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Cas Database

123191-00-4

123191-00-4

Identification

  • Product Name:1H-Indole,1-[tris(1-methylethyl)silyl]-

  • CAS Number: 123191-00-4

  • EINECS:

  • Molecular Weight:273.494

  • Molecular Formula: C17H27 N Si

  • HS Code:2933990090

  • Mol File:123191-00-4.mol

Synonyms:1-(Triisopropylsilyl)indole;1-Triisopropylsilyl-1H-indole

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TCI Chemical
  • Product Description:1-(Triisopropylsilyl)indole >94.0%(GC)
  • Packaging:1g
  • Price:$ 279
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:1-(Triisopropylsilyl)-1H-indole 95+%
  • Packaging:5g
  • Price:$ 686
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  • Manufacture/Brand:Chem-Impex
  • Product Description:1-(Triisopropylsilyl)indole,≥94%(GC) ≥94%(GC)
  • Packaging:1G
  • Price:$ 318.94
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  • Manufacture/Brand:Chemenu
  • Product Description:1-(Triisopropylsilyl)-1H-indole 95%
  • Packaging:5g
  • Price:$ 648
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:1-(TRIISOPROPYLSILYL)INDOLE 95.00%
  • Packaging:1G
  • Price:$ 534.45
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  • Manufacture/Brand:Alichem
  • Product Description:1-(Triisopropylsilyl)-1H-indole
  • Packaging:5g
  • Price:$ 693
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  • Manufacture/Brand:AK Scientific
  • Product Description:1-(Triisopropylsilyl)indole
  • Packaging:1g
  • Price:$ 441
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  • Manufacture/Brand:AHH
  • Product Description:1-(Triisopropylsilyl)indole 94%
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Relevant articles and documentsAll total 18 Articles be found

The synthesis of 4-substituted indoles via arenetricarbonylchromium(0) complexes

Beswick,Greenwood,Mowlem,Nechvatal,Widdowson

, p. 7325 - 7334 (1988)

-

A Highly Enantioselective Asymmetric Hydrogenation Route to β-(2R,3S)-Methyltryptophan

Hoerrner, R. Scott,Askin, David,Volante, R. P.,Reider, Paul J.

, p. 3455 - 3458 (1998)

Asymmetric hydrogenation of a protected (Z)-dehydro-β-methyltryptophan derivative 2 with (R,R)-Me-DuPHOS-Rh catalysis was achieved in 97percent ee.Deprotection then afforded (2R,3S)-β-methyltryptophan 1.

NOVEL PYRIDIN-2(1H)ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE FOR THE TREATMENT OF PAIN

-

Page/Page column 15; 22-23, (2021/04/10)

The present invention concerns novel pyridin-2(1H)one derivatives, their process of preparation and their use in therapeutics, in particular as agents for treating and/or preventing pain.

Pyridin-2(1H)one derivatives: A possible new class of therapeutics for mechanical allodynia

Abrunhosa-Thomas, Isabelle,Anizon, Fabrice,Artola, Alain,Dallel, Radhouane,Descheemaeker, Amélie,Giraud, Francis,Moreau, Pascale,Nauton, Lionel,Pinto-Pardo, Nicolas,Théry, Vincent,Visseq, Alexia

, (2019/12/24)

Mechanical Allodynia (MA), a frequent chronic pain symptom caused by innocuous stimuli, constitutes an unmet medical need, as treatments using analgesics available today are not always effective and can be associated with important side-effects. A series of 3,5-disubstituted pyridin-2(1H)-ones was designed, synthesized and evaluated in vivo toward a rat model of inflammatory MA. We found that the series rapidly and strongly prevented the development of MA. 3-(2-Bromophenyl)-5-(phenylamino)pyridin-2(1H)-one 69, the most active compound of the series, was also able to quickly reverse neuropathic MA in rats. Next, when 69 was evaluated toward a panel of 50 protein kinases (PK) in order to identify its potential biological target(s), we found that 69 is a p38α MAPK inhibitor, a PK known to contribute to pain hypersensitivity in animal models. 3,5-Disubstituted pyridin-2(1H)-ones thus could represent a novel class of analgesic for the treatment of MA.

Boronic Acid Accelerated Three-Component Reaction for the Synthesis of α-Sulfanyl-Substituted Indole-3-acetic Acids

Das, Amrita,Watanabe, Kenji,Morimoto, Hiroyuki,Ohshima, Takashi

supporting information, p. 5794 - 5797 (2017/11/10)

Boronic acid was used to accelerate a three-component reaction of indoles, thiols, and glyoxylic acids for the synthesis of α-sulfanyl-substituted indole-3-acetic acids. Boronic acid catalysis to activate the α-hydroxy group in α-hydroxycarboxylic acid in

Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Nemoto, Koji,Tanaka, Shinya,Konno, Megumi,Onozawa, Satoru,Chiba, Masafumi,Tanaka, Yuuki,Sasaki, Yosuke,Okubo, Ryo,Hattori, Tetsutaro

, p. 734 - 745 (2016/01/15)

Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.

4-Substituted Pyrrolo[2,3-d]pyrimidine Compound and Use Thereof

-

Paragraph 0045; 0046; 0071; 0072; 0095; 0096, (2016/12/07)

The invention relates to a 4-substituted pyrrolo[2,3-d]pyrimidine compound and the use thereof in preparing medications for treating JAK-targeted diseases such as rheumatoid, immune system diseases, and tumor. The 4-substituted pyrrolo[2,3-d]pyrimidine compound of the invention is as shown in chemical formula I. The activity experimental results of the invention show that the new compound has obvious effect and activity in inhibition of Janus kinases, JAK-STAT, cell proliferation of human lymphocytoma, and rheumatoid arthritis.

Process route upstream and downstream products

Process route

indole
120-72-9

indole

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

Conditions
Conditions Yield
indole; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;
100%
indole; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 1.5h;
100%
With n-butyllithium; In tetrahydrofuran; at -78 ℃;
98%
indole; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 0.5h;
triisopropylsilyl chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;
97%
indole; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 1h;
triisopropylsilyl chloride; In tetrahydrofuran; hexane; for 2h;
91%
indole; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 0.166667h; Inert atmosphere;
triisopropylsilyl chloride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;
88%
indole; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;
81%
With n-butyllithium; Yield given; 1.) THF, -20 deg C, 1 h; 2.) YHF, -20 deg C, 1 h;
With sodium hydride; Yield given. Multistep reaction; 1.) DMF, 2.) DMF, overnight;
With n-butyllithium; Multistep reaction; 1.) THF, hexane, -78 deg C to -10 deg C, 15 min, 2.) THF, hexane, -50 deg C then 3 h, 0 deg C;
indole; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.0833333h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;
indole; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1.25h; Inert atmosphere;
triisopropylsilyl chloride; at 20 ℃; Inert atmosphere;
indole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; at -78 ℃; for 1h;
Triisopropyl borate
5419-55-6

Triisopropyl borate

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole
148249-36-9

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

(1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid
208655-73-6

(1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid

Conditions
Conditions Yield
3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole; With n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; for 1h;
Triisopropyl borate; In tetrahydrofuran; hexane; at -60 - 20 ℃; for 21h; Overall yield = 427 mg;
5-bromo-1-triisopropylsilyl-1H-indole
128564-66-9

5-bromo-1-triisopropylsilyl-1H-indole

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-indole
690631-97-1

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-indole

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

Conditions
Conditions Yield
With triethylamine; palladium diacetate; CyJohnPhos; In 1,4-dioxane; at 80 ℃; for 2h;
82%
6%
pyrrolidine
123-75-1

pyrrolidine

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole
148249-36-9

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

2-[3'-(N-triisopropylsilyl)-indolyl]-Δ<sup>1</sup>-pyrroline

2-[3'-(N-triisopropylsilyl)-indolyl]-Δ1-pyrroline

Conditions
Conditions Yield
With tert-butylethylene; RhCl(CO)(PFur3)2; caesium carbonate; In 1,4-dioxane; at 120 ℃; for 14h;
31%
Triisopropyl borate
5419-55-6

Triisopropyl borate

water
7732-18-5

water

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole
148249-36-9

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

(1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid
208655-73-6

(1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid

Conditions
Conditions Yield
3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole; With n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; for 1h; Inert atmosphere;
Triisopropyl borate; In tetrahydrofuran; hexane; at -60 - 20 ℃; for 21h;
water; With ammonium chloride; In toluene;
(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene
108030-46-2

(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole
148249-36-9

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

1-triisopropylsilyl-3-(4-nitro-1,3-butadienyl)indole
327163-16-6

1-triisopropylsilyl-3-(4-nitro-1,3-butadienyl)indole

Conditions
Conditions Yield
3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.333333h;
(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene; In tetrahydrofuran; pentane; at -78 - 20 ℃;
95%
3.2%
indole
120-72-9

indole

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

Conditions
Conditions Yield
indole; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;
100%
indole; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 1.5h;
100%
With n-butyllithium; In tetrahydrofuran; at -78 ℃;
98%
indole; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 0.5h;
triisopropylsilyl chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;
97%
indole; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 1h;
triisopropylsilyl chloride; In tetrahydrofuran; hexane; for 2h;
91%
indole; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 0.166667h; Inert atmosphere;
triisopropylsilyl chloride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;
88%
indole; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;
81%
With n-butyllithium; Yield given; 1.) THF, -20 deg C, 1 h; 2.) YHF, -20 deg C, 1 h;
With sodium hydride; Yield given. Multistep reaction; 1.) DMF, 2.) DMF, overnight;
With n-butyllithium; Multistep reaction; 1.) THF, hexane, -78 deg C to -10 deg C, 15 min, 2.) THF, hexane, -50 deg C then 3 h, 0 deg C;
indole; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.0833333h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;
indole; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1.25h; Inert atmosphere;
triisopropylsilyl chloride; at 20 ℃; Inert atmosphere;
indole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;
triisopropylsilyl chloride; In tetrahydrofuran; at -78 ℃; for 1h;
Triisopropyl borate
5419-55-6

Triisopropyl borate

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole
148249-36-9

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

(1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid
208655-73-6

(1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid

Conditions
Conditions Yield
3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole; With n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; for 1h;
Triisopropyl borate; In tetrahydrofuran; hexane; at -60 - 20 ℃; for 21h; Overall yield = 427 mg;
5-bromo-1-triisopropylsilyl-1H-indole
128564-66-9

5-bromo-1-triisopropylsilyl-1H-indole

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-indole
690631-97-1

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-indole

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

Conditions
Conditions Yield
With triethylamine; palladium diacetate; CyJohnPhos; In 1,4-dioxane; at 80 ℃; for 2h;
82%
6%
pyrrolidine
123-75-1

pyrrolidine

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole
148249-36-9

3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole

1-(triisopropylsilyl)-1H-indole
123191-00-4

1-(triisopropylsilyl)-1H-indole

2-[3'-(N-triisopropylsilyl)-indolyl]-Δ<sup>1</sup>-pyrroline

2-[3'-(N-triisopropylsilyl)-indolyl]-Δ1-pyrroline

Conditions
Conditions Yield
With tert-butylethylene; RhCl(CO)(PFur3)2; caesium carbonate; In 1,4-dioxane; at 120 ℃; for 14h;
31%

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