Trichloroacetonitrile
(Synonyms: 三氯乙腈) 目录号 : GC63614
Trichloroacetonitrile 是饮用水中氯与背景有机物反应产生的一系列污染物之一。Trichloroacetonitrile 是芳基硼酸异丙醇羟基化为酚类化合物的有效活化剂。
Cas No.:545-06-2
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Trichloroacetonitrile is among a number of contaminants found in drinking water produced by reactions of chlorine with background organic material. Trichloroacetonitrile is an efficient activating agent for the ipso-hydroxylation of arylboronic acids to phenolic compounds[1][2].
[1]. Fang Y, et al. Trichloroacetonitrile as an efficient activating agent for the ipso-hydroxylation of arylboronic acids to phenolic compounds. Org Biomol Chem. 2019;17(32):7558-7563. [2]. Smith MK, et al. Teratogenic effects of trichloroacetonitrile in the Long-Evans rat. Teratology. 1988;38(2):113-120.
| Cas No. | 545-06-2 | SDF | |
| 别名 | 三氯乙腈 | ||
| 分子式 | C2Cl3N | 分子量 | 144.39 |
| 溶解度 | DMF : 100 mg/mL (692.57 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 6.9257 mL | 34.6284 mL | 69.2569 mL |
| 5 mM | 1.3851 mL | 6.9257 mL | 13.8514 mL |
| 10 mM | 0.6926 mL | 3.4628 mL | 6.9257 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
N-Cyanation of Secondary Amines Using Trichloroacetonitrile
Org Lett 2016 Nov 4;18(21):5528-5531.PMID:27753288DOI:10.1021/acs.orglett.6b02775.
A one-pot N-cyanation of secondary amines has been developed using Trichloroacetonitrile as an inexpensive cyano source. A diverse range of cyclic and acyclic secondary amines can be readily transformed into the corresponding cyanamides in good isolated yields, with the method successfully utilized in the final synthetic step of a biologically active rolipram-derived cyanamide. This approach exhibits distinct selectivity when compared to the use of highly toxic cyanogen bromide.
Electrochemical Synthesis of Cyanoformamides from Trichloroacetonitrile and Secondary Amines Mediated by the B12 Derivative
J Org Chem 2021 Nov 19;86(22):16134-16143.PMID:34137621DOI:10.1021/acs.joc.1c00837.
The B12 derivative, heptamethyl cobyrinate, -mediated electrochemical synthesis of cyanoformamides has been developed. Aerobic oxygenation of the carbon-centered radical initiated in situ generation of the reactive acyl chloride intermediate, which led to cyanoformamides in the presence of an amine. This one-pot and scalable synthetic method has been demonstrated with 41 examples up to 94% yields with 21 new compounds. The mechanism of electrolysis mediated by the B12 derivative has been proposed based on the DFT calculations.
One-pot expeditious synthesis of glycosylated esters through activation of carboxylic acids using Trichloroacetonitrile
Carbohydr Res 2022 Nov;521:108674.PMID:36126412DOI:10.1016/j.carres.2022.108674.
Acetimidates, a valuable intermediate has been well explored as versatile synthon in a number of organic transformations particularly as suitable donors in glycosylation reactions. Herein, we explored acetimidates to furnish high-to-excellent yield of diverse glycosylated esters under one-pot mild reaction condition. The commercially available Trichloroacetonitrile is implemented for the activation of carboxylic acid via in situ generation of trichloroacetimidate, which was subsequently attacked by sugar alcohols to deliver high-to-excellent yields of desired glycosylated esters. The devised method has some notable features such as metal-free condition, one-pot mild reaction condition, easy-handling, high-to-excellent yields, and broad substrate scope.
Tetraarylphosphonium salt-catalyzed formal [3+2] cycloaddition between epoxides and Trichloroacetonitrile for the synthesis of β-amino alcohol derivatives
Chem Commun (Camb) 2022 Oct 20;58(84):11819-11822.PMID:36189849DOI:10.1039/d2cc03782c.
Efficient regioselective synthesis of β-amino alcohol derivatives, including enantioenriched ones, by a tetraarylphosphonium salt-catalyzed coupling reaction of epoxides with Trichloroacetonitrile is described. Formal [3+2] cycloaddition, followed by hydrolysis, proceeded smoothly to afford N-protected β-amino alcohols in good yields.
Trichloroacetonitrile as an efficient activating agent for the ipso-hydroxylation of arylboronic acids to phenolic compounds
Org Biomol Chem 2019 Aug 28;17(32):7558-7563.PMID:31373339DOI:10.1039/c9ob01568j.
A metal-free and base-free Cl3CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.