[bis(tert-butoxy)methyl]dimethylamine

• ChemBase ID: 137350
• Molecular Formular: C11H25NO2
• Molecular Mass: 203.3217
• Monoisotopic Mass: 203.18852905
• SMILES: CC(C)(C)OC(N(C)C)OC(C)(C)C
• Canonical SMILES: CN(C(OC(C)(C)C)OC(C)(C)C)C
• InChI: InChI=1S/C11H25NO2/c1-10(2,3)13-9(12(7)8)14-11(4,5)6/h9H,1-8H3
• InChIKey: DBNQIOANXZVWIP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [bis(tert-butoxy)methyl]dimethylamine
• IUPAC Traditional name: [bis(tert-butoxy)methyl]dimethylamine
• Synonyms: 1,1-Di-tert-butoxy-N,N-dimethylmethylamine; 1,1-Di-tert-butoxytrimethylamine; N,N-Dimethylformamide di-tert-butyl acetal; N,N-二甲基甲酰胺二叔丁基乙缩醛; 1,1-二叔丁氧基三甲胺; 1,1-双-叔-丁氧基-N,N-二甲基甲胺; N,N-二甲基甲酰胺二叔丁基缩醛

Database IDs

• CAS Number: 36805-97-7
• EC Number: 253-222-7
• MDL Number: MFCD00015002
• Beilstein Number: 969629
• PubChem SID: 162231613; 24865104; 24864634; 24862028
• PubChem CID: 547712

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.8162808
• LogD (pH = 7.4): 2.9155564
• Log P: 2.916981
• Molar Refractivity: 59.9252 cm^3
• Polarizability: 23.900274 Å^3
• Polar Surface Area: 21.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 56-57 °C/8 mmHg(lit.); 75-77°C/12mm
• Flash Point: 33°C(91°F); 35 °C; 95 °F
• Density: 0.848 g/mL at 25 °C(lit.); 0.850
• Refractive Index: 1.4110; n20/D 1.413(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38; 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥90%; ≥90% (GC); tech. 90%
• Grade: for GC derivatization; technical; technical grade
• Linear Formula: (CH3)2NCH[OC(CH3)3]2

DETAILS

Sigma Aldrich - 358800

Packaging
1, 10 mL in glass bottle

Sigma Aldrich - 395005

Application
Reagent used for the preparation of indolizines via intermolecular cyclization of picolinium salts.1
Packaging
10×1, 5, 25 mL in ampule

Sigma Aldrich - 40263

Other Notes
Review;1 synthesis of tert-butyl esters.2
Packaging
10, 50 mL in glass bottle

REFERENCES

• The conversion of carboxylic acids to their esters using DMF acetals (see for example, N,N-Dimethylformamide dimethyl acetal, A15350) can be extended to the preparation of t-butyl esters by using excess reagent in benzene or toluene as solvent: Synthesis, 135 (1983).