3-Phenyl-2-propenoyl chloride
Cinnamoyl chloride
CAS: 102-92-1
Molecular Formula: C9H7ClO
3-Phenyl-2-propenoyl chloride - Names and Identifiers
| Name | Cinnamoyl chloride |
| Synonyms | Cinnamic chloride Cinnamoyl chloride Phenylacrylchloride Phenylacrylyl chloride TRANS-CINNAMOYL CHLORIDE 3-phenyl-acryloylchloride 3-phenyl-2-propenoylchlorid beta-Phenylacryloyl chloride 3-Phenyl-2-propenoyl chloride 3-phenylprop-2-enoyl chloride (2E)-3-phenylprop-2-enoyl chloride (2E)-3-Phenyl-2-propenoyl chloride [(1E)-3-chloroprop-1-en-1-yl]benzene |
| CAS | 102-92-1 |
| EINECS | 203-065-5 |
| InChI | InChI=1/C9H7ClO/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H/b7-6+ |
3-Phenyl-2-propenoyl chloride - Physico-chemical Properties
| Molecular Formula | C9H7ClO |
| Molar Mass | 166.6 |
| Density | d445.3 1.1617 |
| Melting Point | 35-37 °C (lit.) |
| Boling Point | 256-258 °C (lit.) |
| Flash Point | >230°F |
| Water Solubility | DECOMPOSES |
| Solubility | dioxane: 0.1g/mL, clear |
| Vapor Presure | 0.0143mmHg at 25°C |
| Appearance | Pale yellow crystal |
| Color | White to yellow |
| Merck | 13,2323 |
| BRN | 606265 |
| Storage Condition | 2-8°C |
| Refractive Index | nD42.5 1.614 |
| MDL | MFCD00000732 |
| Physical and Chemical Properties | White or yellowish needle-like crystals. Melting point 37-38 ℃, boiling point 257.5 ℃,131 ℃(1.47kPa), relative density 1.167(45/4 ℃), refractive index 1.614(42.5 ℃). Soluble in petroleum ether, carbon tetrachloride and hot ethanol, insoluble in water. Slow decomposition in water. |
| Use | For the determination of trace water, also used as intermediates in organic synthesis |
3-Phenyl-2-propenoyl chloride - Risk and Safety
| Hazard Symbols | C - Corrosive |
| Risk Codes | R34 - Causes burns R29 - Contact with water liberates toxic gas R20 - Harmful by inhalation R14 - Reacts violently with water |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S25 - Avoid contact with eyes. S30 - Never add water to this product. S23 - Do not breathe vapour. S8 - Keep container dry. |
| UN IDs | UN 3261 8/PG 2 |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-21 |
| HS Code | 29163990 |
| Hazard Class | 8 |
| Packing Group | III |
3-Phenyl-2-propenoyl chloride - Introduction
Very soluble in petroleum ether, soluble in carbon tetrachloride, ester, dioxane and hot ethanol, insoluble in water. Slowly decomposed in water.
Last Update：2022-10-16 17:11:34
3-Phenyl-2-propenoyl chloride - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| preparation of polyvinyl cinnamate | polyvinyl cinnamate adhesive is abbreviated as PVAC, which is a linear polymer compound with a molecular weight of 15,000~20,000. it is obtained by esterification reaction of polyvinyl alcohol and cinnamoyl chloride. 5-nitro acenaphthene and the organic solvent cyclohexanone are added to prepare a photosensitive adhesive, that is, the double bond of the molecule is opened under ultraviolet light and cured. It has important uses in the manufacture of integrated circuits and micro components. polycinnamic acid ester photoresist polyvinyl alcohol cinnamic acid ester is synthesized by polyvinyl alcohol and cinnamoyl chloride in pyridine solvent, and the prepared photoresist is called KPR. Under the action of ultraviolet rays, the double bonds of cinnamate undergo a photochemical dimerization reaction to form cross-linking and transform into insoluble substances. KPR is the earliest photoresist used in photolithography, usually with 5-nitro acenaphthene as a photosensitizer. Photoresist, also known as photoresist, can be used as a photosensitive polymer in photoprocessing technology. At present, it is widely used in lithography technology in printing plate making and electronic industry. Its working principle is that the light-receiving part is cross-linked to generate a poorly soluble hardened film, which is processed into a negative image (negative glue); or the original insoluble glue becomes soluble after being exposed to light, and is processed into a positive image (Positive glue). |
| uses | as an intermediate in organic synthesis; a reagent for the determination of trace moisture. Used for the determination of trace water and also used as an intermediate in organic synthesis Used in organic synthesis |
| Production method | It is obtained by the reaction of sodium cinnamate and glycolyl chloride. Combine oxalyl chloride and benzene into a solution, and add the dried sodium cinnamate in multiple times under stirring from time to time, each time it is added to the reaction to release carbon dioxide and then add it next time. Then reflux for 2h. After a little cooling, the sodium chloride produced and a trace amount of unreacted sodium cinnamate are filtered out. The filtrate is first evaporated to remove benzene under normal pressure, and then the fraction at 131 ℃(1.47kPa) is collected by distillation under reduced pressure to obtain the product with a yield of 75-90%. When it needs to be purified, it can be recrystallized with carbon tetrachloride. Cinnamic acid reacts with dichlorosulfoxide to produce cinnamoyl chloride. |
Last Update：2024-04-09 21:04:16
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