10489-28-8

Basic information

• Product Name: 2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE
• Synonyms: 2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE;2,2-dimethyl-2,3-dihydro-1H-inden-1-one;1H-Inden-1-one, 2,3-dihydro-2,2-dimethyl-
• CAS NO: 10489-28-8
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21
• Mol File: 10489-28-8.mol

Chemical Properties

• Melting Point: 44-45 °C
• Boiling Point: 240.5 °C at 760 mmHg
• Flash Point: 94.3 °C
• Appearance: /
• Density: 1.044 g/cm³
• Vapor Pressure: 0.0379mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: 2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE(10489-28-8)
• EPA Substance Registry System: 2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE(10489-28-8)

Safety Data

• Hazardous Substances Data: 10489-28-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE is used as an intermediate in the synthesis of various organic compounds. Its unique chemical structure allows it to be a versatile building block for the creation of a wide range of molecules with diverse properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE is used as a key component in the development of new drugs. Its chemical properties make it a valuable candidate for the synthesis of novel therapeutic agents, potentially leading to the discovery of new medications with improved efficacy and reduced side effects.
Used in Agrochemical Industry:
2,3-DIHYDRO-2,2-DIMETHYLINDEN-1-ONE is used as a starting material in the synthesis of experimental rice herbicides, such as 2,2-dimethyl-1-(4-methylthio-5-pyrimidinyl)indane. Its incorporation into these herbicides contributes to their effectiveness in controlling weed growth, ultimately leading to increased crop yields and improved agricultural productivity.

InChI:InChI=1/C11H12O/c1-11(2)7-8-5-3-4-6-9(8)10(11)12/h3-6H,7H2,1-2H3

Upstream product

• 83-33-0 inden-1-one 
• 74-88-4 methyl iodide 
• 62931-24-2 2,2-dimethyl-3-phenylpropanoyl chloride 
• 5669-14-7 2,2-dimethyl-3-phenylpropanoic acid 
• 201230-82-2 carbon monoxide 
• 515-40-2 neophyl chloride 
• 1754-74-1 2-chloro-2-methyl-1-phenylpropane 
• 563-47-3 3-Chloro-2-methylpropene 
• 71-43-2 benzene 
• 17496-14-9 2,3-dihydro-2-methyl-1H-inden-1-one 
• 594-37-6 1,2-dichloro-2-methylpropane 
• 7581-97-7 2,3-dichlorobutane 
• 5408-86-6 2,3-dibromobutane 
• 4279-22-5 2,2-dichlorobutane 

Downstream Products

• 101518-61-0 2,2-dimethyl-3-phenylpropanamide 
• 78926-54-2 2,2-dimethylindan-1-one p-toluenesulphonylhydrazone 
• 372967-84-5 2,3-dihydro-2,2-dimethyl-1-[[2-(phenylethynyl)phenyl]ethynyl]-1H-inden-1-ol 
• 897655-92-4 1-[[2-[(2,6-dibromophenyl)ethynyl]phenyl]ethynyl]-2,3-dihydro-2,2-dimethyl-1H-inden-1-ol 
• 730962-98-8 2-ethyl-2-hydroxy-3,3-dimethyl-1-tetralone 
• 1026161-57-8 acetic acid 2,2-dimethyl-1-(2-phenylethynyl-phenylethynyl)-indan-1-yl ester 
• 131365-85-0 C₁₈H₁₉N₃O 
• 1335195-74-8 1-(3,5-dimethylbenzyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-ol 
• 1335195-73-7 1-(3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-ol 
• 1335195-75-9 1-mesityl-2,2-dimethyl-2,3-dihydro-1H-inden-1-ol 
• 124688-26-2 2,2-Dimethyl-1-(2-phenylsulfanyl-ethylsulfanyl)-indan 
• 372967-92-5 2,2-dimethyl-1-(2-phenylethynyl-phenylethynyl)-indan 
• 20836-11-7 2,3-dihydro-2,2-dimethyl-1H-indene 

Relevant articles and documents

Radical cyclisation onto nitriles

Iminyl radicals, generated by 5-exo cyclisation of alkyl, vinyl and aryl C-centred radicals onto nitriles, undergo β-scission (nitrile translocation), reduction or tandem cyclisation onto alkenes depending on the nature of the α-substituent. 5-exo Cyclisations of aryl radicals onto nitriles undergo nitrile translocation when the α-substituent is CN, CO2R, SO2Ph or CONMe2. The rate of translocation is faster than 5- or 6-exo cyclisation onto alkenes or 1,5-hydrogen abstraction of allylic hydrogens. When the α-substituents are alkyl, the intermediate iminyl radicals do not undergo nitrile translocation. (C) 2000 Elsevier Science Ltd.

The generation of aryl anions by double electron transfer to aryl iodides from a neutral ground-state organic super-electron donor

(Chemical Equation Presented) It takes two to cyclize: Aryl halides are reduced to aryl anions by double electron transfer from the neutral ground-state electron donor 1 (see scheme), as shown by the formation of a cyclic ketone (2). The reduced compound (3) is also formed. Calculations show that the loss of two electrons from 1 is both thermodynamically and kinetically viable and generates a more planar resonance-stabilized structure.

One-pot reduction of aryl iodides using 4-DMAP methiodide salt

An efficient one-pot procedure is described for the reduction of aryl iodides to aryl anions using a structurally simple bis-pyridinylidene electron donor, prepared in situ by treating 4-DMAP methiodide salt with base. The results show (i) that pyridinylidene carbenes can be easily used for intermolecular C-C bond formation, (ii) that bis-pyridinylidenes demonstrate superior robustness compared to electron-donor systems based on bis-imidazolylidenes, and (iii) that electron-donor strength is enhanced in the simplified DMAP-based donor. Deuterated analogues of this donor also provide mechanistic information on the source of protons when the aryl anions are quenched in situ. Georg Thieme Verlag Stuttgart.

Process chemistry related to the experimental rice herbicide 2,2-dimethyl-1-(4-methylthio-5-pyrimidinyl)indane

Two concise syntheses of the experimental rice herbicide 2,2-dimethyl-1-(4-methylthio-5-pyrimidinyl)indane are reported. The initial synthesis relies on a low-temperature addition of 5-lithio-4-methylthiopyrimidine to 2,2-dimethyl-1-indanone to construct the pyrimidinylindane system. Process improvements to this route are described and resulted in the preparation of 90 kg of the title compound on pilot plant scale. Economics dictated the need to identify a new synthetic route which utilized inexpensive raw materials. Detailed herein is the initial discovery of a new route which features a novel combination of dissolving metal reduction/formylation/cyclization to construct the requisite pyrimidine ring. Process improvements to this chemistry have allowed us to deliver an appropriately substituted pyrimidinylindane in a minimal number of synthetic operations.

Sulfur-Based Intramolecular Hydrogen-Bond: Excited-State Hydrogen-Bond On/Off Switch with Dual Room-Temperature Phosphorescence

We report O-H-S hydrogen-bond (H-bond) formation and its excited-state intramolecular H-bond on/off reaction unveiled by room-temperature phosphorescence (RTP). In this seminal work, this phenomenon is demonstrated with 7-hydroxy-2,2-dimethyl-2,3-dihydro-1H-indene-1-thione (DM-7HIT), which possesses a strong polar (hydroxy)-dispersive (thione) type H-bond. Upon excitation, DM-7HIT exhibits anomalous dual RTP with maxima at 550 and 685 nm. This study found that the lowest lying excited state (S1) of DM-7HIT is a sulfur nonbonding (n) to π? transition, which undergoes O-H bond flipping from S1(nπ*) to the non-H-bonded S′1(nπ*) state, followed by intersystem crossing and internal conversion to populate the T′1(nπ*) state. Fast H-bond on/off switching then takes place between T′1(nπ*) and T1(nπ*), forming a pre-equilibrium that affords both the T′1(nπ*, 685 nm) and T1(nπ*, 550 nm) RTP. The generality of the sulfur H-bond on/off switching mechanism, dubbed a molecule wiper, was rigorously evaluated with a variety of other H-bonded thiones, and these results open a new chapter in the chemistry of hydrogen bonds.

Enantioselective Synthesis of Indanes with a Quaternary Stereocenter via Diastereoselective C(sp3)-H Functionalization

A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C-H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey-Bakshi-Shibata (CBS) reduction of indanone derivatives. The subsequent diastereospecific and regioselective rhodium-catalyzed silylation of the methyl C-H bond led to indane derivatives with quaternary centers. This strategy was further applied in syntheses of (nor)illudalane and botryane sesquiterpenoids.

Nickel-Catalyzed Domino Heck-Type Reactions Using Methyl Esters as Cross-Coupling Electrophiles

While esters are frequently used as traditional electrophiles in substitution chemistry, their application in cross-coupling chemistry is still in its infancy. This work demonstrates that methyl esters can be used as coupling electrophiles in Ni-catalyzed Heck-type reactions through the challenging cleavage of the C(acyl)?O bond under relatively mild reaction conditions at either 80 or 100 °C. With the σ-NiII intermediate generated from the insertion of acyl NiII species into the tethered C=C bond, carbonyl-retentive products were formed by domino Heck/Suzuki–Miyaura coupling and Heck/reduction pathways when organoboron and mild hydride nucleophiles are used.

CXCR3 RECEPTOR AGONISTS

Compounds are provided having the structure of the following Formula I: where R, R1, R2, R3a and R3b are as defined herein. Pharmaceutical compositions comprising such compounds, as well as methods related to their manufacture and use, are also provided.

Potent Inhibitors of Plasmodial Serine Hydroxymethyltransferase (SHMT) Featuring a Spirocyclic Scaffold

With the discovery that serine hydroxymethyltransferase (SHMT) is a druggable target for antimalarials, the aim of this study was to design novel inhibitors of this key enzyme in the folate biosynthesis cycle. Herein, 19 novel spirocyclic ligands based on

Silylative Kinetic Resolution of Racemic 1-Indanol Derivatives Catalyzed by Chiral Guanidine

Efficient kinetic resolution of racemic 1-indanol derivatives was achieved using triphenylchlorosilane by asymmetric silylation in the presence of chiral guanidine catalysts. The chiral guanidine catalyst (R,R)-N-(1-(β-naphthyl)ethyl)benzoguanidine was found to be highly efficient as only 0.5 mol % catalyst loading was sufficient to catalyze the reaction of various substrates with appropriate conversion and high s-values (up to 89). This catalyst system was successfully applied to the gram-scale silylative kinetic resolution of racemic 1-indanol with high selectivity.