharm Soc Japan) 71 713, 715 1951, Beilstein 13 IV 806.] | [Toxicity evaluation]
It is primarily metabolized by cytochrome P450 isozymes, and
it forms two o-anisidine–DNA adducts with DNA. It causes
DNA damage by a metabolite in the presence of metals such
as Cu(II). It can also cause Cu(II)-mediated oxidative DNA
damage. |
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