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Merck

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
UNSPSC Code:
12352111
NACRES:
NA.21
PubChem Substance ID:
57647999
EC Number:
200-679-5
Beilstein/REAXYS Number:
605365
MDL number:
MFCD00003284
Assay:
99.8%
Form:
liquid

Key Documents

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grade

anhydrous

Quality Level

300

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%

pH

7 (20 °C, 200 g/L)

bp

153 °C (lit.)

mp

−61 °C (lit.)

density

0.944 g/mL (lit.)

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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

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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

flash_point_f

135.5 °F - closed cup

flash_point_c

57.5 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Class I Designated Chemical Substances

prtr

Group 4: Flammable liquids + Type 2 petroleums + Hazardous rank III + Water soluble liquid

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

227056-12X100ML:4548173119687 + 227056-ND-200LP1SB: + 227056-8L: + 227056-AW-20L-N2: + 227056-2L:4548173119724 + 227056-20L: + 227056-20L-N2: + 227056-PZ: + 227056-18L:4548173119694 + 227056-6X1L:4548173119748 + 227056-AW-200LP1SB: + 227056-200L:4548173119717 + 227056-4X2L:4548173119731 + 227056-BULK: + 227056-1L:4548173119700 + 227056-VAR: + 227056-100ML:4548173119670 + 227056-AW-50L-RC: + 227056-250ML:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT6189
SHBT4953
SHBT2977
SHBT2262
SHBT1561

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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
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)
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)
W P Inskeep et al.
Plant physiology, 77(2), 483-485 (1985-02-01)
We found inconsistencies in the commonly used data for chlorophyll analysis in 80% acetone. Recently developed extinction coefficients for chlorophyll b in N,N-dimethylformamide (DMF) based on values from 80% acetone are low as a result of these inconsistencies. We determined
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