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Merck
CN

227056

N,N-Dimethylformamide

anhydrous, 99.8%

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
Beilstein:
605365
EC Number:
200-679-5
MDL number:
MFCD00003284
UNSPSC Code:
12352111
PubChem Substance ID:
57647999
NACRES:
NA.21

Key Documents

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grade

anhydrous

Quality Level

300

vapor density

2.5 (vs air)

vapor pressure

2.7 mmHg ( 20 °C)

Assay

99.8%

form

liquid

autoignition temp.

833 °F

expl. lim.

15.2 %

impurities

<0.005% water

evapn. residue

<0.0005%

refractive index

n20/D 1.430 (lit.)

pH

7 (20 °C, 200 g/L)

bp

153 °C (lit.)

mp

−61 °C (lit.)

density

0.944 g/mL (lit.)

SMILES string

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

InChI

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

InChI key

ZMXDDKWLCZADIW-UHFFFAOYSA-N

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General description

N,N-Dimethylformamide (DMF) is the commonly employed solvent for chemical reactions. DMF is a useful solvent employed for the isolation of chlorophyll from plant tissues. It is widely employed reagent in organic synthesis. It plays multiple roles in various reactions such as solvent, dehydrating agent, reducing agent as well as catalyst. It is a multipurpose building block for the synthesis of compounds containing O, -CO, -NMe2, -CONMe2, -Me, -CHO as functional groups.
N,N-Dimethylformamide is a polar solvent commonly used in organic synthesis. It also acts as a multipurpose precursor for formylation, amination, aminocarbonylation, amidation and cyanation reactions.

Application

N,N-Dimethylformamide (anhydrous) has been used as solvent for the synthesis of cytotoxic luteinizing hormone-releasing hormone (LH-RH) conjugate AN-152 (a chemotherapeutic drug) and fluorophore C625 [4-(N,N-diphenylamino)-4′-(6-O-hemiglutarate)hexylsulfinyl stilbene]. It may be employed as solvent medium for the various organic reduction reactions.
DMF has been used as a solvent in the following processes:
  • Multi-step synthesis of L-azidohomoalanine (L-Aha) during the substitution of the mesylate by sodium azide.
  • Synthesis of phosphine-FLAG®, a detection reagent for metabolic labeling of glycans.
  • Synthesis of per-O-acetylated 6-azidofucose, a per-O-acetylated azido sugar.
Solvent for many hydrophobic organic compounds.

Packaging

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Legal Information

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

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

135.5 °F - closed cup

Flash Point(C)

57.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBT2977
SHBT2262
SHBT1561
SHBT1109
SHBS9116

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A concise and scalable route to L-azidohomoalanine.
Roth S, et al.
Nature Protocols, 5(2), 1967-1973 (2010)
Reference electrode for anhydrous dimethylformamide.
Marple LW.
Analytical Chemistry, 39(7), 844-846 (1967)
X Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(20), 11081-11084 (1999-09-29)
Chemotherapy is commonly used in the treatment of cancers. However, the mechanism of action of many of these agents is not well understood. We present the synthesis of a two-photon fluorophore (C625) and its biological application when chemically linked to
Metabolic labeling of glycans with azido sugars and subsequent glycan-profiling and visualization via Staudinger ligation.
Laughlin ST and Bertozzi CR.
Nature Protocols, 2(11), 2930-2944 (2007)
Peter H Huy et al.
Chemical science, 10(31), 7399-7406 (2019-09-07)
A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts
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Solvent Miscibility Table

Substances are said to be miscible in one another if they dissolve to form a uniform solution. Bookmark or download our miscibility table for common lab solvents.

溶剂混溶性表

如果物质相互溶解形成均匀的溶液，就可以说它们相互混溶。收藏或下载我们的常见实验室溶剂混溶性表。

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