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41532-84-7 Usage

Chemical Properties

yellow to brown crystalline powder

Uses

1,1,2-Trimethyl-1H-benzo[e]indole can be used as an indole pH fluorescent probe and can be used for intracellular pH detection and cell marking. It can also be used as a novel nanocarrier-based near-infrared optical probes for in-vivo tumor imaging.

Check Digit Verification of cas no

The CAS Registry Mumber 41532-84-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,5,3 and 2 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 41532-84:
(7*4)+(6*1)+(5*5)+(4*3)+(3*2)+(2*8)+(1*4)=97
97 % 10 = 7
So 41532-84-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H15N/c1-10-15(2,3)14-12-7-5-4-6-11(12)8-9-13(14)16-10/h4-9H,1-3H3

41532-84-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (B21804)  1,1,2-Trimethyl-1H-benzo[e]indole, 97%   

  • 41532-84-7

  • 1g

  • 187.0CNY

  • Detail
  • Alfa Aesar

  • (B21804)  1,1,2-Trimethyl-1H-benzo[e]indole, 97%   

  • 41532-84-7

  • 5g

  • 378.0CNY

  • Detail
  • Alfa Aesar

  • (B21804)  1,1,2-Trimethyl-1H-benzo[e]indole, 97%   

  • 41532-84-7

  • 25g

  • 532.0CNY

  • Detail
  • Sigma-Aldrich

  • (03024)  1,1,2-Trimethylbenz[e]indole  ≥98.0% (HPLC)

  • 41532-84-7

  • 03024-25G-F

  • 1,081.08CNY

  • Detail

41532-84-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1,2-Trimethylbenz[e]Indole

1.2 Other means of identification

Product number -
Other names 1,1,2-Trimethyl-1H-benz[e]indole

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:41532-84-7 SDS

41532-84-7Synthetic route

3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

1-naphthylhydrazine hydrochloride
2243-56-3

1-naphthylhydrazine hydrochloride

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

Conditions
ConditionsYield
With acetic acid at 20℃; for 6.5h; Reflux;95%
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

2-hydrazinonaphthalene
2243-57-4

2-hydrazinonaphthalene

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

Conditions
ConditionsYield
With benzene und Behandeln das entstandene β-Naphtylhydrazon mit wasserfreier Oxalsaeure in alkoh.Loesung;
With acetic acid 1.) 20 deg C, 0.5 h, 2.) reflux, 2 h; Multistep reaction;
methyl iodide
74-88-4

methyl iodide

2.3-dimethyl-4.5-benzo-indole

2.3-dimethyl-4.5-benzo-indole

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

Conditions
ConditionsYield
at 100℃;
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

2-naphthylhydrazine hydrochloride
2243-58-5

2-naphthylhydrazine hydrochloride

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

Conditions
ConditionsYield
With acetic acid at 100℃; for 24h; Fischer Indole Synthesis;
cyclosporin A

cyclosporin A

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

Conditions
ConditionsYield
Stage #1: cyclosporin A With tetrabutylammonium acetate; butanone
Stage #2: In methanol
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

methyl iodide
74-88-4

methyl iodide

1,1,2,3-tetramethyl-1H-benz[e]indol-3-ium iodide
58464-25-8

1,1,2,3-tetramethyl-1H-benz[e]indol-3-ium iodide

Conditions
ConditionsYield
In acetonitrile at 110℃; for 48h; Inert atmosphere;100%
In methanol; acetonitrile at 50℃; for 2h;95%
at 20℃; for 24h;94%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

6-bromohexanoic acid
4224-70-8

6-bromohexanoic acid

3-(5-carboxypentyl)-1,1,2-trimethyl-1H-benzo-[e]indol-3-ium bromide

3-(5-carboxypentyl)-1,1,2-trimethyl-1H-benzo-[e]indol-3-ium bromide

Conditions
ConditionsYield
With potassium iodide In acetonitrile Heating;100%
In nitromethane at 110℃; for 2h; Inert atmosphere; Microwave irradiation;95%
In nitromethane at 110℃; for 2h; Inert atmosphere; Microwave irradiation;95%
1,4-butane sultone
1633-83-6

1,4-butane sultone

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate
63149-24-6

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate

Conditions
ConditionsYield
at 120℃; for 2h;99%
In sulfolane at 120 - 130℃;92%
With 1,2-dichloro-benzene In diethyl ether at 120℃; for 18h; Inert atmosphere; Darkness;90%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

6-bromohexanoic acid
4224-70-8

6-bromohexanoic acid

C21H27NO2

C21H27NO2

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;98%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

ethyl iodide
75-03-6

ethyl iodide

3-ethyl-1,2,2,-trimethyl-benz[e]-1[H]indolium iodide
80566-25-2

3-ethyl-1,2,2,-trimethyl-benz[e]-1[H]indolium iodide

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;97%
In acetonitrile for 48h; Heating;91%
In acetonitrile91%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

ethyl 5-bromovalerate
14660-52-7

ethyl 5-bromovalerate

3-(4-ethoxycarbonylbutyl)-1,1,2-trimethyl-1H-benzo[e]indolium bromide

3-(4-ethoxycarbonylbutyl)-1,1,2-trimethyl-1H-benzo[e]indolium bromide

Conditions
ConditionsYield
With potassium iodide In acetonitrile at 80℃; for 96h;97%
at 120℃; for 1h;26%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

8-bromooctanoic acid
17696-11-6

8-bromooctanoic acid

C23H31NO2

C23H31NO2

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;97%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

9-bromononanoic acid
41059-02-3

9-bromononanoic acid

C24H33NO2

C24H33NO2

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;97%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

10-bromodecanoic acid
50530-12-6

10-bromodecanoic acid

C25H35NO2

C25H35NO2

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;97%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

methyl 4-(iodomethyl)benzoate
94224-92-7

methyl 4-(iodomethyl)benzoate

3-(4-methoxycarbonylbenzyl)-1,1,2-trimethyl-1H-benzo[e]indolium iodide

3-(4-methoxycarbonylbenzyl)-1,1,2-trimethyl-1H-benzo[e]indolium iodide

Conditions
ConditionsYield
In acetonitrile at 80 - 85℃; for 6h; Time;96.4%
1,3-propanesultone
1120-71-4

1,3-propanesultone

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

3-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)propane-1-sulfonate
63666-10-4

3-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)propane-1-sulfonate

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 155℃; for 1h; air-tight flask;96%
95%
94%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

methyloxirane
75-56-9, 16033-71-9

methyloxirane

1-(2-hydroxypropyl)-2,3,3-trimethyl-3H-benzo[e]indolium perchlorate

1-(2-hydroxypropyl)-2,3,3-trimethyl-3H-benzo[e]indolium perchlorate

Conditions
ConditionsYield
Stage #1: 2,3,3-trimethylbenzo[e]indole; methyloxirane With hydrogen bromide In acetic acid at 100℃; for 1h;
Stage #2: With sodium perchlorate
96%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

7-bromoheptanoic acid
30515-28-7

7-bromoheptanoic acid

C22H29NO2

C22H29NO2

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;95%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

(3-bromopropyl)amine
18370-81-5

(3-bromopropyl)amine

3-(3-aminopropyl)-1,1,2-trimethyl-1H-benz[e]indolium bromide
1036378-19-4

3-(3-aminopropyl)-1,1,2-trimethyl-1H-benz[e]indolium bromide

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 110℃; for 0.5h;94%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

1-Iodododecane
4292-19-7

1-Iodododecane

3-dodecyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide
1570368-82-9

3-dodecyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide

Conditions
ConditionsYield
for 18h; Heating;94%
In acetonitrile Inert atmosphere; Reflux;90%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

amyl iodide
628-17-1

amyl iodide

1-pentyl-2,3,3-trimethylbenz[e]indolium iodide

1-pentyl-2,3,3-trimethylbenz[e]indolium iodide

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;94%
at 145℃; for 0.166667h; Microwave irradiation;82%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

3-bromopropylamine hydrochloride
5003-71-4

3-bromopropylamine hydrochloride

3-(3-Aminopropyl)-1,1,2-trimethylbenz(e)indolium bromide.HBr

3-(3-Aminopropyl)-1,1,2-trimethylbenz(e)indolium bromide.HBr

Conditions
ConditionsYield
at 140℃; for 10h;93%
at 140 - 150℃; for 20h;
1-iodo-butane
542-69-8

1-iodo-butane

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

3-butyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide
137107-72-3

3-butyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;93%
In nitromethane at 20℃; for 12h;90%
In acetonitrile for 24h; Reflux;87%
1,2-oxathiane-2-oxide
24308-29-0

1,2-oxathiane-2-oxide

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate
63149-24-6

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate

Conditions
ConditionsYield
at 120℃; for 2h;93%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

1-Iodohexane
638-45-9

1-Iodohexane

3-hexyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide

3-hexyl-1,1,2-trimethyl-1H-benzo[e]indol-3-ium iodide

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;93%
In butanone at 70℃; for 18h;
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

1-iodo-propane
107-08-4

1-iodo-propane

1-propyl-2,3,3-trimethylbenz[e]indolium iodide
1421009-71-3

1-propyl-2,3,3-trimethylbenz[e]indolium iodide

Conditions
ConditionsYield
In toluene Inert atmosphere; Reflux;93%
at 140℃; for 0.166667h; Microwave irradiation;83%
Reflux;
3-Bromopropionic acid
590-92-1

3-Bromopropionic acid

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

3-(2-carboxyethyl)-1,1,2-trimethyl-1H-benzo[e]indole iodide salt
6761-95-1

3-(2-carboxyethyl)-1,1,2-trimethyl-1H-benzo[e]indole iodide salt

Conditions
ConditionsYield
With potassium iodide In 1,2-dichloro-benzene at 110℃; for 16h;92.5%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

6-bromo-hexanoic acid ethyl ester
25542-62-5

6-bromo-hexanoic acid ethyl ester

3-(5-ethoxycarbonylpentyl)-1,1,2-trimethyl-1H-benz[e]indolenium bromide
190714-35-3

3-(5-ethoxycarbonylpentyl)-1,1,2-trimethyl-1H-benz[e]indolenium bromide

Conditions
ConditionsYield
With potassium iodide In acetonitrile at 80℃; for 96h;92%
at 120℃; for 2h;63%
In 1,2-dichloro-benzene
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

bromobutyric acid
2623-87-2

bromobutyric acid

C19H23NO2

C19H23NO2

Conditions
ConditionsYield
In toluene Inert atmosphere; Reflux;92%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

1-Iodoheptane
4282-40-0

1-Iodoheptane

C22H30N(1+)*I(1-)

C22H30N(1+)*I(1-)

Conditions
ConditionsYield
In nitromethane Inert atmosphere; Reflux;92%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

3-hydroxy-3-methyl-1-cyano-1-butyne
32837-87-9

3-hydroxy-3-methyl-1-cyano-1-butyne

(Z)-2-[9,9,10a,11,11-pentamethyl-10a,11-dihydrobenzo[e]oxazolo[3,2-a]indol-8(9H)-ylidene]acetonitrile

(Z)-2-[9,9,10a,11,11-pentamethyl-10a,11-dihydrobenzo[e]oxazolo[3,2-a]indol-8(9H)-ylidene]acetonitrile

Conditions
ConditionsYield
at 20 - 25℃; for 36h; regioselective reaction;92%
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-(1,1-dimethyl-1,3-dihydro-2H-benzo[e]indol-2-ylidene)malonaldehyde

2-(1,1-dimethyl-1,3-dihydro-2H-benzo[e]indol-2-ylidene)malonaldehyde

Conditions
ConditionsYield
Stage #1: 2,3,3-trimethylbenzo[e]indole; N,N-dimethyl-formamide With trichlorophosphate for 1h; Cooling with ice;
Stage #2: for 3h; Reflux;
91%
Stage #1: 2,3,3-trimethylbenzo[e]indole; N,N-dimethyl-formamide With trichlorophosphate at 95℃; for 9h;
Stage #2: With sodium hydroxide
2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

2-(4-bromobutyl)isoindoline-1,3-dione
5394-18-3

2-(4-bromobutyl)isoindoline-1,3-dione

3-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-1,1,2-trimethyl-1H-benzo[e]indolium; bromide

3-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-1,1,2-trimethyl-1H-benzo[e]indolium; bromide

Conditions
ConditionsYield
at 140℃; sealed tube;90%
at 140℃; for 10h;
3-Bromopropionic acid
590-92-1

3-Bromopropionic acid

2,3,3-trimethylbenzo[e]indole
41532-84-7

2,3,3-trimethylbenzo[e]indole

1-(2-hydroxycarbonylethyl)-2,3,3-trimethylbenzo[e]indoleninium bromide

1-(2-hydroxycarbonylethyl)-2,3,3-trimethylbenzo[e]indoleninium bromide

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 100℃; for 20h;90%
In 1,2-dichloro-ethane at 100℃; for 20h;90%
In 1,2-dichloro-benzene at 110℃; for 18h;88%

41532-84-7Relevant articles and documents

Synthesis and spectroscopic study of highly fluorescent β-enaminone based boron complexes

Kumbhar, Haribhau S.,Gadilohar, Balu L.,Shankarling, Ganapati S.

, p. 80 - 87 (2015)

The newly synthesized 1, 1, 2-trimethyl-1H benzo[e]indoline based β-enaminone boron complexes exhibited the intense fluorescence (Fmax = 522-547 nm) in solution as well as in solid state (Fmax = 570-586 nm). These complexes exhibited large stoke shift, excellent thermal and photo stability when compared to the boron dipyrromethene (BODIPY) colorants. Optimized geometry and orbital distribution in ground states were computed by employing density functional theory (DFT). The cyclic voltammetry study revealed the better electron transport ability of these molecules than current electroluminescent materials like tris(8-hydroxyquinoli-nato)-aluminium (Alq3) and BODIPY, which can find application in electroluminescent devices.

Synthesis of advanced fluorescent probes — water-soluble symmetrical tricarbocyanines with phosphonate groups

Podrugina,Temnov,Doroshenko,Kuzmin,Nekipelova,Proskurnina,Zefirov

, p. 2722 - 2728 (2016)

A method for the synthesis of a series of water-soluble heptamethine indocyanine dyes containing a phosphonate group in the substituent bonded to the quaternary nitrogen atom of the indolenine moiety has been developed.

Adenine-based flower-elite probe and preparation method and application thereof

-

Paragraph 0013; 0023-0024; 0033-0034; 0039-0040, (2022/01/07)

The present invention belongs to the field of chemical analysis testing, specifically relates to an adenine-based flower cyanine probe and preparation method and application thereof. The CY5.5 dye is synthesized by a four-step reaction. The CY5.5 dye was then reacted with adenine under N, N'-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) conditions, and the resulting crude product was separated by thin layer chromatography to obtain the final product. The flower probe obtained by the present invention has excellent optical properties and the role of recognizing hemoglobin, which is conducive to the detection of hemoglobin.

Evaluation of asymmetric orthogonal cyanine fluorophores

Boutkan, Michael S.,Buckle, Tessa,Hensbergen, Albertus W.,Welling, Mick M.,Wester, Hans-Jürgen,de Kleer, Mathijs A. C.,van Leeuwen, Fijs W. B.,van Willigen, Danny M.,van der Wijk, Felicia A.

, (2020/08/24)

Pentamethine cyanine (Cy5) fluorophores have proven to be versatile imaging agents (i.e., tracers) for a range of micro- and macroscopic imaging applications, including image-guided surgery. In this study the relationship between the structure of asymmetric Cy5 fluorophores and their photophysical properties was studied. To this end, seven Cy5 analogues, bearing orthogonal N-indole substituents (H, SO3?, or benzene), were synthesised and evaluated. In-depth analysis revealed that introduction of sulfonates enhanced the fluorescence brightness and photostability, while reducing the lipophilicity, serum binding and stacking tendency. The addition of benzene moieties induced a bathochromic shift of 10–20 nm, increased the lipophilicity (LogP = -1.56–1.23) and serum binding (67.3–93.8percent bound), as well as negatively impacted the brightness (0.74–42.9 · 103 M?1 cm?1), photostability (24.4–90.6percent remaining), and stacking tendency. Chemical stability was uninfluenced by the substitution pattern. Additionally, the generation of a c[RGDyK]-based hybrid tracer based on one of these fluorophores in combination with a diethylenetriaminepentaacetic acid (DTPA) chelate and an 111In-isotope was reported. This compound was evaluated in vitro using αvβ3-overexpressing Geβ3 cells and in vivo using a 4T1 mouse tumour model. Overall, the presented results imply that alterations of the asymmetrical orthogonal Cy5 fluorophore structure have impact on the (photo)physical properties. Furthermore, the orthogonal Cy5 fluorophore framework can readily be applied in tracer development.

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