This compound belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
190.070 g/mol
XLogP3
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Exact Mass
189.011 Da
Monoisotopic Mass
189.011 Da
Topological Polar Surface Area
12.000 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
126.000
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
2
Lösungsrechner
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Application Protocols
No biological assay protocols (WB, IHC, IF, FC) are applicable to this small-molecule building block. For synthetic use, see the Reaction Conditions and Synthetic Utility sections for representative procedures and setup guidance. Always adapt conditions to your specific substrates and consult the primary literature.
Biological Roles
This product is a small-molecule heteroaromatic building block intended for research and synthesis. No biological/clinical use is claimed. General context for the isoindoline motif (literature perspective):
Structural role: Isoindoline and isoindolinone cores occur in diverse natural products and research tool compounds; they often serve as conformationally restricted aniline surrogates.
Physicochemical properties: The basic nitrogen (protonated here as the HCl salt) can modulate aqueous solubility and ionization behavior of derivatives, influencing permeability and binding in chemical biology programs.
Reactivity handle: The 5-chloro substituent allows late-stage diversification via cross-coupling to install bioprobes (e.g., fluorophores through boronate intermediates) or affinity tags.
Metabolism (general for secondary anilines/benzannulated amines): oxidative N-dealkylation or ring oxidation pathways are common in microsomal systems; exact ADME for this specific compound is not established here.
Use restrictions
For research use only. Not for human or veterinary use.
Because this is a synthetic intermediate and not a buffer or biomolecule, its primary relevance in biology is as a precursor to more complex probes or ligands rather than as a functional biological agent on its own.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare defined pH buffer systems. It is a protonated amine salt used primarily as a synthetic building block.
If aqueous handling is required, dissolve in water or alcohol/water mixtures and, if needed, adjust pH with appropriate laboratory buffers (e.g., phosphate, HEPES) external to this compound.
For extraction or phase-transfer steps, the hydrochloride salt can be converted to the free base by adding a suitable base and then back to the salt to aid isolation, but this is not a buffering application.
Green Alternatives
Greener practice considerations focus on solvent choice, salt handling, and coupling methodologies. The compound itself is a fixed structure; process choices drive sustainability.
Prefer greener solvents when feasible (general guidance):
Water/ethanol for dissolving the hydrochloride salt in workups or ion-exchange steps.
Replace DMF/NMP with acetonitrile, ethanol, 2-MeTHF, or propylene carbonate where chemistry allows.
Cross-coupling improvements:
Use ligand/catalyst systems active for aryl chlorides to avoid halogen exchange steps (e.g., Pd with bulky biaryl phosphines). Lower temperatures and shorter cycles reduce energy use.
Consider aqueous micellar catalysis for Suzuki/Miyaura-type couplings to reduce organic solvent volumes (employ surfactants like TPGS-750-M; literature).
Base and neutralization:
Employ milder, inorganic bases (K2CO3, KOAc) instead of strong alkoxides when compatible, minimizing exotherms and improving safety.
Workup/waste minimization:
Crystallize as the hydrochloride salt directly from alcohol/water to avoid chlorinated solvent usage where possible.
Comparison (general, qualitative):
DMF vs acetonitrile/ethanol: DMF highly effective but problematic for EHS; MeCN/EtOH are greener with trade-offs in solubility and removal.
Dioxane vs 2-MeTHF/CPME: ethers like 2-MeTHF/CPME offer better environmental profiles; assess peroxide risks and stability (peroxide testing schedule recommended for ethers; general safety guidance).
Note: No item-specific green certifications are claimed or specified.
Pharmaceutical Uses
No therapeutic or clinical claims are made. From a manufacturing/formulation perspective (general):
Role: 5-Chloroisoindoline hydrochloride is best regarded as a synthetic intermediate for discovery chemistry and process development, enabling access to isoindoline-derived APIs or research probes. It is not an approved excipient.
Advantages of the HCl salt form:
Improved handling (reduced volatility, often crystalline) versus the free base.
Facilitates salt metathesis or crystallization-driven purifications in process routes.
Typical operations in process chemistry (general):
Salt switching: conversion between hydrochloride and other counterions (e.g., sulfate, mesylate) to optimize isolation of downstream intermediates.
Late-stage diversification at the aryl chloride using robust cross-coupling platforms to elaborate structure–activity relationships.
Compliance/monographs: No pharmacopeial monograph is indicated for this item. Any use in cGMP settings would require internal specification setting and full characterization.
Item-specific excipient status, residual solvent limits, elemental impurities, and bioburden/endotoxin specifications: Not specified for this item; refer to CoA/Spec Sheet and quality agreements if applicable.
Physical Properties
Note: Item-specific specifications are not provided in the Product Data. Values below are general/literature expectations for guidance only and are not specifications.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~190.07 g/mol (C8H9Cl2N; literature/computed for the hydrochloride salt)
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Aromatic amine hydrochlorides often exhibit sharp melting/softening with decomposition, literature generally reports salt MPs rather than BPs.)
Boiling point: Not applicable/typically not reported for hydrochloride salts (decompose before boiling at 1 atm). Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable (solid); not specified for this item.
pKa (conjugate acid of the isoindoline nitrogen): literature for related benzannulated secondary amines typically pKaH ~8–10 in water; specific value for 5-chloroisoindoline not established here. Not specified for this item; refer to primary literature.
Solubility (general expectations, literature): hydrochloride salts are usually freely soluble in water and polar protic solvents (e.g., methanol, ethanol) and in polar aprotics (DMF, DMSO). The free base is more soluble in organic solvents and less in water at neutral pH.
LogP/LogD: Not specified for this item; refer to CoA/Spec Sheet.
Always consult the item’s CoA/SDS for authoritative, lot-specific physical data before designing processes.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and residual solvent limits.
What “hydrochloride salt” implies for quality and use:
Enhanced handling: the HCl salt form typically offers improved stability toward air/CO2 and reduced volatility versus the free base, aiding accurate weighing and dosing.
Purification: salts often crystallize well, enabling purification by recrystallization and providing sharper melting behavior for identity checks (actual MP not specified for this item).
Typical quality controls for heteroaromatic building blocks (general):
Identity confirmation by 1H/13C NMR (D2O, DMSO-d6), HRMS/ESI in positive mode (observing protonated free base or salt-related adducts), and, where relevant, chlorine isotope pattern.
Purity by HPLC/UPLC with UV detection; for salts, report assay on anhydrous basis and note counterion content.
Water content by Karl Fischer (important for hygroscopic salts) and residual organic solvents by GC; Not specified for this item.
Stabilizers/inhibitors: none typically required for amine hydrochlorides; Not specified for this item.
UV cutoff/trace metals/peroxides: Not specified for this item; refer to CoA/Spec Sheet.
For regulated or analytical workflows, consult the current CoA for lot-specific assay, residuals, and acceptance criteria.
Reaction and Applications
As a 5-chloro-substituted isoindoline salt, this compound serves as a versatile building block for heteroaromatic diversification. The following are general/literature-use cases (not item-specific claims):
Aryl chloride diversification at C-5:
Cross-coupling: Pd-catalyzed Suzuki–Miyaura (after borylation) or direct Miyaura borylation (B2pin2) of the 5-chloro position to access 5-boryl isoindoline for further C–C coupling.
Buchwald–Hartwig amination: amination at C-5 to introduce anilines or diarylamines (ligands such as BrettPhos, XPhos; bases like NaOtBu or Cs2CO3).
Direct SNAr: possible only with highly activated nucleophiles and conditions; the isoindoline ring is not strongly activating toward SNAr, so cross-coupling is preferred.
Nitrogen-centered transformations (operate on the free base):
N-alkylation/acylation: generate the free base (e.g., K2CO3, NaH) to introduce protecting groups (Boc, Cbz) or install substituents on nitrogen.
Oxidation to isoindolinone: controlled oxidation (e.g., with O2/metal catalyst or peracids) affords isoindolinone frameworks valuable in materials and medicinal chemistry.
Reductive functionalization: formation of tertiary amines or quaternary ammonium salts.
Orthogonal strategies:
Sequential N-protection, Pd-catalyzed aryl C–X activation, then deprotection to furnish differentially substituted isoindoline scaffolds.
Practical notes:
Begin from the hydrochloride for robust handling; neutralize to the free base immediately prior to transformations requiring a non-protonated amine.
Control of ring electronics (via the chloro substituent) can modulate coupling rates; optimized catalysts/ligands for aryl chlorides are typically required.
Reaction Conditions
Illustrative literature-style conditions for common transformations of 5-chloro-substituted isoindolines (guidance only; optimize per substrate). Item-specific conditions are not specified.
Liberation of the free base:
Dissolve the hydrochloride in water; basify to pH ~10 with Na2CO3 or NaOH at 0–25°C; extract with CH2Cl2 or EtOAc; dry and use immediately.
Miyaura borylation at C-5 (to form aryl–Bpin derivative):
Pd(dppf)Cl2 (2–5 mol%), B2pin2 (1.5 equiv), KOAc (3 equiv), 1,4-dioxane or 2-MeTHF, 70–90°C, 6–16 h under N2. Typical isolated yields for aryl chlorides often 60–85% (literature ranges).
Suzuki–Miyaura coupling (from aryl–Bpin):
Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI, K3PO4 (2–3 equiv), dioxane/H2O or MeOH/H2O, 60–85°C, 2–12 h. Aryl/heteroaryl/vinyl partners commonly used.
Buchwald–Hartwig amination at C-5:
Pd2(dba)3 (1–2 mol% Pd), BrettPhos or XPhos (2–4 mol%), NaOtBu or Cs2CO3 (2–3 equiv), toluene or dioxane, 80–110°C, 6–20 h. For challenging amines, use BrettPhos/BINAP variants.
N-protection (free base required):
Boc protection: Boc2O (1.1–1.5 equiv), Et3N or NaHCO3, THF/MeOH or CH2Cl2, 0–25°C, 1–4 h; quench and isolate.
Oxidation to isoindolinone (representative):
Aerobic oxidation with Cu or Pd catalysis in DMSO or MeOH at 25–80°C; or peracid oxidations (mCPBA) at 0–25°C with careful control.
Always monitor reactions by TLC/LC–MS. Adjust base/ligand sets to accommodate the amine’s coordination properties and salt state.
Safety and Handling
Safety summary (general guidance; always consult the SDS for authoritative information):
GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
Likely hazards (generic for arylamine hydrochlorides): may cause skin/eye irritation; dust may irritate respiratory tract. The hydrochloride salt is acidic and can be corrosive to some metals in the presence of moisture.
Recommended PPE: laboratory coat, safety glasses or goggles, appropriate gloves (e.g., nitrile). Use in a fume hood to control dust and vapors during any neutralization steps.
Handling notes:
Avoid generating dust. Do not breathe dust. Prevent contact with skin/eyes.
Hygroscopicity: many amine hydrochlorides are moderately hygroscopic; keep container tightly closed to minimize water uptake (general guidance).
Incompatibilities: strong bases (will liberate the free base and HCl), strong oxidizers, and reactive acid-sensitive materials. Avoid contact with reactive metals in wet conditions.
First aid (overview; follow SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; seek medical attention if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Spill response: avoid dust formation; collect solids with minimal dusting; place in appropriate container for disposal.
Fire safety: organic hydrochloride salts can decompose to release HCl and nitrogen/halogenated vapors when heated; use suitable extinguishing media (CO2, dry chemical). Refer to SDS for detailed firefighting measures.
Solvent Selection
This product is a small-molecule heteroaromatic ammonium chloride. Practical solvent guidance (general/literature-based; not specifications):
Polarity/miscibility profile:
Water: hydrochloride salts are typically freely soluble; solubility may increase with mild warming.
Alcohols: methanol and ethanol generally dissolve the salt well.
Polar aprotics: DMSO and DMF provide excellent solubility for stock solutions; acetonitrile is often moderately effective.
Nonpolar/ethers: limited solubility as the HCl salt; prepare the free base for solubility in Et2O, MTBE, toluene, etc.
Choosing salt vs free base:
Use the hydrochloride salt for aqueous-phase chemistry, ion-exchange, or where controlled protonation is needed.
Generate the free base in situ (e.g., with Na2CO3, K2CO3, triethylamine) for N-alkylation/acylation or to enhance solubility in less polar organic media.
Practical tips:
For analytical HPLC, water/MeCN with 0.1% formic acid often gives good peak shape for protonated amines.
For preparative work in organic solvents, neutralize and extract the free base into dichloromethane or ethyl acetate, dry, and proceed.
Comparison (general):
DMSO vs DMF: DMSO offers broader solubility and lower volatility; DMF is easier to remove but has regulatory burdens.
Water/alcohols: greener and safer; consider if reaction/assay tolerates protic media.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Keep tightly closed in a dry place. Store away from incompatible materials (strong bases, strong oxidizers). Shipment: Normal.
Stability (general guidance for amine hydrochloride salts): hydrochloride salts are typically stable to air and ambient light; prolonged exposure to moisture may increase water content and caking. If long-term storage is planned, consider desiccation.
Reconstitution/preparation of solutions:
Aqueous: Dissolve the salt directly in deionized water to prepare stock solutions; mild warming may aid dissolution.
Organic: For DMSO or methanol stocks, dissolve directly. For solubility in less polar solvents, first convert to the free base (neutralize with Na2CO3 or NaOH in water, extract into an organic solvent, dry) and then prepare solutions as required.
Filtration: Use 0.2–0.45 µm PTFE or PVDF filters for particulate removal when preparing analytical stocks.
Freeze–thaw guidance: Not typically required for solids. If storing solutions, keep tightly capped under inert gas where appropriate and avoid repeated freeze–thaw cycles; prepare single-use aliquots.
Specifications such as water content, peroxide content, UV cutoff, or exact solubility: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only.
Structure and Identity
Brief overview: 5-Chloroisoindoline hydrochloride is a protonated isoindoline (bicyclic benzannulated 5-membered nitrogen heterocycle) bearing a chloro substituent on the aromatic ring (position 5), isolated as the hydrochloride salt for stability and handling.
SKU: C195790
Product name: 5-Chloroisoindoline hydrochloride
CAS: 912999-79-2
PubChem CID: 49853502
InChIKey: 341713 (as provided; full-length InChIKey not specified for this item)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: C8H9Cl2N (literature/computed for the HCl salt)
Core: isoindoline (a benzene ring fused to a saturated 5-membered ring containing a secondary amine). The nitrogen is protonated in the hydrochloride salt.
Substitution: one chloro substituent on the benzene ring at the 5-position (para to the ring fusion nitrogen in common numbering conventions for isoindolines).
Ionization: exists as an ammonium chloride salt (R–NH2+ Cl−) under ambient conditions; the free base is obtained upon neutralization with base.
Stereochemistry: none (achiral, no stereocenters).
2D depiction in words: a fused bicyclic framework with an aniline-like ring bearing Cl, fused to a partially saturated ring whose nitrogen (secondary amine) is protonated and paired with chloride counterion.
Synthetic Utility
Key functional elements and how they are leveraged (general/literature guidance):
Aryl chloride at C-5 (electrophile):
Cross-coupling gateway: Pd-catalyzed borylation (B2pin2/KOAc) to an aryl boronate, enabling Suzuki–Miyaura coupling with aryl/heteroaryl/vinyl partners.
Direct amination: Buchwald–Hartwig amination to install anilines/diarylamines (BrettPhos, RuPhos, or XPhos ligands; strong base, controlled temperature).
C–S/C–O bond formation: Pd- or Cu-catalyzed thiolation/aryloxylation to produce thioethers/arylethers.
Secondary amine (nucleophile, as free base):
N-acylation/alkylation to access tertiary amines, amides, ureas, carbamates (e.g., Boc/Cbz protections to mask basicity during cross-coupling).
Quaternization to yield ammonium salts for phase-transfer or materials applications.
Orthogonal strategy examples:
Protect N (Boc2O, Et3N) → Pd-catalyzed C-5 coupling → deprotect (TFA) → further N-functionalization.
Convert C-5 to boronate → iterative Suzuki couplings for rapid analog build-out.
Retrosynthetic value: Serves as a linchpin that unites isoindoline core assembly with modular diversification at C-5, shortening routes to complex benzannulated amines.
Note: Start from the hydrochloride salt for storage and handling, then liberate the free base just prior to N-centered reactions to avoid salt interference and to improve solubility in aprotic organic media.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen, epitope, clone, isotype, or species reactivity information applies.
Häufig gestellte Fragen
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 912999-79-2, the molecular formula is C8H9Cl2N, and the molecular weight is 190.07 g/mol. InChIKey SPDKLINCVDBABZ-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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