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40263

Sigma-Aldrich

N,N-Dimethylformamide di-tert-butyl acetal

technical, ≥90% (GC)

Synonym(s):

1,1-Di-tert-butoxy-N,N-dimethylmethylamine, 1,1-Di-tert-butoxytrimethylamine

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About This Item

Linear Formula:
(CH3)2NCH[OC(CH3)3]2
CAS Number:
36805-97-7
Molecular Weight:
203.32
Beilstein:
969629
EC Number:
253-222-7
MDL number:
MFCD00015002
UNSPSC Code:
12352100
PubChem Substance ID:
329755963
NACRES:
NA.22

grade

technical

Quality Level

100

Assay

≥90% (GC)

form

liquid

refractive index

n20/D 1.413 (lit.)

bp

56-57 °C/8 mmHg (lit.)

density

0.848 g/mL at 25 °C (lit.)

functional group

amine
ether

SMILES string

CN(C)C(OC(C)(C)C)OC(C)(C)C

InChI

1S/C11H25NO2/c1-10(2,3)13-9(12(7)8)14-11(4,5)6/h9H,1-8H3

InChI key

DBNQIOANXZVWIP-UHFFFAOYSA-N

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Application

N,N-Dimethylformamide di-tert-butyl acetal may be used in the synthesis of following:
  • (S)-2-(1-tert-butoxycarbonyl-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}ethylamino)benzoic acid methyl ester
  • 3-O-tert-butylmorphine
  • tert-butylesters of pyrrole- and indolecarboxylic acids

Other Notes

Review; synthesis of tert-butyl esters.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

95.0 °F - closed cup

Flash Point(C)

35 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD4190
BCBW4988
BCBR2521V
BCBL8077V
BCBC0265V

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U. Widmer
Synthesis, 135-135 (1983)
Convenient synthesis of pyrrole-and indolecarboxylic acid tert-butylesters.
Ludwig J and Lehr M.
Synthetic Communications, 34(20), 3691-3695 (2004)
E Mohacsi et al.
Journal of medicinal chemistry, 25(10), 1264-1266 (1982-10-01)
3-O-tert-Butylmorphine (5) was prepared from 6-O-acetylmorphine (3) via alkylation with N,N-dimethylformamide di-tert-butyl acetal, followed by hydrolytic removal of the 3-(dimethylamino)-2-propenoate group. The same process was used to prepare the tert-butyl ether of levorphanol (6), (-)-3-tert-butoxy-N-methylmorphinan (8). Both 5 and 8
William B Mathews et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 46(10), 1719-1726 (2005-10-06)
The goal of this study was to synthesize and evaluate in vivo the peroxisome proliferator-activated receptor-gamma (PPARgamma) agonist (11)C-GW7845 ((S)-2-(1-carboxy-2-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}ethylamino)benzoic acid methyl ester) ((11)C-compound 1). PPARgamma is a member of a family of nuclear receptors that plays a central role
R.F. Abdulla et al.
Tetrahedron, 35, 1675-1675 (1979)

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