Isochroman

Base Information

• Chemical Name: Isochroman
• CAS No.: 493-05-0
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 29329990
• European Community (EC) Number: 207-774-0
• NSC Number: 63362
• UNII: 2CA7RAZ2PM
• DSSTox Substance ID: DTXSID50197757
• Nikkaji Number: J6.065H
• Wikidata: Q27115605
• Metabolomics Workbench ID: 54877
• Mol file: 493-05-0.mol

Synonyms:Isochroman;493-05-0;Isochromane;3,4-dihydro-1H-2-benzopyran;3,4-Dihydro-1H-isochromene;1H-2-Benzopyran, 3,4-dihydro-;2CA7RAZ2PM;EINECS 207-774-0;MFCD00006913;NSC-63362;3,4-dihydro-1H-benzo[c]pyran;NSC63362;Isochroman, 99%;UNII-2CA7RAZ2PM;SCHEMBL8262;1H-2-Benzopyran,4-dihydro-;3,4-Dihydro-1H-2-benzopyrane;3,4-Dihydro-1H-isochromene #;CHEBI:33225;DTXSID50197757;NSC 63362;AKOS009157107;AC-5320;AM85788;CS-W002017;PS-4588;SY018228;1,2,3,4-TETRAHYDROBENZO(C)PYRAN;3,4-Dihydro-1H-2-benzopyran;isochromane;FT-0614301;I0514;EN300-52549;A871817;Q27115605;Z756090080

Chemical Property of Isochroman

Chemical Property:

• Appearance/Colour: clear colorless to yellowish liquid
• Vapor Pressure: 0.112mmHg at 25°C
• Melting Point: 4.35°C
• Refractive Index: n20/D 1.545(lit.)
• Boiling Point: 228.3 °C at 760 mmHg
• Flash Point: 65.6 °C
• PSA: 9.23000
• Density: 1.053 g/cm³
• LogP: 1.75930
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 111

Purity/Quality:

99% ^*data from raw suppliers

Isochroman ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1COCC2=CC=CC=C21
• Uses: Isochroman is a mycotoxins that inhibits the growth of Bacillus thuringiensis and causes morphological abnormalities in the cells.

Technology Process of Isochroman

There total 95 articles about Isochroman 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%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-phenylethanol (60-12-8) → isochromane (493-05-0)

Guidance literature:

With hydrogenchloride; In water; at 36 ℃; for 20h;

Reference yield: 84.0%

1-(2-methoxyethoxy)methoxy-2-phenylethane (81616-92-4) → isochromane (493-05-0)

Guidance literature:

titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)96149-5

Reference yield: 81.0%

2-(2-hydroxyethyl)benzyl alcohol (6346-00-5) → isochromane (493-05-0)

Guidance literature:

With [(C₆H₆)(PCy₃)(CO)RuH]⁺*BF₄^?; In chlorobenzene; at 50 ℃; for 3h;

DOI:10.1021/cs5012537

upstream raw materials:

1H-isochromene

formaldehyd

2-phenylethanol

2-(2-hydroxyethyl)benzyl alcohol

Downstream raw materials:

1-Bromoisochromane

3,4-Dihydro-1-phenyl-1H-benzopyran

2-(2-chloromethylphenyl)-ethanol acetate

2-phenyl-1,2,3,4-tetrahydroisoquinoline

Refernces

Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent

10.1021/acs.joc.5b01136

The research focuses on reductive lithiation, a method for preparing organolithium compounds, typically involving the use of aromatic radical-anions or lithium metal in the presence of an aromatic electron transfer catalyst. The study explores the reductive lithiation of alkyl phenyl thioethers, alkyl chlorides, acrolein diethyl acetal, and isochroman using lithium dispersion as a source of lithium metal, absent of an electron transfer agent. The experiments involved various substrates with different alkyl group sizes to investigate the steric effect on the reaction's efficiency and selectivity. The analyses included DFT calculations to understand the bond dissociation energies and adsorption geometries on the lithium surface, as well as traditional organic chemistry techniques such as NMR spectroscopy and mass spectrometry to characterize the products and monitor the progress of the reactions. The results showed that lithium dispersion could achieve reductive lithiation efficiently and that the reactivity order was reversed when comparing the presence or absence of an electron transfer agent, with smaller alkyl groups exhibiting greater reactivity. This discovery challenges the prevailing understanding of reductive lithiation and highlights the significance of steric effects in these reactions.