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(アセチルアミノ)ベンゼン

(アセチルアミノ)ベンゼン 化学構造式
103-84-4
CAS番号.
103-84-4
化学名:
(アセチルアミノ)ベンゼン
别名:
(アセチルアミノ)ベンゼン;フェナルギン;N-アセチルベンゼンアミン;N-アセチルアニリン;N-(フェニル)アセトアミド;アンチフェブリン;フェナルジン;N-フェニルアセトアミド;アセトアニリド;フェナルゲン;アセチルアミノベンゼン;アセタニル;アセトアニリド (アセチルアニリン);アセトアニリド標準品
英語化学名:
Acetanilide
英語别名:
ACETANIL;usafek-3;NSC 7636;Phenalgin;USAF ek-3;ANTIFEBRIN;Phenalgene;Acetanilid;NSC 203231;ACETANILIDE
CBNumber:
CB9444812
化学式:
C8H9NO
分子量:
135.16
MOL File:
103-84-4.mol

(アセチルアミノ)ベンゼン 物理性質

融点 :
113-115 °C(lit.)
沸点 :
304 °C(lit.)
比重(密度) :
1,121 g/cm3
蒸気密度:
4.65 (vs air)
蒸気圧:
1 mm Hg ( 114 °C)
屈折率 :
1.5700 (estimate)
闪点 :
173 °C
貯蔵温度 :
Store below +30°C.
溶解性:
5g/l
外見 :
Powder
酸解離定数(Pka):
0.5(at 25℃)
色:
Off-white to beige to grayish-blue
PH:
5-7 (10g/l, H2O, 25℃)
水溶解度 :
5 g/L (25 ºC)
Merck :
14,50
BRN :
606468
安定性::
Stable. Combustible. Incompatible with strong oxidizing agents, caustics, alkalies.
CAS データベース:
103-84-4(CAS DataBase Reference)
NISTの化学物質情報:
Acetamide, N-phenyl-(103-84-4)
EPAの化学物質情報:
Acetanilide (103-84-4)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn
Rフレーズ  22-36/37/38
Sフレーズ  22-26-36
WGK Germany  1
RTECS 番号 AD7350000
自然発火温度 540 °C
TSCA  Yes
HSコード  29242995
有毒物質データの 103-84-4(Hazardous Substances Data)
毒性 LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger)
化審法 一般化学物質
絵表示(GHS)
注意喚起語 Warning
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
H335 呼吸器への刺激のおそれ 特定標的臓器毒性、単回暴露; 気道刺激性 3 警告
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P304+P340 吸入した場合:空気の新鮮な場所に移し、呼吸しやすい 姿勢で休息させること。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。
P405 施錠して保管すること。

(アセチルアミノ)ベンゼン 価格 もっと(36)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBQE-9001 アセトアニリド
Acetanilide
103-84-4 5g ¥3600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBQE-9001 アセトアニリド
Acetanilide
103-84-4 25g ¥5400 2021-03-23 購入
関東化学株式会社(KANTO) 01018-31 アセトアニリド >98.0%(T)
Acetanilide >98.0%(T)
103-84-4 25g ¥2000 2021-03-23 購入
関東化学株式会社(KANTO) 01018-01 アセトアニリド >98.0%(T)
Acetanilide >98.0%(T)
103-84-4 500g ¥4600 2021-03-23 購入
Sigma-Aldrich Japan 1003042 United States Pharmacopeia (USP) Reference Standard
Acetaminophen Related Compound D United States Pharmacopeia (USP) Reference Standard
103-84-4 50mg ¥232000 2021-03-23 購入

(アセチルアミノ)ベンゼン MSDS


Acetanilide

(アセチルアミノ)ベンゼン 化学特性,用途語,生産方法

外観

白色の結晶性粉末

溶解性

水に微溶 (1g/20mL, 水100℃)。エタノール, アセトン, エーテルに可溶。エタノール及びアセトンに溶けやすく、水に溶けにくい。

解説

N-phenylacetamide.C8H9NO(135.17).C6H5NHCOCH3.アニリンと氷酢酸,無水酢酸あるいは塩化アセチルとを反応させると容易に得られる.また,アニリンとケテンからも得られる.無色の板状結晶(水).融点113~115 ℃,沸点304~305 ℃.d1541.219.熱水,エタノール,エーテルなどに可溶.各種有機化合物の原料になる.LD50 800 mg/kg(ラット,経口).[CAS 103-84-4]
森北出版「化学辞典(第2版)

用途

医薬品原料、塗料原料

用途

各種有機化合物の原料、医薬品(解熱剤、頭痛薬)、染料、過酸化水素の安定剤。

用途

アニリン系化合物です。シク ロオキシゲナーゼ(COX)活性を阻害し、プ ロスタグランジン生合成阻害作用を示しま す。

用途

アニリン系化合物です。シク ロオキシゲナーゼ(COX)活性を阻害し、プ ロスタグランジン生合成阻害作用を示しま す。

化学的特性

Acetanilide orthorhombic plates or scales; or white, shining, crystalline solid or powder. Odorless

化学的特性

Acetanilide, also known as Nphenylacetamide, acetanil, or acetanilide is a white to gray solid with molecular formula CH3CONHC6H5. It is an odorless colorless, glossy, crystalline powder or flakes. Acetanilide was the first aniline derivative found to possess analgesic as well as antipyretic properties and was quickly introduced into medical practice (Weast, 1981; Gnanasambandan et al., 2014). Later, it was established that in the human body it is mostly metabolized to paracetamol, this compound being responsible for the analgesic and antipyretic properties of acetanilide (Bertolini et al., 2006; Gnanasambandan et al., 2014). In addition, it was discovered that it has unacceptable toxic effects, so that acetanilide is no longer used as a drug.
Acetanilide flakes
Acetanilide is mainly used as an intermediates in the synthesis of pharmaceuticals and dyes, as an additive for hydrogen peroxide and cellulose ester varnishes, and as a plasticizer in polymer industry as well as accelerator in the rubber industry.

来歴

The department of internal medicine at the University of Strassburg in the 1880s was noted for its investigations into intestinal worms. Adolf Kussmaul, the director, asked two young assistants, Arnold Cahn and Paul Hepp, to treat patients with naphthalene as it had been used elsewhere as an internal antiseptic. The young doctors were disappointed with the initial results, but Hepp persevered with the naphthalene treatment in a patient suffering from a variety of complaints besides worms. Surprisingly, the fever chart revealed a pronounced antipyretic effect from this treatment. This had not been observed before, but further investigation revealed that Hepp had wrongly been supplied by Kopp’s Pharmacy in Strassburg with acetanilide instead of naphthalene! Cahn and Hepp lost no time in publishing a report on their discovery of a new antipyretic.
For many years after its discovery in 1886, Acetanilide was used as an alternative to aspirin (i.e. acetyl salicylate) - an analgesic (painkiller) and antipyretic (fever reducing) drug to relieve e.g. headache, menstrual pain, and rheumatic pain. Under the name “Acetanilide” it formerly appeared in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that Acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately causing damage to the liver and kidneys. Thus, Acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen (i.e. paracetamol), which is a metabolite of Acetanilide and whose use Axelrod and Brodie suggested in the same study.

使用

Acetanilide is used as an intermediate in the synthesis of rubber accelerator, dyes and camphor. It is also used in the synthesis of penicillin and other pharmaceutical products. It is involved in the preparation of 4-acetamidobenzenesulfonyl chloride, which is an intermediate during the synthesis of sulfa drugs. Further, it is employed as a experimental photographic developer. In addition to this, it is used to stabilize cellulose ester varnishes.

使用

manufacture of medicinals and dyes; stabilizer for H2O2 solution; as addition to cellulose ester varnishes.

使用

Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and to stabilize cellulose ester varnishes. It is also used in the intermediation of rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis. Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs. It is also a precursor in the synthesis of penicillin and other pharmaceuticals. In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.
Acetanilide is used as a EOF (electroosmotic flow) marker in the studies of affinity capillary electrophoresis for drug–protein binding.
Acetanilide undergoes palladium-catalyzed cross-coupling reaction to form ortho-acylacetanilide.

定義

ChEBI: A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.

製造方法

Acetanilide is medicinally important as it is used as febrifuge (antifibrin).
Synthesis of Acetanilide from aniline
In a 100 ml round bottom flask fitted with a reflux condensor place 5ml of aniline and 10 ml of 1:1 acetic acid and acetic anhydride mixture (5ml acetic acid and 5 ml acetic anhydride). Heat the mixture gently under reflux for 15-20 minutes on oil bath and then pour the contents while still hot with stirring into a 200ml beaker containing 100ml ice cold water. Stir the mixture vigorously to hydrolyse the excess acetic anhydride. After all the acetanilide has precipitated, collct it on buchner funnel and wash with cold water. Recrystallise the crude product from boiling water. If the product is excessively coloured add a pinch of animal charcoal to hot water and filter hot through glass wool/ cotton plug. Pure colourless crystals of acetanilide melts at 114°C (5-5.5g).

世界保健機関(WHO)

Acetanilide, a para-aminophenol derivative with analgesic, antipyretic and weak antiinflammatory activity, was introduced into medicine in 1886. It subsequently proved to be excessively myelosuppressive and has been superseded by safer alternatives.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 4533, 1983 DOI: 10.1016/S0040-4039(00)85947-X

一般的な説明

White to gray solid.

空気と水の反応

Acetanilide is sensitive to prolonged exposure to air . Water insoluble.

反応プロフィール

Acetanilide is an amide. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

火災危険

Acetanilide is combustible.

安全性プロファイル

A human poison by an unspecified route. Poison by ingestion and intravenous routes. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: hallucinations and dstorted perceptions, sleepiness, constipation, cyanosis, respiratory stimulation, hdney damage, me themoglobinemiacarboxyhemoglobinemia, and decreased body temperature. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,. Combustible when exposed to heat or flame. See also ANILINE.

職業ばく露

This amide compound is used in rubber industry as accelerator, in plastics industry as cellulose ester stabilizer, in pharmaceutical manufacture, stabilizer for hydrogen peroxide, azo dye manufacture

輸送方法

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

純化方法

Recrystallise acetanilide from water, aqueous EtOH, *benzene or toluene. [Beilstein 12 IV 373.]

不和合性

Dust may form explosive mixture with air. 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, alkyl nitrates, alkalis (liberate aniline), chloral hydrate, phenols, ferric salts

廃棄物の処理

Add to flammable solvents (alcohol or benzene) and incinerate. Oxides of nitrogenmay be scrubbed from combustion gases with alkaline solution

(アセチルアミノ)ベンゼン 上流と下流の製品情報

原材料

準備製品


(アセチルアミノ)ベンゼン 生産企業

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103-84-4((アセチルアミノ)ベンゼン)キーワード:


  • 103-84-4
  • ACETIC ACID ANILIDE
  • ACETYLAMINOBENZENE
  • ACETYLANILINE
  • ACETANIL
  • ACETANILIDE
  • AKOS BBS-00004291
  • 'LGC' (4002)
  • 'LGC' (2605)
  • 'LGC' (2404)
  • ANTIFEBRIN
  • PHENYL ACETYLAMINE
  • N-PHENYLACETAMIDE
  • Phenalgene
  • Phenalgin
  • USAF ek-3
  • usafek-3
  • N-phenylethanamide
  • Acetanilide (Acetylaniline)
  • Acetanilide purified by subliMation, >=99.9%
  • Acetanilide zone-refined, purified by subliMation, >=99.95%
  • Acetanilide melting point standard
  • Acetanilide (Acetaminophen RCD)
  • Acetanilide puriss. p.a., >=99.5% (CHN)
  • Acetanilide99%up
  • Acetaminophen impurity 5
  • Paracetamol EP Impurity D
  • Paracetamol Impurity 4(Paracetamol EP Impurity D)
  • Paracetamol EP Impurity D(Acetanilide)
  • zone-refined, purified by sublimation
  • Acetamidobenzene
  • (アセチルアミノ)ベンゼン
  • フェナルギン
  • N-アセチルベンゼンアミン
  • N-アセチルアニリン
  • N-(フェニル)アセトアミド
  • アンチフェブリン
  • フェナルジン
  • N-フェニルアセトアミド
  • アセトアニリド
  • フェナルゲン
  • アセチルアミノベンゼン
  • アセタニル
  • アセトアニリド (アセチルアニリン)
  • アセトアニリド標準品
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