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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: zsinger on January 11, 2014, 10:53:16 PM

Title: Use of HMPT
Post by: zsinger on January 11, 2014, 10:53:16 PM

All,
I am looking at a synthesis that calls for the solvent HMPT (hex-methyl-phosphoric triamide), and I am wondering if there is a good substitute.  From the literature, I gathered that HMPT is mostly used for its promotion of Sn2 attack by the anionic species.  While I used this solvent once in undergrad, we were basically under a watchful eye, as I know it is quite dangerous and carcinogenic, if I'm not mistaken.  Any suggestions for an equally good solvent would be greatly appreciated.  Thanks.
           -Zack

Title: Re: Use of HMPT
Post by: AlphaScent on January 12, 2014, 02:09:13 PM

DMSO

Title: Re: Use of HMPT
Post by: zoork34 on January 15, 2014, 04:35:09 PM

You could also try dimethylformamide (DMF), dimethylacetamide (DMAc), or dimethylimidazolidinone (DMI).  All good polar-aprotic solvents. 

Title: Re: Use of HMPT
Post by: Dan on January 16, 2014, 03:28:36 AM

Also:

DMPU (1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone)
DMI (1,3-Dimethyl-2-imidazolidinone)
NMP (N-Methyl-2-pyrrolidone)

Title: Re: Use of HMPT
Post by: zsinger on January 16, 2014, 12:06:00 PM

Great stuff……I got a 66% Theoretical using DMSO, versus a 79% in the paper referenced with HMPT.  I am going to try it in DMF as well in the next few weeks, and will post how I do.  Thanks for all the great advice guys…….Ive never heard of some of these crazy solvents!  Just goes to show you how much there is to know about O-Chem.