4-Chlorocinnamic acid
4-Chlorocinnamic acid
CAS: 1615-02-7
Molecular Formula: C9H7ClO2
4-Chlorocinnamic acid - Names and Identifiers
| Name | 4-Chlorocinnamic acid |
| Synonyms | 4-Chlorociamic acid 4-Chlorocinnamic acid 4-Chlorocinncmic Acid PARA-CHLOROCINNAMICACID 4-Chlorophenyl acrylic acid (2E)-3-(4-chlorophenyl)acrylic acid (2E)-3-(4-chlorophenyl)prop-2-enoate (2E)-3-(4-chlorophenyl)prop-2-enoic acid 4-chlorocinnamic acid, predominantly trans 2-propenoic acid, 3-(4-chlorophenyl)-, (2E)- 4-Chlorocinnamic acid,trans-3-(4-Chlorophenyl)propenoic acid (2E)-3-(4-Chlorophenyl)prop-2-enoic acid, (2E)-3-(4-Chlorophenyl)acrylic acid |
| CAS | 1615-02-7 |
| EINECS | 216-564-8 |
| InChI | InChI=1/C9H7ClO2/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6H,(H,11,12)/p-1/b6-3+ |
| InChIKey | GXLIFJYFGMHYDY-ZZXKWVIFSA-N |
4-Chlorocinnamic acid - Physico-chemical Properties
| Molecular Formula | C9H7ClO2 |
| Molar Mass | 182.6 |
| Density | 1.2377 (rough estimate) |
| Melting Point | 248-250°C(lit.) |
| Boling Point | 260.71°C (rough estimate) |
| Flash Point | 150.5°C |
| Solubility | DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| Vapor Presure | 9.47E-05mmHg at 25°C |
| Appearance | Crystallization |
| Color | White |
| BRN | 1365308 |
| pKa | 4.41(at 25℃) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.5426 (estimate) |
| MDL | MFCD00004396 |
| Physical and Chemical Properties | Colorless crystals. There are two kinds of cis and trans. Soluble in ethanol, CIS melting point 110.5 ℃, trans melting point 249-250 ℃. |
| Use | For the synthesis of herbicides |
4-Chlorocinnamic acid - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S36 - Wear suitable protective clothing. S28A - S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | GD8490000 |
| HS Code | 29163990 |
| Hazard Note | Irritant |
4-Chlorocinnamic acid - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | p-chlorocinnamic acid is a common organic synthesis intermediate, which is used to synthesize p-chlorophenylpropionic acid and produce herbicide madizan. In addition, cinnamic acid derivatives also have good effects on antibacterial and anti-tumor. Knoevenagel method is a common synthesis method of cinnamic acid derivatives. Cinnamic acid was synthesized by Knoevenagel method in pyridine medium with hexahydropyridine as condensing agent. Using toluene and pyridine as solvents and aniline and piperidine as catalysts, p-hydroxycinnamic acid was synthesized by Knoevenagel method. |
| preparation | 1.41g(0.01mol) of p-chlorobenzaldehyde, 1.27g(0.011mol) of malonic acid and 0.77g(0.01mol) of ammonium acetate were added to a 100mL three-neck round bottom flask and mixed evenly. Connect a thermometer and a spherical condenser tube and put it into a microwave reactor for reaction. After the reaction was completed, 5mL of hot water was added to the flask, and unreacted p-chlorobenzaldehyde was removed by steam distillation. Add 10% sodium hydroxide solution 5mL ~ 6mL, add activated carbon to remove color, filter, transfer the filtrate to a beaker, acidify with concentrated hydrochloric acid until Congo red test paper turns blue or pH = 3~4. Cooling to precipitate crystals, suction filtration, washing the precipitate with a small amount of water, draining, and drying the crude product. Recrystallized with water-ethanol (volume ratio 1 ∶ 3) and dried. The yield was calculated. The optimal synthesis conditions were as follows: the material ratio was n (p-chlorobenzaldehyde) ∶n (malonic acid) ∶n (ammonium acetate) = 1.0 ∶ 1.1 ∶ 1.0, the reaction time was 13min, and the power was 800W. Under these conditions, the yield was 85.8%. Melting point determination and infrared spectrum analysis were carried out. Compared with traditional methods, it has the advantages of short time, high yield and less pollution. |
| uses | organic synthesis intermediate, used to synthesize p-chlorophenylpropionic acid, to produce the herbicide Maidi San. for synthetic herbicide |
| Production method | It is obtained by the reaction of p-chlorobenzaldehyde and acetic anhydride. The p-chlorobenzaldehyde, acetic anhydride and sodium acetate were reacted together at 180 ℃ for 13h. After the reaction is finished, it is slightly cold, pour into water, filter, wash the filter cake with water, and dissolve it repeatedly with ammonia water until only a small amount of brown-yellow viscous remains. The obtained ammonium salt solution is filtered, p-chlorocinnamic acid is re-precipitated with 3N dilute sulfuric acid, and the product is filtered and dried. The yield is about 80%. |
Last Update：2024-04-09 02:00:07
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