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Cas Database

814-68-6

814-68-6

Identification

  • Product Name:Acrylyl chloride

  • CAS Number: 814-68-6

  • EINECS:212-399-0

  • Molecular Weight:90.5092

  • Molecular Formula: C3H3ClO

  • HS Code:29161980

  • Mol File:814-68-6.mol

Synonyms:Prop-2-enoyl chloride;2-Propenoyl chloride;HSDB 6330;Acrylic acid chloride;Propenoyl chloride;Acryloyl chloride;Chlorid kyseliny akrylove [Czech];NSC 93770;Acryloyl Acid;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,VeryT+

  • Hazard Codes:F,T+

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH314 Causes severe skin burns and eye damage H330 Fatal if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Irritating materials/

  • Fire-fighting measures: Suitable extinguishing media Use water spray to cool unopened containers. When heated to decomposition, it emits toxic fumes of chlorides. Decomposes in water. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: 2 - 8°C Light sensitive. Reacts violently with water.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:TRC
  • Product Description:Acryloyl chloride
  • Packaging:25g
  • Price:$ 195
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride ≥97%, contains ~400ppm phenothiazine as stabilizer
  • Packaging:5g
  • Price:$ 57
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride ≥97%, contains ~400ppm phenothiazine as stabilizer
  • Packaging:100g
  • Price:$ 134
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride (stabilised with phenothiazine) for synthesis
  • Packaging:100 mL
  • Price:$ 124
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride (stabilised with phenothiazine) for synthesis. CAS No. 814-68-6, EC Number 212-399-0., (stabilised with phenothiazine) for synthesis
  • Packaging:8008260100
  • Price:$ 120
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride 97.0%, contains <210ppm MEHQ as stabilizer
  • Packaging:5g
  • Price:$ 62
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride ≥97%, contains ~400ppm phenothiazine as stabilizer
  • Packaging:1kg
  • Price:$ 893
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride 97.0%, contains <210ppm MEHQ as stabilizer
  • Packaging:500g
  • Price:$ 526
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride ≥97%, contains ~400ppm phenothiazine as stabilizer
  • Packaging:500g
  • Price:$ 473
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acryloyl chloride (stabilised with phenothiazine) for synthesis. CAS No. 814-68-6, EC Number 212-399-0., (stabilised with phenothiazine) for synthesis
  • Packaging:8008260500
  • Price:$ 398
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Relevant articles and documentsAll total 90 Articles be found

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.

Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent-Based Switch in Stereopreference

Lazzarotto, Mattia,Hartmann, Peter,Pletz, Jakob,Belaj, Ferdinand,Kroutil, Wolfgang,Payer, Stefan E.,Fuchs, Michael

supporting information, p. 3138 - 3143 (2021/04/28)

The substrate scope of the asymmetric allylation with zinc organyls catalyzed by 3,3-bis(2,4,6-triisopropylphenyl)-1,1-binaphthyl-2,2-diyl hydrogenphosphate (TRIP) has been extended to non-cyclic ester organozinc reagents and ketones. Tertiary chiral alcohols are obtained with ee's up to 94% and two stereogenic centers can be created. Compared to the previous lactone reagent the stereopreference switches almost completely, proving the fact that the nature of the organometallic compound is of immense importance for the asymmetry of the product. (Figure presented.).

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.

Zinc-Catalyzed β-Functionalization of Cyclopropanols via Enolized Homoenolate

Sekiguchi, Yoshiya,Yoshikai, Naohiko

supporting information, p. 18400 - 18405 (2021/11/16)

We report herein a zinc-catalyzed β-allylation of cyclopropanols with Morita-Baylis-Hillman (MBH) carbonates with retention of the cyclopropane ring. The reaction is promoted by a zinc aminoalkoxide catalyst, affording cyclopropyl-fused α-alkylidene-δ-valerolactone derivatives in moderate to good yields. Mechanistic experiments suggest that the present reaction does not proceed via direct β-C-H cleavage of the cyclopropanol, but involves zinc homoenolate and its enolization to generate a key bis-nucleophilic species. α-Allylation of this "enolized homoenolate"with MBH carbonate would be followed by regeneration of the cyclopropane ring and irreversible lactonization. The enolized homoenolate mechanism has also been proven to allow for β-functionalization with alkylidenemalononitrile as the reaction partner. A sequence of the present reaction and known cyclopropanol transformation provides an opportunity to transform a simple cyclopropanol into α,β- or β,β-difunctionalized ketones.

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

Process route upstream and downstream products

Process route

acrylic acid
79-10-7

acrylic acid

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

Conditions
Conditions Yield
With thionyl chloride; In N,N-dimethyl-formamide; at 80 ℃; for 0.416667h; under 2068.65 Torr; Reagent/catalyst; Pressure;
94%
4%
With trichlorophosphate; In N,N-dimethyl-formamide; at 80 ℃; for 0.00833333h; Reagent/catalyst; Temperature;
6%
91%
With thionyl chloride; N,N-dimethyl-formamide; In neat (no solvent); at 60 ℃; for 0.0166667h; Reagent/catalyst; Temperature; Time; Catalytic behavior; Flow reactor;
acrylic acid
79-10-7

acrylic acid

C<sub>6</sub>H<sub>7</sub>ClO<sub>3</sub>

C6H7ClO3

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

Conditions
Conditions Yield
With thionyl chloride; In N,N-dimethyl-formamide; at 60 ℃; for 0.0166667h; Reagent/catalyst;
11%
82%
7%
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

chloroethylene
75-01-4,9002-86-2

chloroethylene

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

3-Chloro-propen-1-one; hydrochloride

3-Chloro-propen-1-one; hydrochloride

Conditions
Conditions Yield
In solid matrix; at -263.2 ℃; Irradiation;
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

chloroethylene
75-01-4,9002-86-2

chloroethylene

carbon monoxide
201230-82-2

carbon monoxide

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

3-Chloro-propen-1-one; hydrochloride

3-Chloro-propen-1-one; hydrochloride

Conditions
Conditions Yield
In solid matrix; at -263.2 ℃; Mechanism; Irradiation;
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

chloroethylene
75-01-4,9002-86-2

chloroethylene

carbon monoxide
201230-82-2

carbon monoxide

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

3-chloro-1,2-propenone
204848-50-0

3-chloro-1,2-propenone

Conditions
Conditions Yield
In solid matrix; Mechanism; Irradiation;
acrylic acid
79-10-7

acrylic acid

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

Conditions
Conditions Yield
With thionyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Reagent/catalyst; Temperature;
100%
With thionyl chloride;
98%
With oxalyl dichloride; N,N-dimethyl-formamide; at 20 - 40 ℃; for 0.166667h; Product distribution / selectivity;
96.2%
With pyridine; thionyl chloride; 4-methoxy-phenol; at 75 ℃; for 1h; Reagent/catalyst; Temperature;
96%
With bis(trichloromethyl) carbonate; dimethyl sulfoxide; copper(l) chloride; In chloroform; dimethyl sulfoxide; at 70 ℃; for 9h; Reagent/catalyst; Solvent;
95%
With thionyl chloride; In dichloromethane; for 4h; Inert atmosphere; Reflux;
86%
With thionyl chloride; hydroquinone; sodium hydroxide; at 55 ℃; for 3h; Reflux;
82%
With thionyl chloride; In dichloromethane; for 4h; Inert atmosphere; Reflux;
81%
With thionyl chloride; at 0 - 80 ℃; for 12.75h; Inert atmosphere;
80%
With thionyl chloride; N,N-dimethyl-formamide; at 60 ℃; for 4h;
80%
With thionyl chloride; N,N-dimethyl-formamide; at 60 ℃; for 4h; Time; Reagent/catalyst;
79.8%
With thionyl chloride; N,N-dimethyl-formamide; at 20 - 60 ℃; for 0.166667h; Product distribution / selectivity;
75%
With benzoyl chloride; hydroquinone; at 80 ℃; for 2h; Inert atmosphere; Reflux;
65%
With thionyl chloride; hydroquinone; In N,N-dimethyl-formamide; at 40 ℃; for 0.5h; Inert atmosphere;
60%
With thionyl chloride; at 80 ℃;
54%
With thionyl chloride; hydroquinone; copper(I) chloride; In N,N-dimethyl-formamide;
39%
With benzoyl chloride; at 70 - 72 ℃;
26%
With oxalyl dichloride; at 20 - 40 ℃; for 0.166667h; Product distribution / selectivity;
5.7%
With thionyl chloride;
With phosphorus trichloride; at 60 - 70 ℃;
With benzoyl chloride; at 150 ℃;
With benzoyl chloride; hydroquinone; at 110 ℃;
With thionyl chloride; at 60 - 70 ℃;
With phosphorus trichloride; Heating;
With thionyl chloride; at 60 ℃;
With benzoyl chloride; Heating;
With thionyl chloride; hydroquinone; In N,N-dimethyl-formamide; at 60 ℃; for 6h;
With thionyl chloride; for 15h; Heating;
With benzoyl chloride; hydroquinone;
With thionyl chloride; In benzene; Heating;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 2h;
With benzoyl chloride; Heating;
With thionyl chloride; In N,N-dimethyl acetamide; at -5 ℃;
With thionyl chloride; hydroquinone; In N,N-dimethyl-formamide; at 59.84 ℃; for 6h;
With oxalyl dichloride; In N,N-dimethyl-formamide; benzene;
With oxalyl dichloride; In N,N-dimethyl-formamide; benzene;
With n-dodecanoyl chloride; at 100 ℃; for 18h;
With Cl3Pd; at 50 ℃; for 4h;
With benzoyl chloride;
With thionyl chloride;
With benzoyl chloride;
With oxalyl dichloride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
With thionyl chloride; In dichloromethane; at 40 ℃; for 4h;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; Inert atmosphere; Cooling;
With thionyl chloride; at 70 ℃; for 3h;
With thionyl chloride; at 75 ℃; for 8h;
With oxalyl dichloride; In N,N-dimethyl-formamide; for 0.5h;
With thionyl chloride; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
With oxalyl dichloride; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;
With benzoyl chloride; hydroquinone; Heating;
With thionyl chloride; at 80 ℃; for 0.5h; Inert atmosphere;
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene; In chloroform-d1; at 20 ℃; Inert atmosphere;
96 %Spectr.
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 2h;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 1.5h;
With trichlorophosphate;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h;
With thionyl chloride;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3h;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 0.166667h;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 3h; Inert atmosphere;
With benzoyl chloride; N,N-dimethyl-formamide; In neat (no solvent); at 60 ℃; for 0.05h; Reagent/catalyst; Temperature; Time; Catalytic behavior; Flow reactor;
With trichlorophosphate; at 80 ℃;
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; for 2h;
With thionyl chloride; at 0 - 60 ℃; for 6h; Inert atmosphere; Schlenk technique;
With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃;
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.5h;
With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 0 - 20 ℃;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3h;
With thionyl chloride; at 0 - 60 ℃; for 6h;
With thionyl chloride; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; for 2h;
With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3h;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3h;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3.08333h;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 12h;
With thionyl chloride; In dichloromethane; for 4h; Cooling with ice; Inert atmosphere; Reflux;
ethyl vinyl ether
109-92-2,25104-37-4

ethyl vinyl ether

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

Conditions
Conditions Yield
ethyl vinyl ether; With oxalyl dichloride; at 0 - 20 ℃; for 1h; Inert atmosphere;
at 120 ℃; for 0.5h; Inert atmosphere;
89%
3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

Conditions
Conditions Yield
With P(MeNCH2CH2)3N; In acetonitrile; at 25 ℃; for 0.0833333h;
90%
(trichloromethyl)mesitylene
707-74-4

(trichloromethyl)mesitylene

acrylic acid
79-10-7

acrylic acid

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

mesitylene-2-carboxylic acid chloride
938-18-1

mesitylene-2-carboxylic acid chloride

Conditions
Conditions Yield
With iron(III) chloride; In n-heptane; at 100 ℃; for 4h; Inert atmosphere;
3.2 kg
1.3 kg
benzoyl chloride
98-88-4

benzoyl chloride

acrylic acid
79-10-7

acrylic acid

acryloyl chloride
814-68-6,25189-84-8

acryloyl chloride

Conditions
Conditions Yield
With hydroquinone;
With hydroquinone; Heating;

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