Tert-butyl 4-(2-propynylamino)benzoate

Base Information

• Chemical Name: Tert-butyl 4-(2-propynylamino)benzoate
• CAS No.: 112888-76-3
• Molecular Formula: C14H17NO2
• Molecular Weight: 231.294
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID70435345
• Wikidata: Q72504167
• Mol file: 112888-76-3.mol

Synonyms:112888-76-3;TERT-BUTYL 4-(2-PROPYNYLAMINO)BENZOATE;Tert-butyl 4-(prop-2-ynylamino)benzoate;tert-Butyl 4-(prop-2-yn-1-ylamino)benzoate;SCHEMBL433863;DTXSID70435345;AMY15432;Benzoic acid, 4-(2-propyn-1-ylamino)-, 1,1-dimethylethyl ester;CS-M1332;FD7135;MFCD11973652;AKOS015912299;t-Butyl 4-(prop-2-ynylamino)benzoate;Tert-butyl-4-(2-propynylaMino)benzoate;AS-49293;tert-Butyl4-(prop-2-yn-1-ylamino)benzoate;tert-Butyl 4-[(prop-2-yn-1-yl)amino]benzoate;Benzoic acid, 4-(2-propynylamino)-, 1,1-dimethylethyl ester;Benzoic acid,4-(2-propyn-1-ylaMino)-,1,1-diMethylethyl ester

Chemical Property of Tert-butyl 4-(2-propynylamino)benzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.557
• Boiling Point: 357.651 ºC at 760 mmHg
• PKA: 0.41±0.50(Predicted)
• Flash Point: 170.102ºC
• PSA: 38.33000
• Density: 1.085 g/cm³
• LogP: 2.76000
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 231.125928785
• Heavy Atom Count: 17
• Complexity: 300

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl4-(Prop-2-ynylamino)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1=CC=C(C=C1)NCC#C

Technology Process of Tert-butyl 4-(2-propynylamino)benzoate

There total 4 articles about Tert-butyl 4-(2-propynylamino)benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.4%

O-t-butyl 4-(trifluoroacetamido)benzoate (1262414-95-8) + propargyl bromide (106-96-7) → tert-butyl p-[N-(prop-2-ynyl)amino]benzoate (112888-76-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; toluene; at 40 ℃; for 24h;

Reference yield: 46.0%

tert-butyl 4-aminobenzoate (18144-47-3) + propargyl bromide (106-96-7) → tert-butyl p-[N-(prop-2-ynyl)amino]benzoate (112888-76-3)

Guidance literature:

With potassium carbonate; In toluene; at 50 ℃; for 3.5h;

DOI:10.1021/jm00083a008

Reference yield:

tert-butyl 4-aminobenzoate (18144-47-3) → tert-butyl p-[N-(prop-2-ynyl)amino]benzoate (112888-76-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 24 h / 0 - 20 °C / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide; toluene / 24 h / 40 °C

With pyridine; potassium carbonate; In N,N-dimethyl-formamide; toluene;

upstream raw materials:

tert-butyl 4-aminobenzoate

propargyl bromide

O-t-butyl 4-(trifluoroacetamido)benzoate

Downstream raw materials:

4-prop-2-ynylamino-benzoic acid

tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Refernces

• 1、 -. "Quinazoline thymidylate synthase inhibitors". . . Retrieved 2008/06/13.
• 2、 Bisset, Graham M. F.,Pawelczak, Krzysztof,Jackman, Ann L.,Calvert, A. Hilary,Hughes, Leslie R.. "Syntheses and Thymidylate Synthase Inhibitory Activity of the Poly-γ-glutamyl Conjugates of N--2-thenoyl>-L-glutamic Acid (ICI D1694) and Other Quinazoline Antifolates". . p. 859 - 866. Retrieved 2007/10/02.