≥97% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Store at 2-8°C,Argon charged,Desiccated Ships Wet ice Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Vue d’ensemble
2,6-Difluorophenyl isothiocyanate (1,3-Difluoro-2-isothiocyanatobenzene), an aryl isocyanate, can be prepared from difluoroaniline.1H-[1,2,4]triazole-3,5-diamine undergoes acylation with 2,6-difluorophenyl isothiocyanate to form the corresponding 1-acyl-1H-[1,2,4]triazole-3,5-diamine.
Application：
2,6-Difluorophenyl isothiocyanate is used as chemical, organic and pharmaceutical intermediate.
This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached to a benzene ring.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Sensibilité
Moisture sensitive
Indice de réfraction
1.604(lit.)
Point d'éclair (°F)
219°F
Point d'éclair (°C)
104°℃
Point d'ébullition (°C)
217 °C(lit.)
Poids moléculaire
171.170 g/mol
XLogP3
3.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Exact Mass
170.995 Da
Monoisotopic Mass
170.995 Da
Topological Polar Surface Area
44.500 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
169.000
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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Application Protocols
No antibody/assay protocols are provided for this small-molecule reagent. For chemical applications, see Reaction Conditions and Application notes. If using for amine derivatization in analytical workflows, validate labeling conditions (buffer, pH, solvent proportion, reagent excess) on your target matrix.
Biological Roles
This is a synthetic small molecule reagent. It does not have a native biological role. The following points are general, research-oriented considerations for aryl isothiocyanates (not product-specific and not medical claims):
Bioconjugation handle: The –N=C=S group reacts selectively with primary amines on biomolecules (e.g., lysine side chains) to form thioureas under mild, near-neutral conditions, enabling tagging for analytical workflows (LC–UV/LC–MS) or materials functionalization.
Fluorine effects: Ortho-difluorination increases hydrophobicity and can modulate membrane interactions of conjugates; in analytical proteomics, fluorinated tags often alter chromatographic retention and MS ionization behavior (literature observation).
Stability in aqueous media: Isothiocyanates hydrolyze slowly in water and faster under basic conditions; buffered organic–aqueous systems are used to balance reactivity and selectivity for amine labeling.
Enzyme/protein studies: Thiourea formation can influence hydrogen bonding and secondary structure in peptide conjugates; these effects are exploited in affinity materials and supramolecular assemblies.
All uses are for laboratory research only. This product is not intended for diagnostic, therapeutic, or other clinical applications.
Buffer Applications
This compound is not a buffering agent. However, it is sometimes used to derivatize amines in mixed aqueous/organic media. Practical guidance (literature/general, not item-specific):
Aqueous compatibility: Use minimal water to limit hydrolysis; 10–30% organic co-solvent (MeCN, DMF, DMSO) can solubilize the reagent while maintaining amine reactivity in buffered systems.
pH control: For labeling primary amines, mildly basic conditions (pH 8.0–9.0) promote nucleophilicity. Common buffers: carbonate/bicarbonate (50–200 mM), borate (50–100 mM). Avoid primary amine-containing buffers (e.g., Tris) that can consume reagent.
Procedure sketch (general): Dissolve the isothiocyanate in dry MeCN or DMF; add slowly to the buffered amine solution under stirring; react at room temperature for 15–120 min; quench or proceed to purification.
Interferences: Excess water, thiols, or amine-containing additives will compete. Degas if sensitive analytes require oxygen control.
For purely synthetic transformations, anhydrous, non-buffered organic solvents are preferred (see Solvent Selection).
Green Alternatives
Greener strategy focuses on solvent choice and process design; the isothiocyanate functional group is already an efficient coupling partner for amines under mild conditions (low energy input).
Prefer greener solvents where compatible:
Replace DCM with ethyl acetate or 2-MeTHF for amine–isothiocyanate couplings.
Use MeCN (relatively benign) instead of DMF/DMSO when polarity suffices.
Comparison (literature/general):
DCM vs Ethyl acetate:
EHS: DCM (halogenated, potential carcinogen) vs EtOAc (biodegradable, low toxicity).
Performance: EtOAc often dissolves aryl isothiocyanates and aliphatic amines adequately; reaction rates may be modestly slower.
THF vs 2-MeTHF:
EHS: 2-MeTHF derived from biomass; lower peroxide tendency and easier aqueous workup than THF.
Performance: Comparable rates for amine additions; solubility of polar amines sometimes improved in THF.
Process intensification:
Run at ambient temperature without catalysts where possible to cut energy input.
Use slight reagent excess and high-solids or solvent-lean conditions to reduce solvent volumes.
Implement in-line IR or HPLC monitoring to minimize overreaction and waste.
Note: Alternative coupling chemistries (e.g., forming ureas via carbonyldiimidazole or phosgene surrogates) may avoid sulfur but typically require harsher reagents; tradeoffs should be evaluated case-by-case.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this listing. This product is supplied for research use only.
General, non-clinical context for this reagent class (literature; not product-specific):
Process chemistry/building block: Aryl isothiocyanates are used to prepare thiourea motifs found in agrochemical and medicinal chemistry candidates, ion-pairing receptors, and intermediates en route to heterocycles (e.g., thiohydantoins, benzothiazoles).
Analytical derivatization: Employed to derivatize trace amines in API intermediates for improved UV or MS detection during process control (e.g., reaction monitoring, impurity profiling).
Material modification: Surface functionalization via thiourea linkages (e.g., on amine-terminated polymers or silica) for affinity or capture applications in drug development labs.
If regulatory or GMP use is contemplated, request full CoA specifications and perform internal qualification; otherwise, use strictly in research settings.
Physical Properties
Item-specific properties (this listing):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Physical data (literature/general for 2,6-difluorophenyl isothiocyanate or closely related aryl isothiocyanates; not item specifications):
Molecular formula: C7H3F2NS (computed from structure)
Molecular weight: ~171.16 g/mol (calculated)
Expected state: low–moderate volatility organic liquid or low-melting solid depending on purity and temperature (general behavior of aryl isothiocyanates)
Solubility: Miscible with common organic solvents such as dichloromethane, acetonitrile, THF, toluene, ethyl acetate; negligible solubility in water (literature, aryl isothiocyanates)
LogP: Isothiocyanates on aryl rings are generally moderately lipophilic; difluoro substitution typically increases hydrophobicity versus unsubstituted phenyl isothiocyanate (qualitative literature trend)
Refractive index/density/BP/MP: Not widely tabulated for this exact difluoro isomer; consult primary literature or CoA for definitive values.
Notes for practitioners:
Fluorine substituents can increase thermal stability vs unsubstituted analogs but do not preclude moisture sensitivity of the –N=C=S group.
Handle under dry conditions; the isothiocyanate carbon is electrophilic and can slowly react with adventitious nucleophiles (water, amines) even at ambient temperature.
Quality and Grades
Item-specific quality fields:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Context for this reagent class (general guidance):
Research grade aryl isothiocyanates are typically assessed by GC/LC purity and NMR to confirm absence of starting aniline and thiourea byproducts. Low water content is desirable to limit hydrolysis of the –N=C=S.
UV behavior: Many aryl isothiocyanates have significant UV absorbance; when used for derivatization (e.g., HPLC detection), low-UV background solvents and verified purity are important.
Stabilization: Unlike acid-sensitive acid chlorides, aryl isothiocyanates usually do not require added stabilizers; stability depends mainly on dryness and oxygen exclusion. This item is specified to be supplied/kept under argon and desiccated.
Documentation: For lot-specific assay, residual aniline, water content, and chromatographic purity, consult the Certificate of Analysis. Where applicable, spectral data (1H/13C/19F NMR, IR with ν(N=C=S) ~2050–2100 cm−1; literature) are used to confirm identity.
Practical recommendations:
Open only in a dry environment; promptly recap and reblanket with argon. If long-term work requires low-UV background, request or verify HPLC suitability on the CoA.
Reaction and Applications
Aryl isothiocyanates are versatile electrophiles that rapidly react with nucleophiles; the 2,6-difluoro substitution enhances electrophilicity and can influence product conformations.
Key applications (literature/general; expand as applicable to this scaffold):
Primary and secondary amines add to the isothiocyanate carbon to afford thioureas under mild conditions (0–25°C) in aprotic solvents.
Uses: Building blocks for H-bonding organocatalysts, ligands, heterocycles (e.g., thiazoles via cyclization/oxidation), and as analytical derivatization tags to enhance UV response and MS detectability.
Thiol additions → dithiocarbamates: Base-catalyzed addition of thiolates to give S-alkyl dithiocarbamates, useful as protecting groups or intermediates.
Alcohol additions → thiocarbamates: Slower; typically require base or catalysts (e.g., DBU) and heat.
Cyclization chemistry: Intramolecular nucleophile capture (e.g., anilines/diamines) leads to benzothiazolinones, thiohydantoins, and other S,N-heterocycles after appropriate activation (literature).
Isotope/labeling workflows: Aryl isothiocyanates serve in tagging primary amines in peptides or metabolites for LC–UV or LC–MS profiling; fluorine atoms can modulate lipophilicity and chromatographic retention.
Practical tips:
Maintain anhydrous conditions; premix base with amine salts to liberate the free amine before addition.
Use slight excess (1.05–1.2 equiv) of isothiocyanate for complete conversion; monitor by IR (disappearance of ν(N=C=S) ~2050–2100 cm−1; literature) or LC/MS.
Ortho-fluorines can promote intramolecular H-bonding in products; consider this in crystallization and NMR interpretation.
Reaction Conditions
Typical conditions for representative transformations (literature/general guidance; not product-specific specifications):
Primary amine → thiourea:
Solvent: DCM or MeCN (anhydrous).
Stoichiometry: 1.0 equiv amine, 1.05–1.2 equiv isothiocyanate, 1.0–1.5 equiv base if amine is protonated (Et3N, DIPEA).
Temperature/time: 0–25°C, 0.5–4 h (many aliphatic amines complete within 1 h at rt).
Workup: Quench with dilute aqueous base; extract; concentrate; purify by crystallization or silica (hexanes/EtOAc).
Yields: Often 70–95% for unhindered amines (literature range).
Secondary amine → N,N′-disubstituted thiourea: Similar to above; may require longer time or higher polarity solvent (MeCN, DMF); 20–60°C as needed.
Thiol → dithiocarbamate:
Solvent: THF or MeCN.
Base: NaH, KOtBu, or organic base to generate thiolate.
Temperature: 0–25°C; typically rapid.
Alcohol → thiocarbamate:
Solvent: MeCN or toluene; base (DBU) or catalysts; 50–100°C prolonged times.
Monitoring/analytics:
IR: Disappearance of ν(N=C=S) ~2050–2100 cm−1.
NMR: 13C signals for thiocarbonyl ~180–190 ppm; 19F NMR retains two ortho-F signals (often complex due to coupling).
Always conduct small-scale trials to optimize equivalents, base, and solvent for the specific nucleophile.
Safety and Handling
Item-specific hazard fields (this listing):
Signal word: Not specified for this item; refer to SDS.
H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.
General safety guidance for aryl isothiocyanates (literature; not product-specific):
Hazard profile: Often irritating to skin, eyes, and respiratory tract; may be sensitizers. Some members are lacrimatory. Avoid inhalation and skin contact.
PPE: Chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles; use in a properly functioning chemical fume hood.
First aid (overview):
Skin/eye contact: Immediate decontamination with copious water for ≥15 min; remove contaminated clothing; seek medical attention.
Inhalation: Move to fresh air; obtain medical evaluation if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Reactivity notes: The –N=C=S carbon is electrophilic; uncontrolled contact with amines can result in exothermic thiourea formation. Add reagents slowly and control temperature.
Peroxide formation: Not applicable (no ether functionality).
Storage and handling (item-specific where provided):
Store at 2–8°C, argon charged, desiccated (as specified). Keep container tightly closed. Minimize headspace exchanges; purge with inert gas after use. Shipments are on wet ice (as specified). Always consult the product SDS for authoritative safety information.
Solvent Selection
Applicability: This compound is a moisture-sensitive electrophile; solvent choice primarily supports controlled nucleophilic additions and stability.
Solvent classes commonly used (literature/general):
Aprotic, anhydrous solvents (preferred): Dichloromethane (DCM), acetonitrile (MeCN), tetrahydrofuran (THF), toluene, ethyl acetate. These balance solubility of both reagent and nucleophiles and limit side hydrolysis.
Polar aprotics for less reactive nucleophiles: DMF, DMSO (ensure dryness and manage downstream workup).
Alcohols/water: Generally avoided as bulk solvents due to competing formation of thiocarbamates or hydrolysis; may be used intentionally for specific transformations.
Miscibility and polarity notes (literature):
DCM and toluene provide good solubility for aryl isothiocyanates and minimize background reactivity.
MeCN and THF improve rates with hindered amines; both are readily dried.
Selection guidance:
For amine → thiourea couplings: DCM or MeCN at 0–25°C; add base (e.g., Et3N) as needed to neutralize amine salts.
For thiol additions: THF or MeCN with a mild base (e.g., DIPEA) to form dithiocarbamates.
For solid-phase derivatization: DMF is common for swelling polymer supports; rigorously dry.
Green considerations: Where feasible, substitute DCM with 2-MeTHF or ethyl acetate; MeCN has a favorable EHS profile vs DMF/DMSO but requires acetonitrile waste segregation.
Storage and Reconstitution
Item-specific storage/shipping:
Store at 2–8°C, argon charged, desiccated (as provided in Product Data).
Shipped on wet ice (as provided).
Handling guidance (general for aryl isothiocyanates; not product-specific):
Minimize exposure to air and moisture. After dispensing, purge headspace with argon and recap promptly.
Use dry syringes or positive-displacement pipettes; avoid wet spatulas or caps.
If viscosity/crystallization complicates handling at 2–8°C, allow to warm in a sealed container to ambient before opening; do not heat uncapped.
Store in amber glass away from strong bases, amines, and oxidizers. Secondary containment recommended.
Reconstitution: Not applicable; supplied neat as a reactive organic reagent. If a stock solution is required, prepare freshly in anhydrous solvent (e.g., DCM, MeCN, THF). For short-term use, solutions can be stored under argon at 2–8°C for hours to a few days depending on dryness; verify integrity by IR (presence of νN=C=S) or test reaction before critical applications.
Always refer to the product SDS and lot-specific CoA for definitive handling and stability information.
Structure and Identity
A fluorinated aryl isothiocyanate useful as an electrophilic amine-derivatization and thiourea-forming reagent.
Product name (item-specific): 2,6-Difluorophenylisothiocyanate (SKU: D588056)
CAS (item-specific): 207974-17-2
PubChem CID (item-specific): 4031601
InChIKey (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Arene core: Monosubstituted benzene bearing two ortho fluorines (positions 2 and 6), creating a 1,3,5-arrangement of ring substituents relative to hydrogen atoms.
Functional group: An isothiocyanate moiety (–N=C=S) attached via the nitrogen to the aryl ring (aryl–N=C=S), providing a polarized C=S double bond and an electrophilic central carbon.
Electronic characteristics: Two ortho fluorines withdraw electron density inductively and through resonance, typically increasing isothiocyanate electrophilicity and decreasing aryl nucleophilicity relative to phenyl isothiocyanate.
2D structure in words: A benzene ring with fluorine atoms at the two ortho positions; the ring nitrogen-bonded isothiocyanate group projects linearly (Ar–N=C=S), with S at the terminus. No stereocenters; planar aromatic core with a linear N=C=S.
Synthetic Utility
Functional group reactivity (literature/general):
Electrophilic carbon of –N=C=S: Undergoes nucleophilic addition by amines (fast), thiolates (fast), and alkoxides (slower). Products include thioureas, dithiocarbamates, and thiocarbamates, respectively.
Ortho-difluoro substitution:
Increases electrophilicity, often improving conversions with less nucleophilic amines (anilines, hindered amines).
Can bias conformations and hydrogen-bonding patterns in thioureas, influencing crystallinity and binding in supramolecular assemblies.
Downstream transformations:
Cyclizations to heterocycles (e.g., thiazoles, benzothiazolinones) via intramolecular capture and oxidation.
Desulfurization (e.g., with Hg(II) salts or safer modern reagents) to convert thioureas to ureas (literature), retaining the difluorophenyl moiety.
S-alkylation of thioureas to isothiourea salts as phase-transfer catalysts or intermediates.
Retrosynthetic value:
Provides a direct route from amines to thiourea-containing scaffolds without external coupling reagents or high temperatures, enabling late-stage functionalization of complex molecules and polymers bearing amine handles.
Operational notes:
Use slight excess isothiocyanate for complete amine consumption; remove residual reagent by silica plug (strong UV band) or scavenging with excess ethanolamine followed by extraction.
Monitor by IR (νN=C=S ~2050–2100 cm−1; disappearance upon conversion) and 19F NMR to track the aryl fragment (literature).
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and does not possess antibody/bioreceptor target specificity. No clone, isotype, antigen, or species reactivity data apply.
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