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Spécifications

Spécifications et pureté

≥98%

Conditions de stockage de stockage

Room temperature

Pureté

≥98%

Noms et identifiants

Sourires canoniques

CCNCC.C1=CC=C(C=C1)CC(C(=O)O)NC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4

IUPAC Name

N-ethylethanamine;(2S)-3-phenyl-2-(tritylamino)propanoic acid

InChIKey

BSLKHJZVHGFJPR-SNYZSRNZSA-N

INCHI

1S/C28H25NO2.C4H11N/c30-27(31)26(21-22-13-5-1-6-14-22)29-28(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;1-3-5-4-2/h1-20,26,29H,21H2,(H,30,31);5H,3-4H2,1-2H3/t26-;/m0./s1

Isomères SMILES

CCNCC.C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4

PubChem CID

14283984

Documentation

📋 Fiche de données de sécurité (FDS)

Document complet couvrant les dangers, la manipulation, le stockage et la conformité réglementaire.

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✅ Certificat d'analyse (COA)

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📊 Fiche technique

Résumé de référence rapide des spécifications et applications du produit.

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🔬 Fiche de spécifications

Attributs de qualité complets et critères d'acceptation pour cette qualité.

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Données avancées

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Benzenoids
  - Classe Triphenyl compounds

Kingdom	Organic compounds
Superclass	Benzenoids
Classe	Triphenyl compounds
Subclass	Not available
Intermediate Tree Nodes	Not available
Direct Parent	Triphenyl compounds
Alternative Parents	Phenylalanine and derivatives Phenylpropanoic acids L-alpha-amino acids Amphetamines and derivatives Aralkylamines Quaternary ammonium salts Carboxylic acid salts Monocarboxylic acids and derivatives Dialkylamines Carboxylic acids Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic cations
Molecular Framework	Not available
Substituents	Triphenyl compound - Phenylalanine or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - L-alpha-amino acid - Aralkylamine - Monocyclic benzene moiety - Quaternary ammonium salt - Carboxylic acid salt - Carboxylic acid derivative - Secondary amine - Carboxylic acid - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organic salt - Carbonyl group - Hydrocarbon derivative - Organic oxide - Amine - Organic cation - Aromatic homomonocyclic compound
Description	This compound belongs to the class of organic compounds known as triphenyl compounds. These are aromatic compounds containing a triphenyl moiety.
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. DOI: 10.1186/s13321-016-0174-y

Structure 3D

Certificats (CoA, COO, BSE/TSE et tableau d'analyse)

C of A & Other Certificates(BSE/TSE, COO):

Analytical Chart:

Propriétés chimiques et physiques

Poids moléculaire	480.600 g/mol
XLogP3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	10
Exact Mass	480.278 Da
Monoisotopic Mass	480.278 Da
Topological Polar Surface Area	61.400 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	503.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

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Application Protocols

No item‑specific, tested biological application protocols are provided for this product. For synthetic use, general workflows include: • Dissolve the compound in dry DMF or DCM under inert atmosphere. • For coupling, add base (e.g., DIPEA) and an activating reagent (HATU/HBTU/EDC) at 0–25 C; stir until completion by LC. • For detritylation, treat with TFA/DCM and appropriate scavengers; monitor by LC/UV for trityl cation. • Purify by aqueous workup and silica chromatography or preparative HPLC, as appropriate. These are general literature practices; tailor conditions to your substrate set and consult the CoA/SDS for any item‑specific constraints.

Biological Roles

Item-specific biological data are not provided. This product is sold for research use only.

General biochemical context (informational): • Phenylalanine is an essential aromatic amino acid incorporated into proteins; however, the trityl‑protected derivative is not a natural metabolite and is not biologically active in standard pathways. • Protection rationale: Trityl masking of the α‑amine increases hydrophobicity and blocks biological interactions, enabling selective synthetic transformations before re‑exposing the amine. • Analytical relevance: During deprotection, the trityl cation exhibits strong UV absorbance, which can be exploited for monitoring in synthetic workflows but has no physiological role.

No clinical or therapeutic claims are made or implied. For any biological testing, use appropriate controls and remove protecting groups as required to restore the native amino functionality.

Buffer Applications

Not typically applicable. As a hydrophobic, protected amino acid, this compound is not used to prepare aqueous laboratory buffers. If aqueous handling is necessary (e.g., analytical sampling), dissolve first in a miscible organic solvent such as DMF or DMSO, then dilute—ensuring final organic content is compatible with the assay. For buffer selection relevant to peptide work, refer instead to sections on Reaction & Applications and Reaction Conditions.

Green Alternatives

Green chemistry considerations focus on solvent and reagent selection during coupling and detritylation rather than on the solid reagent itself.

Opportunities (literature/guidance): • Replace DCM/chloroform with greener media: – Ethyl acetate or 2‑MeTHF as an alternative for extractions or some coupling steps if solubility permits. – Dimethyl carbonate or CPME as less hazardous options for workups. • DMF/NMP replacements: – Polar, safer amide alternatives such as PC/GBL mixtures, Cyrene (dihydrolevoglucosenone), or propylene carbonate may be used case‑by‑case; verify solubility and compatibility with coupling reagents. • Safer coupling systems: – Use OxymaPure with EDCI (HOAt‑free) to reduce hazardous byproducts; avoid HOBt/HOAt where safety risk is significant. • Waste minimization: – Implement solvent recovery for high‑boiling polar aprotics; use solid‑phase scavengers to reduce aqueous waste.

Note: Validate reaction rates, solubility, and stereochemical integrity when changing media; run small pilots before scale‑up.

Pharmaceutical Uses

Item-specific regulatory or pharmacopeial status is not provided for this product.

General context (informational, non‑clinical): • Role: Protected amino acids such as N‑trityl phenylalanine are used as synthetic intermediates in the manufacture of peptide drug candidates and peptidomimetics, enabling orthogonal protection strategies. • Formulation/excipient use: The protected derivative is not used as an excipient; deprotected and purified peptides may eventually be formulated, but this intermediate is strictly for process chemistry. • Quality considerations for process development: Low levels of racemization, defined residual solvents, and tight control of aromatic impurities facilitate downstream purification and regulatory filings. • Documentation: For GMP‑aligned development, suppliers often provide expanded quality packages (impurity profiles, stability data). None are specified here; consult the CoA/Spec Sheet and inquire if GMP support is required.

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

Physical Properties

Item-specific properties from Product Data: • Appearance: Not specified for this item; refer to CoA/Spec Sheet. • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. • Molecular weight/formula: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for N‑trityl amino acids (informational, not specifications): • Physical form: Typically white to off‑white crystalline solid or foam, with high aromatic content. • Solubility (literature): Sparingly soluble in nonpolar hydrocarbons; soluble in chlorinated solvents (DCM, CHCl3), moderately to well soluble in polar aprotics (DMF, DMSO, NMP), limited in alcohols and very low in water due to multiple aryl rings. • Acid/base: Carboxylic acid pKa typically ~2–3 (suppressed by neighboring aryl groups is minor); the trityl‑protected amine is nonbasic. • Partitioning: High apparent logP due to trityl (literature qualitative). • Melting point: Many N‑trityl amino acids display Mp in the 100–170 C range, often decomposition before clear melt; exact value is compound‑specific and must be confirmed on CoA. • UV characteristics: Strong absorbance in the UV (aryl π–π*), commonly used to monitor trityl cation release during detritylation; exact λmax/ε depend on solvent and are not specified here.

Note: Do not use the above as acceptance criteria. For precise BP/MP, density, refractive index, water/peroxide/metal content, and UV cutoffs, refer to the item’s CoA/Spec Sheet and SDS.

Quality and Grades

Item-specific quality information from Product Data: • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Context and expectations for peptide building blocks (general guidance): • Typical grades: – Peptide synthesis grade: Tight control of residual solvents, low water, and limits on inorganic/metal contaminants; LC/HPLC purity typically ≥95% area for protected amino acids (varies by supplier/spec). – Research grade: Suitable for general synthetic work, with broader acceptance criteria. • Documentation: CoA generally includes assay/purity (e.g., HPLC), identity (NMR/HRMS/IR), and key residuals (water by KF, residual solvents). For chiral building blocks, optical rotation or chiral HPLC may be provided to establish enantiomeric excess. • Stabilizers/additives: Trityl derivatives rarely require stabilizers; however, some suppliers include trace acid scavengers or specify packaging under inert atmosphere. Any stabilizer, if present, will be disclosed on the CoA—none is specified here. • UV suitability: If intended for chromatographic use or UV monitoring, low baseline bleed is desirable; confirm with CoA data.

Acceptance criteria: Because item‑specific specs are not provided, set your in‑house QC thresholds based on your application (SPPS vs solution‑phase synthesis) and verify against the product’s CoA/Spec Sheet.

Reaction and Applications

This item is positioned as a protected amino acid building block for peptide and amide synthesis. Without item‑specific specs, the following are literature‑based best practices.

Applications: • Amide bond formation: Coupling to amines/alcohols under carbodiimide (EDC/DIC) or uronium/phosphonium reagents (HATU, HBTU, PyBOP). The Trt protects the α‑amine, leaving the carboxylate to be activated. • Segment coupling: Useful in convergent peptide assembly where orthogonal protection is required. • Chiral pool derivatization: The L‑center (if L‑Phe derived) propagates stereochemistry into products such as peptidomimetics and heterocycles.

Mechanistic/practical notes: • Racemization control: Use HOAt/Oxyma as additives; keep activation times short and temperatures low. • Base choice: DIPEA/Pr2NEt in DMF or NMP is common; avoid excessive base during prolonged activations. • Detritylation: Trityl is acid‑labile; TFA/DCM liberates the trityl cation (orange/red). Employ appropriate scavengers (TIPS, anisole, thioanisole) to minimize cationic alkylation of nucleophiles. • Monitoring: UV–Vis tracking of the trityl cation is possible during deprotection; TLC with anisaldehyde or ninhydrin (post‑detritylation) may be used.

Workup/purification: • After coupling, acidic aqueous washes remove bases and urea byproducts; avoid strong base to prevent epimerization. • Silica gel chromatography is feasible; however, the polar acid can tail—pre‑neutralize or use buffered eluents if needed.

Note: Confirm the absolute configuration and protection pattern on the CoA to ensure orthogonality with your synthetic route.

Reaction Conditions

The following conditions are literature‑style guidance for Trt‑protected amino acid chemistry; they are not product specifications.

Typical amide couplings: • Solvent: DMF or NMP (dry). • Base: DIPEA (2–3 equiv). • Activators: – HATU (1.0–1.2 equiv) or HBTU, with OxymaPure (0.5–1.0 equiv) to suppress racemization; or – EDC·HCl (1.2–1.5 equiv) + Oxyma/HOAt; or – DIC (1.2–1.5 equiv) + Oxyma. • Temperature/time: 0–25 C, 0.5–4 h for solution phase; monitor by LC/TLC. • Expected outcomes: High conversions with minimal epimerization when activation times are short and temperatures are controlled (yields vary by substrate).

Detritylation (to liberate the α‑amine): • Reagent: TFA in DCM (20–50% v/v) with scavenger (e.g., triisopropylsilane 2–5% v/v; anisole or thioanisole as alternatives). • Conditions: 0–25 C, minutes to 1 h depending on sterics; monitor for orange/red trityl cation formation. • Quench/workup: Evaporate volatiles under reduced pressure; co‑evaporate with toluene or Et2O to remove residual TFA; neutralize carefully if required.

Racemization control tips: • Pre‑activate briefly; add nucleophile promptly. • Maintain pH below strongly basic regimes; avoid prolonged exposure to DBU/NaH. • Use low‑temperature protocols for hindered couplings.

Note: If the product has special protecting‑group patterns or salts, adjust conditions accordingly based on the CoA.

Safety and Handling

Item-specific hazard data from Product Data: • GHS Classification: Not specified for this item; refer to SDS. • Signal word: Not specified for this item; refer to SDS. • H‑statements/Pictograms: Not specified for this item; refer to SDS.

General safety guidance for trityl‑protected amino acids (informational; defer to SDS): • Expected hazards: Generally low to moderate acute toxicity; may cause skin/eye irritation and dust‑related respiratory irritation. Avoid inhalation of dust and contact with skin/eyes. • PPE: Safety glasses, lab coat, and chemically resistant gloves (e.g., nitrile). Use in a fume hood when weighing or during acid detritylation (TFA vapors). • Incompatibilities: Strong oxidizers; strong bases can induce side reactions (e.g., racemization during coupling). During detritylation, acid generates the orange/red trityl cation—manage acidic waste appropriately; avoid contact with bases until neutralized to prevent exotherms. • First aid (overview): – Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists. – Inhalation: Move to fresh air; seek medical attention if symptoms occur. – Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

Handling tips: • Use dry techniques; moisture can affect coupling reagents and promote hydrolysis. • If performing TFA/DCM detritylation, ensure adequate ventilation and use TFA‑compatible materials. • Always consult the product‑specific SDS for definitive hazard and response information.

Solvent Selection

Applicability: This product functions as an aromatic, hydrophobic, protected amino acid. Solvent choice strongly affects dissolution and coupling performance.

General/literature guidance (not product specifications): • Polarity class: Nonpolar to moderately polar organic; multiple aryl rings increase hydrophobicity. • Preferred solvents for dissolution and handling: – Dichloromethane (DCM), chloroform: Good solubility; common for detritylation monitoring and workup. – DMF, NMP, DMSO: Excellent solubility; ideal for amide bond formation (carbodiimide/uronium chemistry). – THF/EtOAc: Moderate solubility; may require warming or co‑solvent with DMF. – Alcohols (MeOH/EtOH): Limited solubility; risk of esterification under acid; generally avoided for storage of activated species. – Water: Poorly soluble due to trityl; use water‑miscible polar aprotics if aqueous processing is needed.

Selection tips: • For SPPS or solution coupling, DMF/NMP are preferred to maintain homogeneity with coupling reagents (HATU/HBTU/EDC). • For acidolytic deprotection (detritylation), DCM with TFA is common; add small amounts of scavengers (e.g., TIPS) as required. • For crystallization or trituration, hexanes/Et2O/EtOAc mixtures can help remove nonpolar impurities.

Small comparison (literature): – DMF vs DCM: DMF maximizes coupling efficiency; DCM facilitates rapid TFA detritylation and easy solvent removal. – DMSO: Strong solvator but high boiling; consider for problematic solubility only.

Storage and Reconstitution

Item-specific conditions from Product Data: • Storage conditions: Room temperature. • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance: • Protection from moisture: Keep container tightly closed in a dry place; trityl derivatives and coupling reagents used with them are moisture‑sensitive in practice. • Light and air: Store in original, opaque/amber container if provided; inert atmosphere is generally not mandatory for the solid, but beneficial if long‑term storage is planned. • Stability: Trityl‑protected amino acids are typically stable at ambient temperatures when dry; avoid prolonged exposure to strong acids or bases. • Reconstitution: – For stock solutions, dissolve in dry DMF, DCM, or DMSO at a convenient concentration (e.g., 0.05–0.5 M depending on solubility). – Filter if particulates are present; use within a few days for highest integrity. – Store solutions at 2–8 C under inert gas if needed; bring to room temperature before use to avoid precipitation. • Freeze–thaw: Avoid repeated freeze–thaw of solutions; aliquot if long‑term storage is necessary.

Always consult the product’s CoA and SDS for definitive storage, stability, and handling instructions.

Structure and Identity

Item-specific identifiers from Product Data: • CAS: 3226-92-4 • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. • 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.

Interpretive notes (general/literature context, not a product specification): • Name context: “Trt‑Phe‑OH” is commonly used to denote an N‑trityl protected phenylalanine with a free carboxylic acid (Phe carboxylate intact; α‑amine masked by the trityl, Trt = triphenylmethyl). The suffix “Dea” in catalog listings often indicates a derivative or packaging designation; structural meaning should be confirmed on the product CoA. • Structural features (typical for N‑trityl phenylalanine): – One α‑amino acid backbone (–NH–CH(R)–CO2H) bearing an L‑configured benzylic side chain (R = –CH2–Ph). – The α‑amine is protected as an N‑trityl amine (–N–C(Ph)3), a bulky, acid‑labile protecting group. – Aromatic content includes the phenylalanine side‑chain ring plus three phenyl rings of trityl. • Stereochemistry: When derived from L‑phenylalanine, the α‑center is S in the CIP system (literature). Confirm enantiomeric form on the specific CoA.

IMPORTANT: Because structure strings (SMILES/InChI) and formula are not provided in the Product Data, treat the above as contextual guidance only; rely on the item’s CoA/Spec Sheet for definitive identity.

Synthetic Utility

Functional group landscape (general for Trt‑protected amino acids): • Reactive handle: Carboxylic acid enables amide/ester formation via activation (e.g., acid chlorides, anhydrides, uronium/carbodiimide coupling). • Masked nucleophile: α‑Amine is protected as trityl—robust to bases and many nucleophiles, labile to mild acid (e.g., TFA). • Aromatic side chain: Phenyl group participates in π–π interactions and can be elaborated (e.g., electrophilic aromatic substitutions) when conditions are compatible with Trt.

Strategic uses: • Orthogonal protection schemes: Combine Trt on nitrogen with base‑labile Fmoc elsewhere, or acid‑stable groups on side chains, to orchestrate selective deprotections. • Convergent assembly: Prepare fragments bearing protected amines for late‑stage unmasking and coupling. • Chiral induction: Preserve stereochemistry during coupling by minimizing base strength and residence time; employ racemization suppressants (Oxyma, HOAt). • Temporary hydrophobic tag: Trityl can improve solubility in organic media to facilitate isolations and crystallizations; subsequently removed to reveal the free amine.

Downstream transformations: • Detritylation to liberate the amine, followed by acylation/alkylation/urea formation. • Conversion of the acid to activated esters (NHS/PNP) for bioconjugation workflows (post‑detritylation as needed).

Target Specificity

Not applicable. This product is a small‑molecule synthetic building block, not a biological targeting reagent (e.g., antibody, ligand probe). No antigen, epitope, species reactivity, clone, or isotype information applies.

Foire aux questions

How should this product be stored?

Store at room temperature.

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.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 3226-92-4. InChIKey BSLKHJZVHGFJPR-SNYZSRNZSA-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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