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498289

Sigma-Aldrich

3-Ethynylaniline

≥98%

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About This Item

Linear Formula:
HC≡CC6H4NH2
CAS Number:
Molecular Weight:
117.15
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
assay:
≥98%

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In StockDetails


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Quality Level

assay

≥98%

reaction suitability

reaction type: click chemistry

storage temp.

2-8°C

SMILES string

Nc1cccc(c1)C#C

InChI

1S/C8H7N/c1-2-7-4-3-5-8(9)6-7/h1,3-6H,9H2

InChI key

NNKQLUVBPJEUOR-UHFFFAOYSA-N

General description

3-Ethynylaniline is a terminal alkyne that can be prepared by the reduction of 3-ethylnylnitrobenzene.[1]

Application

3-Ethynylaniline may be used in the synthesis of the following benzoxazine monomers:[2]
  • 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
  • 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.[3]
  • As a reagent in the multi-step synthesis of erlotinib hydrochloride.[4]
  • To prepare 3-(3-ethynylphenyl)-6-methyl-2H, 4H-benzo[e]1,3-oxazine.[5]
  • To prepare 3-[3-(4-acetylamino-benzyl)-[1,2,4]oxadiazol-5- yl]-N-(3-ethynyl-phenyl)-propionamide.[6]

pictograms

FlameExclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

138.2 °F - closed cup

flash_point_c

59 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Synthesis, analgesic and anti-inflammatory activities of novel 3-(4-acetamido-benzyl)-5-substituted-1,2,4-oxadiazoles.
Farooqui M, et al.
European Journal of Medicinal Chemistry, 44(2), 794-799 (2009)
Modified synthesis of erlotinib hydrochloride.
Barghi L, et al.
Advanced Pharmaceutical Bulletin, 2(1), 119-122 (2012)
Qilin Mei et al.
Polymers, 12(5) (2020-05-03)
Benzoxazine resin has been paid more attention in the fields of aviation, electronics, automobiles and new energy industries because of its excellent comprehensive performance. Further application is limited, however, by shortcomings such as high brittleness and high curing temperature. Furthermore
Diacetylene-Containing Polymers III. Poly (m,m'-butadiynylenesuccindianilide) and Poly (m,m'-butadiynylene sebacodianilide): Novel Materials for Preparation of Transparent Polydiacetylene Containing Films.
Fomine S and Ogawa T
Polymer Journal, 26(1), 93-98 (1994)
Preparation of 2'-aminoacetophenones: a one-pot hydration and reduction of 1-ethynyl-2-nitrobenzenes.
Bosch E and Jeffries L.
Tetrahedron Letters, 42(46), 8141-8142 (2001)

Questions

  1. There is no expiry date on the analysis certificate of the 3-ethnylaniline product with serial number MKCP6127

    1 answer
    1. This product does not contain an expiration date or recommended retest date. Products with no expiration date or recommended retest date should be routinely inspected by customers to ensure they perform as expected. These products are also subject to a one year warranty from the date of shipment. For more information you may access the "Product Dating Information" document under "ADDITIONAL USEFUL DOCUMENTS ABOUT OUR PRODUCTS" at the bottom of the Quality Services page with this link: https://www.sigmaaldrich.com/US/en/life-science/quality-and-regulatory-management/quality-services

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