1,1-Dimethylindan , CAS No.4912-92-9

CAS: 4912-92-9 Cat. No.: D1343494 Formula: C₁₁H₁₄ Peso molecolare: 146.23

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CC1(CCC2=CC=CC=C21)C
• IUPAC Name: 3,3-dimethyl-1,2-dihydroindene
• InChIKey: UTTMVTDJCFSOFF-UHFFFAOYSA-N
• INCHI: 1S/C11H14/c1-11(2)8-7-9-5-3-4-6-10(9)11/h3-6H,7-8H2,1-2H3
• Peso molecolare: 146.23

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Indanes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Indanes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Indanes
• Alternative Parents: Aromatic hydrocarbons Polycyclic hydrocarbons Unsaturated hydrocarbons
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Indane - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as indanes. These are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 146.230 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 146.11 Da
• Monoisotopic Mass: 146.11 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 146.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

• Not applicable. No tested bioassay protocols (e.g., WB, IHC, IF, FC) are relevant to this small-molecule hydrocarbon.
• For chemical applications, refer to the Reaction & Applications and Reaction Conditions sections for general laboratory guidance.

Biological Roles

• This product is a hydrophobic aromatic hydrocarbon used as a synthetic/building-block substrate. It does not have a known endogenous biological role.
• Literature context (general):
  • Alkylated indanes are occasionally used as hydrophobic probe molecules or calibration standards in analytical chemistry (e.g., GC retention indexing) and as model substrates in mechanistic studies of hydrocarbon oxidation.
  • Due to its nonpolar nature and absence of functional groups, specific biochemical interactions are expected to be minimal, aside from nonspecific partitioning into lipid phases (general property of hydrophobic aromatics).

Note: No clinical or biomedical claims are made. For research use only (as stated in Product Data).

Buffer Applications

• Not typically applicable. 1,1-Dimethylindan is a nonpolar hydrocarbon and does not function as a buffering agent or pH control component.
• Practical note: When used in aqueous systems (e.g., biphasic oxidations), buffers may be employed for the aqueous phase, but the compound itself resides in the organic phase. Choose buffers that are compatible with chosen oxidants/catalysts (e.g., phosphate or acetate under aerobic oxidation), and ensure adequate phase transfer if needed.

Green Alternatives

While 1,1-dimethylindan itself is a hydrocarbon substrate, greener choices concern the reaction medium and oxidants/halogenation methods used with it.

• Greener solvent options (general literature guidance):

  • Replace chlorinated solvents (DCM, CHCl3, CCl4) with CPME, 2-MeTHF, toluene, or ethyl acetate when compatible with the catalyst and mechanism.
  • For high-temp processes, consider isododecane or anisole to reduce VOC volatility and flammability risk versus hexanes.

• Greener oxidants/halogenation:

  • Prefer O2/air or H2O2/TBHP in water-reduced systems over stoichiometric Cr(VI)/Mn(VII) oxidants. Use Co/Mn/Br aerobic systems or TEMPO/copper catalysis where applicable.
  • Use photoredox/NBS in acetonitrile or solvent-free conditions instead of NBS/CCl4 for benzylic bromination.

• Energy and safety:

  • Apply flow photochemistry for radical reactions to improve mass/heat transfer and minimize solvent volume.
  • Employ mechanochemistry (ball milling) for selected EAS or metalation steps to reduce solvent use (case-dependent).

Comparison snapshot (general):

• DCM → CPME/2-MeTHF: lower chlorinated waste; similar solvency; watch peroxide formation in ethers (test/mitigate).
• CCl4 (radical bromination) → MeCN or solvent-free photoredox: eliminates ozone-depleting substance; maintains selectivity with modern catalysts.
• Cr(VI) oxidants → O2/TBHP catalysis: reduces toxic waste; may require catalyst optimization for conversion/selectivity.

Pharmaceutical Uses

• No pharmacopeial excipient status or formulation role is indicated for this item.
• General, non-clinical context:
  • Alkylbenzenoid hydrocarbons can be used as process probes, impurity reference standards, or reaction solvents/models in development labs, but 1,1-dimethylindan is primarily a research chemical substrate.

Note: For research use only; not for human or veterinary use. No therapeutic claims are made.

Physical Properties

• Item-specific from Product Data:

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Literature values and general characteristics (for reference; not item specifications):

  • Aggregate state: typically a colorless, hydrophobic liquid at ambient conditions for C11 indanes.
  • Molecular formula: C11H14 (literature)
  • Molecular weight: ~146.23 g/mol (literature)
  • Boiling point: commonly reported for 1,1-dimethylindane in the approximate range of 200–220 °C at 1 atm (literature; consult primary sources for exact values).
  • Melting point: often below 0 °C for similar indane derivatives (literature; exact value should be verified).
  • Density (20–25 °C): expected around 0.85–0.90 g/mL for comparable alkyl indanes (literature; verify experimentally).
  • Refractive index (nD20): typically ~1.49–1.52 for related arylcycloalkanes (literature guidance only).
  • Solubility: practically insoluble in water; miscible with nonpolar organic solvents (hexanes, toluene, diethyl ether) and soluble in moderately polar aprotic media (THF, dichloromethane) (literature).
  • LogP: expected high (>>3) due to hydrocarbon nature (literature estimates for indane derivatives).

Notes:

• Do not treat the above as item specifications. For rigorous experimental planning, confirm with primary literature data or measure under your lab conditions.

Quality and Grades

• Item-specific from Product Data:

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on interpretation (general):

  • For hydrocarbon building blocks, grades may distinguish between general laboratory grade, ≥95–99% purity, GC assay, or spectral grade (low UV background). In the absence of a declared grade, verify impurity profile (e.g., GC area %, residual solvents, aromatic isomers) on the accompanying CoA.
  • If low-UV absorbance is needed (e.g., as a GC/LC system suitability standard), request HPLC/GC-grade material or confirm UV cutoff/background on the CoA.
  • Stabilizers: Not typically required for saturated indane derivatives; no stabilizer is listed for this item. If your application involves photolysis or radical chemistry screening, confirm absence of inhibitors.
  • Batch-to-batch quality: For kinetic or mechanistic studies (C–H activation, autoxidation), even trace benzylic oxidation products can bias results. Consider brief passage through neutral alumina or distillation under reduced pressure to remove peroxides/oxidation byproducts, verifying by GC/MS or 1H NMR.

Reaction and Applications

• Representative research uses (general; expand based on indane chemistry):

  • Model substrate for studying benzylic C–H functionalization where the 1,1-gem-dimethyl group blocks the bridgehead (C-1) and biases reactivity to the 2- and 3-positions (benzylic to the aromatic ring or on the ring itself).
  • Electrophilic aromatic substitution (EAS): nitration, sulfonation, halogenation, Friedel–Crafts acylation/alkylation on the benzene ring. The electron-donating inductive effect of the tert-alkyl substituent typically directs to ortho/para positions relative to the fused junction.
  • Radical benzylic halogenation: NBS or NCS under photolysis or AIBN/benzoyl peroxide initiation targeting benzylic methylenes (not the quaternary C-1). Useful to access benzyl halides for further substitution/elimination.
  • Benzylic oxidation: catalytic Co/Mn/Br with O2 or TBHP; KMnO4/CrO3 historically; modern metal–organic or organocatalytic aerobic methods convert to ketones/aldehydes on the side chain (e.g., 2-oxo derivatives).
  • Dehydrogenation to indenes: Pd/C or Pt/C at elevated temperature or with DDQ to generate 1,1-dimethylindene.
  • Directed lithiation/metalation on the arene ring under strong base (s-BuLi/TMEDA) followed by electrophile trapping (requires careful temperature control to avoid ring opening).

• Practical tips:

  • Dry, oxygen-free conditions improve selectivity in radical/catalytic reactions; sparge with N2/Ar and use inhibitor-free solvents.
  • Monitor by GC-FID/MS; characteristic benzylic signals in 1H NMR assist in positional analysis after functionalization.

Reaction Conditions

General literature guidance (for planning; not item specifications):

• Electrophilic aromatic substitution (EAS):

  • Halogenation: Br2/FeBr3 or NBS/H+; 0–25 °C in DCM or AcOH; monitor to suppress polyhalogenation.
  • Nitration: HNO3/H2SO4 (mixed acid) at 0–5 °C; quench into ice; work up to avoid oxidation of benzylic sites.
  • Friedel–Crafts acylation: RCOCl/AlCl3 (1.1–1.5 equiv AlCl3), 0 °C to rt in DCM/CS2/nitrobenzene; typical times 1–6 h.

• Benzylic halogenation (radical):

  • NBS (1.1–1.3 equiv), AIBN (5–10 mol%) or hv (365 nm), solvent MeCN, toluene, or solvent-free; 25–80 °C or photochemical; 1–6 h. Avoid CCl4 on green chemistry grounds.

• Benzylic oxidation:

  • TBHP (70% aq or in decane, 2–4 equiv), Co(acac)2/Mn(acac)2 (1–5 mol% each), 60–90 °C in toluene or acetonitrile; O2/air sparging can enhance turnover. Typical 6–24 h.
  • Alternative: DDQ (1.2–2.0 equiv) in DCM or toluene, 0–25 °C, 1–4 h for dehydrogenation/oxidation to indenes/ketones (substrate dependent).

• Dehydrogenation to indenes:

  • Pd/C (5–10 wt%), 180–220 °C under inert or vacuum; or catalytic transfer dehydrogenation with DDQ at rt–reflux.

• Directed metalation:

  • s-BuLi (1.1–1.5 equiv) with TMEDA at −78 to −40 °C in THF or 2-MeTHF; quench with electrophiles (CO2, DMF, B(OMe)3). Stringent anhydrous/inert techniques required.

Notes:

• Regioselectivity should be verified by NMR/GC-MS. Reaction scales benefit from calorimetry due to exotherms under EAS and radical conditions.

Safety and Handling

• Item-specific from Product Data:

  • Storage conditions: Room temperature
  • Hazard information (signal word, H-statements, GHS classification, pictograms): Not specified for this item; refer to SDS.

• General safety considerations for alkylated indanes/hydrocarbons (literature/industry practice; consult SDS for authoritative guidance):

  • Likely to be a combustible/flammable liquid with narcotic effects at high vapor concentrations typical of aromatic hydrocarbons. Use away from ignition sources; ground/bond during transfer.
  • Ventilation: handle in a fume hood to avoid inhalation of vapors and to control exposure during heating or distillation.
  • PPE: safety glasses or goggles, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Avoid skin and eye contact and prolonged inhalation.
  • Incompatibilities: strong oxidizers (risk of exothermic reactions), strong electrophiles under Friedel–Crafts conditions (uncontrolled alkylation/acylation), and halogenating agents under radical conditions.
  • Peroxide formation: not an ether; peroxide formation is not a typical hazard. However, autoxidation at benzylic sites can occur upon prolonged air/heat exposure—keep containers tightly closed.
  • First aid (summary; defer to SDS): remove to fresh air after inhalation; rinse skin with soap/water upon contact; flush eyes with water for several minutes; seek medical attention if symptoms persist. In case of fire: use dry chemical, CO2, or foam; avoid water jets that may spread burning liquid.

Solvent Selection

This product is a hydrocarbon substrate rather than a routine solvent. However, choosing a suitable reaction or dissolution medium is key for handling and transformations.

• Polarity/miscibility (literature/general):

  • Strongly nonpolar; miscible with nonpolar and weakly polar organics (hexanes, heptane, cyclohexane, toluene, diethyl ether, MTBE, CPME) and soluble in DCM/CHCl3 and THF.
  • Practically insoluble in water.

• Selecting media for typical uses:

  • Electrophilic aromatic substitution (EAS): use inert aromatic or chlorinated solvents (toluene, DCM, nitrobenzene) under Lewis/Brønsted acid catalysis to control regioselectivity and heat dissipation.
  • Benzylic functionalization (radical bromination/oxidation): CCl4 or DCM historically used; greener options include solvent-free or toluene/MeCN with NBS under photoredox.
  • Transition-metal C–H activation/borylation: polar aprotic solvents (THF, 1,4-dioxane, MTBE, CPME, or isododecane) depending on catalyst solubility.
  • Analytical dissolution: hexane or isooctane for GC; toluene or DCM for NMR (CDCl3 for 1H/13C).

• Comparison note (general):

  • Toluene vs hexanes: toluene improves solubility and heat capacity but increases aromatic background. Hexanes facilitate GC cleanup but may limit substrate concentration.
  • CPME/2-MeTHF often balance solubility, safety, and sustainability compared to DCM/THF.

Storage and Reconstitution

• Item-specific from Product Data:

  • Storage conditions: Room temperature
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General handling recommendations (hydrocarbon liquids):

  • Store tightly closed in an inert, compatible container in a well-ventilated area away from heat, sparks, and oxidizing agents.
  • Protect from prolonged air exposure and light if performing sensitive oxidation/radical studies; consider nitrogen blanket for long-term storage.
  • If material partially solidifies at low temperature, allow to warm to ambient and mix thoroughly before use. No reconstitution is required; use as supplied or dilute in a suitable organic solvent (e.g., hexanes, toluene, DCM) immediately prior to use.

• Stability/testing:

  • Periodically confirm purity by GC or 1H NMR if stored for extended periods, especially before kinetic/mechanistic experiments.

• Research use note: For research use only (as stated in Product Data).

Structure and Identity

• Item-specific from Product Data:

  • SKU: D1343494
  • Product name: 1,1-Dimethylindan
  • CAS: 4912-92-9
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Note: value provided in feed appears incomplete.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/Computed identifiers (for reference; not item specifications):

  • Synonym: 1,1-Dimethylindane
  • Molecular formula (literature): C11H14
  • Molecular weight (literature): ~146.23 g/mol
  • Representative SMILES (literature): CC1(C)CCc2ccccc12

• Structural features (general chemistry description):

  • Hydrocarbon consisting of a benzene ring fused to a cyclopentane (indane scaffold) with a gem-dimethyl (tert-alkyl) substitution at the bridgehead C-1 of the five-membered ring.
  • Functional groups: nonpolar aryl–alkyl framework; no heteroatoms; no formal functionality beyond benzylic C–H sites.
  • Stereochemistry: none (achiral, symmetric substitution at C-1). 2D depiction can be described as a benzocyclopentane core with two methyl groups on the quaternary bridgehead carbon adjacent to the aromatic ring.

• Category context:

  • Nonpolar aromatic hydrocarbon building block/model substrate; useful in studies of benzylic C–H activation, electrophilic aromatic substitution (EAS), and hydrocarbon oxidation chemistry.

Synthetic Utility

• Strategic features:

  • The gem-dimethyl (Thorpe–Ingold) effect at C-1 influences conformational preference and can bias reactivity, offering a handle to study steric and inductive effects on EAS and benzylic transformations.
  • Multiple benzylic C–H sites (excluding the quaternary carbon) enable stepwise installation of halogens, oxygen, or carbon substituents, furnishing diversified indane derivatives.

• Transformations (literature/general):

  • EAS on the arene: halogenation, nitration, sulfonylation, Friedel–Crafts acylation to give regioisomers directed by the tert-alkyl substituent.
  • Benzylic oxidation to ketones/aldehydes/acids (via O2/TBHP with Co/Mn catalysts or DDQ), giving access to indanones and indane carboxylates.
  • Benzylic halogenation (NBS/NCS) enabling nucleophilic substitution (SN1/SN2 at secondary benzylic centers) to amines, ethers, and thioethers.
  • Dehydrogenation to 1,1-dimethylindene for further hydrofunctionalization (e.g., epoxidation/hydroboration on the exocyclic double bond after isomerization) or metallocatalyzed additions.
  • Directed metalation (s-BuLi/TMEDA, low temperature) allowing formylation, borylation, or silylation after trapping with electrophiles or via transmetalation and cross-coupling.

• Retrosynthetic value:

  • Serves as a protected/sterically biased indane core, where the gem-dimethyl group blocks overfunctionalization at C-1 while enabling selective derivatization elsewhere on the framework.

Target Specificity

• Not applicable. This product is a small-molecule hydrocarbon and is not an antibody, enzyme, or biological targeting reagent. No antigen/epitope/clone/isotype information applies.