920-46-7 Usage
Uses
Methacryloyl chloride is used in the preparation of polymeric materials. It reacts with L-histidine and forms functional monomer. It is also used to prepare monomer 2-methacrylamido-caprolactam, amide monomers by amidation.
Application
Methacryloyl chloride is used in the manufacture of polymers:Monomer 2-methacrylamido-caprolactam was prepared by reacting methacryloyl chloride with racemic a-amino-e-caprolactam.Functional monomer was prepared by reacting methacryloyl chloride and L-histidine.A series of amide monomers were synthesized by amidation of methacryloyl chloride with amines and grafted onto commercial poly(ether sulfone) (PES) membranes using irradiation from atmospheric pressure plasma (APP).Reaction of methacryloyl chloride with the hydroxyl groups on the surfaces of HEMA/NVP microspheres was performed, leading to the introduction of polymerisable double bonds onto the surfaces of microspheres.Star-shaped poly(d,l-lactide) oligomers with 2, 3 and 6 arms were synthesised, end-functionalised with methacryloyl chloride and photo-crosslinked in the presence of ethyl lactate as a non-reactive diluent.
General Description
Methacryloyl chloride is the clear to slightly colored acid chloride of methacrylic acid. It appears as a liquid of density 1.07g/cm3, boiling point 95-96°C, and flash point 55°F. Highly toxic. Supplied in technical grades of varying purity. Monomethyl ether hydroquinone is added as a stabilizer to prevent auto polymerization. Reaction with diisopropyl ether in presence of metal salts is rigorous.
Air & Water Reactions
Highly flammable. Reacts with water to produce gaseous hydrogen chloride (corrosive and toxic).
Reactivity Profile
Methacryloyl chloride is incompatible with strong oxidizing agents, alcohols, bases (including amines). Can polymerize violently; but the polymerization reaction can be inhibited by the addition of phenolthiazine. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Hazard
Flammable and corrosive liquid.
Purification Methods
Purify the ester by fractional distillation. If it contains the acid (OH bands in the IR) then add redistilled SOCl2 (with cooling) and cuprous chloride (ca to 2%), reflux the mixture gently for 1hour and fractionate it through a 1metre column packed with glass helices. Redistillation then provides the acid chloride in high purity as a colourless liquid. It is necessary to keep the apparatus moisture free (use CaCl2 tubes), Stabilise it with 0.05% of 2,6-di-tert-butyl-4-methylphenol. [Lal & Green J Org Chem 20 1032 1955, Beilstein 2 IV 1537.]
Check Digit Verification of cas no
The CAS Registry Mumber 920-46-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 0 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 920-46:
(5*9)+(4*2)+(3*0)+(2*4)+(1*6)=67
67 % 10 = 7
So 920-46-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H5ClO/c1-3(2)4(5)6/h1H2,2H3
920-46-7Relevant articles and documents
Rhodium(III)-Catalyzed Aerobic Oxidative C-H Olefination of Unsaturated Acrylamides with Unactivated Olefins
Logeswaran, Ravichandran,Jeganmohan, Masilamani
supporting information, p. 767 - 771 (2021/02/06)
A rhodium(III)-catalyzed aerobic oxidative cross-coupling of acrylamides with unactivated alkenes via vinylic C-H activation has been developed. The present cross-coupling reaction was examined with a variety of differently functionalized acrylamides and unactivated olefins. In these reactions, highly valuable amide-functionalized butadienes were prepared in good to excellent yields. This protocol was also compatible with Weinreb amides. A possible reaction mechanism involving the chelation-assisted vinylic C-H activation via a carboxylate-assisted deprotonation pathway is proposed.
Rhodium(III)-catalyzed chemodivergent annulations between phenyloxazoles and diazos via C–H activation
Zhang, Xueguo,Wang, Peigen,Zhu, Liangwei,Chen, Baohua
supporting information, p. 695 - 699 (2020/06/28)
Acid-controlled, chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(III)-catalyzed C[sbnd]H activation. Diazo compounds act as a carbene precursor, and coupling occurs in one-pot process, where adipic acid and trimethylacetic acid promote chemodivergent cyclizations.
Unified total syntheses of (±)-sessilifoliamides B, C, and D
Olivier, Wesley J.,Bissember, Alex C.,Smith, Jason A.
supporting information, p. 3437 - 3441 (2021/05/10)
The first total syntheses of the Stemona alkaloids sessilifoliamides B and D and the second synthesis of sessilifoliamide C have been completed from a simple pyrrole substrate. The bicyclic lactam core was prepared on a gram scale via a Br?nsted acid mediated cyclization and controlled oxidation with Dess-Martin periodinane. This delivered sessilifoliamide C (and its C-11 epimer) in 24% yield over 11 steps, and sessilifoliamides B and D in 13 and 17 steps, respectively.
