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498289

Sigma-Aldrich

3-Ethynylaniline

≥98%

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About This Item

Linear Formula:
HC≡CC6H4NH2
CAS Number:
54060-30-9
Molecular Weight:
117.15
EC Number:
258-944-6
MDL number:
MFCD00014779
UNSPSC Code:
12352100
PubChem Substance ID:
24873187
NACRES:
NA.22

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

Related Categories

General description

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

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
  • 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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

138.2 °F - closed cup

Flash Point(C)

59 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

498289-VAR:
498289-5G:
498289-BULK:
498289-500G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Modified synthesis of erlotinib hydrochloride.
Barghi L, et al.
Advanced Pharmaceutical Bulletin, 2(1), 119-122 (2012)
Paul L Chariou et al.
Nature nanotechnology, 14(7), 712-718 (2019-05-22)
Large doses of chemical pesticides are required to achieve effective concentrations in the rhizosphere, which results in the accumulation of harmful residues. Precision farming is needed to improve the efficacy of pesticides, but also to avoid environmental pollution, and slow-release
Side-chain type benzoxazine-functional cellulose via click chemistry.
Agag T, et al.
Journal of Applied Polymer Science, 125(2), 1346-1351 (2012)
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