13324-66-8

Basic information

• Product Name: N-BENZYLCYCLOPROPYLAMINE
• Synonyms: N-BENZYLCYCLOPROPYLAMINE;N-BENZYL-N-CYCLOPROPYLAMINE;N-Benzylcyclopropymaine;N-Cyclopropylbenzylamine;N-BENZYLCYCLOPROPANAMINE
• CAS NO: 13324-66-8
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• Mol File: 13324-66-8.mol

Chemical Properties

• Melting Point: 97-98.5 °C
• Boiling Point: 229.8°C at 760 mmHg
• Flash Point: 92.8°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 0.0681mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.47±0.20(Predicted)
• CAS DataBase Reference: N-BENZYLCYCLOPROPYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BENZYLCYCLOPROPYLAMINE(13324-66-8)
• EPA Substance Registry System: N-BENZYLCYCLOPROPYLAMINE(13324-66-8)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 13324-66-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzylcyclopropylamine is utilized as a building block for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agricultural Industry:
In addition to its pharmaceutical applications, N-Benzylcyclopropylamine is also employed in the manufacture of pesticides and other agricultural products. Its chemical properties make it suitable for use in these applications, helping to improve crop protection and yield.
Used in Organic Chemistry Research:
Due to its versatile structure, N-Benzylcyclopropylamine is a valuable compound for research in organic chemistry. It can be used to explore new reactions, mechanisms, and the synthesis of complex organic molecules, further expanding the understanding and capabilities within the field.

InChI:InChI=1/C10H13N/c1-2-4-9(5-3-1)8-11-10-6-7-10/h1-5,10-11H,6-8H2

Upstream product

• 15205-35-3 N-cyclopropylbenzamide 
• 3187-77-7 N-benzylidenecyclopropylamine 
• 88048-45-7 N-carbobenzyloxy-N-benzylcyclopropylamine 
• 100-39-0 benzyl bromide 
• 765-30-0 Cyclopropylamine 
• 100-52-7 benzaldehyde 
• 2521-01-9 ethyl N-benzyl-N-cyclopropylcarbamate 
• 100-46-9 benzylamine 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 75-19-4 cyclopropane 
• 100-47-0 benzonitrile 
• 1396164-75-2 C₁₁H₁₂F₃NO₂S 
• 1007780-01-9 N-benzyl-N-cyclopropylbenzenesulfonamide 

Downstream Products

• 3187-77-7 N-benzylidenecyclopropylamine 
• 1396164-75-2 C₁₁H₁₂F₃NO₂S 
• 5291-77-0 1-benzyl-2-pyrrolidone 

Relevant articles and documents

Effect of N-Bound Organic Moiety in Dithiocarbamate (R2NCS-2) and trans Influence of Triphenylphosphine on NiS2PN Chromophore

Three square planar Ni(II) complexes of the composition [Ni(bzcprdtc)2](1), [Ni(bzcprdtc)(NCS)(PPh3)](2) and [Ni(bzcprdtc)(PPh3)2]ClO4 (3)[(where bzcprdtc = N-benzyl-N-cyclopropyl-dithiocarbamate)] ha

Analgesic Properties of Opioid/NK1 Multitarget Ligands with Distinct in Vitro Profiles in Naive and Chronic Constriction Injury Mice

The lower efficacy of opioids in neuropathic pain may be due to the increased activity of pronociceptive systems such as substance P. We present evidence to support this hypothesis in this work from the spinal cord in a neuropathic pain model in mice. Biochemical analysis confirmed the elevated mRNA and protein level of pronociceptive substance P, the major endogenous ligand of the neurokinin-1 (NK1) receptor, in the lumbar spinal cord of chronic constriction injury (CCI)-mice. To improve opioid efficacy in neuropathic pain, novel compounds containing opioid agonist and neurokinin 1 (NK1) receptor antagonist pharmacophores were designed. Structure-activity studies were performed on opioid agonist/NK1 receptor antagonist hybrid peptides by modification of the C-terminal amide substituents. All compounds were evaluated for their affinity and in vitro activity at the mu opioid (MOP) and delta opioid (DOP) receptors, and for their affinity and antagonist activity at the NK1 receptor. On the basis of their in vitro profiles, the analgesic properties of two new bifunctional hybrids were evaluated in naive and CCI-mice, representing models for acute and neuropathic pain, respectively. The compounds were administered to the spinal cord by lumbar puncture. In naive mice, the single pharmacophore opioid parent compounds provided better analgesic results, as compared to the hybrids (max 70% MPE), raising the acute pain threshold close to 100% MPE. On the other hand, the opioid parents gave poor analgesic effects under neuropathic pain conditions, while the best hybrid delivered robust (close to 100% MPE) and long lasting alleviation of both tactile and thermal hypersensitivity. The results presented emphasize the potential of opioid/NK1 hybrids in view of analgesia under nerve injury conditions.

Continuous flow heterogeneous catalytic reductive aminations under aqueous micellar conditions enabled by an oscillatory plug flow reactor

Despite the fact that continuous flow processing exhibits well-established technical advances, aqueous micellar chemistry, a field that has proven extremely useful in shifting organic synthesis to sustainable water-based media, has mostly been explored under conventional batch-based conditions. This is particularly because of the fact that the reliable handling of slurries and suspensions in flow has been considered as a significant technical challenge. Herein, we demonstrate that the strategic application of an oscillatory plug flow reactor enables heterogeneous catalytic reductive aminations in aqueous micellar media enhancing mass transport and facilitating process simplicity, stability and scalability. The micellar flow process enabled a broad range of substrates, including amino acid derivatives, to be successfully transformed under reasonably mild conditions utilizing only very low amounts of Pd/C as a readily available heterogeneous catalyst. The preparative capabilities of the process along with the recyclability of the heterogenous catalyst and the aqueous reaction media were also demonstrated. This journal is

Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades

The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.

Triazole compound, and application thereof in agriculture

The invention provides a triazole compound, and an application thereof in agriculture, and concretely provides a compound represented by formula (I), a preparation method thereof, a composition containing the compound, and an application of the compound or the composition as a bactericide. R, X, R, R, n, R, R, R, R, R and R in the formula (I) are as defined in the description.

Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer

Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.

Direct Reductive Amination of Carbonyl Compounds with H2 Using Heterogeneous Catalysts in Continuous Flow as an Alternative to N-Alkylation with Alkyl Halides

A general continuous-flow procedure for direct reductive amination of secondary and primary amines with aromatic and aliphatic aldehydes as well as ketones is reported. The use of hydrogen gas and commercially available Pt/C as a heterogeneous catalyst is a key. In addition to exhibiting an excellent functional group tolerance, this method allows the fast formation of C?N bonds without production of any hazardous chemical waste. Applications to the synthesis of key intermediates toward active pharmaceutical ingredients (Donepezil and Arformoterol/Tamsulosin) are also described. (Figure presented.).

Triazole compounds and their use in agriculture (by machine translation)

The present invention provides a triazole compound and its application in agriculture; in particular, the invention provides compounds of formula (A) indicated by the compound and its preparation method; the composition containing these compounds and preparation and their use as fungicides; wherein R1 , R2 , R3 , W, R4 , R5 , R6 , R7 , R8 , R9 , Ra , Rb And in the event of x has the meanings given by the invention. (by machine translation)

Acidic solvent-free removal of amine-protecting diphenylmethyl groups in the presence of camphorsulfonic acid

We developed novel reaction conditions for the removal of the diphenylmethyl group, which is one of the most important protecting groups for amines. The reaction was promoted by adding one equivalent of camphorsulfonic acid in aqueous media, and no acidic

Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing

The reductive aminase from Aspergillus oryzae (AspRedAm) was combined with a single alcohol dehydrogenase (either metagenomic ADH-150, an ADH from Sphingobium yanoikuyae (SyADH), or a variant of the ADH from Thermoanaerobacter ethanolicus (TeSADH W110A)) in a redox-neutral cascade for the biocatalytic alkylation of amines using primary and secondary alcohols. Aliphatic and aromatic secondary amines were obtained in up to 99 % conversion, as well as chiral amines directly from the racemic alcohol precursors in up to >97 % ee, releasing water as the only byproduct.