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3-ETHYNYLANILINE

3-ethynylaniline

CAS: 54060-30-9

Molecular Formula: C8H7N

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3-ETHYNYLANILINE - 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-ETHYNYLANILINE - Physico-chemical Properties

Molecular FormulaC8H7N
Molar Mass117.15
Density1.04
Melting Point27°C
Boling Point92-93 °C (2 mmHg)
Flash Point138°F
Water SolubilityInsoluble in water.
Solubility Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (
Vapor Presure0.0379mmHg at 25°C
AppearanceLiquid
Specific Gravity1.12
ColorClear yellow to brown
BRN2935417
pKa3.67±0.10(Predicted)
Storage Condition2-8°C
StabilityLight Sensitive
Refractive Index1.614-1.616
UseFor the synthesis of aviation, aerospace, military and other fields of high-grade resin and synthesis of new anticancer drugs important intermediates

3-ETHYNYLANILINE - Risk and Safety

Risk Codes36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS26 - 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 IDsUN 1993 3/PG 3
WGK Germany3
TSCAYes
HS Code29214990
Hazard Class3
Packing GroupⅢ

3-ETHYNYLANILINE - 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
3-ETHYNYLANILINE
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Tel: +86-17551318830
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Guangzhou Yuanda New Material Co.,Ltd
Product Name: 3-Aminophenylacetylene Request for quotation
CAS: 54060-30-9
Tel: +86 19849939632
Email: 2470479589@qq.com
Mobile: +86 19849939632
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Jiangsu Pules Biotechnology Co.,Ltd.
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CAS: 54060-30-9
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
Hubei YoungXin Pharmaceutical Tech Co.,Ltd.
Spot supply
Product Name: Erlotinib Impurity 42 Visit Supplier Webpage Request for quotation
CAS: 54060-30-9
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052 Click to send a QQ message
Wechat: 15671228036
Hefei TNJ Chemical Industry Co.,Ltd.
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 Click to send a QQ message
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Wuhan Boye Science And Technology Development Co., Ltd.
Multiple Specifications
Product Name: 3-Aminophenylacetylene Request for quotation
CAS: 54060-30-9
Tel: 86-10-10086 81625225
Email: yeqim@boyechemicals.com
Mobile: 86-15387090420
QQ: 1377812380 Click to send a QQ message
Wechat: 15387090420
Shanghai Worldyang Chemical Co.,Ltd.
Product Name: 3-Aminophenylacetylene Request for quotation
CAS: 54060-30-9
Tel: +86-21-56795779
Email: charles7788@worldyachem.com
Mobile: +86-13651600618
QQ: 2850607228 Click to send a QQ message
Wechat: 13651600618
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3-ETHYNYLANILINE
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