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227056

N,N-Dimethylformamide

Name: <I>N,N</I>-Dimethylformamide
Brand: SIAL

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

eCl@ss:

39031202

Assay:

99.8%

Form:

liquid

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Properties

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

Description

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

Solvent for many hydrophobic organic compounds.

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.

Packaging

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Legal Information

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

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pictograms

GHS02,GHS08,GHS07

signalword

Danger

hcodes

H226,H312 + H332,H319,H360D

pcodes

P210 - P280 - P303 + P361 + P353 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313

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.

68-12-2

CAS No.

svhc

68-12-2

CAS No.

rmu

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Articles

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.

A chemically labeled cytotoxic agent: two-photon fluorophore for optical tracking of cellular pathway in chemotherapy.

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

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)

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Global Trade Item Number

SKU	GTIN
227056-1L	04061837531460
227056-4X2L	04061837531484
227056-ND-200LP1SB	04065267932040
227056-100ML	04061837531446
227056-12X100ML	04061837531453
227056-18L	04061838252593
227056-200L	04061838161215
227056-250ML	04061837531477
227056-2L	04061838780546
227056-6X1L	04061837531491
227056-AW-200LP1SB	04065267932033
227056-PZ	04061823900379

Key Documents

N,N-Dimethylformamide

anhydrous, 99.8%

Select a Size

About This Item

grade

Quality Level

vapor density

vapor pressure

assay

form

autoignition temp.

expl. lim.

impurities

evapn. residue

refractive index

pH

bp

mp

density

SMILES string

InChI

InChI key

General description

Application

Packaging

Legal Information

Still not finding the right product?

Safety Information

pictograms

signalword

hcodes

pcodes

Hazard Classifications

Storage Class

flash_point_f

flash_point_c

ppe

Regulatory Listings

68-12-2

68-12-2

Documentation

Certificates of Analysis (COA)

Already Own This Product?

Protocols and Articles

Articles

Peer Reviewed Papers

Global Trade Item Number