3-Aminophenylacetylene
3-ethynylaniline
CAS: 54060-30-9
Molecular Formula: C8H7N
3-Aminophenylacetylene - Names and Identifiers
| Name | 3-ethynylaniline |
| Synonyms | M-ETHYNYLANILINE 3-ethynylaniline m-ethynylaniline 3-ETHYNYLANILINE 3-ethynyl-benzenamin 3-ethynylbenzeneamine 3-ETHYNYL-PHENYLAMINE 3-ethynyl-Benzenamine 3-ETHYNYLBENZENEAMINE 3-ethynyl-phenylamine 3-aminophenylacetylene 3-AMINOPHENYLACETYLENE m-aminophenyl acetylene M-AMINOPHENYL ACETYLENE Benzenamine, 3-ethynyl- Aminophenylacetylene, 3- |
| CAS | 54060-30-9 |
| EINECS | 258-944-6 |
| InChI | InChI=1/C8H7N/c1-2-7-4-3-5-8(9)6-7/h1,3-6H,9H2 |
| InChIKey | NNKQLUVBPJEUOR-UHFFFAOYSA-N |
3-Aminophenylacetylene - Physico-chemical Properties
| Molecular Formula | C8H7N |
| Molar Mass | 117.15 |
| Density | 1.04 |
| Melting Point | 27°C |
| Boling Point | 92-93 °C (2 mmHg) |
| Flash Point | 138°F |
| Water Solubility | Insoluble in water. |
| Solubility | Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate ( |
| Vapor Presure | 0.0379mmHg at 25°C |
| Appearance | Liquid |
| Specific Gravity | 1.12 |
| Color | Clear yellow to brown |
| BRN | 2935417 |
| pKa | 3.67±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Light Sensitive |
| Refractive Index | 1.614-1.616 |
| Use | For the synthesis of aviation, aerospace, military and other fields of high-grade resin and synthesis of new anticancer drugs important intermediates |
3-Aminophenylacetylene - Risk and Safety
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 1993 3/PG 3 |
| WGK Germany | 3 |
| TSCA | Yes |
| HS Code | 29214990 |
| Hazard Class | 3 |
| Packing Group | Ⅲ |
3-Aminophenylacetylene - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| properties | m-aminophenylacetylene is a colorless to pale yellow transparent liquid. |
| Introduction | m-aminophenylacetylene, also known as 3-acetylaniline, has two functional groups, amino and alkyne, which can derive a series of important intermediates. In recent years, with the deepening of research, m-aminophenylacetylene has been applied more and more widely in the fields of new materials, biomedicine and chemical pharmacy. It is an important intermediate for the synthesis of anticancer drugs erlotinib (Erlotinib) and icotinib (Icotinib). |
| Use | m-aminophenylacetylene itself has good mechanical properties and high mechanical strength, can withstand a fairly high twisting force, and has high temperature resistance and wear resistance. Very good, the polyimide compound produced by its reaction with maleic anhydride is extremely important. The resin made of this polymer has high thermal stability and high mechanical strength, it is a high-end resin used in the synthesis of aviation, aerospace, military and other fields. It can be applied to the tail of aircraft and the shell of missiles; m-aminophenylacetylene and quinazoline compounds react to generate compounds with anti-tumor activity, such as Icotinib, erlotinib, etc. It is used to synthesize high-grade resins in aviation, aerospace, military and other fields and important intermediates for the synthesis of new anticancer drugs |
| Preparation | Method 1: Using m-haloaniline and 2-methyl-3-butyne-2-ol as starting materials, the Sonogashira coupling reaction under the catalysis of triphenylphosphine, palladium acetate and cuprous iodide generates 1-(3-aminophenyl)-3-methyl-3-hydroxy-1-butyne, the elimination reaction is then heated under strong alkali conditions to obtain the target product m-aminobenzene acetylene. The method uses expensive palladium catalyst, and the elimination reaction needs to be heated, which will produce a large number of polymerization reaction by-products, the yield is low, so it is not suitable for industrial production. In addition, similar to the use of m-bromine or m-haloaniline, m-iodide nitrobenzene, etc. and protected dihydroxypropylyne as starting materials have been reported in the literature, and the above unfavorable factors also exist. Method 2: Using m-nitroacetophenone as the starting material, phosphorus oxychloride and anhydrous DMF were mixed to prepare a vilsmiere reagent, and m-nitroacetophenone was added in batches to prepare β-chloro-m-nitrophenylpropanal, then eliminated by strong alkali to prepare m-nitrophenylacetylene, and finally reduced nitro to prepare m-aminophenylacetylene. The first step of the method is very hot, it is difficult to control, eliminate the reaction side reaction more, the final product separation needs distillation, the yield is low, so it is not suitable for industrial production. Method 3: Using m-nitroiodobenzene and trimethylsilyl acetylene as raw materials, (3-nitrophenyl)-(trimethylsilyl)-acetylene was obtained by coupling under the catalysis of bis (triphenylphosphine) palladium dichloride and cuprous iodide or cuprous chloride, and then the target compound m-aminophenylacetylene was obtained by reduction of molybdenum hexacarbonyl/1,8-diazocyclo [5.4.0] undeca-7ene (DBU) under microwave radiation. The raw materials used in this method are expensive, complicated to operate, and the total yield is about 67%. Method 4: Using m-nitrobenzaldehyde as the starting material, first condensed with malonic acid in an ethanol solvent through a basic catalyst, and then decarboxylated to obtain m-nitrocinnamic acid, and then brominated in acetic acid solution to obtain α,β-dibromo-3-(3 '-nitrophenyl) propionic acid, and then decarboxylated by weak base and selective debromination, (Z)-1-(2-bromoethylene)-3-nitrobenzene was prepared, and then completely debrominated by strong alkali to obtain m-alkynyl nitrobenzene, and finally reduced by iron powder and further rectified Purification of m-aminobenzene acetylene. There are a total of five-step reactions. The reaction conditions of the selective debromination process are difficult to control, and a large number of reaction by-products will be produced. In addition, high vacuum distillation is required in the end, which requires high equipment requirements and low yield 58%, resulting in higher product costs. Therefore, it is not suitable for industrial production. In addition, m-alkynyl nitrobenzene is used as the starting material to directly reduce m-aminobenzene acetylene, which is not easy to obtain. Method 5: Using α,β-dibromo-3-(3 '-nitrophenyl) propionic acid as raw material, m-nitrophenylacetylene was obtained by elimination reaction under alkaline conditions, and then m-aminobenzene acetylene was obtained by reduction. This route is simple and economical, but according to the methods reported in the current literature, it is difficult to control the elimination of side reactions, many by-products and the need to use microwaves to promote dehalogenation reactions and other factors limit the industrial use of this route. Method 6: Using m-nitrobenzaldehyde as the starting material, m-nitrocinnamic acid was first generated by Perkin reaction, then 2, 3-dibromo-3-(3-nitrophenyl) propionic acid was prepared by bromine addition, and then (Z)-1-bromo-2-(3-nitrobenzene) ethanthin was obtained by debromination of hydrogen and carboxyl group at the same time, then sodium hydride was debrominated to obtain m-nitrophenylacetylene, and finally m-aminophenylacetylene was obtained by iron powder reduction. The method is easy to obtain raw materials, a total of five steps, but the selective debromination process reaction conditions are difficult to control, will produce a large number of reaction by-products, the yield is low 45%, resulting in higher product costs, so it is not suitable for industrial production. |
| Application | m-aminophenylacetylene is an important intermediate for the synthesis of new quinazoline anti-cancer drugs and nicotinic acid herbicides; it is also used as a thermosetting polyimide resin Modified active end-sealing base raw material, the made material has excellent heat resistance and mechanical properties, no volatile substances are generated during curing and molding, the product has small porosity and good wear resistance, it is a high-end resin used in aerospace and military fields; as an excellent film antifogging agent, this product and its derivatives can effectively improve the clarity of various negatives; in immunoassay, indole derived from m-aminophenylacetylene Compound is an important fluorescent marker; in addition, this product can also be used alone as a high-temperature resistant adhesive or a high-temperature resistant varnish. |
Last Update：2024-04-09 15:16:46
Supplier List
Featured Products
Product Name: 3-ethynylaniline Request for quotationCAS: 54060-30-9
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Spot supply
Product Name: 3-ethynylaniline Request for quotationCAS: 54060-30-9
Tel: +86-18721521379
Email: 18721521379@163.com
Mobile: +86-18721521379
Wechat: 18721521379
Spot supply
Product Name: 3-ethynylaniline Request for quotationCAS: 54060-30-9
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Wechat: chemical6666
Spot supply
Product Name: 3-Ethynylaniline Visit Supplier Webpage Request for quotationCAS: 54060-30-9
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
Product Name: 3-Aminophenylacetylene Request for quotation
CAS: 54060-30-9
Tel: +86 19849939632
Email: 2470479589@qq.com
Mobile: +86 19849939632
QQ: 2470479589
CAS: 54060-30-9
Tel: +86 19849939632
Email: 2470479589@qq.com
Mobile: +86 19849939632
QQ: 2470479589
Multiple Specifications
Product Name: 3-Aminophenylacetylene Request for quotationCAS: 54060-30-9
Tel: 86-10-10086 81625225
Email: yeqim@boyechemicals.com
Mobile: 86-15387090420
QQ: 1377812380
Spot supply
Product Name: 3-Aminophenylacetylene Visit Supplier Webpage Request for quotationCAS: 54060-30-9
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185
Wechat: chinaskyrun
Spot supply
Product Name: 3-Ethynylaniline Visit Supplier Webpage Request for quotationCAS: 54060-30-9
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
WhatsApp: +86-18621343501
Product Name: 3-ethynylaniline Request for quotation
CAS: 54060-30-9
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
CAS: 54060-30-9
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Spot supply
Product Name: 3-Ethynylaniline Visit Supplier Webpage Request for quotationCAS: 54060-30-9
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328
WhatsApp: +86-18821248368
Featured Products
Product Name: 3-ethynylaniline Request for quotationCAS: 54060-30-9
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Spot supply
Product Name: 3-ethynylaniline Request for quotationCAS: 54060-30-9
Tel: +86-18721521379
Email: 18721521379@163.com
Mobile: +86-18721521379
Wechat: 18721521379
Spot supply
Product Name: 3-ethynylaniline Request for quotationCAS: 54060-30-9
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Wechat: chemical6666
Spot supply
Product Name: 3-Ethynylaniline Visit Supplier Webpage Request for quotationCAS: 54060-30-9
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
Product Name: 3-Aminophenylacetylene Request for quotation
CAS: 54060-30-9
Tel: +86 19849939632
Email: 2470479589@qq.com
Mobile: +86 19849939632
QQ: 2470479589
CAS: 54060-30-9
Tel: +86 19849939632
Email: 2470479589@qq.com
Mobile: +86 19849939632
QQ: 2470479589
Multiple Specifications
Product Name: 3-Aminophenylacetylene Request for quotationCAS: 54060-30-9
Tel: 86-10-10086 81625225
Email: yeqim@boyechemicals.com
Mobile: 86-15387090420
QQ: 1377812380
Spot supply
Product Name: 3-Aminophenylacetylene Visit Supplier Webpage Request for quotationCAS: 54060-30-9
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185
Wechat: chinaskyrun
Spot supply
Product Name: 3-Ethynylaniline Visit Supplier Webpage Request for quotationCAS: 54060-30-9
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
WhatsApp: +86-18621343501
Product Name: 3-ethynylaniline Request for quotation
CAS: 54060-30-9
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
CAS: 54060-30-9
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Spot supply
Product Name: 3-Ethynylaniline Visit Supplier Webpage Request for quotationCAS: 54060-30-9
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328
WhatsApp: +86-18821248368
View History
3-Aminophenylacetylene
kako red rl base
(S)-BENZYL 2-AMINO-3-(1H-IMIDAZOL-5-YL)PROPANOATE BIS(4-METHYLBENZENESULFONATE)
kako red rl base
(S)-BENZYL 2-AMINO-3-(1H-IMIDAZOL-5-YL)PROPANOATE BIS(4-METHYLBENZENESULFONATE)