814-68-6 Usage
Description
Acrylyl chloride, also known as 2-propenoyl chloride, is a colorless liquid with a pungent odor. It is a reactive chemical compound that is widely used in the production of various polymers and plastics. Its high reactivity is due to the presence of a chlorine atom attached to a double bond, which allows it to readily undergo addition and substitution reactions.
Uses
Used in Plastics and Polymers Industry:
Acrylyl chloride is used as a monomer for the production of acrylate polymers and plastics. It is an important building block for the synthesis of various polymers, such as poly(methyl methacrylate) (PMMA), which is commonly known as acrylic or Plexiglas. These polymers are known for their excellent transparency, strength, and weather resistance, making them suitable for a wide range of applications, including automotive parts, glazing, and signage.
Used in Organic Synthesis:
Acrylyl chloride is used as a reagent in organic synthesis for the introduction of acrylic groups into other compounds. This allows for the creation of a variety of new molecules with different properties and applications. The acrylic group can be incorporated into pharmaceuticals, dyes, and other specialty chemicals, expanding the range of products that can be synthesized using acrylyl chloride.
Used in Cross-Metathesis Reactions:
Acrylyl chloride also acts as a substrate for cross-metathesis reactions, which are a type of olefin metathesis reaction. These reactions involve the exchange of olefinic groups between molecules, leading to the formation of new products. Cross-metathesis is a powerful tool in organic chemistry, allowing for the synthesis of complex molecules from simpler precursors. Acrylyl chloride's role as a substrate in these reactions further demonstrates its versatility and importance in the field of chemical synthesis.
Air & Water Reactions
Polymerizes readily upon exposure to oxygen in the air. Reacts exothermically with water to give hydrochloric acid and acrylic acid.
Reactivity Profile
Acrylyl chloride is incompatible with strong oxidizing agents, alcohols, amines, alkali. Polymerizes readily upon exposure to oxygen. 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].
Fire Hazard
When heated to decomposition, Acrylyl chloride emits toxic fumes of chlorides. Decomposes in water.
Potential Exposure
May be used as a monomer in preparation of specialty polymers or as a chemical intermediate
Shipping
UN3383 Poisonous Toxic by inhalation liquid, flammable, n.o.s. with an LC50 # 200 mL/m3 and saturated vapor concentration ≥500 LC50, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid, Technical Name Required, Inhalation Hazard Zone A. UN2924 Flammable liquids, corrosive, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, 8-Corrosive material, Technical Name Required
Incompatibilities
Use MEHQ (monomethyl ether of hydroquinone) as an inhibitor. Incompatible with oxidizers, polymerizes on contact with oxygen; alcohols, amines, alkalis. Reacts violently with water, releasing hydrochloric acid and acrylic acid. Attacks some metals.
Check Digit Verification of cas no
The CAS Registry Mumber 814-68-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,1 and 4 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 814-68:
(5*8)+(4*1)+(3*4)+(2*6)+(1*8)=76
76 % 10 = 6
So 814-68-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H3ClO/c1-2-3(4)5/h2H,1H2
814-68-6Relevant articles and documents
The molecular design of photo-curable and high-strength benzoxazine for 3D printing
Lu, Yong,Ng, Kok Wei Joseph,Chen, Hui,Chen, Xuelong,Lim, Song Kiat Jacob,Yan, Weili,Hu, Xiao
supporting information, p. 3375 - 3378 (2021/04/07)
Low viscosity photo-curable benzoxazines (BZs) are designed and synthesized for use in stereolithography 3D printing. An initial investigation shows that the thermally polymerized polybenzoxazines (PBZs) have remarkably highTg(264 °C) and flexural modulus (4.91 GPa) values. Subsequently, the formulated photoprintable resins are employed for use in high-resolution projection micro-stereolithography (PμSL) printing. Complex PBZ 3D structures can be achieved from the as-printed objects after they are thermally treated. These findings advance the design of BZ monomers for photopolymerization-based 3D printing and offer a method for the efficient fabrication of high-performance thermosets for various demanding engineering applications.
Synthesis and Biological Evaluation of Celastrol Derivatives with Improved Cytotoxic Selectivity and Antitumor Activities
Feng, Jia-Hao,He, Qi-Wei,Hou, Ji-Qin,Hu, Xiao-Long,Long, Huan,Wang, Bao-Lin,Wang, Hao,Wang, Quan,Wang, Rong,Ye, Wen-Cai,Zhang, Li-Xin,Zhang, Xiao-Qi
, p. 1954 - 1966 (2021/07/20)
Cdc37 associates kinase clients to Hsp90 and promotes the development of cancers. Celastrol, a natural friedelane triterpenoid, can disrupt the Hsp90-Cdc37 interaction to provide antitumor effects. In this study, 31 new celastrol derivatives, 2a - 2d , 3a - 3g , and 4a - 4t , were designed and synthesized, and their Hsp90-Cdc37 disruption activities and antiproliferative activities against cancer cells were evaluated. Among these compounds, 4f , with the highest tumor cell selectivity (15.4-fold), potent Hsp90-Cdc37 disruption activity (IC50= 1.9 μM), and antiproliferative activity against MDA-MB-231 cells (IC50= 0.2 μM), was selected as the lead compound. Further studies demonstrated 4f has strong antitumor activities both in vitro and in vivo through disrupting the Hsp90-Cdc37 interaction and inhibiting angiogenesis. In addition, 4f exhibited less toxicity than celastrol and showed a good pharmacokinetics profile in vivo. These findings suggest that 4f may be a promising candidate for development of new cancer therapies.
An efficient approach for the synthesis of new (±)-coixspirolactams
Nascimento, Vinicius R.,Suenaga, Melissa L. S.,Andrade, Leandro H.
supporting information, p. 5458 - 5465 (2020/08/03)
Coixspirolactams, spiro[oxindole-γ-lactones], are found in adlay seeds and exhibit anticancer activity. A novel synthetic methodology was developed to enable an easy access to (±)-coixspirolactam A and a large number of new coixspirolactams in excellent overall yields. The exquisite exploitation of formamide reactivity was essential for the construction of oxindole and lactone scaffolds. This journal is