Contact Manager: Emma Song Email Address: emma@coreychem.com
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Items |
Specifications |
Test Result |
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Appearance |
Colorless or light yellow oily liquid |
Colorless oily liquid |
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Identification |
IR: chromatograph conforms to the characteristic peak of R.S. |
Conforms |
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HPLC: retention time of sample should be concordant with that of reference standard. |
Conforms |
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Water |
≤0.5% |
0.10% |
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Ignition residue |
≤0.2% |
0.03% |
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Related substances (HPLC) |
3-AMINOSTYRENE |
≤0.01% |
N.D. |
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4-(3-AMINOPHENYL)-2-METHYL-3-BUTYN-2-OL |
≤0.15% |
0.03% |
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3-Bromoaniline |
≤0.05% |
0.01% |
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Max. individual impurity |
≤0.15% |
0.01% |
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Total impurities |
≤1.0% |
0.06% |
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Purity |
≥99.0% |
99.94% |
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Assay |
98.0%-102.0% |
100.3% |
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Residual solvent |
Methanol |
≤3000ppm |
20.8ppm |
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Ethanol |
≤5000ppm |
N.D. |
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Methylene chloride |
≤600ppm |
N.D. |
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Toluene |
≤890ppm |
463.4ppm |
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Acetone |
≤5000ppm |
1304.2ppm |
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3-Ethynylaniline Usage And Synthesis:
Chemical Properties Clear yellowish to brown liquid
Uses: Reagent in the preparation of a labelled metabolite of Erlotinib (E625000).
Uses: 3-Aminophenylacetylene is used as a pharmaceutical intermediate.
Application:
3-Ethynylaniline may be used in the synthesis of the following benzoxazine monomers: bis{4-[3-(3-ethynylphenyl)(2H,4Hbenzo[3,4-e]1,3-oxazin-6-yloxy)]phenyl}phenylphosphino-1-one, [3-(3-ethynylphenyl)(2H,4Hbenzo[3,4-e]1,3-oxazaperhydroin-6-yl)][3-(3-ethynylphenyl)(2H,4H-benzo[3,4-e]1,3-oxazin-6-yl)]phenylphosphino-1-one, and bis[3-(3-ethynylphenyl)(2H,4Hbenzo[3,4-e]1,3-oxazin-6-yl)oxy]phenylphosphino-1-one.
It may be used: To synthesize succin(m-ethynyl)dianilide and sebaco(m-ethynyl)dianilide. As a reagent in the multi-step synthesis of erlotinib hydrochloride. To prepare 3-(3-ethynylphenyl)-6-methyl-2H, 4H-benzo[e]1,3-oxazine. To prepare 3-[3-(4-acetylamino-benzyl)-[1,2,4]oxadiazol-5- yl]-N-(3-ethynyl-phenyl)-propionamide.
General Description: 3-Ethynylaniline is a terminal alkyne that can be prepared by the reduction of 3-ethylnylnitrobenzene.
Reaction suitability reaction type: click chemistry
Synthesis Starting with m-nitrocinnamic acid:
First, it undergoes an addition reaction with liquid bromine in glacial acetic acid to generate 3-(3-nitro)phenyl-2,3-dibromopropionic acid; subsequently, it undergoes dehydrobromination and decarboxylation reactions under the action of an organic base (such as DBU) to generate the key intermediate m-nitrophenylacetylene; finally, the nitro group is reduced to an amino group using iron powder in an acidic aqueous ethanol solution to obtain the target product 3-Ethynylaniline.
3-Ethynylaniline Preparation Products And Raw materials
Raw materials Ethanol–>Hydrazinium hydroxide solution–>Stannous chloride dihydrate–>Activated carbon–>Iron chloride hexahydrate–>3-NITROPHENYLACETYLENE
Preparation Products Erlotinib–>(3aR,6aR)-N-(4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)-1-methylhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxamide–>3-Vinylaniline–>Benzenamine, 3-ethynyl-N-methyl- (9CI)–>3-(2H-1,2,3-triazol-4-yl)aniline
