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D158550

N,N-Dimethylformamide

ReagentPlus®, ≥99%

Synonym(s):

DMF, NSC 5356

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About This Item

Linear Formula:
HCON(CH3)2
CAS Number:
68-12-2
Molecular Weight:
73.09
UNSPSC Code:
12352111
NACRES:
NA.21
PubChem Substance ID:
329798705
EC Number:
200-679-5
Beilstein/REAXYS Number:
605365
MDL number:
MFCD00003284
Assay:
≥99%
Bp:
153 °C (lit.)
Vapor pressure:
2.7 mmHg ( 20 °C)

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Product Name

N,N-Dimethylformamide, ReagentPlus®, ≥99%

InChI key

ZMXDDKWLCZADIW-UHFFFAOYSA-N

InChI

1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3

SMILES string

[H]C(=O)N(C)C

vapor density

2.5 (vs air)

vapor pressure

2.7 mmHg ( 20 °C)

product line

ReagentPlus®

assay

≥99%

form

liquid

autoignition temp.

833 °F

expl. lim.

15.2 %

dilution

(for general lab use)

impurities

≤0.1% Water (Karl Fischer)

refractive index

n20/D 1.430 (lit.)

pH

6.7

bp

153 °C (lit.)

mp

−61 °C (lit.)

density

0.944 g/mL (lit.)

Quality Level

100

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1 of 4

This Item
3312031993772438
N,N-Dimethylformamide ReagentPlus®, ≥99%

Sigma-Aldrich

D158550

N,N-Dimethylformamide

N,N-Dimethylformamide puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.8% (GC)

Sigma-Aldrich

33120

N,N-Dimethylformamide

N,N-Dimethylformamide ACS reagent, ≥99.8%

Sigma-Aldrich

319937

N,N-Dimethylformamide

N,N-Dimethylformamide analytical standard

Supelco

72438

N,N-Dimethylformamide

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

assay

≥99%

assay

≥99.8% (GC)

assay

≥99.8%

assay

≥99.9% (GC)

form

liquid

form

liquid

form

liquid

form

-

pH

6.7

pH

7 (20 °C, 200 g/L)

pH

7 (20 °C, 200 g/L)

pH

-

refractive index

n20/D 1.430 (lit.)

refractive index

n20/D 1.4290-1.4310, n20/D 1.430 (lit.)

refractive index

n20/D 1.430 (lit.)

refractive index

n20/D 1.430 (lit.)

expl. lim.

15.2 %

expl. lim.

15.2 %

expl. lim.

15.2 %

expl. lim.

15.2 %

Application

N,N-Dimethylformamide has been used in the to prepare pure polyurethane as well as nanocomposite solutions.
It may be used in the following processes:
  • Synthesis of gold nanoparticles.[1]
  • Capillary electrophoresis.[2]
  • Regioselective synthesis of N,N-dimethylaminopyridzines.[3]
  • Synthesis of urea-N,N-dimethylformamide, a 3:1 solvate with urea.[4]
Solvent for many hydrophobic organic compounds.

General description

N,N-Dimethylformamide (DMF) is a polar organic solvent with a wide range of industrial applications.[5] It is a precursor for numerous reactions such as formylation, aminocarbonylation, amination, amidation and cyanation.[6] Along with phosphorus oxychloride, it forms Vilsmeier reagent used in the formylation of reactive aromatic and heteroaromatic substrates.[7] Dielectric relaxation experiments on DMF have been conducted between 238.15 K and 338.15K.[8] The thermophysical properties of the molecular interactions between DMF and the ionic liquids, ammonium salts and imidazolium salts have been studied.[9] The characteristics of solute-solvent interactions between ammonium nitrate and DMF have been investigated.[10]

Other Notes

A Greener alternative is available for many DMF applications, Cyrene (807796)

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 1B

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

135.5 °F - closed cup

flash_point_c

57.5 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT4464
SHBT2518
SHBT1772
0000468540
0000468540

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Urea-N,N-dimethylformamide (3/1).
Fernandes P, et al.
Acta Crystallographica Section E, Structure Reports Online, 63(12), 4861-4861 (2007)
Capillary electrophoresis in N,N-dimethylformamide.
Porras SP and Kenndler E.
Electrophoresis, 26(17), 3279-3291 (2005)
N,N-dimethylformamide as a reaction medium for metal nanoparticle synthesis.
Pastoriza-Santos I and Liz-Marzan LM.
Advances in Functional Materials, 19(5), 679-688 (2009)
Reaction of chloropyridazines with N,N -dimethylformamide.
Lee WS, et al.
Journal of Heterocyclic Chemistry, 37(6), 1591-1591 (2000)
N,N-Dimethylformamide: much more than a solvent.
Muzart J.
Tetrahedron, 65(40), 8313-8323 (2009)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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