3587-60-8

Basic information

• Product Name: Benzylchloromethyl ether
• Synonyms: (CHLOROMETHOXYMETHYL)BENZENE;BENZYLOXYMETHYL CHLORIDE;BENZYL CHLOROMETHYL ETHER;Benzene, [(chloromethoxy)methyl]-;(Chloromethoxymethyl)benzene, Benzyloxymethyl chloride;Chloromethyl benzyl ether;Benzyl chloromethyl ether ,98%;α-Chloromethoxytoluene
• CAS NO: 3587-60-8
• Molecular Formula: C₈H₉ClO
• Molecular Weight: 156.61
• EINECS: 252-527-2
• Product Categories: Building Blocks;C8;Chemical Synthesis;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 3587-60-8.mol

Chemical Properties

• Boiling Point: 102 °C14 mm Hg(lit.)
• Flash Point: 91 °C
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.126 g/mL at 20 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.527
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water [2.7 g/L (25 C)]
• BRN: 1364034
• CAS DataBase Reference: Benzylchloromethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Benzylchloromethyl ether(3587-60-8)
• EPA Substance Registry System: Benzylchloromethyl ether(3587-60-8)

Safety Data

• Hazard Codes: T,Xn,N
• Statements: 45-22-23-37/38-41-48/22-36/37/38-20/21/22-50-43
• Safety Statements: 53-26-39-45-36/37/39-36-61
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 19-21
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 3587-60-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzylchloromethyl ether is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its ability to introduce benzoyloxy and hydroxymethyl groups allows for the creation of new drug candidates with improved pharmacological properties, such as enhanced solubility, stability, and bioavailability.
Used in Agrochemical Industry:
In the agrochemical industry, Benzylchloromethyl ether is utilized as a key component in the synthesis of novel agrochemicals. The introduction of benzoyloxy and hydroxymethyl groups can lead to the development of more effective and environmentally friendly pesticides, herbicides, and other crop protection agents.
Used in Specialty Chemicals:
Benzylchloromethyl ether is also employed in the synthesis of specialty chemicals, such as fragrances, dyes, and other fine chemicals. Its unique reactivity allows for the creation of new compounds with specific properties, catering to the diverse needs of various industries.

Synthesis Reference(s)

Synthesis, p. 762, 1983 DOI: 10.1055/s-1983-30506

InChI:InChI=1/C16H16Cl2O/c17-15(11-13-7-3-1-4-8-13)19-16(18)12-14-9-5-2-6-10-14/h1-10,15-16H,11-12H2

Upstream product

• 538-86-3 benzyl methyl ether 
• 50-00-0 formaldehyd 
• 100-51-6 benzyl alcohol 
• 110-88-3 1,3,5-Trioxan 
• 52132-66-8 Benzyl-methylthiomethylether 
• 31600-55-2 benzyl methoxymethyl ether 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 56-23-5 tetrachloromethane 
• 7782-50-5 chlorine 
• 20194-18-7 sodium phenyl-methanolate 

Downstream Products

• 89268-01-9 (phenylmethoxy)methylphosphonic acid diethyl ester 
• 31600-55-2 benzyl methoxymethyl ether 
• 92495-85-7 formaldehyde-(benzyl-phenyl-acetal) 
• 79983-47-4 (α-chloro-benzyl)-chloromethyl ether 
• 948587-89-1 3-O-benzyloxymethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 53164-28-6 1-benzyloxymethyl-3-carbamoyl-pyridinium; chloride 
• 57866-74-7 acetylamino-(benzylsulfanyl-methyl)-malonic acid diethyl ester 
• 2749-70-4 bis(benzyloxy)methane 
• 56822-99-2 2-benzyloxymethyl-5-ethoxy-[1,2,4]thiadiazol-3-one 
• 58460-96-1 (3-Chloro-2,3-dimethyl-butoxymethyl)-benzene 
• 61674-96-2 4-(benzyloxy)-3,3-dimethylbutan-2-one 
• 58460-99-4 [5-Chloro-2-(1-chloro-1-methyl-ethyl)-5-methyl-hexyloxymethyl]-benzene 
• 61378-01-6 4-benzyloxymethyl-7c-hydroxy-2ξ-(4-methoxy-phenyl)-13-methyl-(6ac)-7,11-dihydro-6aH-4r,11ac-azaethano-[1,3,5]dithiazepino[5,4-a]indole-5,12-dione 
• 5537-89-3 1-Benzyloxy-ethan-tricarbonsaeure-(2,2,2)-trimethylester 

Relevant articles and documents

Development of Acidic Imidazolium Ionic Liquids for Activation of Kraft Lignin by Controlled Oxidation: Comprehensive Evaluation and Practical Utility

A novel, eco-friendly method for the activation of lignin by controlled oxidation was studied. The results obtained for six acidic imidazolium ionic liquids containing the hydrogen sulfate anion were compared. The key goal of this research was to increase the content of carbonyl groups in the lignin structure because these may play the main role in the transport of protons and electrons in active materials for electrochemical applications. By means of a variety of analytical techniques (FTIR, 13C CP/MAS NMR, and X-ray photoelectron spectroscopy; selected reactions to determine the presence of carbonyl groups; SEM; zeta-potential analysis; thermogravimetric analysis/differential thermogravimetric analysis; and porous structure analysis), it was determined that the product obtained after treatment with 3-cyclohexyloxymethy-1-methylimidazolium hydrogen sulfate had favorable properties, in terms of the target application. Electrochemical tests proved that the obtained materials could be used as anodes in lithium batteries. The results show that the activation of lignin with ionic liquids can increase its capacity and maintain stability.

6-Cyclohexylmethyl-3-hydroxypyrimidine-2,4-dione as an inhibitor scaffold of HIV reverase transcriptase: Impacts of the 3-OH on inhibiting RNase H and polymerase

3-Hydroxypyrimidine-2,4-dione (HPD) represents a versatile chemical core in the design of inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H and integrase strand transfer (INST). We report herein the design, synthesis and biological evaluation of an HPD subtype (4) featuring a cyclohexylmethyl group at the C-6 position. Antiviral testing showed that most analogues of 4 inhibited HIV-1 in the low nanomolar to submicromolar range, without cytotoxicity at concentrations up to 100?μM. Biochemically, these analogues dually inhibited both the polymerase (pol) and the RNase H functions of RT, but not INST. Co-crystal structure of 4a with RT revealed a nonnucleoside RT inhibitor (NNRTI) binding mode. Interestingly, chemotype 11, the synthetic precursor of 4 lacking the 3-OH group, did not inhibit RNase H while potently inhibiting pol. By virtue of the potent antiviral activity and biochemical RNase H inhibition, HPD subtype 4 could provide a viable platform for eventually achieving potent and selective RNase H inhibition through further medicinal chemistry.

New compound for sequencing by synthesis

The present invention provides deoxynucleoside tri - or tetraphosphate comprising a 3' nitrate and a detectable label covalently bound to the oxygen atom of a oxymethyl or oxyallyl or oxypropargyl substitution of a nucleobase. Such compounds provide new possibilities for future Sequencing by Synthesis technologies.

The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives

With the goal of eventually synthesizing [5]radialene (3), the still missing member of the parent radialene hydrocarbons, we have prepared the pentaacetates 21 and 31, the pentabromide 29 and the hexabromide 32. In principle these should be convertible by elimination reactions to the desired target molecule.

6-Benzoyl-3-hydroxypyrimidine-2,4-diones as dual inhibitors of HIV reverse transcriptase and integrase

N-3-Hydroxylation of pyrimidine-2,4-diones was recently found to yield inhibitors of both HIV-1 reverse transcriptase (RT) and integrase (IN). An extended series of analogues featuring a benzoyl group at the C-6 position of the pyrimidine ring was synthesized. Through biochemical studies it was found that these new analogues are dually active against both RT and IN in low micromolar range. Antiviral assays confirmed that these new inhibitors are active against HIV-1 in cell culture at nanomolar to low micromolar range, further validating 3-hydroxypyrimidine-2,4-diones as a viable scaffold for antiviral development.

3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase

Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (INIs). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure-activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

6-(AMINOALKYL)INDAZOLES

6-(Aminoalkyl) indazoles of formula (I) and the salts thereof have renin-inhibiting properties and can be used as antihypertensive, and renal, cardiac and vascular protecting medicinally active ingredients.

Practical synthesis of an orally active renin inhibitor aliskiren

A convergent synthesis of aliskiren was accomplished via the use of Segment AB as the key intermediate, which was prepared via the coupling of the Grignard reagent derived from Segment B with Segment A, followed by subsequent oxidative lactonization.

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