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1-BOC-2-CHLORO-3-FORMYL-INDOLE is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 180922-71-8 Structure
  • Basic information

    1. Product Name: 1-BOC-2-CHLORO-3-FORMYL-INDOLE
    2. Synonyms: 1-BOC-2-CHLORO-3-FORMYL-INDOLE
    3. CAS NO:180922-71-8
    4. Molecular Formula: C14H14ClNO3
    5. Molecular Weight: 279.72
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 180922-71-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 1-BOC-2-CHLORO-3-FORMYL-INDOLE(CAS DataBase Reference)
    10. NIST Chemistry Reference: 1-BOC-2-CHLORO-3-FORMYL-INDOLE(180922-71-8)
    11. EPA Substance Registry System: 1-BOC-2-CHLORO-3-FORMYL-INDOLE(180922-71-8)
  • 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: 180922-71-8(Hazardous Substances Data)

180922-71-8 Usage

Type of compound

Chemical compound

Derivative of

Indole (bicyclic heterocyclic organic compound)

Formyl group

Attached to the 3rd position of the indole ring

Chlorine atom

Attached to the 2nd position of the indole ring

BOC protecting group

Attached to the 1st position (tert-butoxycarbonyl)

Reactivity

Versatile, can participate in various chemical reactions

Applications

a. Intermediate in the synthesis of pharmaceuticals
b. Intermediate in the synthesis of other organic compounds

Usage

Commonly used in the field of medicinal chemistry and drug development

Check Digit Verification of cas no

The CAS Registry Mumber 180922-71-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,0,9,2 and 2 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 180922-71:
(8*1)+(7*8)+(6*0)+(5*9)+(4*2)+(3*2)+(2*7)+(1*1)=138
138 % 10 = 8
So 180922-71-8 is a valid CAS Registry Number.

180922-71-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butyl 2-chloro-3-formylindole-1-carboxylate

1.2 Other means of identification

Product number -
Other names 1-Boc-2-Chloro-3-formyl-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:180922-71-8 SDS

180922-71-8Relevant articles and documents

Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to access dihydrothiopyran-fused benzosulfolane skeletons bearing three contiguous stereocenters

Yang, Lei,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Yuan, Wei-Cheng

, p. 12363 - 12366 (2020)

The first organocatalytic diastereo- and enantioselective tandem sulfa-Michael/aldol reaction of 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes with benzo[b]thiophene sulfones was developed. With multiple hydrogen-bonding thiourea as a catalyst, a wide range of polycyclic dihydrothiopyran-fused benzosulfolanes were smoothly obtained with excellent results (up to 99% yield, 420 : 1 dr and 99% ee) under mild reaction conditions.

A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes

Yang, Lei,Zhou, Shun,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng

supporting information, p. 3678 - 3686 (2021/05/05)

The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.

Method for simply and efficiently synthesizing caulerpin

-

Paragraph 0043; 0045, (2018/07/30)

The invention belongs to the field of organic chemical synthesis and discloses a method for simply and efficiently synthesizing caulerpin. The method comprises the following steps: by taking 2-indolone as a raw material, firstly, performing halogenated acylation on the 2-indolone, protecting amino on indole, performing nucleophilic substitution at a site 2 of the amino, connecting malonic acid dimethyl, further performing decarboxylation and protection group removal so as to obtain 3-formyl-2-indole methyl acetate, and finally performing cyclization between two molecules, so as to obtain caulerpin. Compared with a disclosed method for synthesizing caulerpin, the method disclosed by the invention is simple in synthesis process, low in raw material cost, gentle in reaction condition, high inproduct purity, high in yield and easy in industrialization, and has a very high medical value and a wide market prospect.

Synthesis of an azabicyclic framework towards (±)-actinophyllic acid

Mortimer, Danny,Whiting, Matthew,Harrity, Joseph P.A.,Jones, Simon,Coldham, Iain

, p. 1255 - 1257 (2014/02/14)

Lewis acid mediated intramolecular Mannich reaction between an azocinone and a 3-formylindole was investigated as part of a study towards the synthesis of actinophyllic acid. The intramolecular Mannich reaction resulted in a single diastereomer of the 1-azabicyclo[4.2.1]nonan-5-one core framework, although single crystal X-ray structure analysis revealed that this had the undesired stereochemistry in comparison with the natural product.

The tertiary amino effect: An efficient method for the synthesis of α-Carbolines

Majumder, Swarup,Bhuyan, Pulak J.

experimental part, p. 173 - 176 (2011/03/22)

Functionalized annelated α-Carbolines have been synthesized from oxindole following a tertiary amino effect reaction strategy. Georg Thieme Verlag Stuttgart New York.

An efficient one-pot, three-component reaction: Synthesis of complex-annelated α-carbolines via an intramolecular [3+2]-dipolar cycloaddition reaction

Majumder, Swarup,Bhuyan, Pulak J.

experimental part, p. 1547 - 1550 (2011/08/04)

Novel annelated α-carbolines have been synthesized from oxindole using three components in a one-pot procedure involving an intramolecular [3+2]-dipolar cycloaddition reaction of azides to nitriles. Georg Thieme Verlag Stuttgart ? New York.

Control of competing N-H insertion and Wolff rearrangement in dirhodium(II)-catalyzed reactions of 3-indolyl diazoketoesters. Synthesis of a potential precursor to the marine 5-(3-indolyl)oxazole martefragin A

Davies, James R.,Kane, Peter D.,Moody, Christopher J.,Slawin, Alexandra M. Z.

, p. 5840 - 5851 (2007/10/03)

Dirhodium(II)-catalyzed reaction of 3-indolyl α-diazo-β- ketoester 25 in the presence of hexanamide results in competing metal carbene N-H insertion and Wolff rearrangement. The corresponding phenyl diazoketoester 32, on the other hand, gives only the product of N-H insertion, suggesting that the indole moiety is more prone to 1,2-rearrangement. The competing processes were investigated in a range of 3-indolyl α-diazo-β-ketoesters (36, 38, 40, 44); these studies established that the Wolff rearrangement could be effectively suppressed by the presence of a strong electron-withdrawing group on the indole nitrogen. Dirhodium(II) catalysts were also more effective than copper or Lewis acid catalysts in favoring the insertion process. The products of N-H insertion, the ketoamides (26, 47, 49, 51, 53), were readily cyclodehydrated to the corresponding 5-(3-indolyl)-oxazoles. The N-H insertion/cyclodehydration methodology was used in a formal synthesis of the marine natural product martefragin A. Thus the N-Boc homoisoleucine amide 23, prepared by asymmetric hydrogenation of a dehydro amino acid, underwent N-H insertion with the rhodium carbene derived from the N-nosyl indolyl diazoester 40, followed by cyclodehydration and deprotection to give the 5-(3-indolyl)oxazole martefragin A precursor 75.

A new approach to the synthesis of rare thiazino[6,5-b]indol-4-one derivatives. First total synthesis of the indole phytoalexin cyclobrassinon

Kutschy, Peter,Suchy, Mojmír,Andreani, Aldo,Dzurilla, Milan,Ková?ik, Vladimír,Alf?ldi, Juraj,Rossi, Maddalena,Gramatová, Mária

, p. 9029 - 9039 (2007/10/03)

The first synthesis of the indole phytoalexin cyclobrassinon and some of its analogues, possessing a thiazino[6,5-b]indol-4-one tricyclic ring system was performed starting from 1-substitued 2-chloroindole-3-carboxaldehydes. The route employed the intramolecular Et3N-mediated or photochemical nucleophilic substitution of a chlorine atom in the 2-position of the indole ring with a sulfur atom as a key step. Examination of biological activity against the selected tumor cell lines, bacteria and fungi revealed no expressive activity of synthesized compounds.

1,3-Thiazino[6,5-b]indol-4-one derivatives. The first synthesis of indole phytoalexin cyclobrassinon

Suchy, Mojmír,Kutschy, Peter,Dzurilla, Milan,Ková?ik, Vladimír,Andreani, Aldo,Alf?ldi, Juraj

, p. 6961 - 6963 (2007/10/03)

The first synthesis of indole phytoalexin cyclobrassinon in six steps, in 12% overall yield and some of its analogues, possessing a 1,3-thiazino[6,5-b]indol-4-one tricyclic ring system was performed, starting from 2-chloroindole-3-carboxaldehyde and employing the intramolecular Et3N-mediated nucleophilic substitution of a chlorine atom in the 2-position of an indole ring with sulfur as a key step.

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