22774-32-9

Basic information

• Product Name: 4‐methyl‐N,N‐di(prop‐2‐yn‐1‐yl)aniline
• Synonyms: 4‐methyl‐N,N‐di(prop‐2‐yn‐1‐yl)aniline
• CAS NO: 22774-32-9
• Molecular Weight: 183.253
• Mol File: 22774-32-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4‐methyl‐N,N‐di(prop‐2‐yn‐1‐yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4‐methyl‐N,N‐di(prop‐2‐yn‐1‐yl)aniline(22774-32-9)
• EPA Substance Registry System: 4‐methyl‐N,N‐di(prop‐2‐yn‐1‐yl)aniline(22774-32-9)

Safety Data

• Hazardous Substances Data: 22774-32-9(Hazardous Substances Data)

Upstream product

• 106-49-0 p-toluidine 
• 106-96-7 propargyl bromide 
• 116507-14-3 N-(5-methoxy-2-furfuryl)-p-toluidine 
• 16156-58-4 prop-2-yn-1-ol methanesulfonate 

Relevant articles and documents

Pyrrolylmethyl functionalized o-carborane derivatives

The reactions of the 16e half-sandwich complex CpCoS2C2B10H10 (1), diazo esters, and various 1,6-diynes (3a-i; PhN(CH2C CH)2, 4-Me-PhN(CH2C CH)2, 4-OMe-PhN(CH2C CH)2, 4-F-PhN(CH2C CH)2, BzN(CH2C CH)2, O(CH2C CH)2, C(Ac)2(CH2C CH)2, N(CH2C CH)3, NH(CH2C CH)N(CH2C CH)2) were investigated, in which two novel types of B-H activated products CpCoS2B10H9(CH2CO2Et)C5H3N(R)(CHCHCO2Et) (4a-c; R = Ph, 4-Me-Ph, 4-OMe-Ph) and the key intermediate CpCoS2B10H9(CHCO2Me) (CH2CO2Me) (9) were isolated. 9 features a reactive Co-B bond, which triggers insertion of various 1,6-diynes to further lead to different final products. Substrates 3a-c are activated by the Co-B bond to produce o-carborane derivatives 4a-c which are functionalized by a cobalt-complexed 3-pyrrolylmethyl group. The pyrrole ring is formed by in situ ring closure of 1,6-diynes. Control experiments and isolation of the intermediate CpCoS2B10H9(CHCO2Me)(CH2CO2Me)HCC CH2N(4-Me-Ph)(CH2C CH) (10) support the proposed mechanism concerning the formation of 4a-c analogues by oxidation. All of the new complexes were characterized by NMR, IR, elemental analysis, and mass spectrometry. The structures of 4a-6a and 9 were determined by single-crystal X-ray diffraction analysis as well.

Synthesis and characterization of N,N-di(prop-2-ynyl)-p-toluidine

In order to investigate the intramolecular [4 + 2] cycloaddition, we prepared some new tertiary N-(5-substituted-2-furfuryl)-N-prop-2-ynyl-p- toluidines [Hergold-Brundic et al., Acta Cryst C56:e520, 2000; Mance and Jakopcic, Mol Divers 9:229, 2005; Mance,

Direct and selective N-monoalkynylation and N-monoalkenylation of anilines with alky(e)nyl methanesulfonates using methylmagnesium bromide as a base

Several anilines were directly N-monoalkynylated and N-monoalkenylated with alkynyl methanesulfonates and alkenyl methanesulfonates, respectively, using methylmagnesium bromide as a base in good yields with high selectivities.