o-アニシジン 化学特性,用途語,生産方法
外観
無色～暗赤褐色, 澄明の液体
溶解性
水に不溶, アルコール, エーテルに易溶。エタノールに極めて溶けやすく、水にほとんど溶けない。
用途
着色用染料
用途
ファーストレッドBBベース、染料の中間物
用途
有機合成原料(染料)。
使用上の注意
不活性ガス封入
説明
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 ‘anisidines, 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.
化学的特性
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).
物理的性質
Colorless, yellow to reddish liquid with an amine-like odor. Becomes brown on exposure to air.
使用
Similar to other aromatic amines, o-anisidine may cause methemglobinemia and cancer in humans. It is used mainly as an intermediate for the production of azo dyes and pigments. Other industrial uses of o-anisidine include synthesis of other dyes and pharmaceuticals, as a corrosion inhibitor for steel, and as an antioxidant for polymercaptan resins (IARC, 1999; HSDB, 2012).
Intermediate for azo dyes and for guaiacol.
一般的な説明
Clear, yellowish to reddish or brown liquid with an amine (fishy) odor.
空気と水の反応
o-Anisidine darkens on exposure to air. Insoluble in water.
反応プロフィール
o-Anisidine is sensitive to heat. o-Anisidine is also sensitive to exposure to light. o-Anisidine is incompatible with strong oxidizers. o-Anisidine is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. o-Anisidine will attack some forms of plastics, rubber and coatings. .
危険性
Strong irritant. Toxic when absorbed
through the skin. Possible carcinogen.
健康ハザード
o-Anisidine was carcinogenic in
experimental animals.
火災危険
o-Anisidine is combustible.
安全性プロファイル
Confirmed carcinogen.
Moderately toxic by ingestion. Mutation data
reported. When heated to decomposition it
emits toxic fumes of NOx.
職業ばく露
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.
発がん性
o-Anisidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity in experimental animals.
環境運命予測
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).
輸送方法
UN2431 Anisidines, Hazard Class: 6.1; Labels:
6.1-Poisonous materials
純化方法
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.]
廃棄物の処理
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.
o-アニシジン 上流と下流の製品情報
原材料
準備製品
2-メトキシベンゾニトリル
7-ブロモ-N-(2-メトキシフェニル)-3-ホスホノオキシ-2-ナフタレンカルボアミド
Benzoic acid, 2-[[1-amino-7-[[4-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sulfo-2-naphthalenyl]azo]-2-methoxyphenyl]azo]-8-hydroxy-3,6-disulfo-2-naphthalenyl]azo]-5-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sul
3-(2-メトキシフェニル)-5-メトキシ-2-オキソ-2,3-ジヒドロ-1,3,4-オキサジアゾール
o-アセトアニシジド
3,8-ジメチル-1,10-フェナントロリン
2-メトキシ-4-ニトロアニリン
3-ヒドロキシ-2'-メトキシ-2-ナフトアニリド
4-アミノ-3-メトキシフェニルボロン酸, ピナコールエステル
1-(2-メトキシフェニル)ピペラジン臭化水素酸塩
N-(2-メトキシ-4-ニトロフェニル)アセトアミド
イソシアン酸 2-メトキシフェニル
5-[(ジエチルアミノ)スルホニル]-2-メトキシベンゼンジアゾニウム
Reactive Yellow KE-4RN
グアイアコール
2-フルオロアニソール
3,4-DIHYDRO-8-HYDROXY-4-OXOQUINOLINE-3-CARBOXYLIC ACID
ファストレッドBソルト
2-メトキシ-5-ニトロベンゼンジアゾニウム
シリアスイエローGC
2-メトキシベンゼンチオール
4-[[2-メトキシ-4-[(4-ニトロフェニル)アゾ]フェニル]アゾ]フェノール
N-アセトアセチル-o-トルイジン
5-クロロ-2-メトキシアニリン
N-(2-メトキシ-4-アミノフェニル)アセトアミド
N-(5-クロロ-2-メトキシフェニル)-3-ヒドロキシ-2-ナフトアミド
4-HYDROXY-8-METHOXYQUINOLINE-3-CARBOXYLIC ACID
o-アセトアセトアニシジド
キサンツレン酸
3,3'-[カルボニルビス[イミノ(3-メトキシ-4,1-フェニレン)アゾ]]ビス(安息香酸)二ナトリウム
バニリン
ファスト レッド ITR
5-ブロモ-8-メトキシ-2-メチルキノリン
1-(2-メトキシフェニル)ピペラジン
4-ヒドロキシ-8-メトキシキノリン-3-カルボン酸エチル