2-Chloropropionitrile - ≥95% , CAS No.1617-17-0

CAS: 1617-17-0 Cat. No.: C122640 Fórmula: CH₃CH(Cl)CN Peso molecular: 89.52 Número EC: 216-570-0

GRADE & PURITY ≥95%

Synonyms

2-Chloropropionitrile, 95% | J-009853 | DTXSID401030864 | FT-0697777 | (+/-)-2-Chloropropionitrile | PROPANENITRILE, 2-CHLORO- | Propanenitrile, chloro- | 2-Chloropropanenitrile | AKOS001073334 | CH3CHClCN | MFCD00001859 | chloropropionitrile | BCP10983 |

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Sinónimos

2-Chloropropionitrile, 95% | J-009853 | DTXSID401030864 | FT-0697777 | (+/-)-2-Chloropropionitrile | PROPANENITRILE, 2-CHLORO- | Propanenitrile, chloro- | 2-Chloropropanenitrile | AKOS001073334 | CH3CHClCN | MFCD00001859 | chloropropionitrile | BCP10983 |

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

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Pureza

≥95%

Nombres e identificadores

Pubchem Sid

504759021

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504759021

Sonrisas canónicas

CC(C#N)Cl

IUPAC Name

2-chloropropanenitrile

InChIKey

JNAYPRPPXRWGQO-UHFFFAOYSA-N

INCHI

1S/C3H4ClN/c1-3(4)2-5/h3H,1H3

Isómeros SMILES

CC(C#N)Cl

WGK Alemania

3

Número ONU

3275

Peso molecular

89.52

Reaxy-Rn

1736658

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1736658&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Clase Organonitrogen compounds
      • Subclass Organic cyanides

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Clase: Organonitrogen compounds
• Subclass: Organic cyanides
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitriles
• Alternative Parents: Organopnictogen compounds Organochlorides Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Nitrile - Carbonitrile - Organopnictogen compound - Hydrocarbon derivative - Organochloride - Organohalogen compound - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as nitriles. These are compounds having the structure RC#N; thus C-substituted derivatives of hydrocyanic acid, HC#N.
• 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

Propiedades químicas y físicas

• Sensibilidad: heat sensitive
• Índice de refracción: 1.413
• Punto de inflamación (°F): 91.4 °F
• Punto de inflamación (°C): 33 °C
• Punto de ebullición (°C): 120-122°C
• Peso molecular: 89.520 g/mol
• XLogP3: 1.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 89.0032 Da
• Monoisotopic Mass: 89.0032 Da
• Topological Polar Surface Area: 23.800 Ų
• Heavy Atom Count: 5
• Formal Charge: 0
• Complexity: 60.500
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 for this small-molecule reagent. For synthetic use, refer to the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections for practical guidance.

Biological Roles

This product is a synthetic organic intermediate and not intended for biological use in vivo.

General/literature context

• Endogenous role: none known; simple α‑chloro nitriles are not natural metabolites.
• Biotransformation potential: Nitriles can be hydrolyzed by nitrile hydratases/nitrilases in microbial systems to corresponding amides/acids, but the α‑chloro substituent makes this substrate more electrophilic and potentially toxic to enzymes.
• Use in bioconjugation: The reagent is not typically used in bioorthogonal chemistry because the secondary chloride is too reactive and nonspecific toward nucleophilic residues, posing risk of protein denaturation.
• Toxicology note: Many small alkyl chlorides and nitriles exhibit cytotoxicity and irritancy; any in vitro exposure studies (if conducted in research settings) should be carried out with strict containment and without any clinical intent.

Bottom line

• No specific biological signaling or structural roles are associated with 2‑chloropropionitrile. Its value lies in chemical synthesis rather than biochemistry.

Buffer Applications

Not typically applicable. 2‑Chloropropionitrile is a reactive organic reagent and is not used to prepare laboratory buffer systems. For aqueous work, avoid exposing this electrophile to buffer solutions unless hydrolysis or nucleophilic substitution is intended. Select relevant sections such as Reaction & Applications and Reaction Conditions for practical use.

Green Alternatives

Context: 2‑Chloropropionitrile is a halogenated, electrophilic reagent. Green chemistry considerations center on safer leaving groups, solvent choices, and minimizing halogenated waste.

Greener design options (general/literature)

• Leaving group alternatives: Where feasible, replace the chloride with a sulfonate ester (e.g., 2‑tosylpropionitrile prepared upstream). Tosylates can enable cleaner SN2 at lower basicity, reducing elimination and waste from side products. Trade‑off: additional synthetic step and use of sulfonyl chloride.
• Direct access to methacrylonitrile: If elimination is the goal, sourcing stabilized methacrylonitrile directly may avoid base, heat, and HCl handling. Trade‑off: methacrylonitrile has its own hazard profile (toxic, polymerizable).
• Solvent improvements: Substitute DMF/DMSO with 2‑MeTHF, CPME, propylene carbonate, or green acetonitrile grades when compatible. Trade‑offs include solubility and rate.
• Catalysis and PTC: Phase‑transfer catalysis can enable use of inorganic bases (K2CO3) in biphasic systems at lower temperatures, reducing energy input and byproducts.

Comparison snapshot (general guidance)

• DMF/DMSO vs 2‑MeTHF/CPME: similar selectivity can be achieved at lower temperature in ethers with careful base control; ethers are more volatile/recyclable but may form peroxides and require management.
• Chloride vs tosylate: chloride is atom‑economical and readily available; tosylate can provide higher selectivity and yield at milder conditions but increases upstream waste.

Operational tips

• Emphasize closed‑loop solvent recovery; segregate halogenated waste; use minimal excess reagent and monitor conversion closely to curb overreaction and elimination.

Pharmaceutical Uses

This product is provided for research use only and is not intended for human or veterinary applications.

General/literature context

• Role: 2‑Chloropropionitrile may serve as a synthetic intermediate in process chemistry (e.g., to access 2‑substituted propionitriles, amides, or acids) during early route scouting. It is not used as an excipient.
• Regulatory status: No pharmacopeial monograph is commonly associated with this specific reagent. Any use in a GMP setting would require full qualification, impurity profiling, and risk assessment.
• Handling in process development: Because of its alkylating nature and potential for elimination to methacrylonitrile, development groups typically evaluate alternative leaving groups or in situ generation to mitigate handling of neat halides.

Note: No therapeutic or clinical claims are made or implied. Usage, if any, would be confined to non‑clinical synthetic steps under appropriate controls.

Physical Properties

Item-specific specs

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

Literature/general reference values (for context; not item-specific)

• Empirical formula (literature): C3H4ClN
• Formula mass (calculated): 89.53 g/mol
• Physical state: typically a colorless to pale liquid (literature)
• Volatility: moderate; expected to have a mid‑range boiling point for a small nitrile bearing a chloro substituent (literature trend)
• Density and refractive index: available in chemical handbooks; consult literature/SDS for precise values.
• Solubility: low in water; miscible with many organic solvents such as ethers, chlorinated solvents, and polar aprotics (literature trends for α‑chloro nitriles).
• pKa: not applicable (no Brønsted acid/base center in neutral form); conjugate acidity/basicity dominated by nitrile functionality (literature note).
• LogP: expected moderate due to small size and polar nitrile balanced by hydrophobic framework (literature trend).

Notes for practitioners

• Because α‑halo nitriles can undergo base‑promoted elimination, measured boiling points can appear depressed in the presence of strong base or impurities; use neutral/acidic drying agents and avoid basic drying conditions when characterizing (general guidance). Always confirm item‑specific constants on the CoA.

Quality and Grades

Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpreting grades for this reagent (general guidance)

• Research grade vs. analytical grade: For reactive alkyl chlorides like 2‑chloropropionitrile, trace moisture and base can promote elimination or hydrolysis. Higher grades typically control water and acid/base impurities more tightly, leading to improved stability and reproducibility.
• Stabilizers/inhibitors: None specified for this item. Some suppliers ship α‑halo nitriles without stabilizers; if a stabilizer is present in a particular lot, it will be listed on the CoA and may influence certain base‑sensitive reactions.
• UV/GC/HPLC suitability: If using as a standard or in photometric workflows, verify UV absorbance profile and purity on the CoA. For kinetic or polymerization studies (e.g., elimination to methacrylonitrile), confirm residual acid/alkali content and assay by GC.

What to check on receipt (best practice)

• Review assay (%), identity (GC/MS, 1H/13C NMR), and residual solvents/water (Karl Fischer) on the CoA where available.
• Record lot number and date; for moisture-sensitive or base-sensitive operations, consider a quick GC or NMR check before critical experiments.
• If chirality matters, note that material is generally racemic unless an enantiomeric excess is explicitly specified on the label/CoA.

Reaction and Applications

Use cases (general/literature; expand from common practice with α‑chloro nitriles)

• Nucleophilic substitution (SN2): Installation of a 1‑cyanoethyl unit onto heteroatom nucleophiles (RO−, RS−, R2N−), giving 2‑substituted propionitriles with inversion at C‑2. Typical for synthesis of 2‑alkoxy-, 2‑thio-, and 2‑amino‑propionitriles.
• Base‑promoted elimination (E2): Formation of methacrylonitrile under strong base or elevated temperature; relevant for planned dehydrohalogenation or as a competing side reaction to manage during SN2.
• Hydrolysis/functional group interconversion: Stepwise nitrile hydrolysis to amide (acidic or basic conditions) and further to 2‑chloropropionic acid derivatives; 2‑chloropropionamide can serve as a handle for further coupling.
• Carbon–carbon bond construction: Enolate or organometallic chemistry at the α‑position of the nitrile (after substitution) enables access to β‑functionalized nitriles; the chloro group can be replaced first to introduce diversity.
• Asymmetric synthesis: Because C‑2 is stereogenic, chiral phase‑transfer catalysis or chiral amine nucleophiles can furnish enantioenriched products via stereospecific SN2 pathways.

Practical tips

• Suppress elimination by using softer nucleophiles, lower temperatures, and less basic conditions; employ polar aprotic solvents judiciously.
• Avoid strong bases during workup; quench at low temperature and minimize standing time with basic washes.
• For amination, pre-form the amine salt and add base slowly at 0–10°C. For thiolation, use thiolates in ether solvents to improve selectivity.
• Monitor by GC or 1H NMR (disappearance of CH(Cl) signal; appearance of new methine adjacent to CN).

Reaction Conditions

General/literature guidance (not item-specific; optimize per substrate)

• SN2 substitutions

  • Solvents: DMF, DMSO, acetonitrile, sulfolane (fast) or THF/2‑MeTHF/toluene (more selective, cooler).
  • Nucleophiles: alkoxides, thiolates, secondary amines, azide.
  • Base: mild bases (K2CO3, Cs2CO3) for O/S nucleophiles; tertiary amines for amination. Avoid strong bases that drive E2.
  • Temperature: 0 to 50°C; lower temperatures favor SN2 over E2. Typical times 1–16 h depending on nucleophile/solvent.
  • Additives: Phase‑transfer catalysts (e.g., TBAB) can enable K2CO3/NaN3 in biphasic toluene/water.

• E2 elimination to methacrylonitrile

  • Conditions: strong, non‑nucleophilic base (t‑BuOK, DBU) in THF or DMSO, 25–80°C.
  • Notes: Control exotherm; vent for HCl traces; methacrylonitrile is volatile/toxic—trap appropriately.

• Hydrolysis/hydration of nitrile

  • Acidic hydration: H2SO4 or HCl aqueous mixtures, 50–100°C → amide; harsher or prolonged → acid.
  • Basic hydrolysis: NaOH/KOH aqueous alcohol, reflux → acid (via amide). Beware of concurrent elimination under strongly basic, hot conditions.

• Workup/purification

  • Quench bases at 0–10°C. Extract into suitable organic phase; wash with brine, avoid strong basic washes to prevent post‑reaction elimination.
  • Purify by vacuum distillation or flash chromatography; verify by GC, 1H/13C NMR, IR (strong CN stretch ~2250 cm⁻¹; literature).

Safety and Handling

Authoritative classification: Not specified in the Product Data. Always consult the product SDS for definitive GHS classification, pictograms, and H/P statements.

General hazards of α‑chloro nitriles (literature/general guidance)

• Toxicity/irritation: harmful if swallowed, inhaled, or absorbed through skin; vapors and liquid can irritate eyes, skin, and respiratory tract. Many low‑MW alkyl chlorides are lachrymators.
• Reactivity: alkylating electrophile; reacts with strong nucleophiles (amines, thiolates, alkoxides). Bases promote elimination to methacrylonitrile. Hydrolysis under acidic/basic conditions gives amide/acid with HCl evolution; avoid contact with moisture and bases in storage.

PPE and engineering controls

• Wear chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles; handle in a chemical fume hood.
• Avoid inhalation; use local exhaust ventilation. Keep containers tightly closed to minimize vapor.

First-aid overview (consult SDS/medical professional)

• Inhalation: move to fresh air; seek medical attention if symptoms persist.
• Skin contact: remove contaminated clothing; wash with soap/water for ≥15 min.
• Eye contact: rinse cautiously with water for ≥15 min; remove contacts if easy.
• Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Storage incompatibilities and special precautions

• Store at 2–8°C (per Product Data), away from bases, strong nucleophiles, oxidizers, and moisture. Use amber or opaque secondary containment if prolonged light exposure is expected. Ground/bond when transferring flammable liquids. Dispose of waste as halogenated organic.

Solvent Selection

Applicability: 2‑Chloropropionitrile is a reactive substrate/reagent rather than a general-purpose solvent. Solvent choice matters primarily for its use in substitutions, eliminations, and additions.

General solvent guidance (literature/general)

• Polarity: Reactions benefit from polar aprotic media (e.g., acetonitrile, DMF, DMSO, sulfolane) to accelerate SN2 on the secondary chloride, but these conditions also increase the risk of base-promoted E2 elimination to methacrylonitrile.
• Less polar options: Ethers (THF, 2‑MeTHF, MTBE) and toluene can moderate elimination, especially at lower temperature, at the expense of slower substitution.
• Protic solvents: Alcohols can lead to solvolysis (formation of 2‑alkoxypropionitriles) and HCl formation; use intentionally for alkoxylation, otherwise avoid.
• Aqueous media: Limited solubility is expected; biphasic systems with phase-transfer catalysts (PTC) can enable SN2 with inorganic bases/nucleophiles.

When to choose alternatives

• If elimination is problematic, consider switching to a better leaving group precursor (e.g., 2‑tosylpropionitrile prepared in situ) or using milder nucleophiles/solvents.

Small comparison (general)

• Polar aprotic (DMF/DMSO): fastest SN2; highest E2 risk.
• Ethers/aromatics: slower SN2; improved selectivity; better for temperature control.
• PTC biphasic: enables inorganic nucleophiles; scalable with careful heat management.

Storage and Reconstitution

Item-specific storage and shipping (from Product Data)

• Storage Conditions: Store at 2–8°C.
• Shipped In: Wet ice.

General handling and storage best practices (literature/general)

• Keep tightly closed in the original container; protect from moisture and bases to prevent hydrolysis/elimination.
• If frequent access is expected, consider aliquoting under dry nitrogen/argon to minimize headspace moisture and repeated warming cycles.
• Avoid prolonged exposure to heat or light. Use compatible seals (PTFE-lined caps) to resist halogenated organics.
• No reconstitution is required; this reagent is typically supplied neat. If dilution/stock solutions are prepared, use dry, oxygen-free solvents (e.g., anhydrous toluene, THF, or acetonitrile), label clearly, and store cold. Check stability over time by GC before critical runs.
• Freeze–thaw guidance: Not typically frozen; if a solution is frozen for long-term storage, avoid repeated freeze–thaw—prepare single-use aliquots.

Note: For any stabilizer content, water limits, or detailed shelf-life, see the lot-specific CoA/Spec Sheet.

Structure and Identity

Brief description: 2‑Chloropropionitrile is a small, electrophilic α‑chloro nitrile (secondary chloro on C‑2 adjacent to a nitrile). It is commonly used as an alkylating reagent and as a precursor to methacrylonitrile, amides, and acids.

• Product identifiers (from Product Data)
  • SKU: C122640
  • Product Name: 2-Chloropropionitrile
  • CAS: 1617-17-0
  • CID: 519225
  • InChIKey: 164820 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Computed/literature identity (general reference values; not item-specific)
  • Preferred (literature) SMILES: CC(Cl)C#N
  • Molecular formula (literature): C3H4ClN
  • Molecular weight (calculated from formula): 89.53 g/mol
• Structural features (general chemistry description)
  • Functional groups: secondary alkyl chloride (–CH(Cl)–) α to a nitrile (–C≡N).
  • Ring systems: none (acyclic).
  • Stereochemistry: the C‑2 center is stereogenic; commercial material is typically racemic unless otherwise specified.
  • 2D description in words: a three‑carbon chain where C‑1 is a nitrile carbon (–C≡N), C‑2 bears chlorine and a methyl substituent, and C‑3 is a terminal methyl (CH3–CH(Cl)–C≡N).

Synthetic Utility

Key reactivity (general/literature)

• Electrophilic center: Secondary C–Cl adjacent to a nitrile enables SN2 displacement by O, N, S, and C nucleophiles; stereochemical inversion affords access to enantioenriched targets if chiral nucleophiles/catalysts are used.
• Chemoselectivity lever: The nitrile activates the adjacent carbon, increasing the rate of substitution vs non‑activated secondary chlorides; however, it also increases E2 susceptibility.
• Functional group interconversion: Nitrile can be hydrated (to amide) or hydrolyzed (to acid) post‑substitution, enabling rapid diversification to carboxamides/acids with a 2‑substituted motif.

Named/representative transformations

• SN2 alkylations of thiolates to give 2‑(alkylthio)propionitriles (precursors to sulfides/sulfoxides/sulfones).
• Amination to 2‑aminopropionitriles; subsequent hydration to 2‑amino‑propionamides or hydrogenation to β‑aminoethylamines.
• Alcoholate substitution to 2‑alkoxypropionitriles; further hydrolysis to 2‑alkoxypropionic acids (masked lactic‑acid analogs).
• E2 elimination with strong base to methacrylonitrile (feedstock for further polymer chemistry).

Retrosynthetic value

• Serves as a convenient masked equivalent of methacrylonitrile (via E2) or of 2‑substituted propionic acid derivatives (via substitution + nitrile hydrolysis). It enables step‑economic access to β‑functionalized carbonyl compounds via nitrile chemistry.

Target Specificity

Not applicable. This product is a small-molecule reagent and does not possess biological target specificity, antigen/epitope binding, or isotype characteristics. No clone or species reactivity information applies.