Cyclopropanemethanamine， 1-(3-chlorophenyl)- - ≥95% , CAS No.115816-31-4

CAS: 115816-31-4 Cat. No.: C769705 Formula: C₁₀H₁₂NCl Peso molecolare: 181.66 PubChem CID: 15611174

GRADE & PURITY ≥95%

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

C1CC1(CN)C2=CC(=CC=C2)Cl

IUPAC Name

[1-(3-chlorophenyl)cyclopropyl]methanamine

InChIKey

PCAQCRJAVGXMQF-UHFFFAOYSA-N

INCHI

1S/C10H12ClN/c11-9-3-1-2-8(6-9)10(7-12)4-5-10/h1-3,6H,4-5,7,12H2

Isomeri SMILES

C1CC1(CN)C2=CC(=CC=C2)Cl

PubChem CID

15611174

Peso molecolare

181.66

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Chlorobenzenes
• Alternative Parents: Aralkylamines Aryl chlorides Organochlorides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aralkylamine - Chlorobenzene - Aryl halide - Aryl chloride - Organic nitrogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Organochloride - Organohalogen compound - Primary aliphatic amine - Amine - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
• 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: 181.660 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 181.066 Da
• Monoisotopic Mass: 181.066 Da
• Topological Polar Surface Area: 26.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 165.000
• 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 for assay protocols such as WB, IHC, IF, or FC. This item is a small-molecule reagent for chemical synthesis. For practical use, refer to the Reaction & Applications and Reaction Conditions sections for guidance on typical synthetic transformations, and consult primary literature for substrate-specific procedures.

Biological Roles

Item-specific biological data are not provided. The following are general considerations for small arylalkyl primary amines (literature/general; not specific to this item):

• Primary amines participate in Schiff base formation with carbonyls and can engage in ionic interactions with acidic biomolecules when protonated.
• The 3-chlorophenyl group and cyclopropyl motif are common in medicinal chemistry for tuning lipophilicity, metabolic stability, and conformational bias of ligands, but any biological activity depends on the final derivative and target context.
• Protonation state at physiological pH (typically cationic) affects membrane permeability and binding to acidic residues.

No pharmacology, ADME, or bioactivity is claimed for this catalog item. Use strictly for research and chemical synthesis; evaluate any biological properties empirically in your specific system.

Buffer Applications

Not typically applicable. This product is a small organic amine building block, not a dedicated buffering reagent. While primary amines can accept protons, they lack the defined pKa ranges and composition control expected of laboratory buffer systems. For buffer preparation, select validated buffering agents (e.g., phosphate, Tris, HEPES) and refer to appropriate recipes. Use this item in synthetic workflows as outlined under Reaction & Applications and Synthetic Utility.

Green Alternatives

Greener choices often pertain to solvents and reagents used with this amine rather than the amine itself (literature/general):

• Solvent substitution (examples):

  • Replace DCM with EtOAc or 2-MeTHF for extractions and acylations when feasible.
  • Substitute DMF/DMAc with propylene carbonate, MeCN, or 2-MeTHF in coupling steps if reactivity allows.
  • Prefer EtOH/i-PrOH over MeOH for reductive aminations due to lower toxicity and better sustainability profiles.

• Reagent choices:

  • Use OxymaPure/EDC instead of HOBt/HBTU to reduce explosive risk and improve safety in amide couplings.
  • Choose aqueous H2 with Pd/C for imine reductions when compatible, reducing cyanoborohydride waste.

• Processing/workup:

  • Employ acid–base extraction to minimize chromatographic solvent consumption; crystallize amine salts (e.g., HCl, p-TsOH) when possible.

Trade-offs: Greener solvents may alter reaction rates/solubility; small-scale scouting is recommended. No item-specific environmental metrics are provided; consult your organization’s solvent selection guides (e.g., GSK/ACS PMI) to balance safety, health, and environmental impact.

Pharmaceutical Uses

Item-specific pharmacopeial status or excipient use: Not specified for this item; refer to CoA/Spec Sheet.

General context (literature/general):

• Arylalkyl primary amines like this compound are commonly employed as intermediates in API development, enabling preparation of amides, ureas, sulfonamides, and other analog series for SAR studies.
• Salt formation (e.g., hydrochloride) can improve processability, crystallinity, and stability during isolation and storage of intermediates.
• No claims are made regarding this compound’s suitability as a pharmaceutical excipient or active ingredient; it is provided strictly for research and laboratory synthesis.

Physical Properties

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

• Literature/general expectations for an aryl–cyclopropylmethyl primary amine (for context only; verify experimentally):

  • Physical state: often low-melting solid or viscous liquid depending on salt form and purity.
  • Basicity: primary aliphatic amines typically have conjugate acid pKaH ~9–10 (literature, analogous compounds); free-base pKb accordingly weak. Salt formation (e.g., HCl) improves crystallinity and handling.
  • Solubility: free base is generally miscible with many organic solvents (alcohols, ethers, chlorinated solvents); limited solubility in water as free base but highly water-soluble as mineral acid salts (literature, analogous arylalkylamines).
  • Lipophilicity: aryl chloride plus cyclopropyl ring confer moderate hydrophobicity; protonation markedly increases aqueous solubility (literature, analogous compounds).
  • Volatility/odor: primary amines may have characteristic amine odor; volatility depends on molecular weight and hydrogen bonding; handle in fume hood.

Notes: Without a provided CoA/Spec Sheet, do not treat any numeric property as specification. Always confirm mp/bp, density, refractive index, and purity empirically for method development.

Quality and Grades

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

• General notes for amine building blocks in research catalogs (literature/general):

  • Research grade typically targets high chemical purity suitable for synthesis and screening; trace water, residual solvents, and amine value may be reported on CoA.
  • If provided as a salt (e.g., hydrochloride), assay may be reported as free-base equivalent; residual inorganic content (chloride) is inherent to the salt.
  • For analytical applications (e.g., LC/MS), suppliers may offer additional filtration/drying or low UV-absorbing solvent content; absence of such claims implies standard research grade.

• Stabilizers/additives: None are stated for this item. When present in amines, stabilizers are uncommon; if provided, they would be listed on the CoA.

• Recommendation: Confirm identity (NMR, HRMS) and purity (HPLC/GC) upon receipt for critical applications. If chiral information or isomer ratio matters, request supporting documentation from the CoA/Spec Sheet.

Reaction and Applications

This compound is a versatile primary amine bearing a 3-chlorophenyl handle and a cyclopropylmethyl motif, making it useful as a building block in medicinal and materials chemistry (literature/general guidance):

• Derivatization of the amine:

  • Amide formation with acid chlorides/anhydrides or via carbodiimide (DCC/EDC, HOBt/HOAt, Oxyma) or uronium reagents (HATU/HBTU). Control base (DIPEA, NMM) and temperature to minimize overacylation.
  • Sulfonamide/carbamate/urea synthesis using sulfonyl chlorides, chloroformates, or isocyanates; triphosgene can generate symmetrical/unsymmetrical ureas.
  • Reductive amination with aldehydes/ketones (NaBH3CN, NaBH(OAc)3) to access secondary amines while retaining the aryl chloride for later cross-coupling.

• Exploiting the aryl chloride (on the molecule itself):

  • Pd-catalyzed cross-couplings (e.g., Buchwald–Hartwig amination, Suzuki–Miyaura, Negishi) can functionalize the aryl chloride after protecting the native amine (e.g., Boc, Cbz) to avoid self-reaction. Modern ligands (e.g., XPhos, BrettPhos) enable coupling of aryl chlorides.

• Cyclopropane chemistry:

  • The cyclopropyl unit is a compact, lipophilic motif; under strongly acidic or radical conditions, cyclopropane ring-opening pathways can occur—plan conditions accordingly.

• Parallel/array synthesis:

  • As a primary amine, it is well-suited for amide library preparation and for solid-phase coupling to activated esters (after temporary protection if needed).

Always assess chemoselectivity: protect the amine before aryl chloride activation; conversely, retain the aryl chloride as a synthetic handle after amine derivatization.

Reaction Conditions

General conditions for typical transformations of primary arylalkyl amines and aryl chlorides (literature/general; optimize per substrate):

• Amide coupling: HATU or EDC/Oxyma (1.1–1.5 equiv) in DMF, DCM, or 2-MeTHF; base DIPEA (2–3 equiv); 0–25 °C, 1–12 h. Minimize epimerization for chiral acids by using Oxyma and low temperature.

• Sulfonamide formation: RSO2Cl (1.05–1.2 equiv), DIPEA or NaHCO3, DCM/MeCN, 0–25 °C, 1–4 h.

• Carbamate/urea: Boc2O (1.1–1.5 equiv) in THF/MeCN with base; or CDI/triphosgene protocols for ureas; 0–25 °C, 1–6 h.

• Reductive amination: carbonyl (1.0 equiv), amine (1.1–2.0 equiv), NaBH(OAc)3 (2–3 equiv) in MeOH/HOAc or DCE/i-PrOH; rt to 40 °C, 2–16 h. Alternatively, H2/Pd for imine hydrogenation when compatible.

• Aryl chloride cross-coupling (on this scaffold after amine protection):

  • Suzuki–Miyaura: ArB(OH)2 (1.2–1.5 equiv), Pd(dba)2 or Pd-precatalyst (1–3 mol%), XPhos/SPhos ligand, base K3PO4 or Cs2CO3, dioxane/H2O or toluene, 80–110 °C.
  • Buchwald–Hartwig amination: amine partner, Pd2(dba)3 or Pd-precatalyst (1–3 mol%), BrettPhos or RuPhos ligand, NaOtBu or Cs2CO3, toluene/dioxane, 80–110 °C.

• Workup and isolation: acid–base extraction is efficient; for salts, basify to liberate free base or isolate as crystalline HCl salt. Chromatography on silica may require addition of base (0.5–1% Et3N) to suppress tailing.

These conditions are representative; substrate-specific optimization and small-scale scouting are recommended.

Safety and Handling

• Item-specific hazard data: Not specified for this item; refer to SDS. Signal word, H-statements, GHS classification, and pictograms are not provided in the Product Data.

• General safety guidance for primary aliphatic/benzylic amines (literature/general):

  • Potential hazards: skin/eye irritation, respiratory irritation, and sensitization. Amines are basic and may be corrosive to eyes; avoid contact.
  • PPE: wear lab coat, safety glasses or face shield, and appropriate gloves (e.g., nitrile). Use in a certified fume hood to prevent inhalation of vapors and to mitigate odor.
  • Storage incompatibilities: keep away from strong oxidizers, acid chlorides/anhydrides, isocyanates, and strong acids/bases unless intentionally reacting. Amines may absorb CO2 forming carbamates; store tightly closed under inert atmosphere if feasible for free-base form.
  • Spill/response: absorb small spills with inert material (vermiculite), ventilate area; neutralize cautiously if appropriate. For skin/eye contact, rinse with water for at least 15 minutes and seek medical attention per SDS.
  • Fire safety: many amines are combustible; use CO2, dry chemical, or foam. Ensure proper grounding when transferring solvents containing amines.

Always defer to and follow the product-specific SDS for authoritative hazard classification, exposure limits, and first-aid measures.

Solvent Selection

• Polarity and solubility profile (literature/general):

  • Free-base primary arylalkylamines are typically soluble in polar aprotic solvents (DMF, DMSO, acetonitrile), moderately to highly soluble in alcohols (MeOH, EtOH, i-PrOH), and in many ethers (THF, MTBE) and chlorinated solvents (DCM, DCE). Water solubility is limited for the free base but greatly increases upon protonation (e.g., HCl salt).

• Practical selection tips:

  • Reaction media: choose polar aprotic solvents (DMF, DCM, THF, MeCN) for acylation/carbamate/sulfonamide formation; use alcohols for reductive amination with NaBH3CN or NaBH(OAc)3.
  • Workup: dissolve crude in an organic solvent and perform acid–base extraction to partition the amine into aqueous acid, then re-basify and extract—effective for this class of compounds.
  • Analytical: DMSO-d6 or CDCl3 are common NMR solvents; confirm solubility first.

• Comparison (literature/general):

  • DCM vs. EtOAc: DCM offers higher amine solubility and faster phase disengagement; EtOAc is greener and often sufficient for extractions.
  • THF vs. 2-MeTHF: 2-MeTHF can be a greener alternative with similar solvating power for many amine transformations.

Note: No item-specific solvent constraints are provided; tailor solvent choice to your reaction chemistry and downstream isolation.

Storage and Reconstitution

• Item-specific storage: Store at 2–8 °C. Shipped on wet ice. Protect from moisture and CO2 uptake by keeping the container tightly sealed. Follow any additional guidance on the CoA/Spec Sheet.

• General handling (literature/general):

  • If supplied as a free base, consider storing under inert gas (N2/Ar) to minimize oxidation and carbamate formation from atmospheric CO2. Desiccant use is recommended.
  • If supplied as an acid salt (e.g., HCl), store tightly closed to avoid deliquescence; salts typically exhibit improved stability and crystallinity.
  • Allow the container to equilibrate to room temperature before opening to prevent condensation. Reseal promptly after use.

• Reconstitution: No specific protocol is provided for this item. Dissolve in anhydrous organic solvent compatible with the intended use (e.g., DCM, MeOH, THF, DMSO) or prepare an aqueous solution after protonation (e.g., dilute HCl) if needed. Filter if particulates are present. For long-term stock solutions, store in amber vials at 2–8 °C or below, under inert atmosphere when appropriate.

• Stability: Not specified for this item; refer to CoA/Spec Sheet. Verify stability by periodic analytical checks (HPLC/NMR) for critical applications.

Structure and Identity

Brief overview: This item is described as an aryl-substituted cyclopropanemethylamine bearing a 3-chlorophenyl group.

• Item-specific (from Product Data):

  • CAS: 115816-31-4
  • Product Name: Cyclopropanemethanamine, 1-(3-chlorophenyl)-
  • InChIKey: 273500
  • SMILES: 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.

• Structural features (interpretation from the chemical name; literature/general description):

  • Contains a 3-chlorophenyl (meta-chloro) aromatic ring.
  • Contains a cyclopropane ring linked through a methylene to a primary amine (–CH2–NH2) motif (cyclopropanemethanamine).
  • Functional groups: primary aliphatic amine (basic, nucleophilic), aryl chloride (potential cross-coupling handle), strained cyclopropyl ring (engages in ring-opening under certain conditions).
  • Stereochemistry: None explicitly indicated by the name; the structure as named does not require a stereocenter, though substitutions on cyclopropane can lead to diastereotopic environments.

• 2D structure in words (literature/general): A benzene ring bearing a chlorine at the 3-position is attached via a single carbon linker to a cyclopropane ring; a methanamine substituent is attached to the cyclopropane carbon (cyclopropane–CH2–NH2), yielding an aryl–(cyclopropylmethyl)amine framework.

Synthetic Utility

Key features enabling broad synthetic value (literature/general):

• Primary amine handle: readily undergoes acylation to amides, sulfonylation to sulfonamides, carbamoylation to carbamates/ureas, and reductive amination to secondary/tertiary amines. Compatible with solid-phase synthesis (after protection) and parallel library generation.
• Aryl chloride: a versatile synthetic handle for downstream diversification. After protecting the amine (e.g., Boc or Cbz), the aryl chloride can engage in Pd-catalyzed couplings (Suzuki, Buchwald–Hartwig, Negishi, Kumada), allowing late-stage installation of heteroaryl, alkyl, or amino fragments.
• Cyclopropyl motif: adds conformational constraint and lipophilicity. Under acidic or radical conditions, ring-opening transforms the scaffold; this can be exploited or avoided depending on the route.
• Orthogonal strategies:
  • Sequence 1: Protect amine → cross-couple aryl chloride → deprotect → elaborate amine.
  • Sequence 2: Elaborate amine (amide/sulfonamide formation) → retain aryl chloride for final cross-coupling.
• Protecting groups: Boc (acid-labile), Cbz (hydrogenolysis), Fmoc (base-labile) are typical; selection depends on planned aryl chloride activation conditions.

Overall, the combination of nucleophilic amine, a cross-coupling handle, and a strain-bearing ring makes this a compact, high-information-content building block for lead optimization.

Target Specificity

Not applicable. This product is a small-molecule amine building block, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with defined target, or oligonucleotide). No target, epitope, or species reactivity information is provided or implied for this item.

Domande frequenti

How should this product be stored?

Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.