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4-((Trimethylsilyl)ethynyl)aniline, with the molecular formula C11H15NSi, is a yellow to orange colored solid chemical compound. It is sparingly soluble in water but exhibits greater solubility in organic solvents. Characterized by a trimethylsilyl group and an ethynyl group, 4-((Trimethylsilyl)ethynyl)aniline is recognized for its versatility in participating in a variety of chemical reactions, making it a valuable intermediate in the synthesis of organic compounds. Its unique structure also endows it with potential antibacterial and antifungal properties, which broadens its applicability in medical and agricultural sectors.

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  • 75867-39-9 Structure
  • Basic information

    1. Product Name: 4-((Trimethylsilyl)ethynyl)aniline
    2. Synonyms: 1-aMino-4-triMethylsilylethynylbenzene;[(4-Aminophenyl)ethynyl]trimethylsilane, (4-Aminophenyl)(trimethylsilyl)acetylene;4-[2-(Trimethylsilyl)ethynyl]aniline;p-(2-Trimethylsilylethynyl)aniline;4-[(Trimethylsilyl)ethynyl]aniline 96%;4-[2-(Trimethylsilyl)ethynyl]benzenamine
    3. CAS NO:75867-39-9
    4. Molecular Formula: C11H15NSi
    5. Molecular Weight: 189.33
    6. EINECS: N/A
    7. Product Categories: Amines;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Alkynes;Building Blocks;C10 to C11;Chemical Synthesis;Internal;Nitrogen Compounds;Organic Building Blocks
    8. Mol File: 75867-39-9.mol
  • Chemical Properties

    1. Melting Point: 94-98℃
    2. Boiling Point: 258.873°C at 760 mmHg
    3. Flash Point: >110°C
    4. Appearance: /
    5. Density: 0.973g/cm3
    6. Vapor Pressure: 0.013mmHg at 25°C
    7. Refractive Index: 1.532
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. PKA: 5.13±0.10(Predicted)
    11. CAS DataBase Reference: 4-((Trimethylsilyl)ethynyl)aniline(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-((Trimethylsilyl)ethynyl)aniline(75867-39-9)
    13. EPA Substance Registry System: 4-((Trimethylsilyl)ethynyl)aniline(75867-39-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 75867-39-9(Hazardous Substances Data)

75867-39-9 Usage

Uses

Used in Organic Synthesis:
4-((Trimethylsilyl)ethynyl)aniline is utilized as a building block in organic synthesis for the preparation of a diverse array of functionalized materials and pharmaceuticals. Its unique structural features allow it to engage in multiple chemical reactions, contributing to the creation of complex organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-((Trimethylsilyl)ethynyl)aniline is used as a versatile intermediate for the synthesis of various medicinal compounds. Its ability to participate in a range of reactions facilitates the development of new drugs with specific therapeutic properties.
Used in Material Science:
4-((Trimethylsilyl)ethynyl)aniline is employed in material science for the development of novel functional materials. Its structural attributes make it suitable for the creation of materials with tailored properties for specific applications.
Used in Medical and Agricultural Industries:
Due to its antibacterial and antifungal properties, 4-((Trimethylsilyl)ethynyl)aniline is used in the medical and agricultural industries as a potentially valuable compound for combating infections and controlling the growth of harmful microorganisms.

Check Digit Verification of cas no

The CAS Registry Mumber 75867-39-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,5,8,6 and 7 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 75867-39:
(7*7)+(6*5)+(5*8)+(4*6)+(3*7)+(2*3)+(1*9)=179
179 % 10 = 9
So 75867-39-9 is a valid CAS Registry Number.
InChI:InChI=1/C11H15NSi/c1-13(2,3)9-8-10-4-6-11(12)7-5-10/h4-7H,12H2,1-3H3

75867-39-9 Well-known Company Product Price

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  • Aldrich

  • (686360)  4-[(Trimethylsilyl)ethynyl]aniline  96%

  • 75867-39-9

  • 686360-1G

  • 1,113.84CNY

  • Detail
  • Aldrich

  • (686360)  4-[(Trimethylsilyl)ethynyl]aniline  96%

  • 75867-39-9

  • 686360-5G

  • 3,732.30CNY

  • Detail

75867-39-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(2-trimethylsilylethynyl)aniline

1.2 Other means of identification

Product number -
Other names 1-amino-4-trimethylsilylethynylbenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:75867-39-9 SDS

75867-39-9Relevant articles and documents

Photogenerated charge collection on diamond electrodes with covalently linked chromophore monolayers

Artemenko, A.,Cermák, J.,Haenen, K.,Kavan, L.,Kromka, A.,Krysova, H.,Lopez-Carballeira, D.,Maes, W.,Nicley, S. S.,Raymakers, J.,Rezek, B.,Verstraeten, F.

, (2020)

Encouraged by its rich surface chemistry and excellent electrochemical properties, boron-doped nanocrystalline diamond (B:NCD) is a promising p-type photoelectrode in dye-sensitized solar cells. One method of diamond surface functionalization using stable carbon-carbon bonds involves the electrochemical grafting of diazonium salts. However, this method typically leads to multilayers that may complicate the transport of photogenerated charges. Here, we establish functionalization of B:NCD electrodes by a monolayer of ethynylphenyl molecules using sterically hindered 4-(trimethylsilyl)ethynylbenzenediazonium tetrafluoroborate. Both the density and structural orientation of the grafted layer are investigated by angular resolved X-ray photoelectron spectroscopy, confirming the presence of covalently grafted monolayers. After removal of the trimethylsilyl protective groups, the resulting ethynyl functionalities are employed to immobilize organic donor-acceptor chromophores via Sonogashira cross-coupling reactions. Homogenous surface coverage is achieved even on the B:NCD electrode. Atomic scale DFT computing reveals that for the chromophore with the strongest acceptor unit, efficient charge separation of 20 ? is obtained where photogenerated holes move directly into diamond. Yet, photocurrent and photovoltage measurements suggest competitive electron recombination to the diamond electrode via the redox electrolyte. Correlation between the density of the molecular layer and photocurrents/photovoltage provides better understanding of the charge generation and recombination pathways in diamond-organic photoelectrochemical cells.

Synthesis, characterization, photophysics, and anion binding properties of gold(i) acetylide complexes with amide groups

Shi, Hua-Yun,Qi, Jie,Zhao, Zhen-Ze,Feng, Wen-Juan,Li, Yu-Hao,Sun, Lu,Lin, Zhuo-Jia,Chao, Hsiu-Yi

, p. 6168 - 6175 (2014)

A series of mononuclear gold(i) acetylide complexes with amide groups, Ph3PAuCCC6H4NHC(O)C6H4-R-4 (R = NO2 (3a), CF3 (3b), H (3c), and OMe (3d)), has been synthesized and characterized. The crystal structure of Ph3PAuCCC6H4NHC(O)C6H4-NO2-4 (3a) was determined by X-ray diffraction. The photophysical properties of gold(i) acetylide complexes 3b-3d were studied and the complexes show luminescence both in the solid state and in degassed THF solutions at 298 K. The anion-binding abilities of complexes 3a-3d in CDCl3 were also studied through 1H NMR titration experiments. They show similar anion selectivity trends and 3a exhibits the highest binding affinity towards anions due to the strongest electron-withdrawing ability of the NO2 group. In DMSO, 3a shows a dramatic color change upon addition of F-, which provides access to naked eye detection of F-. This journal is

Liquid crystal compound containing butadiyne structure and liquid crystal composition and application thereof

-

Paragraph 0103; 0115-0117, (2021/05/08)

The invention relates to a liquid crystal compound containing a butadiyne structure. The liquid crystal compound is represented by a general formula I. The invention also relates to a liquid crystal composition which at least comprises the compound repres

Development of a Pre-assembled Through-Bond Energy Transfer (TBET) Fluorescent Probe for Ratiometric Sensing of Anticancer Platinum(ll) Complexes

Ang, Wee Han,Ong, Jun Xiang

, (2020/04/02)

Fluorescence microscopy has emerged as an attractive technique to probe the intracellular processing of Pt-based anticancer compounds. Herein, we reported the first through-bond energy transfer (TBET) fluorescent probe NPR1 designed for sensitive detectio

Synthesis and photophysical properties of multilayer emitting π-p-π fluorophores

Wang, Xiaorong,Zhao, Sanxiao,Chen, Yin,Wang, Jingang

, (2019/11/02)

Fluorescence is widely used in biology, medicine, and analytical chemistry. The anthracene framework has received considerable attention for the luminescent molecular design as an attractive building unit. Herein, Luminescent “π-p-π” anthracene crystals with different multilayer stacking modes were conducted by experimental methods and theoretical calculations. It was found that “these anthracene derivatives showed strong fluorescence and stability in both solution and solid-state; A face-to-face π-π stacking arrangement dominated in N9,N10-diphenyl-2,6-bis((trimethylsilyl)ethynyl)anthracene-9,10-diamine (4), while C/N–H … π interactions were observed in the crystal lattice of 2,6-diethynyl-N9,N10-diphenylanthracene-9,10-diamine (5); The excitation processes of S0→S1 of 4 and 5 belonged to Localized Excitation; The number of photons emitted could be nearly equal to the number of photons absorbed below 120K”. This study is expected to assist in the design of photonic materials in the field of optical chemistry.

Synthesis and asymmetric catalytic performance of one-handed helical poly(phenylacetylene)s bearing proline dipeptide pendants

Liu, Lijia,Wang, Yaodong,Wang, Fuqingyun,Zhang, Chunhong,Zhou, Yanli,Zhou, Zhengjin,Liu, Xudong,Zhu, Ruiqi,Dong, Hongxing,Satoh, Toshifumi

, (2019/11/14)

One-handed helical substituted polyacetylene has received extensive attention due to its potential in chiral stationary phases and molecular recognition. Here, three one-handed helical poly(phenylacetylene)s bearing proline or proline dipeptide as the pen

Design, synthesis, and structure-activity relationship of 7-propanamide benzoxaboroles as potent anticancer agents

Zhang, Jiong,Zhang, Jinyi,Hao, Guiyun,Xin, Weixiang,Yang, Fei,Zhu, Mingyan,Zhou, Huchen

, p. 6765 - 6784 (2019/08/20)

Benzoxaboroles, as a novel class of bioactive molecules with unique physicochemical properties, have been shown to possess excellent antimicrobial activities with tavaborole approved in 2014 as an antifungal drug. Although urgently needed, the investigation of benzoxaboroles as anticancer agents has been lacking so far. In this study, we report the design, synthesis, and anticancer structure-activity relationship of a series of 7-propanamide benzoxaboroles. Compounds 103 and 115 showed potent activity against ovarian cancer cells with IC50 values of 33 and 21 nM, respectively. Apoptosis was induced by these compounds and colony formation was effectively inhibited. Furthermore, they also showed excellent efficacy in ovarian tumor xenograft mouse model.

Mild-Base-Promoted Arylation of (Hetero)Arenes with Anilines

Monzón, Diego M.,Santos, Tanausú,Pinacho-Crisóstomo,Martín, Víctor S.,Carrillo, Romen

, p. 325 - 333 (2018/01/15)

Transition metal-free radical arylation of heteroarenes is achieved at room temperature by simply adding aqueous sodium carbonate to a solution of the corresponding heteroarene and arenediazonium salt, which can even be formed in situ. Such an easy, inexpensive and mild methodology has been optimized and applied to the expeditious modification of interesting molecular cores like naphthylimide or bisthienylcyclopentenes.

Palladium catalysed regio- and stereoselective synthesis of (E)-4-aryl-1,3-bis(trimethylsilyl)but-3-en-1-ynes

Rogalski, Szymon,Kubicki, Maciej,Pietraszuk, Cezary

, p. 6192 - 6198 (2018/09/17)

A practical and general synthetic approach to a series of 4-aryl-but-3-en-1-ynes is described. In the presence of palladium complexes a variety of aryl bromides (or iodides) undergo coupling with two equivalents of trimethylsilylacetylene with the formati

Stabilization of High Oxidation State Upconversion Nanoparticles by N-Heterocyclic Carbenes

M?ller, Nadja,Rühling, Andreas,Lamping, Sebastian,Hellwig, Tim,Fallnich, Carsten,Ravoo, Bart Jan,Glorius, Frank

supporting information, p. 4356 - 4360 (2017/04/03)

The stabilization of high oxidation state nanoparticles by N-heterocyclic carbenes is reported. Such nanoparticles represent an important subset in the field of nanoparticles, with different and more challenging requirements for suitable ligands compared to elemental metal nanoparticles. N-Heterocyclic carbene coated NaYF4:Yb,Tm upconversion nanoparticles were synthesized by a ligand-exchange reaction from a well-defined precursor. This new photoactive material was characterized in detail and employed in the activation of photoresponsive molecules by low-intensity near-infrared light (λ=980 nm).

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