14321-27-8

Basic information

• Product Name: N-Ethylbenzylamine
• Synonyms: LABOTEST-BB LTBB000558;N-ETHYLBENZYLAMINE;NEBA;N-BENZYLETHYLAMINE;Benzylamine, N-ethyl-;Benzylethylamine;Ethylbenzylamine;N-Benzyl-N-ethylamine
• CAS NO: 14321-27-8
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• EINECS: 238-265-1
• Product Categories: Polyamines
• Mol File: 14321-27-8.mol
• Article Data: 84

Chemical Properties

• Melting Point: 191-194
• Boiling Point: 191-194 °C(lit.)
• Flash Point: 152 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.909 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.518mmHg at 25°C
• Refractive Index: n20/D 1.511(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: slightly soluble
• PKA: 9.77±0.10(Predicted)
• Water Solubility: slightly soluble
• Sensitive: Air Sensitive
• BRN: 386023
• CAS DataBase Reference: N-Ethylbenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethylbenzylamine(14321-27-8)
• EPA Substance Registry System: N-Ethylbenzylamine(14321-27-8)

Safety Data

• Hazard Codes: C
• Statements: 34-37-52
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 14321-27-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

N-Ethylbenzylamine has been used to demonstrate the reactivity of NDTE (2,5-dihydroxyphenylacetic acid, 2,5-bis-tetrahydropyranyl ether p-nitrophenyl ester) and HLTE (homogentisic gamma-lactone tetrahydropyranyl ether). It has also been used to prepare 2-[(N-Benzyl, N-ethyl)amino]derivative using 2-chloro-4H-pyrido[1,2-a]pyrimidin-4-one.

Synthesis Reference(s)

Chemistry Letters, 15, p. 917, 1986Journal of the American Chemical Society, 91, p. 3996, 1969 DOI: 10.1021/ja01042a078Tetrahedron Letters, 9, p. 61, 1968

InChI:InChI=1/C9H13N/c1-2-10-8-9-6-4-3-5-7-9/h3-7,10H,2,8H2,1H3/p+1

Upstream product

• 75-07-0 acetaldehyde 
• 100-46-9 benzylamine 
• 15481-55-7 4-Nitrobenzenesulfonic acid ethyl ester 
• 97-94-9 triethyl borane 
• 38636-02-1 N-benzyl-O-benzoylhydroxylamine 
• 100-52-7 benzaldehyde 
• 75-04-7 ethylamine 
• 64-19-7 acetic acid 
• 6852-54-6 N-(benzylidene)ethylamine 
• 64-17-5 ethanol 
• 69981-57-3 N-(1-iminoethyl)benzylamine 
• 100-39-0 benzyl bromide 
• 62673-31-8 benzyl(bromo)zinc 
• 98-88-4 benzoyl chloride 

Downstream Products

• 91339-47-8 N-benzyl-2-(ethylamino)ethanol 
• 107418-17-7 ethyl-benzyl-(2-[4]pyridyl-ethyl)-amine 
• 14629-66-4 N-Ethylbenzylamin-N-trimethylsilylether 
• 98924-92-6 1-(Aethyl-benzylamino)-1-desoxy-D-fructose 
• 1132-35-0 N-Ethyl-N-benzylguanidin 
• 14299-71-9 3-(Benzyl-ethyl-amino)-butyric acid 1-prop-2-ynyl-cyclohexyl ester 
• 33778-31-3 4-(benzyl-ethyl-amino)-4-deoxy-rifamycin 
• 35929-09-0 Methyl-β-(N-benzyl-N-ethylamino)-isobutyratmino)-propanol-maleinsaeure-salz 
• 25676-01-1 (2,4-dinitrophenyl) benzyl(ethyl)carbamodithioate 
• 106663-34-7 3-[(Benzyl-ethyl-amino)-methyl]-1,3-diaza-spiro[4.5]decane-2,4-dione 
• 239075-92-4 3-(N-benzyl-N-ethylamino)-5-methylphenol 
• 772-54-3 N,N-diethylbenzylamine 
• 106536-22-5 3,3-bis(3-phenyl-2-propen-1-yl)pentane-2,4-dione 

Relevant articles and documents

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Synthesis and evaluation of Zn(II) dithiocarbamate complexes as potential antibacterial, antibiofilm, and antitumor agents

Four complexes having the formula [Zn(L)2] [L1 = (C18H20NS2 –), N-(4-isopropyl-benzyl)-(benzyl)-dithiocarbamate], [L2 = (C10H12NS2 –), N-(benzyl)-(ethyl)-dithiocarbamate], [L3 = (C19H22ONS2 –), N-(4-isopropyl-benzyl)-(4-methoxy-benzyl)-dithiocarbamate], and [L4 = (C16H16NS2 –), N-(benzyl)-(4-methyl-benzyl)-dithiocarbamate] have been contemplated, synthesized, and characterized by elemental analysis and IR, 1H, 13C NMR and UV–visible absorption spectra. All Zn(II) complexes have similar geometry and coordination number. Complex A2 (with ligand L2) crystallizes in triclinic system with space group P-1 having distorted square pyramidal geometry which was stabilized by weak C–H···π and C–H···S intramolecular interactions. The antibacterial, antibiofilm, and antitumor activities of the complexes have been screened and A2 and A3 showed their prominence. Interestingly, both A2 and A3 showed more killing potential against multi-drug resistant gram-positive isolates with MIC indices of 16 μg mL?1 and 16 μg mL?1, respectively, against both MRSA and MSSA, while the antitumor agent A3 showed its prominence with GI50 and LC50 41.15 and 133.73 μg mL?1, respectively.

Discovery of tert-amine-based RORγt agonists

The nuclear receptor retinoic acid receptor-related orphan receptor gamma-t (RORγt) is a transcription factor regulating Th17 cell differentiation and proliferation from naive CD4+ T cells. Since Th17 cells have demonstrated the antitumor efficacy by eliciting remarkable activation of CD8+ T cells, RORγt agonists could be applied as potential small molecule therapeutics for cancer immunotherapy. Based on the previously reported RORγt agonist 1 and its resolved co-crystal structure, a series of new tertiary amines were designed, synthesized and biologically evaluated, yielding optimal moieties with improved chemical properties and biological responses. The combination of these optimal moieties resulted in identification of novel RORγt agonists such as 8b with further elevated RORγt agonism responses at a target-based level as well as in cell-based assays, which provided some structural knowledge for further optimization of RORγt agonists as small molecule therapeutics for cancer immunotherapy.

Method for preparing amine compound by reducing amide compound

The invention relates to a method for preparing an amine compound by reducing an amide compound, which comprises the following steps: in a protective atmosphere, mixing the amide compound or cyclic amide, a zirconium metal catalyst and pinacol borane, carrying out amide reduction reaction at room temperature, and carrying out aftertreatment by using an ether solution of hydrogen chloride after 12-48 hours to obtain an amine hydrochloride compound. The method is simple to operate, low in cost, good in functional group tolerance and wide in substrate range.

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines

Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.