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261483

Sigma-Aldrich

N,N-Dimethylacetamide dimethyl acetal

90%

Synonym(s):

1,1-Dimethoxy-N,N-dimethylethylamine

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About This Item

Linear Formula:
CH3C(OCH3)2N(CH3)2
CAS Number:
18871-66-4
Molecular Weight:
133.19
Beilstein:
1420865
MDL number:
MFCD00008476
UNSPSC Code:
12352100
PubChem Substance ID:
24855813
NACRES:
NA.22

Assay

90%

form

liquid

refractive index

n20/D 1.411 (lit.)

bp

118 °C (lit.)

density

0.911 g/mL at 25 °C (lit.)

SMILES string

COC(C)(OC)N(C)C

InChI

1S/C6H15NO2/c1-6(8-4,9-5)7(2)3/h1-5H3

InChI key

FBZVZUSVGKOWHG-UHFFFAOYSA-N

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General description

Claisen type reaction of N,N-dimethylacetamide dimethyl acetal using optically active trans-3-penten-2-ol as substrate has been investigated.

Application

N,N-Dimethylacetamide dimethyl acetal has been used as:
  • one carbon inserting synthon in preparation of pyrimido[1,2-a][1,3,5]triazin-6-ones
  • reagent for the synthesis of amides, diacylamines and heterocycles

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 2 - STOT SE 3

Target Organs

Eyes,Central nervous system, Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

46.4 °F - closed cup

Flash Point(C)

8 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The Journal of Organic Chemistry, 57, 7133-7133 (1992)
Nikhil Sachdeva et al.
Organic & biomolecular chemistry, 10(23), 4586-4596 (2012-05-15)
A novel thermal rearrangement, involving pyrimidine ring opening and subsequent ring closure leading to recyclization of the system, was identified in the reaction of (6-oxo-1,6-dihydropyrimidin-2-yl)guanidines 3 (where NR(1)R(2) = NH(2), NH alkyl, NH aralkyl, NHCH(2)Ph(R)) with triethyl orthoacetate, affording 4-substituted-2-methyl-6H-pyrimido[1,2-a][1,3,5]triazin-6-ones
Tetrahedron Letters, 33, 3449-3449 (1992)
Asymmetric induction in the thermal reactions of allylic alcohols with N, N-dimethylacetamide dimethylacetal and triethyl orthoacetate.
Hill RK, et al.
The Journal of Organic Chemistry, 37(23), 3737-3740 (1972)
Tetrahedron, 48, 5227-5227 (1992)
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