Methyl 2-(chloromethyl)acrylate

Base Information

• Chemical Name: Methyl 2-(chloromethyl)acrylate
• CAS No.: 922-15-6
• Molecular Formula: C5H7ClO2
• Molecular Weight: 134.562
• Hs Code.: 2916190090
• European Community (EC) Number: 618-828-1
• DSSTox Substance ID: DTXSID60498661
• Nikkaji Number: J1.291.827E
• Wikidata: Q72489277
• Mol file: 922-15-6.mol

Synonyms:METHYL 2-(CHLOROMETHYL)ACRYLATE;922-15-6;methyl 2-(chloromethyl)prop-2-enoate;methyl2-(chloromethyl)acrylate;(?)-2-Hydroxyisopinocampheol;SCHEMBL882348;DTXSID60498661;MFCD11617809;AKOS006317182;Methyl 2-(chloromethyl)acrylate, 95%;2-(Chloromethyl)acrylic acid methyl ester;AS-33344;AM20120602;CS-0208489;FT-0645546;EN300-7390197;A922778;[1R-(1?,2?,3?,5?)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol

Chemical Property of Methyl 2-(chloromethyl)acrylate

Chemical Property:

• Vapor Pressure: 2.859mmHg at 25°C
• Refractive Index: 1.433
• Boiling Point: 156.659 °C at 760 mmHg
• Flash Point: 58.448 °C
• PSA: 26.30000
• Density: 1.114 g/cm³
• LogP: 0.95440
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 134.0134572
• Heavy Atom Count: 8
• Complexity: 109

Purity/Quality:

98% ^*data from raw suppliers

Methyl 2-(chloromethyl)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 36/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=C)CCl
• Uses: Methyl 2-(chloromethyl)acrylate is a versatile reactant used in the synthesis of hydroxyl-containing dimethacrylate crosslinkers.

Technology Process of Methyl 2-(chloromethyl)acrylate

There total 5 articles about Methyl 2-(chloromethyl)acrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

dichloro bis(acetonitrile) palladium(II) (21264-30-2,90243-59-7,14592-56-4) + methyl 2-hydroxymethylacrylate (15484-46-5) → PdCl2[H2CC(CO2CH3)CH2] + C(2)H3OCH2C(O)CO2CH3 + methyl (α-chloromethyl)acrylate (922-15-6)

Guidance literature:

With d⁽⁴⁾-methanol; In chloroform-d1; byproducts: HCl, Pd(OH)Cl; addn. of CD3OD to CDCl3 soln. of starting compds. and monitoring of react. by (1)H-NMR spectroscopy.; formation of org. compd. after 95 h.;

DOI:10.1016/0022-328X(94)80175-4

Reference yield: 29.0%

dichloro bis(acetonitrile) palladium(II) (21264-30-2,90243-59-7,14592-56-4) + methyl 2-hydroxymethylacrylate (15484-46-5) → PdCl2[H2CC(CO2CH3)CH2] + dichloro palladium(II) methyl(α-hydroxymethyl)acrylate + methyl (α-chloromethyl)acrylate (922-15-6)

Guidance literature:

In chloroform-d1; react. of starting compds. in CDCl3 at 50°C is monitored by (1)H-NMR spectroscopy.; unreacted initial org. material (44%) is remained after 5 days. NMR identification of resulting compds.;

DOI:10.1016/0022-328X(94)80175-4

Reference yield: 17.0%

methanol (67-56-1) + 1,2-propanediene (463-49-0) + carbon monoxide (201230-82-2) → methyl (α-chloromethyl)acrylate (922-15-6) + methyl α-methoxymethylacrylate (25328-81-8)

Guidance literature:

With sodium acetate; copper dichloride; palladium dichloride; at -40 - -30 ℃; for 3h;

DOI:10.1023/A:1020976821007

upstream raw materials:

methacrylic acid methyl ester

methanol

1,2-propanediene

carbon monoxide

Downstream raw materials:

methyl 4-hydroxy-4-methyl-2-methylene-4-phenylbutanoate

C₂₈H₂₈O₇

C₂₄H₂₄O₄

2-Chlormethyl-3-cyclohexylpropionsaeure-methylester

Refernces

• 1、 Hosokawa, Takahiro,Sugafuji, Toshihiro,Yamanaka, Toshio,Murahashi, Shun-Ichi. "Elimination of β-palladium hydroxide in the PdII-catalyzed reaction of methyl(α-hydroxymethyl)acrylate with alcohols". . p. 253 - 256. Retrieved 2007/10/02.