N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide

Base Information

• Chemical Name: N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide
• CAS No.: 134892-18-5
• Molecular Formula: C11H22BNO3
• Molecular Weight: 245.12
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID001201734
• Nikkaji Number: J2.757.075E
• Mol file: 134892-18-5.mol

Synonyms:134892-18-5;N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide;3-(N,N-DIMETHYLAMINO)-3-OXOPROPYLBORONIC ACID PINACOL ESTER;2-(Dimethylaminocarbonyl)ethylboronic acid, pinacol ester;1,3,2-dioxaborolane-2-propanamide, N,N,4,4,5,5-hexamethyl-;2-(DIMETHYLAMINOCARBONYL)ETHYLBORONIC ACID;SCHEMBL15299965;DTXSID001201734;MFCD10700156;AS-55079;CS-0175739;W13749;J-006620;2-(dimethylaminocarbonyl)ethylboronic acid, AldrichCPR;N,N,4,4,5,5-Hexamethyl-1,3,2-dioxaborolane-2-propanamide;N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)propanamide

Chemical Property of N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide

Chemical Property:

• Boiling Point: 286.9±23.0 °C(Predicted)
• PKA: -0.40±0.70(Predicted)
• PSA: 38.77000
• Density: 0.98±0.1 g/cm3(Predicted)
• LogP: 1.55690
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 227.1692737
• Heavy Atom Count: 16
• Complexity: 260

Purity/Quality:

98.5% ^*data from raw suppliers

2-(Dimethylaminocarbonyl)ethylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CCC(=O)N(C)C

Technology Process of N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide

There total 6 articles about N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide 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: 99.0%

N,N-Dimethylacrylamide (2680-03-7,68761-83-1) + bis(pinacol)diborane (73183-34-3) → N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-propanamide (134892-18-5)

Guidance literature:

With methanol; [Pd2(μ-C9H7NPPh2)(μ-O2CCH3)]2; water; caesium carbonate; In tetrahydrofuran; at 25 ℃; for 6h; Inert atmosphere;

DOI:10.1002/chem.200903095

Reference yield: 83.0%

N,N-Dimethylacrylamide (2680-03-7,68761-83-1) → N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-propanamide (134892-18-5)

Guidance literature:

N,N-Dimethylacrylamide; With copper(II) carbonate; (+)-D-glucosamine hydrochloride; sodium hydroxide; In water; at 20 ℃; for 1.25h;

N,N-Dimethylacrylamide; In water; at 60 ℃; for 20h;

Reference yield: 80.0%

N,N-Dimethylacrylamide (2680-03-7,68761-83-1) + 4,8-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,6,2-dioxazaborocane → N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-propanamide (134892-18-5)

Guidance literature:

4,8-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,6,2-dioxazaborocane; With copper(l) chloride; In dichloromethane; for 0.166667h; Inert atmosphere;

N,N-Dimethylacrylamide; In methanol; dichloromethane; at 0 - 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/ol901359n

upstream raw materials:

N,N-Dimethylacrylamide

bis(pinacol)diborane

methanol

water

Downstream raw materials:

3-(3-methoxyphenyl)propanoic acid dimethylamide

Refernces

• 1、 Reilly, Sean W.,Akurathi, Gopalakrishna,Box, Hannah K.,Valle, Henry U.,Hollis, T. Keith,Webster, Charles Edwin. "β-Boration of α,β-unsaturated carbonyl compounds in ethanol and methanol catalyzed by CCC-NHC pincer Rh complexes". . p. 32 - 38. Retrieved 2015/12/23.
• 2、 -. "?-boration of alkene and alkyne intermediates". Paragraph 0071. . Retrieved 2013/10/22.