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140732

N,N-Dimethylformamide dimethyl acetal

technical grade, 94%

Synonym(s):

1,1-Dimethoxy-N,N-dimethylmethylamine, 1,1-Dimethoxytrimethylamine

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25 ML

$64.70

100 ML

$135.00

500 ML

$315.00

2.5 L

$1,430.00

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About This Item

Linear Formula:
(CH3)2NCH(OCH3)2
CAS Number:
Molecular Weight:
119.16
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
EC Number:
225-063-3
Beilstein/REAXYS Number:
506020
MDL number:
Assay:
94%
Form:
liquid

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InChI key

ZSXGLVDWWRXATF-UHFFFAOYSA-N

InChI

1S/C5H13NO2/c1-6(2)5(7-3)8-4/h5H,1-4H3

SMILES string

COC(OC)N(C)C

grade

technical grade

assay

94%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

Quality Level

refractive index

n20/D 1.396 (lit.)

bp

102-103 °C/720 mmHg (lit.)

density

0.897 g/mL at 25 °C (lit.)

functional group

amine, ether

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1 of 4

This Item
14277817853540252
assay

94%

assay

95%

assay

95%

assay

≥95.0% (GC)

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

-

reaction suitability

-

reaction suitability

-

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

bp

102-103 °C/720 mmHg (lit.)

bp

130-133 °C (lit.)

bp

79-80 °C/60 mmHg (lit.)

bp

130-133 °C (lit.)

density

0.897 g/mL at 25 °C (lit.)

density

0.859 g/mL at 25 °C (lit.)

density

0.838 g/mL at 25 °C (lit.)

density

0.859 g/mL at 25 °C (lit.)

refractive index

n20/D 1.396 (lit.)

refractive index

n20/D 1.400 (lit.)

refractive index

n20/D 1.401 (lit.)

refractive index

n20/D 1.397-1.401, n20/D 1.400 (lit.)

Application

N,N-Dimethylformamide dimethyl acetal (DMF-DMA) can be used as: 
  • An organocatalyst for the synthesis of 1,2-disubstituted-3,4-dihydronaphthalenes by the reaction of vinylarenes and electron-deficient alkynes.[1]       
  • A building block for the preparation of heterocyclic compounds such as enamines and amidines via formylation of methylene and amino groups.[2]       
  • A reagent in the synthesis of 1,4-diaryl-piperazine-2,5-diones by reacting with chloroacetamides.[3]        
  • A reagent along with enamine and alkyne for the preparation of 2,3,4,5-tetrasubstituted pyridine derivatives by three-component coupling reaction in the presence of Me3SiCl.[4]

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Eye Dam. 1 - Flam. Liq. 2 - Skin Sens. 1

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

42.8 °F

flash_point_c

6 °C

ppe

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


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A highly efficient cycloaddition of vinylarenes with electron-deficient alkynes affording 1, 2-disubstituted-3, 4-dihydronaphthalenes catalysed by N, N-dimethylformamide dimethyl acetal
Jiang J-L, et al.
Organic & Biomolecular Chemistry, 5(12), 1854-1857 (2007)
Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis
Abu-Shanab FA, et al.
Journal of Heterocyclic Chemistry, 46(5), 801-827 (2009)
Synthesis of 1, 4-Diaryl-piperazine-2, 5-diones: New Behavior of N, N-Dimethylformamide Dimethyl Acetal (DMFDMA)
Abu-Shanab FA, et al.
Synthetic Communications, 38(3), 376-382 (2008)
Wim Schepens et al.
Organic letters, 8(19), 4247-4250 (2006-09-08)
A novel series of analogues of calcitriol (1) is developed featuring a spirocyclic central core resulting from C18/C21-connection and C15/C16-deletion (2a, 2b). The synthesis of the key intermediate involves an Eschenmoser rearrangement of an enantiomerically pure bromo-substituted cyclohexenol.
C Rodier et al.
Chirality, 14(6), 527-532 (2002-07-12)
Two different methods of derivatization were studied in order to select and optimize one for the in situ enantiomeric separation of amino acids present in Martian samples. The method, using DMF-DMA [N,N-dimethylformamide dimethyl acetal], is simple and easily automated. However

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    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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