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3-Bromo-9-hexyl-9H-carbazole is an organic compound with the molecular formula C19H20BrN and a molecular weight of 344.27 g/mol. It is a derivative of carbazole, a tricyclic aromatic compound with a core structure consisting of two benzene rings fused to a pyrrole ring. The presence of a bromine atom at the 3-position and a hexyl chain at the 9-position gives this compound unique chemical and physical properties. It is primarily used in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals due to its potential applications in the development of new drugs and materials. The compound is typically synthesized through various chemical reactions, such as bromination and alkylation, and can be further functionalized to create a range of derivatives with diverse applications in research and industry.

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  • 156972-74-6 Structure
  • Basic information

    1. Product Name: 9H-Carbazole, 3-bromo-9-hexyl-
    2. Synonyms:
    3. CAS NO:156972-74-6
    4. Molecular Formula: C18H20BrN
    5. Molecular Weight: 330.267
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 156972-74-6.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 9H-Carbazole, 3-bromo-9-hexyl-(CAS DataBase Reference)
    10. NIST Chemistry Reference: 9H-Carbazole, 3-bromo-9-hexyl-(156972-74-6)
    11. EPA Substance Registry System: 9H-Carbazole, 3-bromo-9-hexyl-(156972-74-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 156972-74-6(Hazardous Substances Data)

156972-74-6 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 156972-74-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,6,9,7 and 2 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 156972-74:
(8*1)+(7*5)+(6*6)+(5*9)+(4*7)+(3*2)+(2*7)+(1*4)=176
176 % 10 = 6
So 156972-74-6 is a valid CAS Registry Number.

156972-74-6Relevant articles and documents

Single and double branched organic dyes based on carbazole and red-absorbing cationic indolium for p-type dye-sensitized solar cells: A combined experimental and theoretical investigation

Bao, Le Quoc,Ho, Phuong,Chitumalla, Ramesh Kumar,Jang, Joonkyung,Thogiti, Suresh,Kim, Jae Hong

, p. 25 - 36 (2017/10/05)

A series of novel single and double branched carbazole-based red-absorbing cationic dyes without (CSI and CDI) and with (CST and CDT) a thiophene spacer have been synthesized for p-type dye-sensitized solar cells (p-DSSCs). The introduction of the red-absorbing cationic acceptor/thiophene spacer led to the broadening and bathochromic shift of the absorption maxima from an onset of 600 nm for CSI to 800 nm for CDT as well as improved molar absorptivity. The introduction of the double branching/thiophene spacer lowered the lowest unoccupied molecular orbital (LUMO) levels of CDI, CST, and CDT, making their potentials more positive than that of CSI. Among these, the double branched CDI exhibited the highest conversion efficiency of 0.112%. Furthermore, all of the dyes examined outperformed the standard C343 dye (0.062%), measured under similar fabrication conditions. Despite the decreased photovoltaic performance as a result of the introduction of the thiophene spacer, overall, the double branched dyes exhibited better interfacial charge transfer that led to higher JSC and VOC values compared to those of singly branched dyes. Electrochemical impedance spectroscopy analysis showed that double branched dyes have much lower charge transfer resistance and increased hole lifetime than single branched dyes. Density functional theory (DFT) and time-dependent DFT calculations were performed to theoretically characterize the optical and electrochemical properties of the synthesized dyes.

Preparation method of terpyridyl zinc complex and application

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Paragraph 0036; 0037, (2018/06/26)

The invention discloses a preparation method of a terpyridyl zinc complex and application. The preparation method comprises the following steps: in a DMSO (Dimethylsulfoxide) solvent system, performing a substitution reaction on carbazole, bromohexane and a 50% sodium hydroxide solution at 50 DEG C; in a dichloromethane solvent system, performing a local selective bromination reaction on a compound 1 and NBS (N-Bromobutanimide) at 25 DEG C; in a nitrogen environment and in a dried diisopropylamine solution system, performing a Sonogashira coupling reaction on p-bromo benzaldehyde, trimethylsilylacetylene, copper iodide and (beta-4)-platinum at 80 DEG C; in a nitrogen environment and in a dried diisopropylamine and tetrahydrofuran solution system, performing a Sonogashira coupling reactionon a compound 2, a compound 3, copper iodide and (beta-4)-platinum at 80 DEG C; in an ethanol solvent system, performing a Krohnke middle ring formation method reaction on an alkyne-containing compound 4, diacyl pyridine and potassium hydroxide at 25 DEG C; stirring a terpyridyl compound and trifluoro zinc sulfonate in methanol. The preparation method is simple in step and gentle, and water printing of a product is achieved.

Effect of Donor Groups on the Performance of Cyclometalated Ruthenium Sensitizers in Dye-Sensitized Solar Cells

Aghazada, Sadig,Ren, Yameng,Wang, Peng,Nazeeruddin, Mohammad Khaja

supporting information, p. 13437 - 13445 (2017/11/15)

Three new tris-heteroleptic complexes of ruthenium(II) were designed by coordinating the metal center with cyclometalating, anchoring, and auxiliary ligands with different donor substituents. N-Hexylcarbazole, N-hexylphenothiazine, and N-hexyldiphenylamine donor moieties were used as substituents on the auxiliary ligands for SA633, SA634, and SA635, respectively. Complexes were characterized by 1H and 13C 2D-COSY NMR techniques. These complexes provide power conversion efficiencies in the range of 7.6-8.2% when they are employed in state of the art dye-sensitized solar cells (DSCs) with cobalt electrolyte. Various electrochemical and transient techniques were used to unveil the unexpected differences in the performance of these very similar sensitizers.

Hetero aromatic donors as effective terminal groups for DPP based organic solar cells

Reddy, Marri Anil,Kumar, Ch. Pavan,Ashok, Akudari,Sharma, Abhishek,Sharma,Chandrasekharam, Malapaka

, p. 9023 - 9036 (2016/02/05)

Four new solution-processable donor-acceptor-donor (D-A-D) structured low bandgap small molecules (CSDPP5, CSDPP6, CSDPP7 and CSDPP8) with diketopyrrolopyrrole as central acceptor unit and phenoxazine (POZ) or carbazole (CBZ) as terminal units were designed, synthesized and characterized. The new small molecules have been employed as donors along with the PC71BM as electron acceptor in solution processed BHJ organic solar cells, showed broad absorption bands with suitable electrochemical energy levels. When the BHJ active layer was cast from THF solvent, the optimal power conversion efficiencies obtained with CSDPP5, CSDPP6, CSDPP7 and CSDPP8 are 2.97% 3.06%, 2.42% and 2.43% respectively. The PCE of the devices when processed with DIO/THF solvent, have been further enhanced to 4.69%, 4.14% for CSDPP6:PC71BM and CSDPP8:PC71BM active layers respectively. The enhancement in PCE has been attributed to change in nanoscale morphology and more balanced charge transport resulting from increased hole mobility.

Synthesis and properties of novel 'ethyne-linked' compounds containing carbazole and 1, 8-naphthalimide groups

Liu, Yu,Wang, Hai-Ying,Chen, Gang,Xu, Xiao-Ping,Ji, Shun-Jun

scheme or table, p. 934 - 940 (2010/02/17)

A series of the novel 'ethyne-linked' compounds containing carbazole and 1,8-naphthalimide groups have been synthesized by Pd/Cu-catalyzed Sonogashira reaction. These compounds were fully characterized by means of Fourier-transform IR, 1H, 13C NMR, and high resolution mass spectroscopy. The thermal, optical, and electrochemical properties were also investigated. As we expected, the results indicated that these compounds could improve charge-transport ability and fluorescent quantum yield by introducing the electron-transporting emitting moieties naphthalimide and the alkyne group to carbazole moieties.

Synthesis and optical properties of novel compounds containing carbazole and 1,8-naphthalimide groups

Feng, Guo-Liang,Ji, Shun-Jun,Geng, Li-Jun,Bian, Bing,Liu, Yu

scheme or table, p. 137 - 140 (2009/04/10)

A series of novel carbazole-naphthalimide compounds with moieties capable of carrier-balance and electroluminescence were synthesised and characterised, and theirs luminescent properties had been studied.

Synthesis and optical properties of starburst carbazoles based on 9-phenylcarbazole core

Feng, Guo-Liang,Ji, Shun-Jun,Lai, Wen-Yong,Huang, Wei

, p. 2841 - 2845 (2008/02/13)

New well-defined starburst carbazole derivatives, which contain N-phenylcarbazole as the central core joining 9-hexylcarbazole or 9-phenylcarbazole as arms, are presented. All these compounds were obtained via Suzuki cross-coupling in moderate yields. Their structures were confirmed by 1H NMR, MALDI-TOF mass spectrometry and elementary analysis. Moreover, the fluorescence spectra showed that these compounds exhibited good blue fluorescence with the maximum wavelengths ranging from 410 nm to 430 nm. Georg Thieme Verlag Stuttgart.

Synthesis of novel star-shaped carbazole-functionalized triazatruxenes

Feng, Guo-Liang,Lai, Wen-Yong,Ji, Shun-Jun,Huang, Wei

, p. 7089 - 7092 (2007/10/03)

The syntheses of novel well-defined star-shaped carbazole-functionalized triazatruxenes, which consist of six carbazole arms linked with a central triazatruxene core consisting of three carbazoles with one phenyl, are presented. Both 9-hexylcarbazole and 9-phenylcarbazole as arms gave high yields. Their chemical formulas were confirmed by means of 1H NMR, MALDI-TOF mass spectroscopy, and elementary analysis. The fluorescent spectra showed that these compounds exhibit good blue fluorescence. The maximum fluorescence emission wavelengths were between 420 and 430 nm.

Practical syntheses of N-hexylcarbazol-2-yl- and -3-yl-boronic acids, their cross-coupled products and a derived tris-cyclometalated (pyridin-2-yl) carbazole iridium(III) complex

Tavasli, Mustafa,Bettington, Sylvia,Bryce, Martin R.,Batsanov, Andrei S.,Monkman, Andrew P.

, p. 1619 - 1624 (2007/10/03)

The syntheses of N-hexylcarbazol-2-yl- and -3-yl-boronic acids (1 and 2) are described on a ca. 7 g scale, starting from commercially available 2,5-dibromonitrobenzene (4) and carbazole (11), respectively. Compounds 1 and 2 underwent efficient palladium-catalyzed cross-coupling reactions under Suzuki-Miyaura conditions to yield products 17,18 and 20. Compound 18 reacted with IrCl3 to give the tris-cyclometalated (pyridin-2-yl)carbazole iridium(III) complex 21, the X-ray crystal structure of which is reported. Georg Thieme Verlag Stuttgart.

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