40510-88-1

Basic information

• Product Name: Acetic acid 2-chloromethoxy-ethyl ester
• Synonyms: Acetic acid 2-chloromethoxy-ethyl ester;2-(Chloromethoxy)ethyl acetate;2-Acetoxyethyl chloromethyl ether;2-(CHLOROMETHOXY)ETHYL ACETATE(WXG01398)
• CAS NO: 40510-88-1
• Molecular Formula: C₅H₉ClO₃
• Molecular Weight: 152.57616
• Product Categories: pharmacetical
• Mol File: 40510-88-1.mol

Chemical Properties

• Boiling Point: 78-81℃ (6 Torr)
• Appearance: /
• Density: 1.1895 g/cm3(Temp: 200 °C)
• Refractive Index: 1.4373 (589.3 nm 20℃)
• CAS DataBase Reference: Acetic acid 2-chloromethoxy-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid 2-chloromethoxy-ethyl ester(40510-88-1)
• EPA Substance Registry System: Acetic acid 2-chloromethoxy-ethyl ester(40510-88-1)

Safety Data

• Hazardous Substances Data: 40510-88-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Acetic acid 2-chloromethoxy-ethyl ester is used as a solvent and intermediate for the synthesis of various chemicals. Its unique structure allows it to participate in a range of chemical reactions, facilitating the production of different compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, Acetic acid 2-chloromethoxy-ethyl ester is utilized as a reagent in organic synthesis, particularly for the modification of biomolecules. Its ability to interact with biologically relevant molecules makes it a valuable tool in the development of new drugs and therapeutic agents.
Used in Organic Synthesis as a Reagent:
Acetic acid 2-chloromethoxy-ethyl ester is employed as a reagent in organic synthesis, where it aids in the modification of biomolecules. Its chloromethoxy group provides a handle for further chemical reactions, making it a useful component in the creation of complex organic structures.
Safety Considerations:
Due to its classification as a skin sensitizer and irritant, Acetic acid 2-chloromethoxy-ethyl ester requires careful handling to prevent adverse effects on human health. Appropriate safety measures, including the use of personal protective equipment and proper disposal methods, should be implemented when working with this compound.

Upstream product

• 646-06-0 1,3-DIOXOLANE 
• 75-36-5 acetyl chloride 
• 7646-85-7 zinc(II) chloride 

Downstream Products

• 93089-29-3 2-<(2-Acetoxy-aethoxy)-methyl>-3-chlor-3-phenyl-propionsaeure-aethylester 
• 91425-60-4 Essigsaeure-<2-(5-chlor-pent-3-enyloxy)-ethylester> 
• 542-59-6 2-hydroxyethyl acetate 
• 105554-12-9 2-(cyclohex-2-enyloxymethoxy)ethanol 
• 105554-13-0 2-(cyclohex-3-enyloxymethoxy)ethanol 
• 105554-11-8 bis(cyclohex-3-enyloxy)methane 
• 148355-63-9 2-(cyclohex-2-enyloxymethoxy)ethyl acetate 
• 105554-10-7 bis(2-cyclohexen-1-yloxy)methane 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 118966-30-6 5-amino-1-<<2-(acetyloxy)ethoxy>methyl>-1H-imidazole-4-carboxamide 
• 77474-50-1 5-Fluor-1-(2-hydroxyethoxymethyl)-2,4-(1H,3H)pyrimidindion 
• 83702-30-1 4-(2-Acetoxyethoxymethyl)-4H-benzo-1,2,4-triazin-3-one 1-Oxide 
• 119552-61-3 Acetic acid 2-(2-benzyl-benzoimidazol-1-ylmethoxy)-ethyl ester 
• 119552-62-4 Acetic acid 2-[2-(hydroxy-phenyl-methyl)-benzoimidazol-1-ylmethoxy]-ethyl ester 

Relevant articles and documents

Introduction of α-fluorophosphonomethyl ether functionality and its application to the synthesis of fluorinated acyclic phosphonate nucleosides

Introduction of the α-fluorophosphonomethyl ether functionality has been achieved by electrophilic fluorination of the corresponding phosphonomethyl ether carbanion. Coupling of the synthesized 2-[(diethoxyphosphono)fluoromethoxy]ethanol (9) with adenine and 6-chloropurine under Mitsunobu conditions afforded novel fluorinated acyclic phosphonate nucleosides 11a and 11b, respectively. Copyright (C) 1996 Elsevier Science Ltd.

Diversity oriented efficient access of trisubstituted purines via sequential regioselective Mitsunobu coupling and SNAr based C 6 functionalizations

An efficient protocol for the syntheses of diverse 2,6,7- and 2,6,9-trisubstituted purines is reported starting from the guanine precursor, 2amino-6-chloropurine nucleoside through subsequent regioselective, high yielding Mitsunobu coupling and nucleophilic substitutions at C6 with versatile primary and secondary amines. A wide range of 2,6,7- and 2,6,9-trisubstituted purines were accessible in good to excellent yields with remarkable functional group tolerance. Moreover, solvent-free, large scale synthesis of precursors 2 & 3 and facile preparation of organophosphorus side chains 4 & 5 were also accomplished with excellent yields.

Diverse combinatorial design, synthesis and in vitro evaluation of new HEPT analogues as potential non-nucleoside HIV-1 reverse transcription inhibitors

New analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) were synthesized and evaluated for their in vitro activities against HIV-1 in MT-4 cell cultures. Chemical diversity was introduced in 4 of the six positions of the core and the influence of each substituent was studied. This library was built on the basis of a rational diversity analysis with the objective of maximizing diversity and thus, the activity range with a minimum number of synthesized compounds. Among them, 2{1,2,3,1} and 2{1,2,3,4} exhibited the most potent anti-HIV-1 activities (EC50 = 0.015 μg/mL; 0.046 μM, SI >1667) and (EC50 = 0.025 μg/mL; 0.086 μM, SI >1000), respectively, which were about 71-fold and 38-fold more active than the reference compound HEPT (EC50 = 1.01 μg/mL; 3.27 μM, SI >25).

Novel 5-(N -alkylaminouracil) acyclic nucleosides

Protocols for the two-step syntheses of new 5-(N-hydroxyalkyl- and 5-N-benzylamino)uracil acyclic nucleosides bearing various functional groups (alkoxy/hydroxy and cyano/ester) are presented. Two groups of the title compounds were synthesised via aminolysis of 5-bromouracil and, subsequently, either coupling with an alkylating agent (2-chloromethoxyethyl acetate), or Michael-type addition to acrylonitrile/methyl acrylate. The reverse sequences for both syntheses were also studied. The target molecules were designed as non-nucleoside reverse transcriptase inhibitors (NNRTI) and are analogues of 1-(hydroxyethoxymethyl)-6-thiophenylthymine (HEPT) and 3-benzyl-1- cyanomethyluracils. The obtained compounds will be used in screening tests for anti-HIV-1 activity. Georg Thieme Verlag Stuttgart New York.

Antitumor effects of guanosine-analog phosphonates identified by molecular modelling

Aiming to address new drug targets, molecular modelling is gaining increasing importance although the prediction capability of the in silico method is still under debate. For an improved treatment of actinic keratosis and squamous cell carcinoma, inhibitors of human DNA polymerase α (pol α) are developed by docking nucleoside phosphonate diphosphates into the active site of pol α. The most promising prodrugs OxBu and OxHex were then prepared by total synthesis and tested in the squamous cancer cell line SCC25. OxBu and OxHex proved cytotoxic and antiproliferative in the nanomolar concentration range and thus exceeded activity of aphidicolin, the relevant model compound, and 5-fluorouracil, the current standard for the therapy of actinic keratosis. Interestingly, the cytotoxicity in normal human keratinocytes with OxHex was clearly less pronounced and even not detectable with OxBu. Moreover, cytotoxicity of OxBu in particular with the colorectal carcinoma cell line HT29 even surmounted cytotoxicity in SCC25, and other tumor cell lines were influenced, too, by both agents. Taken together, OxBu and OxHex may offer a new approach to cancer therapy, given the agents are sufficiently well tolerated in vivo which is to be suspected beside their chemical structure.

A novel, simple cyclocondensation reaction towards glycosyl triazines

Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and 13C and 1H NMR (COSY, HMBC and HMQC). Georg Thieme Verlag.

PHOSPHONATES, MONOPHOSPHONAMIDATES, BISPHOSPHONAMIDATES FOR THE TREATMENT OF VIRAL DISEASES

Compounds and compositions of Formula (I) are described, useful as anti-proliferative agents, and in particular anti-HPV.

Method for the preparing ?9-12-(Diethoxyphosphonomethoxy)ethyl!adenine and analogues thereof

Unprotected adenine, 6-chloropurine, 2,6-diaminopurine, and 2-amino-6-chloropurine have been directly coupled with 2-(diethoxyphosphonomethoxy)ethanol under a disclosed method to provide acyclic phosphonate nucleotide analogues which are intermediates for antiviral agents such as 9-?2-(phosphonomethoxy)ethyl!adenine (PMEA) and its analogues having a structure of formula I: STR1 wherein Z represents N or CH; R1 represents hydrogen, alkyl, aryl, or arylalkyl; R2 and R3 are independently selected from H, OH, halo, NH2, C6 H5 CH2 O, or R4 R5 N wherein R4 and R5 are independently selected from alkyl, aryl, or arylalkyl.

Antiviral phosphonomethoxyalkylene purine and pyrimidine derivatives

A series of compounds of Formula I which have anti-tumor activity, and are useful in treating viral infections, their compositions and use. STR1 In Formula I B is a purine or pyrimidine base; alk1 alk2 and alk3 are chemical bonds or alkylene groups; Q is hydrogen or hydroxyl; and R1 -R4 are hydrogen or alkyl.

Selective Protection of 1,2- and 1,3-Diols via Acylative Cleavage of Cyclic Formals

An efficient two-step method for the differential functionalization of 1,2- and 1,3-diols, involving regioselective cleavage of five- and six-membered cyclic formals with acetyl chloride followed by conversion of the resulting chloromethyl ether acetate 1 to an alkoxymethyl ether acetate (2), has been developed.When applied to unsymmetrically substituted cyclic formals, the differential functionalization sequence is highly selective and produces an alkoxymethyl ether acetate having the acetate at the less hindered center and the acetal moiety at the more hindered center.Removal of either protecting group affords a selectively monoprotected diol: for the case of an unsymmetrical diol, removal of the acetate gives a product selectively protected with an acetal group at the more hindered hydroxyl.