This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
176.000 g/mol
XLogP3
2.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
174.959 Da
Monoisotopic Mass
174.959 Da
Topological Polar Surface Area
29.400 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
121.000
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
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Recensioni
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Application Protocols
No biological assay protocols (WB, IHC, IF, FC) apply to this small-molecule reagent.
General synthetic handling protocol (example, literature-style):
Dissolve 1.0 equiv 1,3-dichloro-2-nitrosobenzene in dry DCM (0.1–0.5 M) under nitrogen.
Cool to 0–5 °C; add 1.2 equiv of diene dropwise.
Stir 2–6 h while monitoring by TLC/LC–MS.
Warm to rt; wash with sat. NaHCO3, dry, and concentrate.
Purify by silica chromatography (heptane/EtOAc) to afford the oxazine adduct.
This is illustrative, not item-specific. For exact procedures and hazard controls, consult primary literature and the SDS. Research use only.
Biological Roles
This compound is a synthetic, halogenated nitrosoarene and does not have a recognized native biological role.
General chemistry/biochemistry context (literature):
Reactivity toward biomolecules: Aryl nitroso groups are electrophilic and can react with nucleophiles (thiols, amines) to give N–O linked adducts or hydroxylamines; such reactivity underpins use of nitroso reagents in bioconjugation/pericyclic labeling strategies under mild conditions.
Spin trapping/NO chemistry: Some nitroso compounds function as spin traps or engage in NO-related redox processes; however, aryl nitrosoarenes like this one are not standard biological probes without derivatization.
Metabolic fate (general): In vivo, aryl nitroso/hydroxylamine species may be interconvertible via redox enzymes; aryl chlorides may undergo oxidative dehalogenation in certain systems. These are general considerations and not application claims for this product.
All uses must remain strictly in vitro/instrumental research or synthetic contexts. No clinical, diagnostic, or in vivo use is intended or implied.
Buffer Applications
Not typically used as a buffering agent. As a hydrophobic, halogenated aromatic reagent, it has no defined acid/base pair suitable for preparing laboratory buffers. For aqueous work, dissolve or disperse using miscible organic cosolvents (e.g., acetonitrile, DMSO) before dilution into buffered systems if required for an assay. Prior sections on Solvent Selection and Reaction & Applications are more relevant.
Green Alternatives
Consider both solvent and process intensification choices to reduce environmental impact when working with halogenated aromatics.
Greener solvent choices (literature/general):
| Use case | Conventional | Greener alternative | Trade-offs |
|---|---|---|---|
| HDA at rt | DCM, CHCl3 | 2-MeTHF, EtOAc | Slightly lower solubility; may require longer times.
| Thermal ene | Toluene, xylene | Cyclopentyl methyl ether (CPME) | Higher bp can aid; ensure peroxide control for ethers over time.
| Workup/extraction | DCM | EtOAc, MTBE | Partitioning may differ; check product stability.
| Chromatography | Hexane/DCM | Heptane/EtOAc | Similar selectivity with reduced toxicity.
Process considerations:
Concentration/intensification: Continuous-flow HDA or ene reactions can improve heat/mass transfer and minimize solvent volumes.
Catalysis: Employ catalytic hydrogenation for reductions instead of stoichiometric metals when compatible with the chlorides.
Waste segregation: Keep halogenated waste streams separate and minimized; use solvent recovery where possible.
Note: The substrate itself contains chlorine; end-of-life and waste policies should account for halogenated organics. Greener route design might replace the aryl chloride(s) via subsequent coupling to less persistent motifs if life-cycle is a concern.
Pharmaceutical Uses
No excipient or pharmacopeial roles are known for this compound. It is a synthetic intermediate/building block for research and development in medicinal chemistry or process chemistry.
General formulation context (literature):
May serve as a route intermediate toward dichloroanilines or oxazine scaffolds after pericyclic addition/reduction, which can be elaborated into candidate molecules.
If used in screening libraries, stocks are typically prepared in DMSO at millimolar concentrations; confirm stability with LC–MS to monitor potential dimerization (azodioxide) and reduction.
Regulatory note: For research use only. Not for human or veterinary use, not for drug, diagnostic, or household purposes.
Physical Properties
Item-specific specifications are not provided in the Product Data. The following are general/literature descriptors for aryl nitroso compounds of this substitution pattern; verify against the CoA/SDS for this lot.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Melting/boiling point (literature): Not widely tabulated for this exact isomer; nitrosoarenes are often low-melting solids or high-boiling liquids. Use DSC/TGA for precise data if critical.
Density (literature expectation): ca. 1.4–1.6 g/mL for chlorinated aromatics; exact value Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general):
Poorly soluble in water (typical for chlorinated aromatics).
Soluble in organic solvents such as DCM, chloroform, toluene, THF, and ethyl acetate (literature, general behavior).
Partitioning (literature expectation): LogP > 2 typical for dichloro aromatics; exact logP Not specified for this item; refer to CoA/Spec Sheet.
Refractive index (if liquid): Not specified for this item; refer to CoA/Spec Sheet.
UV–vis (literature): Aryl nitroso compounds often display n→π* absorption in the visible/near-UV leading to pale to intense coloration; exact λmax Not specified for this item; refer to CoA/Spec Sheet.
Practical note (general): aryl nitroso species can dimerize (azodioxide formation) reversibly; spectra and melting behavior may depend on equilibrium and sample history.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, related substances, and any stabilizers.
Identity control (typical practices): Vendors commonly confirm aryl nitroso identity by NMR (aromatic region; characteristic nitroso chemical shifts), IR (N=O stretch typically 1500–1600 cm−1 for aryl nitroso; literature), MS (M, M+2, M+4 pattern for two Cl), and melting point if solid. Item-specific acceptance criteria are defined on the CoA.
UV/LC attributes: For use in synthesis or analytical method development, low UV background and defined purity are desirable; if HPLC suitability is critical, request an HPLC-grade specification.
Stabilizers/inhibitors: None specified for this item. If needed, materials are sometimes stored under inert gas or with minimal headspace to limit redox/dimerization; consult the CoA for any declared stabilizer.
What the grade means (general guidance):
“Analytical Reagent/AR” implies tight assay and impurity limits suitable for most lab syntheses.
“Purified/Technical” may have broader impurity profiles; consider pre-purification before sensitive reactions.
Recommendation: For pericyclic or catalytic applications sensitive to trace metals/halides, review the CoA impurity profile; consider an additional recrystallization or chromatography if needed.
Reaction and Applications
As an aryl nitroso bearing two chloro substituents, this reagent is a versatile partner in pericyclic, redox, and cross-coupling sequences.
Hetero-Diels–Alder (HDA): Reacts with conjugated dienes to furnish 1,2-oxazines; the nitroso acts as the dienophile (literature). Regioselectivity can be tuned by diene electronics; subsequent N–O cleavage gives β-amino carbonyl derivatives.
Ene reaction: Under thermal conditions, alkenes bearing allylic hydrogens undergo nitroso-ene addition to yield allylic hydroxylamines, which can be elaborated to ketones/aldehydes or amines (literature).
Radical/trapping chemistry: Aryl nitroso groups can trap carbon-centered radicals to give oxime/hydroxylamine adducts (spin-trap analogs; literature concept).
Reductive transformations: Reduction affords the corresponding aniline (2-amino-1,3-dichlorobenzene) via hydroxylamine intermediates; Zn/AcOH, Fe/NH4Cl, or catalytic hydrogenation are commonly used (literature).
Cross-coupling leverage: The two aryl chlorides enable Pd-catalyzed Suzuki–Miyaura, Buchwald–Hartwig (after N–O management), or Negishi couplings to access densely functionalized anilines/oxazines post-sequence (literature). Electron-withdrawing nitroso can influence oxidative addition rates; choose ligands accordingly.
Nitrosation chemistry: While typically electrophilic nitrosation uses NO+ equivalents, preformed aryl nitroso reagents can participate in N/O-transfer sequences under specific conditions.
Tips:
Control light and temperature to limit azodioxide dimerization prior to use; gentle warming or dilution can revert dimers to monomers.
For HDA reactions, run at 0–25 °C in DCM/toluene; for ene reactions, 60–120 °C in non-protic solvents is common (literature guidance).
Reaction Conditions
General literature guidance; optimize for your substrate set and scale.
Hetero-Diels–Alder (with dienes):
Solvent: DCM, toluene, EtOAc, or 2-MeTHF.
Temperature: 0–25 °C (often exothermic); some systems benefit from –20 to 0 °C for selectivity.
Stoichiometry: 1.0–1.5 equiv nitrosoarene to 1.0 equiv diene.
Time: 0.5–24 h depending on diene reactivity.
Workup: quench with base-washed brine; purify oxazine; subsequent N–O manipulation as needed.
Nitroso-ene (with alkenes):
Solvent: toluene, CPME, or chlorinated solvents.
Temperature: 60–120 °C.
Catalysis: often thermal; Lewis acids (e.g., ZnCl2) occasionally reported to accelerate.
Reduction to aniline:
Conditions: Zn/AcOH (rt–50 °C) or Fe/NH4Cl in EtOH/H2O; catalytic hydrogenation (H2, Pd/C) if C–Cl tolerance acceptable.
Outcome: nitroso → hydroxylamine → aniline; monitor to avoid over-reduction/dehalogenation.
Cross-coupling at C–Cl:
Catalysts/ligands: Pd2(dba)3 or Pd(OAc)2 with bulky, electron-rich ligands (e.g., BrettPhos, XPhos) for aryl chloride activation (literature).
Analytical monitoring: TLC/UPLC with dual-wavelength detection (e.g., 230/320 nm) captures both monomer and azodioxide dimer.
All parameters above are literature-style ranges; verify compatibility with your system.
Safety and Handling
Always handle nitroso- and chlorinated-aromatic reagents in a fume hood. This product is supplied for research use only.
GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
Likely hazards (general chemistry knowledge):
Harmful if swallowed or inhaled; may cause skin/eye irritation typical of chlorinated aromatics.
Aryl nitroso compounds can participate in redox reactions; avoid contact with strong reducing or oxidizing agents unless intended.
PPE: lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid skin contact; prevent aerosol formation.
Engineering controls: use in a certified chemical fume hood; ensure local exhaust when weighing powders.
Incompatibilities (general): strong bases/acids (can accelerate decomposition), strong oxidizers/reductants, active metals. Avoid excessive heat and light.
Special risks: potential for reversible dimerization (azodioxide) and color change upon temperature/light; does not form peroxides like ethers.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; get medical advice.
Ingestion: rinse mouth; do not induce vomiting; obtain medical attention.
Spill/leak: absorb with inert material, avoid dust; collect for disposal per local regulations.
Waste: treat as halogenated organic waste; segregate from non-halogenated streams.
Solvent Selection
This is a moderately nonpolar, chlorinated aromatic with a polar N=O functional group. It dissolves well in many organic solvents but is poorly soluble in water (general behavior, literature).
Preferred solvents (typical): dichloromethane, chloroform, toluene, ethyl acetate, THF, acetone, acetonitrile. For highly polar media, DMF/DMSO can be used.
Avoid: strongly basic aqueous solutions (can promote side reactions) and neat strong acids/oxidants.
Polarity/interaction: aryl nitroso groups engage in dipole–dipole and hydrogen-bond acceptance; chlorinated ring increases van der Waals interactions.
Comparison (general guidance):
DCM vs toluene: DCM maximizes solubility and heat removal for pericyclic additions at 0–25 °C; toluene is suitable for higher-temperature reactions and greener than chloroform.
EtOAc/MTBE: greener options for extractions and workups; may suffice for reactions at modest concentrations.
Practical tips:
Degas oxygen-sensitive setups only if a reducing partner is present; otherwise, ambient air is acceptable for many pericyclic reactions.
If crystallization is desired, use toluene/hexane or EtOAc/hexane mixtures to exploit differential polarity.
For analytical HPLC, acetonitrile/water with a low proportion of water (or MeOH/water) can resolve the parent and potential azodioxide dimer; monitor at 230–350 nm (literature behavior of aryl nitroso UV).
Storage and Reconstitution
Storage temperature (from Product Data): Room temperature.
Container: Keep tightly closed in an amber glass bottle to limit light exposure; minimize headspace if storing for extended periods (general best practice for aryl nitroso compounds).
Atmosphere: Store under dry conditions; inert gas blanket (N2/Ar) recommended for long-term stability (general guidance). Avoid moisture and strong light.
Stability considerations (general): Aryl nitroso compounds can reversibly dimerize to azodioxides; gentle warming or redissolution can regenerate the monomer. Avoid prolonged heating.
Reconstitution/solution prep:
Dissolve in DCM, toluene, THF, EtOAc, acetonitrile, or DMSO to prepare stock solutions. Typical research stocks: 10–100 mM in dry solvent.
Filter (0.2 µm PTFE) if particulates are present. Prepare fresh solutions for sensitive reactions.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Research use note: For research use only; not for human or animal use.
Always defer to the Aladdin CoA and SDS for authoritative storage and handling instructions for the specific lot supplied.
Structure and Identity
A halogenated nitrosoarene building block featuring two chloro substituents and an ortho nitroso group on a benzene ring.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (chemistry description):
Aromatic core: benzene ring bearing three substituents.
Functional groups: an aryl nitroso (–N=O) at the 2-position (ortho) relative to one chloro; two aryl chlorides at the 1- and 3-positions (meta to each other).
Electronic character: the nitroso group is strongly withdrawing and ambident (N/O) reactive; the two chloro substituents further deactivate the ring but enable cross-coupling under Pd catalysis.
2D description: ring positions 1–6 with Cl at C1, nitroso at C2 (–N=O bound via N to the ring), and Cl at C3; remaining ring positions unsubstituted.
Notes:
Identifiers and structure strings above are provided as general literature information for this chemical name; consult the Aladdin CoA/Spec Sheet for item-specific identity confirmation.
Synthetic Utility
Key functional elements and their implications:
Aryl nitroso (–N=O): Enables hetero-Diels–Alder and ene reactions to forge C–N/O–N bonds under mild conditions. Post-cycloaddition N–O bond manipulation (reduction or rearrangement) yields β-amino carbonyls or anilines (literature).
Two aryl chlorides: Serve as handles for Pd-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Negishi). Electron withdrawal from –N=O can facilitate oxidative addition with modern ligands.
Retrosynthetic leverage:
Build densely substituted anilines: HDA with a diene → oxazine → reductive N–O cleavage → β-amino carbonyl → cyclization/aromatization to aniline derivatives.
Orthogonal functionalization: Couple one C–Cl selectively (e.g., C3) using bulky ligands, then manipulate the nitroso group; reduce to an aniline and continue diversification on the remaining C–Cl.
Protecting-group logic:
The nitroso can behave as a transient masked amino function; reduction unveils the aniline without conventional protecting groups.
Analytical handles:
Distinct MS isotopic pattern (Cl2) simplifies tracking in mixtures; UV absorption assists in LC method development.
Caveats:
Control redox environment; unintended reduction may occur with metal reagents.
Manage potential dimerization before coupling or pericyclic steps by ensuring adequate dilution and temperature control (literature best practices).
Target Specificity
Not an antibody, enzyme, or bioactive ligand with defined biological target specificity. This product is a small-molecule chemical reagent/building block used in synthetic and materials chemistry. No antigen/epitope, clone, or isotype information applies.
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