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1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE, commonly known as 1-Boc-3-iodoindole, is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and materials. It features a tert-butoxycarbonyl (Boc) protecting group and an iodine atom attached to the indole core, which can be further functionalized in chemical reactions.

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  • 192189-07-4 Structure
  • Basic information

    1. Product Name: 1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE
    2. Synonyms: 1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE;3-Iodoindole-1-carboxylic acid tert-butyl ester;1-Boc-3-iodoindole, 95%;tert-Butyl 3-iodo-1H-indole-1-carboxylate;N-Boc-3-iodoindole;3-Iodo-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester;1-(Tert-Butoxycarbonyl)-3-iodo-1H-icdole;tert-butyl3-iodoindole-1-carboxylate
    3. CAS NO:192189-07-4
    4. Molecular Formula: C13H14INO2
    5. Molecular Weight: 343.16
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 192189-07-4.mol
  • Chemical Properties

    1. Melting Point: 36-40℃
    2. Boiling Point: 388℃
    3. Flash Point: 189℃
    4. Appearance: /
    5. Density: 1.56
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.61
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
    9. Solubility: N/A
    10. Water Solubility: Insoluble in water.
    11. Sensitive: Light Sensitive
    12. CAS DataBase Reference: 1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE(CAS DataBase Reference)
    13. NIST Chemistry Reference: 1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE(192189-07-4)
    14. EPA Substance Registry System: 1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE(192189-07-4)
  • 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: 192189-07-4(Hazardous Substances Data)

192189-07-4 Usage

Uses

Used in Pharmaceutical Industry:
1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its unique structure allows for the development of new therapeutic agents with potential applications in treating a range of medical conditions.
Used in Ceramic Manufacturing Industry:
1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE is also utilized in the ceramic manufacturing industry, where it may contribute to the development of advanced ceramic materials with improved properties. Its role in this industry could involve enhancing the performance or functionality of ceramic products, although specific applications are not detailed in the provided materials.

Check Digit Verification of cas no

The CAS Registry Mumber 192189-07-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,2,1,8 and 9 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 192189-07:
(8*1)+(7*9)+(6*2)+(5*1)+(4*8)+(3*9)+(2*0)+(1*7)=154
154 % 10 = 4
So 192189-07-4 is a valid CAS Registry Number.
InChI:InChI=1/C13H14INO2/c1-13(2,3)17-12(16)15-8-10(14)9-6-4-5-7-11(9)15/h4-8H,1-3H3

192189-07-4 Well-known Company Product Price

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

  • (H27022)  1-Boc-3-iodoindole, 95%   

  • 192189-07-4

  • 250mg

  • 703.0CNY

  • Detail
  • Alfa Aesar

  • (H27022)  1-Boc-3-iodoindole, 95%   

  • 192189-07-4

  • 1g

  • 1137.0CNY

  • Detail

192189-07-4SDS

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 tert-butyl 3-iodoindole-1-carboxylate

1.2 Other means of identification

Product number -
Other names tert-butyl 3-iodo-1H-1-indolecarboxylate

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:192189-07-4 SDS

192189-07-4Relevant articles and documents

Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 6. 2-Indol-3-yl- and 2-azaindol-3-yl- dipyridodiazepinones

Kelly,McNeil,Rose,David,Shih,Grob

, p. 2430 - 2433 (1997)

Modification of the non-nucleoside inhibitor of HIV-1 reverse transcriptase nevirapine (Viramune) by incorporation of a 2-indolyl substituent confers activity against several mutant forms of the enzyme.

Synthesis of selenium-containing biindolyls and their Diels–Alder reaction toward the synthesis of heteroannulated [a]- and [c]-carbazoles

Wang, Ruei-Yu,Kao, Wei-Ting,Shih, Tzenge-Lien

, p. 829 - 837 (2020)

We reported the first syntheses of 2- and 3-(2-(benzo[b]selenophen-2-yl)-indoles and their Diels–Alder reactions to furnish six unique annulated benzoselenphene carbazoles. This facile route can be used to synthesize selenium-containing biindolyl derivati

INDOLE DERIVATIVES AND USES THEREOF FOR TREATING A CANCER

-

Page/Page column 71-72; 80; 88; 145, (2022/02/06)

The present invention relates to indole derivatives of formula (I') as CK2 inhibitor and pharmaceutical compositions comprising the same. The present invention further relates to the use of such compounds of formula (I) for use for preventing and/or treating a cancer.

Tricepyridinium-inspired QACs yield potent antimicrobials and provide insight into QAC resistance

Garrison, Michelle A.,Mahoney, Andrew R.,Wuest, William M.

supporting information, p. 463 - 466 (2020/10/19)

Quaternary ammonium compounds (QACs) comprise a large class of surfactants, consumer products, and disinfectants. The recently-isolated QAC natural product tricepyridinium bromide displays potent inhibitory activity against S. aureus but due to its unique structure, its mechanism of action remains unclear. A concise synthetic route to access tricepyridinium analogs was thus designed and four N-alkyl compounds were generated in addition to the natural product. Biological analysis of these compounds revealed that they display remarkable selectivity towards clinically-relevant Gram-positive bacteria exceeding that of commercially-available QACs such as cetylpyridinium chloride (CPC) and benzalkonium chloride (BAC) while having little to no hemolytic activity. Molecular modeling studies revealed that tricepyridinium and shorter-chain N-alkyl analogs may preferentially bind to the QacR transcription factor leading to potential activation of the QAC resistance pathway found in MRSA; however, our newly synthesized analogs are able to overcome this liability.

Small-molecule anti-HIV-1 agents based on HIV-1 capsid proteins

Kobayakawa, Takuya,Yokoyama, Masaru,Tsuji, Kohei,Fujino, Masayuki,Kurakami, Masaki,Boku, Sayaka,Nakayama, Miyuki,Kaneko, Moemi,Ohashi, Nami,Kotani, Osamu,Murakami, Tsutomu,Sato, Hironori,Tamamura, Hirokazu

, p. 1 - 14 (2021/02/06)

The capsid of human immunodeficiency virus type 1 (HIV-1) is a shell that encloses viral RNA and is highly conserved among many strains of the virus. It forms a conical structure by assembling oligomers of capsid (CA) proteins. CA dysfunction is expected to be an important target of suppression of HIV-1 replication, and it is important to understand a new mechanism that could lead to the CA dysfunction. A drug targeting CA however, has not been developed to date. Hydrophobic interactions between two CA molecules via Trp184/Met185 in CA were recently reported to be important for stabilization of the multimeric structure of CA. In the present study, a small molecule designed by in silico screening as a dipeptide mimic of Trp184 and Met185 in the interaction site, was synthesized and its significant anti-HIV-1 activity was confirmed. Structure activity relationship (SAR) studies of its derivatives were performed and provided results that are expected to be useful in the future design and development of novel anti-HIV agents targeting CA.

Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization

Xi, Yong-Kai,Zhang, Hongbin,Li, Rui-Xi,Kang, Shi-Yuan,Li, Jin,Li, Yan

supporting information, p. 3005 - 3009 (2019/02/07)

Cyclodipeptide 2,5-diketopiperazines (DKP) are privileged structural units present in drugs and natural alkaloids. This work reports a new method for the synthesis of biologically important DKP scaffolds based on an intramolecular nucleophilic α-addition of general amides towards an alkynamide system. The utility of this umpolung cyclization mediated by trimethyl phosphine and l-glutamic acid is highlighted by its application to the concise total syntheses of 6-methoxyspirotryprostatin B (the first total synthesis), spirotryprostatin A, and spirotryprostatin B.

BENZYLAMINE COMPOUND, AND PHARMACEUTICAL COMPOSITION AND ANTI-HIV AGENT THEREOF

-

Paragraph 0070; 0072-0073, (2020/05/13)

PROBLEM TO BE SOLVED: To provide: a novel benzylamine compound; and a pharmaceutical composition and an anti-HIV agent that are suitable for suppression of HIV activity. SOLUTION: The benzylamine compound is represented by the general formula (1) in the figure. In the general formula (1), R1 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; A represents an oxygen atom or sulfur atom; R2 represents a substituted or unsubstituted alkyl group; and n represents an integer from 1 to 10. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

H-bonding vs Protonation of Alkynes in Regioselective Hydroamination Reactions: A Glimpse into the Reactivity of Arylogous Ynolethers and Ynamines

Abe, Masahiro,Jean, Alexandre,Blanchet, Jér?me,Rouden, Jacques,Maddaluno, Jacques,De Paolis, Micha?l

, p. 15448 - 15475 (2019/11/29)

In this paper is described the competition and transition between hydrogen bonding and protonation of alkynes connected, on one side, to various aromatic rings and to chiral amino ester appendages on the other side. While the first mode of activation indu

Aerobic, Metal-Free, and Catalytic Dehydrogenative Coupling of Heterocycles: En Route to Hedgehog Signaling Pathway Inhibitors

Bering, Luis,Paulussen, Felix M.,Antonchick, Andrey P.

supporting information, p. 1978 - 1981 (2018/04/16)

The nitrosonium ion-catalyzed dehydrogenative coupling of heteroarenes under mild reaction conditions is reported. The developed method utilizes ambient molecular oxygen as a terminal oxidant, and only water is produced as byproduct. Dehydrogenative coupl

SELECTIVE ALPHA-7 NICOTINIC RECEPTOR AGONISTS AND METHODS FOR MAKING AND USING THEM

-

, (2018/09/16)

In alternative embodiments, provided are selective agonists having a high affinity for the alpha7 nicotinic acetylcholine receptor (α7 nAChR), assays for selectivity of nicotinic receptor subtype and ligand-gated ion channel subtype based on receptor occupation and response, behavioral assessments for reversing cognitive impairment after scopolamine treatment, enhancing memory retention over time, pharmaceutical compositions and formulations and devices comprising them, and methods for making and using them, including characterizing and efficiently assaying them for receptor subtype selectivity. In alternative embodiments, provided are substituted anti 1,2,3-triazoles compounds with high affinity, and selective binding, for the alpha7 nicotine acetylcholine receptor (α7 nAChR), as exemplified by 5-(1-(2-(Piperidin-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)-1H-indole (“IND1”), 5-((quinuclid-3-yl)-1H-1,2,3-triazol-4-yl)-1H-indole (“IND8”) and 3-(4-hydroxyphenyl-1,2,3-triazol-1-yl) quinuclidine (“QND8”). In alternative embodiments, provided are products of manufacture such as pumps, devices, syringes and the like comprising a compound, pharmaceutical composition or formulation as provided herein.

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