> chemistry > composés-halogénés > making-methyl-iodide-nilered

Making Methyl Iodide

NileRed - 2016-06-19

Hey guys, today we make a little bit of methyl iodide (iodomethane) using methanol, red phosphorus and iodine. 

I plan to use this in the future to synthesize caffeine. If you guys have any suggestions on how it can be used, let me know!

Chemplayer video: https://www.youtube.com/watch?v=ZB7YSR3CaUE

Erowid: https://www.erowid.org/archive/rhodium/chemistry/methyliodide.html

Nile talks about lab safety:  https://youtu.be/ftACSEJ6DZA

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Adam Harrington - 2016-06-19

Gonna look pretty suspicious when I order a load of Iodine and red phosphorous.😂

Maxence Hirbec - 2018-05-14

Henry Jiang on ebay.de you can get it for about 16€ 250g

Danielle Spargo - 2018-08-27

Dick Hedd been years since i've heard someone use SWIM. They don't even use it on bluelight these days

And the vid mentioned erowid, reminds me of the good ol' days when i got up to no good lol

BackYard Science 2000 - 2020-05-18

Both elements can be found on etsy.com when they are in stock. The virus has slowed things down a lot lately, so it may not be in stock right now. But they usually aren't out of stock long.

nitrous dude - 2020-11-01

@Lone Dawg believe it or not, it comes up on eBay every once in a while.... they ship it in labeled something appropriate like iron oxide. Alternatively, it can be purchased from India.... but if confiscated, you'd likely be in big trouble.

Zack perron - 2021-08-24

@Bill Smathers by this reaction do you mean the video or making meth

Random Username - 2016-06-19

I have a chemistry exam tomorrow and I'm sitting here watching this... Am I being productive or am I procrastinating

NileRed - 2016-06-19

Both :)

Random Username - 2016-06-19

+Nile Red well, I hope I find something that can help me with my other exams as well then :P, as always great job with your video, you always have something interesting to show everybody

Ignacio Carlevaro - 2016-06-20

Great video, as always. I was wondering if you were going to finish your synthesis of 1-octen-3-ol, cause that compound is really interesting.

NileRed - 2016-06-20

There is a story behind that. I made the acrolein but it polymerized. I am taking a different route to it now. It is a little more interesting.

Ignacio Carlevaro - 2016-06-20

Nice! I'm looking forward to that.

Mitchell G - 2016-06-20

It is always a good day when Nile red uploads a video.

Krisztián Szirtes - 2016-06-20

Just a question, if that filter was gone anyways, couldn't you try and oven-dry it and then burn out the phosphorus? M?ight be a bit extreme but you could end up with a clean funnel :D

Ok Ok - 2020-05-19

Reacting iodine with red phosphorous to make something with the word "meth" in it...seems a bit meta.

Mikey - 2016-06-20

im so keen to see this whole caffeine reaction!!!

Nicholi - 2016-06-22

That was neat. Thanks again. Also, the red phosphorous from match books sounds cool. My vote is for that sooner than later.

Jeffrey Schultz - 2016-07-14

I would love to see an alkylation of an alpha-carbon using NaOH in PTC conditions. Would that be a possibility? Acetophenone could be a possibility substrate with only a single alpha-carbon and a high enough pKa to make normal bases too weak for deprotonation.

Humberto Castro - 2016-07-01

awesome video, can't wait for the caffine synthesis from scratch. may I have your patreon info i would like to support.

xXPyro NinjaXx - 2016-06-23

make an overly complicated siphon pot of coffee like in breaking bad

Stevey Bingoluia - 2016-06-25

Great videos, wondering why use 40g of the red phosphorus when you can calculate to see you only need 5g?

Luis Borja - 2020-04-04

Wonderful video, and actually might be helpful to me for a future synthetic step in my research.

Question: Why such a large excess of red P? Was it intentional or a broad overestimation?

LE-Handmade knives - 2016-06-19

Nile when do you do the video of Kclo3 elektrolysis? Ive been waiting for it a long time.

beneric73 - 2016-06-20

thanks for the video, great job as always, i'll be realy happy if u show how to make some quaternary ammonium cation with this, like tetramethylamine or another more interesting quaternary ammonium cation.

NileRed - 2016-06-21

Do you have a use for tetramethylamine?

beneric73 - 2016-06-21

+Nile Red nop, but I read some article on the quaternisation of amonium cation but i'm curious to see how to proceed to achive the réaction.

Nitro - 2016-06-28

A menthol synthesis would be pretty darn cool

Chain Smoker - 2016-06-17

Great video as always! Mercury distillation? Sounds like fun! ;)

ficolas2 - 2016-06-19

Scary as fuck

Steve S - 2018-01-12

Another great video.
I have a question regarding safety.
It is hard to tell from your video but do you use a fume hood or just a well-ventilated area?
Do you take any extra precautions for this substance than you would for most other organics you make?

I am hoping to make some methyl (or ethyl) iodide for a Grignard reaction to make tertiary alcohols from ketones. However reading around about the toxicity it seems like these compounds are nasty ("highly toxic dimethyl mercury can be produced if allowed to contact mercury amalgam" for example). I do wonder if some of these fears are a little overblown but regardless, I don't have access to a fume hood so was hoping to limit my risk by conducting outside and making it on the fly for use in the Grignard. Do you have any thoughts on this?
Sorry its a little wordy but would appreciate your feedback on this :)

2aDDict3d - 2016-06-21

1:50 it said you added red phosporus instead of iodine. Great video though!

Juan Camilo Zschommler - 2017-01-23

+ NileRed
Can you please make a Video how you make this structure formula?

Dönci Terényi - 2016-06-23

You could try to create an organic superconductor, I mean you probably couldn't get the pressure or temperature required to activate them but it would still be cool

2MC - 2020-07-14

To clean red phosphorous from your funnel, just add some dissolved iodine(in alkanes/alcohols/ethers/toluene/acetone/etc). Good as new :)

Ben Brockert - 2016-12-26

Can you convert phosphoric acid into elemental phosphorous? A video turning a few liters of Coke into a few grams of red phosphorous would be interesting.

Pietro Tettamanti - 2017-08-14

1) in coke there is really few phosphoric acid. Maybe 300ppm. By extracting it from coke you would use at least 20L of it to recover 5 ml of phosphoric acid. It would be better extracting phosphate from fertilizers or bones.
2) to reduce the phosphate back to phosphorus you need to use SiO2, elemental carbon and obviously the phosphate. This seems easy, the only problem is that the reaction needs to run at 1500°C.

Matt Gipson - 2016-06-20

when you add iodine for the first time your label says red phosphorus. you might want to throw an annotation over that for ppl who don't listen lol

NileRed - 2016-06-20

I did change it! I wish i noticed it before uploading it though :(

Matt Gipson - 2016-06-20

It happens

Honhei Lee - 2016-06-21

You should keep it in a brown container and then seal it with parafilm.

Alex - 2017-07-06

Yeah dude I'm totally making methyl iodide, what else would I be making?

Dane Zurwell - 2016-06-20

-That appears to be quite the ambitious synthesis pathway :D I have a 1,3,7-trimethylxanthine tattoo on my right shoulder and look very much forward to seeing your progress, fellow chemist!

Casey Crungle - 2016-06-19

you put the caption of red phosphorus instead of 83,3g iodine

NileRed - 2016-06-19

ughhhhhhh

Sand - 2016-06-20

+Nile Red hhhhhhhgu

Charlie Mallindine - 2016-06-30

+Nile Red uurrrrrrrrhhhh

tj hooker - 2017-10-11

STOP dropping in your stirbars!!!! The first time you break the bottom of an expensive multi-neck reaction vessel is not the time to learn this. Turn the flask sideways, place the stirbar in the neck, and right the flask. Now begin adding reagents.

Joey VX - 2016-09-08

Use your phosphorus tribromide or just bromine to clean the funnel!

Libor Tinka - 2019-02-03

Maybe you could clean the sinter with nitric acid (it should react with P to form now water-soluble phosphoric acid).
Another idea is using hot ethanol as P is slightly soluble in it.
But it might not work for physical reasons - polymerized material stuck in fine glass might not react adequately.

Lewis Ho - 2020-02-14

Use the CH3I for synthesis of iodine containing stuff?

Zenix Fire - 2017-11-15

Can this be used to form CH3+ and I- in solution?

Charles Kogan - 2017-06-29

that's a very cute powder at the end 😊😊😊

Blackline - 2016-06-27

If I'm not wrong, with I-Me you can't obtain a secondary amine. I mean, it's a very fast reaction, you will have a pretty precipitate, as a quaternary amine salt... If you want to make a secondary amine you need to use Formol with NaBH3CN or for a primary : use the Gabriel Technic, you see ? So @0:26 I think this is not accurate :p let's discuss about it

rollaroundaparty - 2016-06-20

Any chance of Sodium Azide or Nitroguanidine?
Airbag special :D

Nivedita Priyadarshini - 2016-06-20

hey nile ,
can you pls let us know how to work with a Roto-Evapourators !!!

xWood4000 - 2016-06-20

Could you extract theobrymine if it's possible with your tools?

Cooking With Cows - 2016-06-20

Is there a reason why you used 8-9x as much red phosphorus as you need? I mean if you can recover it, fine, but if you know that the reaction will only consume like 5 grams, then maybe you add 10 grams to have plenty excess, but not 42 grams :P

Ali Mansor - 2020-09-22

Because the reaction is happening on surface of Red-P . So it will speed 9-8x

RadicalFive - 2016-06-23

Could you do a synthesis of nitrogen triiodide?

ALEJANDRO - 2016-06-20

hello nile red
show us how to make the materials of the nickel iron batery!

That's all that needed to be sustainable and cheap energy!

best regards

Ernesto Millan - 2016-06-19

So how come you used phosphorous in that much of an excess?

Mohamed El-Haseen - 2019-11-22

thnx much .. can you make a video to methylation imidazole by methyl iodide to produce 1-methyl imidazole

Tyler Fu - 2020-03-06

Methyl Iodide is also used in geology for separating minerals.

Youtubecomenter365 - 2016-06-20

Extract malic from apples please!!!

Tobias _ - 2017-06-04

NileRed can methyl iodide be used to make dimethyl mercury?

cameron Gibbs - 2016-07-07

would there be a by product of hydrodic acid ?

Jon Durak - 2017-08-26

Get a stainless filtering setup and use 1 micron paper

meganie - 2016-06-20

You have to mention that Methyl Iodide is a very strong carcinogen and you have to wear a respirator or work in a fume hood. A well ventilated area is definitely not enough!

Adam Montoya - 2019-04-09

meganie8 I personally love alkylating my DNA. How else are we supposed to get super powers?

Kevin Byrne - 2016-06-20

Synthesizing caffeine from maleic acid? Wow! You've become Very ambitious.