Difference between revisions of "Dimethylformamide"

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| Name = Dimethylformamide
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| Reference =
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| IUPACName = N,N-Dimethylformamide
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| PIN =
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| SystematicName =
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| OtherNames = N,N-Dimethylmethanamide<br>DMF
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| ImageFile = Dimethylformamide bottle and sample.jpg
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| ImageSize = 280
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| ImageCaption = Dimethylformamide sample and bottle
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| SMILES = C[n](C):c:[o]<br>CN(C)C=O
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless liquid
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| BoilingPt =
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| BoilingPtC = 152 to 154
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 0.948 g/mL
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| Formula = C<sub>3</sub>H<sub>7</sub>NO
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| HenryConstant =
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| LogP = −0.829
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| MolarMass = 73.10 g/mol
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| MeltingPt =
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| MeltingPtC = −60.5
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| Odor = None (fresh)<br>Fishy, amoniacal (old)
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| pKa =
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| Solubility = Miscible
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| SolubleOther = Miscible with [[ethanol]], [[toluene]]
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| VaporPressure = 516 Pa
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| Section4 = {{Chembox Thermochemistry
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| DeltaGf =
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| DeltaHc = −1.9428–−1.9404 MJ mol<sup>−1</sup>
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| DeltaHf = −240.6–−238.2 kJ mol<sup>−1</sup>
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| Entropy =
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| HeatCapacity = 146.05 J K<sup>−1</sup> mol<sup>−1</sup>
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| Section5 = {{Chembox Explosive
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| ShockSens = Non-explosive
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| Section6 = {{Chembox Hazards
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| AutoignitionPt = 445 °C
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| ExploLimits = 2.2–15.2%
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| ExternalMSDS = [http://www.sciencelab.com/msds.php?msdsId=9923813 LabChem]
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| FlashPt = 58 °C
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| LD50 = 1.5 g kg−1 (dermal, rabbit)<br>2.8 g kg−1 (oral, rat)<br>3.7 g/kg (mouse, oral)<br>3.5 g/kg (rat, oral)
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| LC50 = 3092 ppm (mouse, 2 hr)
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| MainHazards = Toxic
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| OtherAnions =
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| OtherCompounds = [[Formamide]]
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'''Dimethylformamide''' or '''N,N-dimethylformamide''' is an organic compound with the formula '''(CH<sub>3</sub>)<sub>2</sub>NC(O)H'''.
 
'''Dimethylformamide''' or '''N,N-dimethylformamide''' is an organic compound with the formula '''(CH<sub>3</sub>)<sub>2</sub>NC(O)H'''.
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
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DMF penetrates most types of plastic and causes them to swell.  
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Reaction of dimethylformamide with a strong base like [[sodium hydroxide]] or strong acid like [[hydrochloric acid]], yields [[dimethylamine]] and [[dimethylamine hydrochloride]] respectively:<ref>Thy Labs, ''Making Dimethylamine: A Chemical Used In Big Pharma,'' [https://www.youtube.com/watch?v=D1pvqXeh3TE https://www.youtube.com/watch?v=D1pvqXeh3TE]</ref>
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: (CH<sub>3</sub>)<sub>2</sub>NC(O)H + NaOH → (CH<sub>3</sub>)<sub>2</sub>NH + HCOONa
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: (CH<sub>3</sub>)<sub>2</sub>NC(O)H + HCl → (CH<sub>3</sub>)<sub>2</sub>NH·HCl + HCOOH
 +
 
 +
DMF has a tendency to penetrate many types of plastic and causes them to swell.
  
 
===Physical===
 
===Physical===
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Dimethylformamide is an odorless, colorless liquid, miscible with water and most organic liquids. Technical grade or degraded samples often have a fishy smell due to impurities, such as dimethylamine.
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Dimethylformamide is an odorless, colorless liquid, miscible with water and most organic liquids. Technical grade or degraded samples often have a fishy smell due to impurities, such as dimethylamine, though obtaining completely 100% odorless DMF is extremely difficult due to dimethylamine's strong odor and is not always done.
  
 
==Availability==
 
==Availability==
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==Preparation==
 
==Preparation==
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Dimethylformamide can be synthesized from [[methyl formate]] and dimethylamine or by reaction of dimethylamine with [[carbon monoxide]].
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Dimethylformamide can be synthesized from [[methyl formate]] and [[dimethylamine]] or by reaction of dimethylamine with [[carbon monoxide]].<ref>Weissermel, K.; Arpe, H.-J. (2003). Industrial Organic Chemistry: Important Raw Materials and Intermediates. Wiley-VCH. pp. 45–46</ref> Another route involves carbon dioxide, hydrogen and dimethylamine, in the presence of CuO/ZnO catalyst.<ref>https://www.researchgate.net/publication/45114772_Synthesis_of_dimethylformamide_from_CO2_H2_and_dimethylamine_over_CuZnO</ref>
  
 
==Projects==
 
==Projects==
 
*Acyl halide synthesis
 
*Acyl halide synthesis
 +
*Make cadaverine
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*Make [[dimethylamine]] and dimethylamine hydrochloride
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*Vilsmeier–Haack reaction
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*Storage of [[acetylene]]
  
 
==Handling==
 
==Handling==
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===Storage===
 
===Storage===
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In closed bottles, away from any acidic vapors. DMF will slowly break down to release dimethylamine.
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DMF should be kept in closed bottles, away from any acidic vapors. DMF will slowly break down to release dimethylamine.
  
 
===Disposal===
 
===Disposal===
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[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Organic compounds]]
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[[Category:Carcinogenic]]
 
 
[[Category:Solvents]]
 
[[Category:Solvents]]
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[[Category:Polar solvents]]
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[[Category:Aprotic solvents]]
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[[Category:Amide solvents]]
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[[Category:Carcinogenic]]
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[[Category:Liquids]]

Latest revision as of 13:57, 26 August 2023

Dimethylformamide
Dimethylformamide bottle and sample.jpg
Dimethylformamide sample and bottle
Names
IUPAC name
N,N-Dimethylformamide
Other names
N,N-Dimethylmethanamide
DMF
Identifiers
Jmol-3D images Image
Properties
C3H7NO
Molar mass 73.10 g/mol
Appearance Colorless liquid
Odor None (fresh)
Fishy, amoniacal (old)
Density 0.948 g/mL
Melting point −60.5 °C (−76.9 °F; 212.7 K)
Boiling point 152 to 154 °C (306 to 309 °F; 425 to 427 K)
Miscible
Solubility Miscible with ethanol, toluene
Vapor pressure 516 Pa
Thermochemistry
−240.6–−238.2 kJ mol−1
Hazards
Safety data sheet LabChem
Flash point 58 °C
Lethal dose or concentration (LD, LC):
1.5 g kg−1 (dermal, rabbit)
2.8 g kg−1 (oral, rat)
3.7 g/kg (mouse, oral)
3.5 g/kg (rat, oral)
3092 ppm (mouse, 2 hr)
Related compounds
Related compounds
 Formamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dimethylformamide or N,N-dimethylformamide is an organic compound with the formula (CH3)2NC(O)H.

Properties

Chemical

Reaction of dimethylformamide with a strong base like sodium hydroxide or strong acid like hydrochloric acid, yields dimethylamine and dimethylamine hydrochloride respectively:[1]

(CH3)2NC(O)H + NaOH → (CH3)2NH + HCOONa
(CH3)2NC(O)H + HCl → (CH3)2NH·HCl + HCOOH

DMF has a tendency to penetrate many types of plastic and causes them to swell.

Physical

Dimethylformamide is an odorless, colorless liquid, miscible with water and most organic liquids. Technical grade or degraded samples often have a fishy smell due to impurities, such as dimethylamine, though obtaining completely 100% odorless DMF is extremely difficult due to dimethylamine's strong odor and is not always done.

Availability

DMF is sold by various chemical suppliers.

Preparation

Dimethylformamide can be synthesized from methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide.[2] Another route involves carbon dioxide, hydrogen and dimethylamine, in the presence of CuO/ZnO catalyst.[3]

Projects

  • Acyl halide synthesis
  • Make cadaverine
  • Make dimethylamine and dimethylamine hydrochloride
  • Vilsmeier–Haack reaction
  • Storage of acetylene

Handling

Safety

DMF has been linked to cancer in humans, and it is thought to cause birth defects.

Storage

DMF should be kept in closed bottles, away from any acidic vapors. DMF will slowly break down to release dimethylamine.

Disposal

DMF should be mixed with a more flammable solvent and safely burned.

References

  1. ↑ Thy Labs, Making Dimethylamine: A Chemical Used In Big Pharma, https://www.youtube.com/watch?v=D1pvqXeh3TE
  2. ↑ Weissermel, K.; Arpe, H.-J. (2003). Industrial Organic Chemistry: Important Raw Materials and Intermediates. Wiley-VCH. pp. 45–46
  3. ↑ https://www.researchgate.net/publication/45114772_Synthesis_of_dimethylformamide_from_CO2_H2_and_dimethylamine_over_CuZnO

Relevant Sciencemadness threads

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