CAS 62637-93-8|TRIMETHYLAMINE-N-OXIDE DIHYDRATE|trimethylamine-n-oxide dihydrate|N,N-dimethylmethanamine oxide dihydrate|N,N-Dimethylmethanamine oxide, Dihydrate|Trimethylamine N-oxide dihydrate|TMA...

General Information

Structure

Molecular Formula

C₃H₁₃NO₃

Molecular Mass

111.14022

Exact Mass

111.08954328

Charge

InChI

InChI=1S/C3H9NO.2H2O/c1-4(2,3)5;;/h1-3H3;2*1H2

InChIKey

PGFPZGKEDZGJQZ-UHFFFAOYSA-N

Canonic Smiles

[O-][N+](C)(C)C.O.O

Isomeric Smiles

O.O.C[N+](C)(C)[O-]

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.9441224

LogD (pH = 7.4)

-0.93434685

Log P

-0.9342057

Molar Refractivity

22.033

Polarizability

7.9283214

Polar Surface Area

23.06

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

TRIMETHYLAMINE-N-OXIDE DIHYDRATEN,N-Dimethylmethanamine oxide, DihydrateTrimethylamine N-oxide dihydrateTMANO三甲胺N-氧化物二水合物三甲基N氧化二水合物

IUPAC Traditional name

trimethylamine-n-oxide dihydrate

IUPAC name

N,N-dimethylmethanamine oxide dihydrate

Names and Identifiers

Registration numbers

CAS Number

62637-93-8

PubChem SID

2489989316209170024889631

EC Number

Beilstein Number

MDL Number

PubChem CID

Merck Index

Registration numbers

Properties

Safety Information

Download link

YH2850000

Room Temperature (15-30°C)

Physical Property

97-100°C

95-99 °C(lit.)

95-99 °C

96-101°C

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02157068

Dihydrate

Sigma Aldrich

T0514

包装
100 g in glass bottle
Application
Reactant for:
• C-H bond cleavage1
• Oxidation reactions (oxidant)2,3
• Decarbonylating agent for solvent-free reactions4

176869

Application
Reactant for:
• C-H bond cleavage1
• Oxidation reactions (oxidant)2,3
• Decarbonylating agent for solvent-free reactions4

92277

Other Notes
Oxidant for the catalytic OsO4 cis-hydroxylation of hindered olefins5; preparation of the unstable, crystalline anhydrous compound6
Application
Reactant for:
• C-H bond cleavage1
• Oxidation reactions (oxidant)2,3
• Decarbonylating agent for solvent-free reactions4

Molecule Details

References

PubChem Literature

From Data Sources

• Compare also 4-Methylmorpholine N-oxide monohydrate, A15996.

• Reviews: Trimethylamine as a useful oxidizing agent: J. Prakt. Chem./ Chem. Ztg., 338, 190 (1996); The utility of N-oxides in synthesis: Synthesis, 263 (1993).

• Has been used in the oxidation of alkyl halides to aldehydes. For a procedure, including dehydration of the N-oxide by distillation of water with DMF, see: Org. Synth. Coll., 5, 872 (1973):

• For an improved procedure using DMSO, see: Tetrahedron Lett., 31, 4825 (1990).

• For use as a reoxidant in the catalytic cis-hydroxylation of alkenes with Osmium(VIII) oxide, 12103, see: Tetrahedron Lett., 21, 449 (1980).

• Also oxidizes alkylboranes to alcohols, giving less interference with other functionality than the more usual H₂O₂: J. Org. Chem., 40, 1776 (1975).

• Reagent for the liberation of organics from their complexes with iron carbonyls. Partial oxidation of CO to CO₂ takes place: J. Chem. Soc., Chem. Commun., 336 (1974).

• Deprotonation by LDA at low temperature gives the unstable azomethine ylide, which undergoes 1,3-dipolar addition, even with unactivated alkenes, to give pyrrolidines: J. Chem. Soc., Chem. Commun., 31 (1983):

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Commercial Catalog

Academic Data

Names and Identifiers

Synonyms

TRIMETHYLAMINE-N-OXIDE DIHYDRATEN,N-Dimethylmethanamine oxide, DihydrateTrimethylamine N-oxide dihydrateTMANO三甲胺N-氧化物二水合物三甲基N氧化二水合物

IUPAC Traditional name

trimethylamine-n-oxide dihydrate

IUPAC name

N,N-dimethylmethanamine oxide dihydrate

Registration numbers

CAS Number

62637-93-8

PubChem SID

2489989316209170024889631

EC Number

Beilstein Number

MDL Number

PubChem CID

Merck Index

Molecule Details

Dihydrate

T0514

包装
100 g in glass bottle
Application
Reactant for:
• C-H bond cleavage1
• Oxidation reactions (oxidant)2,3
• Decarbonylating agent for solvent-free reactions4

176869

Application
Reactant for:
• C-H bond cleavage1
• Oxidation reactions (oxidant)2,3
• Decarbonylating agent for solvent-free reactions4

92277

References

PubChem Literature

From Data Sources

• Compare also 4-Methylmorpholine N-oxide monohydrate, A15996.

• Reviews: Trimethylamine as a useful oxidizing agent: J. Prakt. Chem./ Chem. Ztg., 338, 190 (1996); The utility of N-oxides in synthesis: Synthesis, 263 (1993).

• Has been used in the oxidation of alkyl halides to aldehydes. For a procedure, including dehydration of the N-oxide by distillation of water with DMF, see: Org. Synth. Coll., 5, 872 (1973):

• For an improved procedure using DMSO, see: Tetrahedron Lett., 31, 4825 (1990).

• For use as a reoxidant in the catalytic cis-hydroxylation of alkenes with Osmium(VIII) oxide, 12103, see: Tetrahedron Lett., 21, 449 (1980).

• Also oxidizes alkylboranes to alcohols, giving less interference with other functionality than the more usual H₂O₂: J. Org. Chem., 40, 1776 (1975).

• Reagent for the liberation of organics from their complexes with iron carbonyls. Partial oxidation of CO to CO₂ takes place: J. Chem. Soc., Chem. Commun., 336 (1974).

Bioactivity

PubChem BioAssay

Properties

Safety Information

Download link

YH2850000

Room Temperature (15-30°C)

Physical Property

97-100°C

95-99 °C(lit.)

95-99 °C

96-101°C

Molecule

ID:104753