836-42-0

Basic information

• Product Name: 4-(Benzyloxy)benzyl chloride
• Synonyms: 4-BENZYLOXYBENZYL CHLORIDE;4-CHLOROMETHYL-ALPHA-PHENYLANISOLE;4-CHLOROMETHYL-A-PHENYLANISOLE;TIMTEC-BB SBB000714;1-(Chloromethyl)-4-(Phenylmeth;Benzene, 1-(chloromethyl)-4-(phenylmethoxy)-;4-chloromethyl-α-phenylanisole;4-Benzyloxybenzyl chloride 98%
• CAS NO: 836-42-0
• Molecular Formula: C₁₄H₁₃ClO
• Molecular Weight: 232.71
• EINECS: 212-648-3
• Product Categories: Building Blocks;C14;Chemical Synthesis;Ethers;Organic Building Blocks;Oxygen Compounds;Pyrimidines
• Mol File: 836-42-0.mol

Chemical Properties

• Melting Point: 77-79 °C(lit.)
• Boiling Point: 355.7 °C at 760 mmHg
• Flash Point: 168.5 °C
• Appearance: /
• Density: 1.152 g/cm³
• Vapor Pressure: 0.000721mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: 2-8°C
• Solubility: soluble in Toluene
• BRN: 882526
• CAS DataBase Reference: 4-(Benzyloxy)benzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Benzyloxy)benzyl chloride(836-42-0)
• EPA Substance Registry System: 4-(Benzyloxy)benzyl chloride(836-42-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-19-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 836-42-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-(Benzyloxy)benzyl chloride is used as a reagent in organic synthesis for facilitating various chemical reactions such as nucleophilic substitution and Friedel-Crafts acylation. Its high reactivity allows for the formation of new chemical bonds and the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-(Benzyloxy)benzyl chloride is employed as a key intermediate in the synthesis of various drugs. Its unique structure and reactivity enable the development of new pharmaceutical compounds with specific therapeutic properties.
Used in Agrochemical Production:
4-(Benzyloxy)benzyl chloride is utilized in the agrochemical industry for the synthesis of various agrochemicals, including pesticides and herbicides. Its reactivity and functional groups contribute to the development of effective and targeted agrochemical products.
Used in Specialty Chemicals Production:
In the specialty chemicals sector, 4-(Benzyloxy)benzyl chloride is used as a building block for the synthesis of a wide range of specialty chemicals with specific applications in various industries, such as coatings, adhesives, and polymers. Its versatility and reactivity make it a valuable component in the development of innovative specialty chemicals.
Safety Precautions:
Due to the high reactivity and potential hazards associated with 4-(Benzyloxy)benzyl chloride, it is essential to handle and store this compound with care. Appropriate safety measures, such as wearing personal protective equipment, working in a well-ventilated area, and following proper disposal procedures, should be taken to minimize the risk of accidents and exposure.

InChI:InChI=1/C13H11ClO/c14-10-11-6-8-13(9-7-11)15-12-4-2-1-3-5-12/h1-9H,10H2

Upstream product

• 623-05-2 (4-hydroxyphenyl)methanol 
• 262288-18-6 4-acetylthio-1-(4-benzylbenzyl)pyrrolidin-2-one 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 100-39-0 benzyl bromide 
• 60-29-7 diethyl ether 
• 946-80-5 (benzyloxy)benzene 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-44-7 benzyl chloride 
• 32122-11-5 4-benzyloxy-benzoic acid methyl ester 
• 4397-53-9 p-benzyloxybenzaldehyde 

Downstream Products

• 74447-42-0 2-(4-benzyloxybenzyl)-1,3-dithian 
• 77148-75-5 2-(((4-Benzyloxy)benzyl)thio)-1-methylpyridinium chloride 
• 76003-35-5 methyl 4-(t-Butoxycarbonyl)-2-oxo-3-(4-benzyloxybenzyl)-1-piperazineacetate 
• 74447-49-7 2-(4-benzyloxybenzyl)-<2-(2)H>-1,3-dithian 
• 63659-20-1 1-benzoxy-4-(cyclopropylmethoxymethyl)-benzene 
• 108007-96-1 4-<(cyclobutylmethoxy)methyl>-1-(phenylmethoxy)benzene 
• 114773-13-6 N-<4-(benzyloxy)benzyl>glycine ethyl ester 
• 114799-98-3 1-<4-(benzyloxy)benzyl>-2-butyl-4-chloro-5-(hydroxymethyl)imidazole 
• 76003-32-2 t-Boc-3-(p-benzyloxybenzyl)-piperazinon 
• 84184-50-9 diethyl 2-(4-benzyloxybenzyl)malonate 
• 860818-44-6 1-(4-benzyloxybenzyl)-2-pivaloyl-1,2,3,4-tetrahydroisoquinoline 
• 26697-36-9 α-<4-Benzyloxy-benzyl>-2-nitro-4,5-dimethoxy-benzylcyanid 
• 50816-46-1 O-Benzyl-<1-14C>-tyramin 
• 131719-55-6 diethyl <4-(benzyloxy)benzyl>phosphonate 

Relevant articles and documents

Topochemical polymerisation of assembled diacetylene macrocycle bearing dibenzylphosphine oxide in solid state

Novel diacetylene macrocycles 1 and 2 bearing dibenzylphosphine oxide were synthesised via Eglinton acetylenic intramolecular coupling. The X-ray analysis of crystals of macrocycles 1 and 2 demonstrated that the better-aligned tubular supramolecular structure was formed in macrocycle 1 than in macrocycle 2, which provided the possibility of diacetylene topochemical polymerisation in solid state of macrocycle 1. UV–vis, Raman spectroscopy and X-ray analysis indicated that the crystals of macrocycle 1 could undergo topochemical diacetylene polymerisation only on their surface by light irradiation; differential scanning calorimetry, solid-state 13C NMR spectroscopy and solubility test demonstrated that the crystals of macrocycle 1 could undergo diacetylene topochemical polymerisation inside solid by heat. As expected, based on the topological analysis of crystal structure, the crystals of macrocycle 2 could not undergo diacetylene topochemical polymerisation either by light irradiation or heat.

PO functional group-containing cryptands: From supramolecular complexes to poly[2]pseudorotaxanes

Two types of cryptand-based host-guest complexes were constructed successfully, in which PO functional groups were located at the different positions of the third arms. Consequently, supramolecular poly[2]pseudorotaxanes with almost linear and zigzag shapes were formed in the solid state. This journal is

Fumarate related impurity and preparation method and application thereof (by machine translation)

The preparation method of the related impurities comprises the following steps: No.No.No. STR8No.No. wherein the (I) preparation method, of ,R the related impurities is. shown, in the specification, and the preparation method of, the 1 present, application, further, discloses, the preparation method, and of the related impurities. (by machine translation)

Nickel-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes

Herein, we report a nickel-catalyzed asymmetric two-component reductive dicarbofunctionalization of aryl iodide-tethered unactivated alkenes using benzyl chlorides as the challenging coupling partner. This arylbenzylation reaction enables the efficient synthesis of diverse benzene-fused cyclic compounds bearing a quaternary stereocenter with a high tolerance of sensitive functionalities in highly enantioselective manner. The preliminary mechanistic investigations suggest a radical chain reaction mechanism.

Benzofuran compound and its preparation, use (by machine translation)

The invention relates to a benzofuran compound and its preparation, use, its structural formula such as formula (I) as shown: Wherein R1 , R2 , R4 Are selected from hydrogen, C1 - C5 Alkyl, nitro, halogen, ester, hydroxy, amino, amide base or alkoxyl; R3 Hydrogen, C1 - C5 Alkyl, benzyl, aromatic or heteroaromatic group. The invention also relates to the benzofuran compounds in inhibiting the application of gram-positive to be used repeatedly. The invention relates to 3 - oxime substituted benzene and furan structure aromatic ring as the center, the establishment and optimize the preparation method of the compound, and on the preparation of novel compound of the bacteriostatic screening experiment, through initial bacteriostatic test to confirm that preparation compound has broad-spectrum bacteriostatic activity. (by machine translation)

Beyond the affinity for protein kinase C: Exploring 2-phenyl-3-hydroxypropyl pivalate analogues as C1 domain-targeting ligands

Over the past fifteen years, we reported the design and synthesis of different series of compounds targeting the C1 domain of protein kinase C (PKC) that were based on various templates. Out of the pivalate templates, 2-[4-(benzyloxy)phenyl]-3-hydroxypropyl pivalate (compound 1) emerged as the most potent and promising PKCα ligand, showing a Ki value of 0.7 μM. In the present contribution our efforts are aimed at better understanding which structural modifications of the pivalate template are allowed for its affinity to the C1 domain of PKC to be preserved or increased. To this aim, thirteen novel analogues of 1 were designed and their interaction with the target was evaluated in silico. Designed compounds were then prepared and fully characterized as well as their affinity for the α and δ isoforms of PKC evaluated. Additionally, in order to investigate the role of chirality in the ligand-target interaction, the pure enantiomers of the most interesting PKC ligands were prepared and their affinity for PKC isoforms was determined. Results from our study revealed that: i) the presence of the ester function seems to be essential for the ligand-target interaction; ii) only a few structural modifications at the ester group are allowed for the C1 domain affinity to be preserved; and iii) the [3H]PDBu replacement experiments showed that the C1 domain of PKC does not exhibit enantiopreference for the pure stereoisomers of tested compounds. Altogether our observations provide further insights into the ligand-target interactions of the PKC C1 domain and represent a step-forward in future development of more specific and effective PKC ligands. This journal is

Strategies for large-scale synthesis of coelenterazine for in vivo applications

A new application of two Negishi-type coupling reactions for the synthesis of coelenterazine is reported. The synthesis of coelenterazine in high purity on a gram scale will enable numerous approaches to bioluminescence imaging and possibly photodynamic therapy of deep-seated tumors. Coelenterazine is the substrate for several luciferases, among them Gaussia luciferase (gLuc). This synthesis starts with pyrazin-2-amine and uses inexpensive starting materials and catalysts. Georg Thieme Verlag Stuttgart New York.

Structural insights into the substrate specificity of bacterial copper amine oxidase obtained by using irreversible inhibitors

Copper amine oxidases (CAOs) catalyse the oxidation of various aliphatic amines to the corresponding aldehydes, ammonia and hydrogen peroxide. Although CAOs from various organisms share a highly conserved active-site structure including a protein-derived cofactor, topa quinone (TPQ), their substrate specificities differ considerably. To obtain structural insights into the substrate specificity of a CAO from Arthrobacter globiformis (AGAO), we have determined the X-ray crystal structures of AGAO complexed with irreversible inhibitors that form covalent adducts with TPQ. Three hydrazine derivatives, benzylhydrazine (BHZ), 4-hydroxybenzylhydrazine (4-OH-BHZ) and phenylhydrazine (PHZ) formed predominantly a hydrazone adduct, which is structurally analogous to the substrate Schiff base of TPQ formed during the catalytic reaction. With BHZ and 4-OH-BHZ, but not with PHZ, the inhibitor aromatic ring is bound to a hydrophobic cavity near the active site in a well-defined conformation. Furthermore, the hydrogen atom on the hydrazone nitrogen is located closer to the catalytic base in the BHZ and 4-OH-BHZ adducts than in the PHZ adduct. These results correlate well with the reactivity of 2-phenylethylamine and tyramine as preferred substrates for AGAO and also explain why benzylamine is a poor substrate with markedly decreased rate constants for the steps of proton abstraction and the following hydrolysis. The Authors 2011. Published by Oxford University Press on behalf of the Japanese Biochemical Society. The Authors 2011. Published by Oxford University Press on behalf of the Japanese Biochemical Society. All rights reserved.

An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations

An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives.

Discovery of highly potent and selective benzyloxybenzyl-based peroxisome proliferator-activator receptor (PPAR) δ agonists

A series of 1,4-benzyloxybenzylsulfanylaryl carboxylic acids were prepared and their activities for PPAR receptor subtypes (α, δ, and γ) with potential indications for the treatment of dyslipidemia were investigated. Analog 13a displayed the greatest binding affinity (IC50 = 10 nM) and selectivity (120-fold) for PPARδ over PPARα. Many of the analogs investigated were found to be highly selective for PPARδ and were dependent on the point of attachment of the substituent. In the 1,4-series, analog 28e was found to be the most potent (IC50 = 1.7 nM) and selective (>1000-fold) compound for PPARδ. None of the compounds tested showed appreciable binding affinity for PPARγ.