trichloroacetonitrile

• ChemBase编号: 89276
• 分子式: C2Cl3N
• 平均质量: 144.3871
• 单一同位素质量: 142.90963205
• SMILES: N#CC(Cl)(Cl)Cl
• Canonical SMILES: N#CC(Cl)(Cl)Cl
• InChI: InChI=1S/C2Cl3N/c3-2(4,5)1-6
• InChIKey: DRUIESSIVFYOMK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: trichloroacetonitrile
• IUPAC传统名: trichloroacetonitrile
• 别名: 三氯乙腈; 2,2,2-trichloroacetonitrile; Trichloromethyl cyanide; Trichloroacetonitrile 96%; Trichloroacetonitrile; Trichloroacetonitrile

登记号

• CAS号: 545-06-2
• EC号: 208-885-7
• MDL号: MFCD00001842
• Beilstein号: 605572
• 默克索引号: 149628
• PubChem SID: 24867685; 24889442; 24900271; 162076157
• PubChem CID: 24900271; 11011
• 维基百科标题: Trichloroacetonitrile

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.5869915
• LogD (pH = 7.4): 1.5869915
• Log P: 1.5869915
• 摩尔折射率: 27.1376 cm^3
• 极化性: 10.134492 Å^3
• 极化表面积: 23.79 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: insoluble in water
• 外观: colourless liquid
• 熔点: -42; -42°C; -44°C
• 沸点: 83 - 84°C; 83-84 °C(lit.); 83-84°C; 85-86°C
• 闪点: 195 °C; 195°C (383°F); 383 °F
• 密度: 1.44; 1.44 g/mL; 1.44 g/mL at 25 °C(lit.)
• 折射率: 1.4410; 1.4840; n20/D 1.441; n20/D 1.441(lit.)
• 蒸汽压: 58 mmHg ( 20 °C)

安全信息

• 保存注意事项: Toxic/Lachrymatory
• RTECS编号: AM2450000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有毒(Toxic) (T)
• 联合国危险货物编号: 3276; UN3276
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 23/24/25-51/53
• 安全公开号: 45-61
• TSCA收录: 是
• GHS危险品标识: GHS06; GHS09
• GHS警示词: Danger
• 主要危害: GHS06, GHS09
• GHS危险声明: H301-H311-H331-H411
• GHS警示性声明: P261-P273-P280-P301 + P310-P311; P261-P301+P310-P361-P302+P352-P405-P501A
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3276 6.1/PG 3

产品相关信息

• 纯度: ≥95.0% (GC); 98%
• 级别: analytical standard; purum
• 包装: ampule of 1000 mg
• 线性分子式: Cl3CCN

详细说明

Sigma Aldrich - T53805

Application
用于通过 DBU 催化的烯丙醇加成反应合成三氯乙酰亚胺酯，以及用于 MOM 催化型氮杂-Claisen 重排反应的后续研究。1还可用于由二醇制备双三氯乙酰亚胺酯，再通过酸催化的环化反应生成二氢噁嗪。2
包装
5, 100, 500 g in glass bottle

参考文献

• The combination with PPh₃ is superior to the popular CCl₄-PPh₃ system for conversion of carboxylic acids to acyl chlorides: Tetrahedron Lett., 40, 5323 (1999). It also converts allylic alcohols to the corresponding chlorides: Russ. J. Org. Chem., 31, 1019 (1995).
• In the presence of a base, e.g DBU, reacts with alcohols to form trichloroacetimidates, which are a useful means of protection, readily cleaved by TsOH/MeOH, DBU/MeOH or Zn/NH₄Cl: Synlett, 753(1999). These imidates are activated towards displacement by nucleophiles. Glycosyl imidates, formed in the presence of a base such as K₂CO₃ or DBU, are widely applied as glycosyl donors in oligosaccharide synthesis. Reaction with the free OH of the glycosyl acceptor occurs under mild conditions, promoted by a Lewis acid, e.g. BF₃ etherate or TMS-OTf, to form, respectively, either the ?- or ɑ-glycoside as the major product: Angew. Chem. Int. Ed., 25, 212 (1986). For reviews, see: Chem. Rev., 93, 1503 (1993); Adv. Carbohydr. Chem. Biochem., 50, 21 (1994); Contemp. Org. Synth., 3, 173 (1996). The imidates of allylic alcohols, prepared using NaH, or, more conveniently, KOH under phase-transfer conditions: Tetrahedron Lett., 37, 1481 (1996), undergo a [3,3]-sigmatropic rearrangement to derivatives of allylamines: J. Am. Chem. Soc., 96, 597 (1974); 98, 2901 (1976). For an example, see: Org. Synth. Coll., 6, 507 (1988). Review: Acc. Chem. Res., 13, 218 (1980):
  
• Reacts with hydrogen peroxide, to give, in situ, peroxytrichloroacetamidic acid, a reagent for the epoxidation of alkenes under essentially neutral conditions: J. Org. Chem., 48, 888 (1983).
• Aromatic aldoximes are dehydrated to nitriles by a similar cyclic mechanism: J. Org. Chem., 38, 2241 (1973).
• For a review of the chemistry of trichloroacetonitrile, see: Heterocycles, 43, 1083 (1996).