627-42-9

Basic information

• Product Name: 2-Methoxyethyl chloride
• Synonyms: 1-chloro-2-methoxy-ethan;beta-chloroethylmethylether;Ethane, 1-chloro-2-methoxy-;ethane,1-chloro-2-methoxy;ether,2-chloroethylmethyl;2-CHLOROETHYL METHYL ETHER;2-METHOXYETHYL CHLORIDE;1-CHLORO-2-METHOXYETHANE
• CAS NO: 627-42-9
• Molecular Formula: C₃H₇ClO
• Molecular Weight: 94.54
• EINECS: 210-999-7
• Mol File: 627-42-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: -55 °C
• Boiling Point: 89-90 °C(lit.)
• Flash Point: 59 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.035 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.408(lit.)
• Storage Temp.: Flammables area
• Solubility: 80g/l
• Water Solubility: 60 g/L (20 C)
• BRN: 1731028
• CAS DataBase Reference: 2-Methoxyethyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxyethyl chloride(627-42-9)
• EPA Substance Registry System: 2-Methoxyethyl chloride(627-42-9)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-22
• Safety Statements: 36/37-23-16
• RIDADR: UN 3271 3/PG 2
• WGK Germany: 3
• F: 9
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 627-42-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxyethyl chloride is used as a reagent for the synthesis of Piperonyl Methoxyethyl Ether (P490475), a selective inhibitor of the cytochrome P450-dependent monooxygenase from the housefly. This application is significant in the development of new drugs and therapies targeting specific enzymes and metabolic pathways.
Used in Chemical Synthesis:
2-Methoxyethyl chloride is used as a reagent in the synthesis of acyclic nucleosides of thieno[2,3-d]pyrimidine derivatives. These derivatives have potential applications in various fields, including pharmaceuticals and materials science, due to their unique chemical properties and potential biological activities.

InChI:InChI=1/C3H7ClO/c1-5-3-2-4/h2-3H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 107-07-3 2-chloro-ethanol 
• 67-56-1 methanol 
• 473-29-0 N,N-Dichlorobenzenesulfonamide 
• 74-85-1 ethene 
• 15454-33-8 chloromethanol 
• 109-86-4 2-methoxy-ethanol 
• 99418-55-0 2,2,2-trichloro-acetimidic acid-(2-methoxy-ethyl ester) 
• 110-71-4 1,2-dimethoxyethane 
• 1107601-58-0 NbCl₄(OCH₂CH₂OMe) 
• 107-30-2 chloromethyl methyl ether 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 24053-00-7 2-(sulfanyl-2-methoxyethyl)benzothiazole 
• 349656-01-5 (+)-(R,R)-1,2-N,N'-(2-methoxyethyl)diaminocyclohexane 
• 177478-11-4 tert-butyl 3-(benzyloxy)-2-nitrophenyl(2-methoxyethyl)carbamate 
• 405211-51-0 1-(2-methoxyethyl)-1H-benzo[d]imidazol-2(3H)-one 

Relevant articles and documents

4-anilinoquinazoline derivative and albumin conjugates thereof

a pharmaceutical composition for preventing, treating, or ameliorating one or more symptoms of a malignant tumor associated with EGFR mutation and/or K-RAS mutation is provided. The pharmaceutical composition includes a 4-anilinoquinazoline derivative having a formula (I) where A is iodine when m is 1 and n is zero, or A is albumin when m is an integral ranging from 1 to 7 and n is 1.

Synthesis of novel poly(ethylene glycol)-containing imidazolium-functionalized phosphine ligands and their application in the hydrosilylation of olefins

A series of polyethylene glycol-containing imidazolium-functionalized phosphine ligands (mPEG-im-PPh2) were successfully synthesized and used in the rhodium-catalyzed hydrosilylation of olefins. The results indicate that the RhCl3/mPEG-im-PPh2 catalytic system exhibits both excellent activity and selectivity for the β-adduct. In addition, the catalytic system may be recycled at least six times.

Synthesis and biological assay of erlotinib analogues and BSA-conjugated erlotinib analogue

A series of erlotinib analogues that have structural modification at 6,7-alkoxyl positions is efficiently synthesized. The in vitro anti-tumor activity of synthesized compounds is studied in two non-small cell lung cancer (NSCLC) cell lines (A549 and H1975). Among the synthesized compounds, the iodo compound 6 (ETN-6) exhibits higher anti-cancer activity compared to erlotinib. An efficient method is developed for the conjugation of erlotinib analogue-4, alcohol compound, with protein, bovine serum albumin (BSA), via succinic acid linker. The in vitro anti-tumor activity of the protein attached erlotinib analogue, 8 (ETN-4-Suc-BSA), showed stronger inhibitory activity in both A549 and H1975 NSCLC cell lines.

Further insights into the chemistry of niobium and tantalum pentahalides with 1,2-dialkoxyalkanes: Synthesis of bromo- and iodoalkoxides, spectroscopic and computational studies

The room temperature reactions of a series of 1,2-dialkoxyalkanes ROCH 2CH(R′)OR′′ with MX5 (M = Nb, Ta; X = Br, I) in 1:1 ratio result in single C-O bond cleavage and high-yield formation of the halo-alkoxides MBr4[κ2-OCH 2CH(R′)OR′′] or [NbI4{κ 1-OCH2CH(R′)OR′′}]2, and equimolar amounts of the corresponding alkyl halides RX. The reaction of NbBr5 with 1,2-dimethoxyethane, dme, proceeds with preliminary formation of the ionic species [NbBr4(κ2-dme) (κ1-dme)][NbBr6], 3b, which has been identified by solution NMR at low temperature and conductivity analyses. The gas-phase structure of 3b has been optimized by DFT calculations, confirming that the dme ligands adopt bidentate and monodentate coordination, respectively. Although the formation of NbOBr3(dme), 4b, 1,4-dioxane and MeBr from NbBr 5/dme (ratio 1:2) is an exoergonic process (calculated ΔGr° = -115.96 kcal mol-1), it is inhibited at room temperature. High temperature conditions enhance the production of 1,4-dioxane at the expense of selectivity. The dinuclear species NbOBr3(dme)NbBr5 (Nb-O-Nb), 5b, (X-ray) has been isolated in modest yield as byproduct of the room temperature reaction of NbBr5 with dme. In general, the 1:2 molar reactions of NbX5 (X = Br, I) with ROCH2CH(R′) OR′′ occur with the exclusion of nearly one equivalent of organic reactant.

A systematic study on the activation of simple polyethers by MoCl 5 and WCl6

MoCl5, 1a, and WCl6, 1b, activate 1,3-dioxolane at room temperature in chlorinated solvents: the compound [MoOCl 3{OC(H)OCH2CH2Cl}]2, 2, has been isolated from MoCl5/dioxolane. The mixed oxo-chloro species WOCl 4, 1c, reacts with 1,3-dioxolane, selectively giving the coordination adduct WOCl4(κ1-C3H6O 2), 3. Dimethoxymethane, CH2(OMe)2, undergoes activation including C-H bond cleavage when reacted with 1a to give the molybdenum complexes [MoOCl3{OC(H)OMe}]2, 4, and Mo 2Cl5(OMe)5, 5. The reactions of 1b with CH 2(OR)2 (R = Me, Et) proceed via O-abstraction with formation of the oxo-derivatives WOCl4[O(R)CH2Cl] (R = Me, 6a; R = Et, 6b) in admixture with equimolar amounts of RCl. The reactions of 1a,b with CMe2(OMe)2 lead to mesityl oxide, MeC(O)CHC(Me)2. A series of simple diethers of general formula ROCH2(CHR′)OR′′ are activated by 1a,b in CDCl 3, usually via cleavage of C-O bonds at high temperature. The complex WCl5(OCH2CH2OMe), 7, has been detected in solution as an intermediate species in the course of the degradation of 1,2-dimethoxyethane (dme) by 1b. The activation of CH(OMe)3 by 1 is limited to C-O bonds and selectively gives methyl chloride and methylformate, which has been found coordinated in WOCl4[OC(H)OMe], 8. The organic fragments produced in the reactions have been detected by GC-MS and NMR analyses, upon hydrolysis of the reaction mixtures. Compounds 2 and 5, which have had their molecular structures ascertained by X-ray diffraction, represent rare examples of crystallographically-characterized dinuclear Mo(v) species containing both halides and oxygen ligands.

EFFICIENT AND/OR SELECTIVE METHYLATION BY DIAZOMETHANE OF ALCOHOLS, HALO ALCOHOLS, GLYCOLS, AMINO ALCOHOLS AND MERCAPTO ALCOHOLS WITH THE USE OF A PROTON-EXCHANGED X-TYPE ZEOLITE AS AN ACID-BASE BIFUNCTIONAL CATALYST

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We studied the rate-determining and the product-determining steps of the chlorohydrination of olefins with Cl2/H2O and HOCl.In competitive kinetic experiments with 3-ethylpent-2-ene and cyclohexene we determined the relative rate constants krel=1,5 (with Cl2/H2O) and krel=infinite (with HOCl).This shows that the rate-determining steps of the chlorohydrination with Cl2/H2O and with HOCl are different.In order to investigate the product-determining steps we determined the proportion of alkyl-(2-chloroethyl)-ethers 3 and ethylene chlorohydrine 2 in the reaction of ethylene with Cl2 and with HOCl in alcohol/water-mixtures.The proportion of both the reaction products 3/2 was independent of the chlorinating agent used.Also the proportion of MARKOVNIKOV and anti-MARKOVNIKOV products in the chlorohydrination of propylene with Cl2/H2O or HOCl was independent of the type of chlorinating agent.In the chlorohydrination of cyclohexene both agents (Cl2/H2O and HOCl) yielded only the trans-chlorohydrine.From the results obtained it may be concluded that the product-determining step of chlorohydrination is the same for both the chlorinating agents studied.

Process for preparing vicinal dialkoxyalkanes

A process is disclosed for preparing vicinal dialkoxyalkanes by reacting a vicinal dihaloalkane with an alkanol in the presence of a hydrogen halide absorbing agent which is substantially insoluble in the alkanol.