ブロモベンゼン 化学特性,用途語,生産方法
外観
無色～わずかにうすい褐色, 澄明の液体
溶解性
水に難溶, エタノール, エーテルに可溶。エタノール、エーテル、ベンゼンに可溶。水に不溶。エタノールに溶け、水にほとんど溶けない。
解説
ブロモベンゼン，液体．融点－31 ℃，沸点155～156 ℃，43 ℃(2.4 kPa)．d1515"1.4991．nD15"1.5625．エタノール，エーテルに可溶．ベンゼン，石油系炭化水素などとまざる．臭化ベンゼンマグネシウムはグリニャール試薬として，各種のベンゼン誘導体の合成に使われる．そのほか溶剤に用いられる．高濃度では麻酔性があり，皮膚を刺激する．
森北出版「化学辞典（第2版）
用途
難燃剤、医薬 農薬 香料の中間体
用途
難燃剤、医薬、農薬、香料の中間体、染料、電動機油添加剤として用いられる。
製造
ベンゼンに鉄などの触媒とともに臭素を作用させると得られるブロモベンゼン．
化学的特性
Bromobenzene, also known as phenyl bromide and monobromobenzene, is a benzene halogen derivative generated by benzene being substituted by bromine in the presence of iron powder. The chemical reaction principle is the same as that of chlorination of benzene to produce chlorobenzene. The reaction between bromobenzene and metal magnesium can generate phenylmagnesium bromide, which is a Grignard reagent with important uses in organic synthesis.
物理的性質
Mobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is 4.6 ppm (Mateson, 1955). Insoluble in water, soluble in benzene, alcohol, ether, chlorobenzene and other organic solvents. It is irritating to the skin and anesthetic to the nerves. Its toxicity is stronger than chlorobenzene. Inhalation of its vapors can cause anemia and damage the liver.
使用
Bromobenzene is an additive to motor oils and used as a crystallizing solvent. It is used as an ingredient in the manufacture of phencyclidine, a recreational drug.
定義
ChEBI: Bromobenzene is the simplest member of the class of bromobenzenes, that is benzene in which a single hydrogen has been substituted by a bromine. A liquid at room temperature (m.p. -30℃; b.p.760 156℃), it is used as a solvent, particularly for large-scale crystallisations, and for the introduction of phenyl groups in organic synthesis. It has a role as a non-polar solvent, a hepatotoxic agent and a mouse metabolite. It is a member of bromobenzenes, a bromoarene and a volatile organic compound.
主な応用
The compound is employed as a starting material in organic syntheses in which a Grignard intermediate (phenyl magnesium bromide) is used. The material is a chemical precursor for certain agricultural products and has been used as an additive to motor oils. Bromobenzene has also been used as a high-density solvent for chemical recrystallization processes. especially for crystallizations on a large scale and where a heavy liquid is desirable.
製造方法
Bromobenzene is obtained by reacting benzene with bromine. First add iron powder and benzene into the reactor, slowly add bromine under stirring, keep the reaction at 70-80°C for 1 h after adding, the obtained crude product is washed with water and 5% sodium hydroxide solution, left to stand for stratification, distillation, Drying, filtering, and finally fractional distillation under constant pressure, taking the fraction at 155-157°C to obtain the finished product.
空気と水の反応
Flammable. Insoluble in water.
反応プロフィール
Bromobenzene may be sensitive to light. May react with oxidizing agents .
火災危険
Moderate fire risk. Special Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire.
安全性プロファイル
Moderately toxic by ingestion, subcutaneous, and intraperitoneal routes. LWdly toxic by inhalation. An eye and mucous membrane irritant. Mutation data reported. Flammable liquid when exposed to heat, sparks, or flame. Can react with oxidtzing materials. To fight fire, use water to blanket fire, foam, CO2, water spray or mist, dry chemical. Violent reaction with bromobutane + sodium when heated above 30℃. When heated to decomposition it emits toxic fumes of Br-. See also BROMIDES.
環境運命予測
Bromobenzene will volatilize from dry surfaces, due to its vapor pressure of 4.18mmHg at 25°C, and therefore will exist as a vapor in the environment. Bromobenzene will undergo little hydrolysis in water and little biodegradation by aquatic microorganisms. Bromobenzene is not expected to adsorb to sediment from water due to its soil sorption constant (Koc) of 150 and water solubility of 446 mg l-1. It is also expected to have a high mobility in soil and volatilize easily from moist surfaces due to its Henry’s law constant of 2.47×10-3 atmm3 mol-1 at 25°C. Bioconcentration factors range from low values of 8.8 in carp to moderately high values of 190 in algae.
代謝経路
Bromobenzene and chlorobenzene are metabolized by
human and mouse hepatic microsomes to two
different epoxide intermediates, which rearrange to
form either o- or p-bromo- and o- or p-chlorophenols,
respectively. Humans preferentially metabolize
halobenzenes through the hepatotoxic 3,4-epoxide
pathway, suggesting that humans may be more
susceptible than mice to halobenzene-induced
hepatotoxicity.
合成方法
鉄粉存在下，ベンゼンに臭素を反応させて製造される
純化方法
Wash bromobenzene vigorously with conc H2SO4, then 10% NaOH or NaHCO3 solutions, and H2O. Dry it with CaCl2 or Na2SO4, or pass it through activated alumina, before refluxing with, and distilling from, CaH2, using a glass helix-packed column. [Beilstein 5 IV 670.]
毒性学
The acute toxicity of bromobenzene is lowin test animals. The toxic symptoms includesomnolence, respiratory stimulation, and muscle contraction. The oral LD50 value in rats is2700 mg/kg.
ブロモベンゼン 上流と下流の製品情報
原材料
準備製品
ニメスリド
2-(6-メチル-2-ピリジル)エタノール
(-)-4,5-ビス[ヒドロキシ(ジフェニル)メチル]-2,2-ジメチル-1,3-ジオキソラン
1-ブロモ-4-(トリフルオロメトキシ)ベンゼン
フェニルシラン
(ジフェニルメチレンアミノ)酢酸エチル
ベンゼンセレノール
4-ブロモニトロベンゼン
1-フェニル-1H-イミダゾール
4-ブロモベンゼンスルホンアミド
N-フェニルアントラニル酸
ブチルベンゼン
α,α-ジフェニル-4-ピリジルメタノール
ベンゾイルぎ酸 エチル
3-フェニル酪酸
2-クロロトリチルアルコール
ドキセピン
1,3-DIMETHYL-4-PHENYL-4-PIPERIDINOL
α-(2-ブロモエチル)-α-フェニルベンゼン酢酸
テトラフェニルほう酸ナトリウム
トリエトキシフェニルシラン
p-オクチルベンズアルデヒド
アセトキシトリフェニルスタンナン
イソプロピルジフェニルホスフィン
(+)-4,5-ビス[ヒドロキシ(ジフェニル)メチル]-2,2-ジメチル-1,3-ジオキソラン
4-フェノキシフェノール
4-ブロモ-α-ヒドロキシベンゼン酢酸
2-フェニルベンジルアミン HYDROCHLORIDE
2-メチル-3-クロロビフェニル
トリクロサン
4,5-ジヒドロ-3,3-ジフェニル-2(3H)-フラノン
2-フェニルキノリン
brofluthrinate
brofenvalerate
2-メトキシ-1-フェニルエタノン
9-フェニルアントラセン
ジフェニルジセレニド
アリルベンゼン
p-ターフェニル
2-クロロトリチルクロリド