5'-bromospiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one

Base Information

• Chemical Name: 5'-bromospiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one
• CAS No.: 75822-54-7
• Molecular Formula: C10H8 Br N O3
• Molecular Weight: 270.082
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40369744
• Nikkaji Number: J2.545.335B
• Wikidata: Q82157039
• ChEMBL ID: CHEMBL6720
• Mol file: 75822-54-7.mol

Synonyms:75822-54-7;5'-bromospiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one;5'-Bromospiro[[1,3]dioxolane-2,3'-indolin]-2'-one;5'-bromospiro[1,3-dioxolane-2,3'-1H-indole]-2'-one;MFCD00097597;5'-bromo-1',2'-dihydrospiro[1,3-dioxolane-2,3'-indole]-2'-one;5//'-Bromospiro[1,3-dioxolane-2,3//'-1H-indole]-2//'-one;5-Bromoisatin 3-(ethylene acetal);Maybridge1_007236;CHEMBL6720;Oprea1_430087;Oprea1_713929;MLS001143353;SCHEMBL9097528;HMS562A20;DTXSID40369744;GQAJPVMAVMEQQJ-UHFFFAOYSA-N;HMS2807G03;AC6768;STL483118;AKOS000268276;CCG-249176;MS-0751;SMR000473188;SY248189;CS-0312736;A853671;AG-690/12870161;5-Bromospiro[indoline-3,2'-[1,3]dioxolan]-2-one;5-Bromospiro[1,3-dioxolane-2,3-indol]-2(1H)-one;5-Bromospiro[indoline-3,2'-[1,3]dioxolane]-2-one;5'-Bromospiro[1,3-dioxolane-2,3'-indolin]-2'(1'H)-one;5-BROMOSPIRO[[1,3]DIOXOLANE-2,3-INDOLIN]-2-ONE;5/'-Bromospiro[1,3-dioxolane-2,3/'-1H-indole]-2/'-one;5''-BROMOSPIRO[1,3-DIOXOLANE-2,3''-INDOL]-2''(1''H)-ONE;5'-bromo-1',3'-dihydrospiro[1,3-dioxolane-2,3'-(2'H)-indole]-2'-one;5 inverted exclamation mark -Bromospiro[[1,3]dioxolane-2,3 inverted exclamation mark -indolin]-2 inverted exclamation mark -one

Chemical Property of 5'-bromospiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one

Chemical Property:

• Melting Point: 191-192 °C
• Boiling Point: 451.2±45.0 °C(Predicted)
• PKA: 12.97±0.20(Predicted)
• Flash Point: 226.7oC
• PSA: 47.56000
• Density: 1.81±0.1 g/cm3(Predicted)
• LogP: 1.73880
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 268.96876
• Heavy Atom Count: 15
• Complexity: 290

Purity/Quality:

99% ^*data from raw suppliers

3-(1',3'-DIOXOLYNYL)-5-BROMO-1,3-DIHYDRO-2H-INDOL-2-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2(O1)C3=C(C=CC(=C3)Br)NC2=O

Technology Process of 5'-bromospiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one

There total 6 articles about 5'-bromospiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

5-Bromo-1H-indole-2,3-dione (87-48-9) + ethylene glycol (107-21-1) → 5’-bromo-1‘,2’-dihydrospiro[1,3-dioxolane-2,3’-indole]-2’-one (75822-54-7)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 5h; Reflux;

Reference yield:

5-Bromo-1H-indole-2,3-dione (87-48-9) + 2-bromoethanol (540-51-2) → 5’-bromo-1‘,2’-dihydrospiro[1,3-dioxolane-2,3’-indole]-2’-one (75822-54-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 80 ℃; for 6h;

DOI:10.1039/c9ra08776a

Reference yield:

4-bromo-aniline (106-40-1) → 5’-bromo-1‘,2’-dihydrospiro[1,3-dioxolane-2,3’-indole]-2’-one (75822-54-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 2 h / 85 °C

2: sulfuric acid / 0.5 h / 60 - 90 °C

3: toluene-4-sulfonic acid / toluene / 5 h / 130 °C

With hydrogenchloride; sulfuric acid; hydroxylamine hydrochloride; toluene-4-sulfonic acid; sodium sulfate; In water; toluene;

DOI:10.1016/j.bmc.2012.06.024

upstream raw materials:

5-Bromo-1H-indole-2,3-dione

ethylene glycol

4-bromo-aniline

N-(4-bromophenyl)-2-(hydroxyimino) acetamide

Refernces

• 1、 Burke, Anthony J.,Erxleben, Andrea,Marques, Carolina S.,McArdle, Patrick. "Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction". supporting information. . Retrieved 2020/06/30.
• 2、 Babu, K. Naresh,Kinthada, Lakshmana K.,Pratim Das, Partha,Bisai, Alakesh. "Cu(ii)-: TBu-PHOX catalyzed enantioselective malonate addition onto 3-hydroxy 2-oxindoles: Application in the synthesis of dimeric pyrroloindoline alkaloids". supporting information. p. 7963 - 7966. Retrieved 2018/07/25.