This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
163.260 g/mol
XLogP3
2.500
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
4
Exact Mass
163.136 Da
Monoisotopic Mass
163.136 Da
Topological Polar Surface Area
12.000 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
112.000
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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Recensioni
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Application Protocols
Not applicable. This listing is not an antibody, enzyme, or kit with defined biological assay protocols. No validated applications (e.g., WB, IHC, IF, FC) or recommended dilutions are provided for this small-molecule reagent.
For synthetic uses, see the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections for general laboratory guidance.
Biological Roles
Item-specific: none provided in Product Data; this product is supplied for research use only (non-clinical, non-diagnostic).
General/biochemistry context
(2-Methylbenzyl)propylamine is a synthetic secondary amine; it is not recognized as a natural metabolite or cofactor.
Secondary benzylamines can interact non-specifically with biological membranes due to amphiphilicity (aromatic ring plus basic amine), and they can form protonated species at physiological pH (pKaH for similar amines ~9–10.5, literature), which may drive lysosomal partitioning in cells (general behavior of cationic amphiphiles).
In enzyme or receptor research, benzylamine motifs are sometimes used as handles in probe molecules or as intermediates toward bioactive tertiary amines; however, no target-specific biological role is assigned to this compound without further derivatization.
As with many small aliphatic/aromatic amines, oxidation by monoamine oxidase is typically limited to primary amines; secondary benzylamines may undergo oxidative N-dealkylation in microsomal systems (general xenobiotic metabolism), but actual metabolic fate is system- and structure-dependent.
Compliance note
No medical, diagnostic, or therapeutic use is intended or implied. Any biological testing should follow institutional biosafety and chemical safety procedures.
Buffer Applications
Not typically applicable. (2-Methylbenzyl)propylamine is a hydrophobic secondary amine, not a defined buffering agent with a standardized pKa/pH working range for biochemical buffers.
If pH control is needed in reactions involving this amine, use established buffer systems (e.g., phosphate, acetate, HEPES) appropriate to your pH window. The amine itself can act as a base but does not provide reliable buffering capacity in aqueous media over broad ranges.
Green Alternatives
Assessment context
This product is itself a functional reagent (secondary amine), not a solvent. “Green alternatives” therefore focus on greener media and reagents for reactions employing this amine.
Greener media choices (literature/general guidance)
Prefer ethanol, isopropanol, or water/ethanol mixtures for reductive amination when compatible, instead of chlorinated solvents.
Use 2-MeTHF or CPME as ether alternatives to THF/Et2O; they offer lower peroxide hazard and improved renewability (2-MeTHF from hemicellulose).
Reductive agents and activators
Replace NaBH3CN with NaBH(OAc)3 to avoid cyanide; or use catalytic hydrogenation (H2, Pd/C) under mild conditions where selectivity permits.
Swap acid chlorides for coupling reagents that minimize HCl generation or employ green acyl donors (activated esters) with recyclable byproducts.
Workup/waste minimization
Employ solid-supported scavengers for excess amine or acylating agents to reduce aqueous basic/acidic waste.
Implement acid–base extraction with minimal solvent, and recover/reuse organic solvents through distillation.
Brief comparison (general)
DCM vs EtOAc/2-MeTHF: EtOAc/2-MeTHF reduce halogenated waste but may impact reaction rate/selectivity; pilot on small scale first.
NaBH3CN vs NaBH(OAc)3/H2: safer byproduct profile, though chemoselectivity and stereoselectivity can differ; adjust acid promoter and temperature accordingly.
Pharmaceutical Uses
Item-specific: none provided in Product Data. Research Use Note: For research use only.
General formulation/manufacturing context (non-clinical)
Secondary benzylamines like (2-methylbenzyl)propylamine are more commonly employed as synthetic intermediates toward APIs or advanced intermediates rather than as excipients.
Potential roles in process chemistry include:
Intermediate for tertiary amines via reductive amination/alkylation.
Precursor to amide-bearing scaffolds via acylation/coupling.
Formation of crystalline hydrochloride salts that can be advantageous for isolation and handling during process development.
Pharmacopeial status: no monograph is indicated for this specific compound. If a salt form is generated (e.g., hydrochloride), specifications should be established internally (assay, water, residual solvents, counterion content) in alignment with ICH Q6A/Q3 guidelines.
Quality considerations (general)
Control amine-related impurities (over-alkylated tertiary amines, dibenzylamines), residual solvents, and color/oxidation products.
For scale-up, establish kinetic data for exothermic acylations/alkylations and define safe operating limits (DSC/ARC) as part of process safety.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values for context (not item specifications; consult CoA for release criteria)
Physical state: typically a colorless to pale yellow liquid for related secondary benzylamines.
Boiling point: expected high-boiling organic liquid; secondary benzylamines of similar size typically boil in the 210–240 °C range at 1 atm (literature, class analogue).
Melting point: generally below room temperature for analogous secondary benzylamines (literature, class analogue).
Density (20–25 °C): often around 0.85–0.93 g/mL for similar secondary benzylamines (literature, class analogue).
Refractive index (nD20): typically ~1.49–1.52 for comparable structures (literature, class analogue).
Solubility: miscible with common organic solvents (e.g., alcohols, ethers, chlorinated solvents); limited solubility in water but can form water-soluble ammonium salts upon protonation (general chemistry, amines).
Basicity: secondary benzylamines often show pKaH (conjugate acid) in the ~9–10.5 range (aqueous, literature for class), reflecting good nucleophilicity.
LogP/logD: aromatic secondary amines of this size typically show logP ~2–3 (literature, fragment estimate).
Practical notes (general chemistry)
Forms stable ammonium salts with mineral acids (e.g., HCl), often crystalline and water-soluble.
Free base can absorb CO2 and moisture from air; keep container tightly closed to minimize amine odor and atmospheric uptake.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grade/purity (general guidance)
If specified as “>98%” or similar on the CoA, this typically refers to GC or HPLC area normalization; confirm method and thresholds on the accompanying documentation.
For chromatographic or kinetic applications, low UV-absorbing impurities and low residual water can be important; verify UV cutoff and Karl Fischer only if stated on the CoA (not provided here).
Stabilizers: none indicated in Product Data. If present, stabilizers or acid inhibitors would be disclosed on the label/CoA; these affect reactivity in acylation/alkylation steps.
Recommended incoming QC (practical tips)
Identity: confirm by 1H/13C NMR (benzylic CH2 ~3.7–4.0 ppm; N–CH2 of propyl ~2.6–3.1 ppm; aromatic multiplets 6.9–7.3 ppm; o-methyl singlet ~2.2–2.4 ppm), and MS (M+H+ expected at m/z ~164, literature/computed).
Purity: GC or HPLC to monitor residual toluenes/xylene, dibenzylamine, and tertiary amine byproducts. Inspect for color; slight yellowing can indicate oxidation.
Water/amine equivalency: for stoichiometric applications (e.g., acylations), titrate basicity (e.g., HClO4 in acetic acid) if needed to determine exact amine content.
Reaction and Applications
Typical reaction families (general/literature)
N-acylation to amides using acyl chlorides/anhydrides or coupling agents (EDC/HATU). Secondary amine gives tertiary amide products.
N-alkylation to tertiary amines via SN2 with primary halides (e.g., benzyl/allyl/alkyl halides) under basic conditions; Eschweiler–Clarke not applicable (secondary amines cannot be dimethylated this way).
Reductive amination: serve as nucleophile toward aldehydes/ketones to form iminium, then reduce (NaBH3CN/NaBH(OAc)3 or catalytic H2) to give tertiary amines.
Carbamate/urea formation with chloroformates or isocyanates, respectively.
N–Boc or N–Cbz protection may be used for temporary masking when orthogonal selectivity is needed.
Benzyl-specific features (general chemistry)
Benzylic activation facilitates formation of iminium species; the ortho-methyl adds steric bulk that can modulate selectivity in acylations/alkylations.
Hydrogenolysis: N-benzyl groups can be cleaved under Pd/C and H2 in certain tertiary/benzylic configurations; for secondary benzylamines, oxidative or transfer-hydrogen routes can lead to deprotection, potentially yielding o-xylene as the benzyl fragment product (conditions-dependent; literature).
Practical tips
Drying: if water-sensitive transformations are planned, dry the amine over K2CO3 or molecular sieves (3 Å) and use anhydrous solvents.
Base behavior: the amine can act as both nucleophile and base; control equivalents to avoid over-alkylation.
Analytical tracking: TLC with ninhydrin or KMnO4 stain; GC-MS provides rapid assessment of alkylation/reductive amination outcomes.
Use cases in synthesis (examples from literature classes)
Installing a bulky, benzylic-tertiary amine motif in lead-like scaffolds.
Forming tertiary amide auxiliaries where the o-methylbenzyl group biases conformation/stereochemical induction.
Reaction Conditions
General conditions (literature guidance; optimize per substrate)
N-Acylation: RCOCl (1.05–1.2 eq), base (Et3N or DIPEA, 1.5–2 eq), DCM or THF, 0 °C to rt, 1–3 h; monitor by TLC/GC. Coupling reagents (EDC/HATU) in DMF or DCM for acid counterparts, with catalytic DMAP as needed.
N-Alkylation (SN2): Alkyl bromide/iodide (1.1–1.5 eq), K2CO3 or Na2CO3 (2–3 eq), MeCN/acetone/DMF, 20–60 °C, 2–16 h. Suppress over-alkylation by limiting electrophile equivalents and reaction time; phase-transfer catalysis (TBAB) can accelerate in biphasic toluene/aqueous K2CO3.
Reductive amination: Carbonyl (1.05–1.5 eq), NaBH(OAc)3 (1.5–2 eq), AcOH (0.2–0.5 eq), DCE/MeCN/MeOH, rt to 40 °C, 2–18 h. Alternatively, H2 (1–5 bar), Pd/C (5–10 wt%), EtOH or MeOH, rt to 40 °C.
Carbamate/urea formation: Chloroformate (1.1–1.2 eq) or isocyanate (1.0–1.1 eq), base (Et3N), DCM or toluene, 0 °C to rt.
Workup and isolation
Quench acylations with saturated aqueous NaHCO3 to neutralize HCl; separate layers, dry, and concentrate.
For amine bases, switch to hydrochloride salt by HCl in ether to aid crystallization and removal of neutral/aromatic impurities.
Expected outcomes (typical ranges from literature)
N-acylations: often 70–95% isolated yield.
Reductive aminations: 60–90% depending on sterics/electrophile.
SN2 alkylations: 50–85% with primary halides; lower with secondary due to E2 competition.
Analytical monitoring
GC or LC-MS to follow consumption of starting amine and appearance of tertiary products; 1H NMR to verify disappearance of NH signal upon tertiary amine formation.
Safety and Handling
Item-specific hazard data (from Product Data)
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety guidance for secondary aliphatic/benzyl amines (informational; defer to SDS for this product)
Hazards: Basic, corrosive to eyes/skin at high concentrations, strong odor; vapors may be irritating to respiratory tract. High-boiling amines may have moderate flammability with elevated flash points; avoid ignition sources.
PPE: use chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles; work in a fume hood to control vapors/odor.
Storage incompatibilities: keep away from strong oxidizers, acid chlorides/anhydrides, isocyanates, and strong acids/bases that can cause exothermic reactions. Amines can react with carbonyl activators to form imines/amide derivatives.
Handling tips: purge with inert gas if storing long-term to minimize oxidation/discoloration. Avoid copper/brass in transfer lines; amines can corrode certain metals.
First aid overview: in case of skin/eye contact, rinse with plenty of water for ≥15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always follow your institutional SOPs and the product SDS.
Spill response: absorb with inert material (vermiculite, sand), ventilate area, and dispose of as organic amine waste per local regulations.
Solvent Selection
Polarity and miscibility (general chemistry)
Secondary benzylamines are moderately polar, basic organics.
Miscible with many organic solvents (alcohols, ethers, aromatics, chlorinated solvents). Limited miscibility with water as free base; fully water-miscible as ammonium salts under acidic conditions.
Choosing solvents for handling/reaction (general guidance)
For acylation/alkylation: dichloromethane, acetonitrile, THF, toluene, or EtOAc are common; add a base (e.g., DIPEA) as needed unless the amine itself acts as base.
For reductive amination: protic solvents (MeOH, EtOH, i-PrOH) with NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation; alternatively, MeCN or DCE with borohydride reagents.
For salt formation/purification: dissolve base in ether/EtOAc and treat with HCl in ether or HCl(g) to precipitate the amine hydrochloride; recrystallize from alcohol/ether mixtures.
Comparison and practical considerations
Ethers (THF/Et2O): enhance nucleophilicity; watch for peroxide formation in ethers (general solvent caution).
Chlorinated solvents (DCM/DCE): excellent for acylation but consider environmental and safety profiles.
Alcohols: convenient for reductive amination and for quenching acylation reactions; may form ammonium alkoxides/transesterify under strong conditions.
Workup tips
Acid–base extraction: partition the amine as its hydrochloride in aqueous phase, wash organics, then basify and re-extract to obtain the free base.
Avoid strongly acidic aqueous washes if you wish to keep the free base in the organic layer; brief contact is usually fine.
Storage and Reconstitution
Item-specific (from Product Data)
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for secondary benzylamines (informational)
Store tightly closed under air- and moisture-minimizing conditions to reduce odor emission and prevent uptake of CO2/moisture. Amber glass recommended to limit light-induced discoloration.
If long-term storage is anticipated, consider keeping an inert gas blanket (N2/Ar). Avoid contact with acidic vapors and strong oxidants.
Secondary amines may slowly oxidize/darken; if discoloration occurs, pass through a short plug of basic alumina or convert to a crystalline hydrochloride salt for more robust storage.
Reconstitution/handling
Appearance is not specified for this item; if received as a solid salt, dissolve in suitable solvent (e.g., ethanol, methanol, DCM, or ethyl acetate) as required. If received as a neat liquid, use directly or prepare stock solutions in dry solvent.
To obtain the free base from a hydrochloride salt: dissolve the salt in water, basify with 2–3 M NaOH to pH >12, extract with an organic solvent (Et2O/MTBE/EtOAc), dry, and concentrate under reduced pressure.
Stability note
Always consult the product CoA/SDS for definitive storage and handling instructions. For research use only.
Structure and Identity
Brief description: (2-Methylbenzyl)propylamine is a secondary benzylamine bearing a 2-methyl (ortho-methyl) substituent on the aromatic ring and a propyl substituent on nitrogen.
Item-specific (from Product Data)
SKU: M1358445
Product Name: (2-Methylbenzyl)propylamine
CAS: 807343-02-8
CID: 4722397
InChIKey: 91912 (as provided)
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.
Literature/computed (for identification/context; not item specifications)
Typical molecular formula (computed from structure name): C11H17N
2D structure (verbal): a benzene ring bearing a methyl at the ortho position relative to a benzylic methylene that connects to a secondary amine nitrogen; the nitrogen bears a propyl chain (–CH2–CH2–CH3) and a hydrogen.
Structural features (general chemistry)
The benzylic C–N bond increases basicity and nucleophilicity relative to anilines; the ortho methyl introduces steric hindrance near the benzylic site.
The secondary amine can be acylated, alkylated (to tertiary amines), or oxidized to N-oxides (under appropriate conditions).
The benzylic position adjacent to nitrogen stabilizes iminium intermediates, facilitating reductive amination and Mannich-type chemistry.
Retrosynthetic value
Accessible via reductive amination of 2-methylbenzaldehyde (o-tolualdehyde) with propylamine followed by N-alkylation, or directly by reductive amination of 2-methylbenzaldehyde with propylamine under conditions favoring secondary amine formation.
Alternatively, N-alkylation of 2-methylbenzylamine with n-propyl electrophiles (e.g., 1-bromopropane) under basic conditions affords the secondary amine.
Selectivity and sterics
The ortho-methyl increases steric bulk near the benzylic site, sometimes improving selectivity for N- vs C-acylation and reducing over-alkylation rates; however, it can also slow certain substitutions.
Transformations leveraging the benzyl group
Temporary benzyl masking on nitrogen can, under hydrogenolysis/oxidative conditions, be removed to regenerate a less substituted amine; in this case, specialized conditions may cleave the N–CH2Ar bond to give propylamine with formation of o-xylene (literature precedent for N-debenzylation; reaction- and substrate-dependent).
Purification advantages
Formation of crystalline acid salts (HCl, p-TsOH) enables non-chromatographic purification and resolution of tertiary amine impurities through differential solubility.
Target Specificity
Not applicable. This product is a small-molecule amine, not a biological affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information is relevant or provided.
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