Names | |||
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Preferred IUPAC name 2-Methoxyaniline [1] | |||
Other names ortho-Anisidine 2-Anisidine ortho-Aminoanisole o-Methoxyaniline 2-Methoxy-1-aminobenzene 2-Methoxyphenylamine | |||
Identifiers | |||
3D model (JSmol) | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.001.785 | ||
EC Number |
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KEGG | |||
PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 2431 | ||
CompTox Dashboard (EPA) | |||
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Properties [2] | |||
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) | ||
1.5 g/100 ml | |||
Solubility | soluble in ethanol, diethyl ether, acetone, benzene | ||
-80.44·10−6 cm3/mol | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | potential occupational carcinogen [3] | ||
GHS labelling: | |||
Danger | |||
H301, H311, H331, H341, H350 | |||
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) | ||
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). |
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.
It is prepared via methanolysis of 2-chloronitrobenzene: [5]
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.
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]
Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.
Chromium(III) chloride (also called chromic chloride) describes any of several chemical compounds with the formula CrCl3 · xH2O, where x can be 0, 5, and 6. The anhydrous compound with the formula CrCl3 is a violet solid. The most common form of the trichloride is the dark green hexahydrate, CrCl3 · 6 H2O. Chromium chlorides find use as catalysts and as precursors to dyes for wool.
2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.
Allyl alcohol (IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.
meta-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and o-cresol.
2-Chloroethanol is a chemical compound with the formula HOCH2CH2Cl and the simplest chlorohydrin. This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional groups.
Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.
1,2-Dichloroethene, commonly called 1,2-dichloroethylene or 1,2-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a highly flammable, colorless liquid with a sharp, harsh odor. It can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have few industrial applications, although they are fundamental given their simple stoichiometries.
Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.
1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an organic compound with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.
2-Tolidine (orthotolidine, o-tolidine; not to be confused with o-toluidine) is an organic compound with the chemical formula (C6H4(CH3)NH2)2. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as the hydrochloride, which is commercially available.
m-Anisidine is an organic compound with the formula CH3OC6H4NH2. A clear light yellow or amber color liquid, commercial samples can appear brown owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.
p-Anisidine (para-anisidine) is an organic compound with the formula CH3OC6H4NH2. A white solid, commercial samples can appear grey-brown owing to air oxidation. It is one of three isomers of anisidine, methoxy-containing anilines. It is prepared by reduction of 4-nitroanisole.
Terphenyls are a group of closely related aromatic hydrocarbons. Also known as diphenylbenzenes or triphenyls, they consist of a central benzene ring substituted with two phenyl groups. There are three substitution patterns: ortho-terphenyl, meta-terphenyl, and para-terphenyl. Commercial grade terphenyl is generally a mixture of the three isomers. This mixture is used in the production of polychlorinated terphenyls, which were formerly used as heat storage and transfer agents.
4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including common antioxidants found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.
ortho-Cresol, also called 2-methylphenol, or 2-hydroxytoluene, is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.
4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.
3-Nitrotoluene or meta-nitrotoluene is a yellow liquid. It is used in the manufacture of meta-toluidine. It is an intermediate in the production of various dyes.
2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.
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’.