62637-93-8

Basic information

• Product Name: Trimethylamine N-oxide dihydrate
• Synonyms: methanamineoxide,n,n-dimethyl,dihydrate;n,n-dimethylmethanamineoxide,dihydrate;trimethylammoniumoxidhydrat;TMO;TRIMETHYLAMINE N-OXIDE DIHYDRATE;TRIMETHYLAMINE OXIDE DIHYDRATE;TMANO ;TrimethylamineN-oxidedihydrate,98%
• CAS NO: 62637-93-8
• Molecular Formula: C₃H₉NO*2H₂O
• Molecular Weight: 111.14
• EINECS: 214-675-6
• Product Categories: Oxidation;Synthetic Organic Chemistry;Amines;Catalyst
• Mol File: 62637-93-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 95-99 °C(lit.)
• Flash Point: 95 °C
• Appearance: White to off-white/Fine Crystalline Powder
• Density: 1.157 g/cm3
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Sparingly)
• Water Solubility: Soluble in water, ethanol, dimethyl sulfoxide and methanol. Sparingly soluble in hot chloroform. Insoluble in diethyl ether, ben
• Merck: 14,9711
• BRN: 3612927
• CAS DataBase Reference: Trimethylamine N-oxide dihydrate(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethylamine N-oxide dihydrate(62637-93-8)
• EPA Substance Registry System: Trimethylamine N-oxide dihydrate(62637-93-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: YH2850000
• F: 4.10
• TSCA: Yes
• Hazardous Substances Data: 62637-93-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 62637-93-8 differently. You can refer to the following data:
1. Trimethylamine N-Oxide Dihydrate is as an oxygen transfer agent used to promote heterometallic cluster catalyzing coordinative hydrogenation. Trimethylamine N-Oxide Dihydrate is also used as a catalyst in the preparation of thermally stable TiO2 nanorod incorporated polymers and semiconductor/metal nanocomposites.
2. Oxidizing reagent in organic synthesis.
3. Trimethylamine N-oxide dihydrate is used as an oxidizing agent in organic synthesis. It is also used to make quaternary ammonium compounds and a warning agent for flammable gas. Further, it acts as a flavoring agent or adjuvant. It serves as an oxidant for the catalytic osmium tetraoxide cis-hydroxylation of hindered olefins. In addition to this, it is used as a reactant for C-H bond cleavage and decarbonylating agent for solvent-free reactions.

General Description

Trimethylamine N-oxide (TMAO) is an amphiphilic osmolyte that can counteract the denaturing effects of urea, pressure, and ice and stabilize the proteins.

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

Synthetic route

dimanganese decacarbonyl (10170-69-1) + trimethylamine-N-oxide dihydrate (62637-93-8) + toluene (108-88-3) → {{Mn(μ3-OH)(CO)3}4}*2toluene

Conditions	Yield
In tetrahydrofuran; toluene stirring Mn2(CO)10 with Me3NO*2H2O in THF (18 h), solvent removal; recrystn. (hot toluene);	100%
In toluene byproducts: trimethylammonium carbonate; treatment of Mn2(CO)10 with 6 equivs. of Me3NO, boiling of product in MePh; hot filtration, crystn. (5°C); second crop from mother liquor; elem. anal.;	98%

C5H5(CO)2P(C4H9)3Fe(1+)*BF4(1-)={C5H5(CO)2P(C4H9)3Fe}BF4 + trimethylamine-N-oxide dihydrate (62637-93-8) → C5H5(CO)P(C4H9)3Fe(CH3CN)(1+)*BF4(1-)={C5H5(CO)P(C4H9)3Fe(CH3CN)}BF4

Conditions	Yield
In acetonitrile byproducts: CO2, NMe3; addn. of solid ONMe3*H2O to the soln. of the Fe-compd., gasdevelopment; volatile parts are removed, resolving with CH2Cl2, drying over MgSO4, filtn., drying in vacuum, elem. anal.;	99%

Os3(μ-H,μ-O=CNMe2)(CO)10 + trimethylamine-N-oxide dihydrate (62637-93-8) → 1,2-μ-hydrido-1,2-μ-(N,N-dimethylcarbamoyl)-1-trimethylamino-1,1,2,2,2,3,3,3,3-nonacarbonyl-triangulo-triosmium (313689-14-4)

Conditions	Yield
In methanol; diethyl ether under Ar; addn. of methanolic soln. of Me3NO*2H2O to stirred soln. of complex in Et2O over 20 min, keeping react. mixt. for 2 h; diln. with hexane, column chromy. (silica gel, CH2Cl2), evapn., crystn.from CHCl3-hexane at 2°C;	96%
In methanol; diethyl ether under dry Ar atm.; soln. of HOs3(OCNMe2)(CO)10 in Et2O was treated with;soln. of Me3NO*2H2O in MeOH; mixt. stirred at ambient temp.; monitored by TLC chromy. (hexane-CH2Cl2 2:1); soln. diluted with hexane;filtered through two short silica columns; solvent removed (vac.);	96%

trimethylamine-N-oxide dihydrate (62637-93-8) → trimethylamine-N-oxide (1184-78-7)

Conditions	Yield
With N,N-dimethyl-formamide distillation;	94%

η(4)-(Z)-1,3-pentadiene tricarbonyliron + trimethylamine-N-oxide dihydrate (62637-93-8) + triethyl phosphite (122-52-1) → dicarbonyl{1-4-η-((Z)-penta-1,3-diene)}(triethoxyphosphine)iron

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	93%

tricarbonyl(η(4)-buta-1,3-diene)iron (522611-42-3, 12078-32-9, 139687-42-6, 71435-61-5) + trimethylamine-N-oxide dihydrate (62637-93-8) + triethylphosphine (554-70-1) → (η4-buta-1,3-diene)dicarbonyl(triethylphosphine)iron (12154-18-6)

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	93%

1,10-Phenanthroline (66-71-7) + trimethylamine-N-oxide dihydrate (62637-93-8) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → (1,10-phenanthroline)molybdenum tetracarbonyl (15740-78-0)

Conditions	Yield
In benzene N2-atmosphere; stoichiometric amts., room temp.;	93%

[Ru(CO)3(OC2H4C4(C(O)OCH3)2Ru(CO)3)] + trimethylamine-N-oxide dihydrate (62637-93-8) → [(CH3)3NRu(CO)2(OC2H4C4(C(O)OCH3)2Ru(CO)3)]

Conditions	Yield
In tetrahydrofuran Ar, stirred for 1 h at ambient temp.; solvent removed (vac.), chromy. (silia gel, hexane/ethyl acetate); elem.anal.;	93%

cis-dichlorobis(dimethylsulfoxide)platinum(II) (75992-73-3, 25794-47-2, 30729-25-0, 15274-33-6, 22840-91-1, 14568-13-9) + trimethylamine-N-oxide dihydrate (62637-93-8) → trans-{Pt(DMSO)(NMe3)Cl2} (120272-54-0)

Conditions	Yield
In acetone refluxing (1 min); cooling, removal of solvent (vac.), addn. of isopropanol, filtration, reprecipitation from soln. in MeCN on addn. of ether; elem. anal.;	92%

{RhRe(CH3)(CO)2(μ-CO)2(dppm)2}{CF3SO3} + trimethylamine-N-oxide dihydrate (62637-93-8) + acetonitrile (75-05-8) → {RhRe(CH3)(μ-carbonyl)2(acetonitrile)2(dppm)2}{CF3SO3}

Conditions	Yield
With CH3CN In dichloromethane; acetonitrile dissolving complex in CH2Cl2; addn. of 2 equiv. Me3NO*H2O in CH3CN; stirring for 1 h; removal of solvents in vac.; recrystn. (CH2Cl2/Et2O); elem. anal.;	91%

tricarbonyl[(2-5-η)-(2E,4E)-hexa-2,4-dienal]iron + trimethylamine-N-oxide dihydrate (62637-93-8) + phosphorous acid trimethyl ester (121-45-9) → dicarbonyl{2-5-η-((2E,4E)-hexa-2,4-dienal)}(trimethoxyphosphine)iron

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent, elem. anal.;	90%

tricarbonyl[(2-5-η)-(2E,4E)-hexa-2,4-dienal]iron + trimethylamine-N-oxide dihydrate (62637-93-8) + triethylphosphine (554-70-1) → dicarbonyl{2-5-η-((2E,4E)-hexa-2,4-dienal)}(triethylphosphine)iron

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	90%

(+/-)iron tricarbonyl(CH3CHCHCHCHCOOH) methyl ester + trimethylamine-N-oxide dihydrate (62637-93-8) + triethylphosphine (554-70-1) → dicarbonyl{2-5-η-(methyl(2E,4E)-hexa-2,4-dienoate)}(triethylphosphine)iron

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	90%

tricarbonyl[(2-5-η)-(2E,4E)-hexa-2,4-dienal]iron + trimethylamine-N-oxide dihydrate (62637-93-8) + triethyl phosphite (122-52-1) → dicarbonyl{2-5-η-((2E,4E)-hexa-2,4-dienal)}(triethoxyphosphine)iron

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent, elem. anal.;	90%

ammonium hexafluorophosphate + dicarbonylcyclopentadienylbromoiron(II) + trimethylamine-N-oxide dihydrate (62637-93-8) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (1,2-bis(diphenylphosphino)ethane)carbonyl(η5-cyclopentadienyl)iron(1+) hexafluorophosphate

Conditions

Yield

In acetone; toluene a mixt. of Fe-complex and dppe was heated under reflux in toluene for 2h, cooled, filtered under N2, solid was washed with toluene, suspended in wet acetone contg. NH4PF6, Me3NO*2H2O was added, mixt. was stirred for 1 h; solvent was removed under reduced pressure, extd. with CH2Cl2, soln. was washed with H2O, decanted, dried over CaCl2, filtered, concd., Et2O was added, cooled to -30°C;

90%

2-(N,N-dimethylamino)ethanol (108-01-0) + decacarbonyldirhenium(0) (14285-68-8) + trimethylamine-N-oxide dihydrate (62637-93-8) → [tricarbonylrhenium(I)(η2-(2-(dimethylamino)ethoxide))(μ-OH)tricarbonylrhenium(I)(η2-(2-(dimethylamino)ethanol))]

Conditions	Yield
In tetrahydrofuran; methanol N2, a soln. of Re compd. (THF) added at room temp. to a soln. of ligand and N-oxide, stirred for 4 h at ambient temp.; solvent removed (vac.), recrystd. (CH2Cl2-hexane) by slow evapn. at roomtemp.; elem. anal.;	90%
In tetrahydrofuran N2, a soln. of Re compd. (THF) added at room temp. to a soln. of ligand and N-oxide, stirred for 4 h at ambient temp.; solvent removed (vac.), recrystd. (CH2Cl2-hexane) by slow evapn. at roomtemp.; elem. anal.;	55%

aqueous NaHSO3 + cis-1,4-diacetoxy-2-cyclopentene (54664-61-8) + trimethylamine-N-oxide dihydrate (62637-93-8) → 3α,5α-diacetoxy-1β,2β-cyclopentanediol (115420-61-6)

Conditions	Yield
With osmium(VIII) oxide In tetrahydrofuran; water; acetone	89.5%

tungsten hexacarbonyl (14040-11-0) + trimethylamine-N-oxide dihydrate (62637-93-8) + acetonitrile (75-05-8) → W(CO)5NMe3 (15228-32-7) + pentacarbonyl(acetonitrile)tungsten (15096-68-1)

Conditions	Yield
In neat (no solvent) addn. of Me3NO*2H2O to a suspn. of W(CO)6 in CH3CN, stirring under aspirator vac. 5 min, under N2, 5 min; filtration in air, vac. evapn., yellow powder, taken up in CH3CN, filtered (through a pad of silica gel), washed (CH3CN), vac. evapn.;	A n/a B 89%

{Fe(CO)3(η4-CH3(CH)4CH3)} (164457-02-7, 52993-12-1, 93482-06-5, 52993-16-5, 12108-38-2) + trimethylamine-N-oxide dihydrate (62637-93-8) + triethylphosphine (554-70-1) → dicarbonyl{2-5-η-((2E,4E)-hexa-2,4-diene)}(triethylphosphine)iron (127454-43-7)

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	89%

Os3(CO)11(P(C2H5)3) (28688-45-1) + trimethylamine-N-oxide dihydrate (62637-93-8) → Os3(CO)10(CH3CN)P(C2H5)3 (121483-79-2)

Conditions	Yield
In dichloromethane; acetonitrile (CH3)2NO*H2O is added to a soln. of Os-compd. (N2); stirring at room temp. for 30 min.; the initial yellow colour turnes to orange; filtration through silica; removal of solvent in vacuo; recrystn. from hexane-dichloromethane at -15°C; elem. anal.;	88%

η(4)-(E)-1,3-pentadiene tricarbonyliron + trimethylamine-N-oxide dihydrate (62637-93-8) + phosphorous acid trimethyl ester (121-45-9) → dicarbonyl{1-4-η-((E)-penta-1,3-diene)}(trimethoxyphosphine)iron

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	87%

(μ-pyridyl)(μ-hydrido)dirhenium octacarbonyl + trimethylamine-N-oxide dihydrate (62637-93-8) → (μ-hydrido)(μ-pyridyl)(trimethylamine N-oxide)dirhenium heptacarbonyl (84538-00-1) + trimethylamine (75-50-3)

Conditions	Yield
In dichloromethane Re complex dissolved in CH2Cl2, excess Me3NO*2H2O added, stirred vigorously at room temp. for 10 h; filtered, filtrate washed with water, hexane added, slowly evapd.; elem. anal.;	A 84% B n/a

[Os(II)(tris(1-pyrazolyl)methane)(Cl)2(NS)](PF6) + trimethylamine-N-oxide dihydrate (62637-93-8) → Os(III)(tris(1-pyrazolyl)methane)(Cl)2(NSO) * 2 H2O

Conditions	Yield
In acetonitrile excess Me3NO, stirring for 30 min (pptn.); collection (filtration), washing (MeCN, Et2O); elem. anal.;	84%

(+/-)iron tricarbonyl(CH3CHCHCHCHCOOH) methyl ester + trimethylamine-N-oxide dihydrate (62637-93-8) + triethyl phosphite (122-52-1) → dicarbonyl{2-5-η-(methyl(2E,4E)-hexa-2,4-dienoate)}(triethoxyphosphine)iron

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	83%

{RhRe(CH3)(CO)2(μ-CO)2(dppm)2}{CF3SO3} + trimethylamine-N-oxide dihydrate (62637-93-8) + acetonitrile (75-05-8) → {RhRe(CH3)(CO)2(μ-CO)(CH3CN)(dppm)2}{CF3SO3}

Conditions	Yield
In dichloromethane dissolving complex in CH2Cl2; addn. of Me3NO*H2O in CH3CN; stirring for 1 h; removal of solvents in vac.; recrystn. (CH2Cl2/Et2O); elem. anal.;	83%

[Cr(CO)4(1,10-phenanthroline)] (14168-63-9) + trimethylamine-N-oxide dihydrate (62637-93-8) + bis-diphenylphosphinomethane (2071-20-7) → Cr(CO)3(C12H8N2)((C6H5)2PCH2P(C6H5)2) (108854-16-6)

Conditions	Yield
In acetonitrile N2-atmosphere; molar ratio Mo(CO)4(phen):Me3NO:dppm = 1:1.5:1, room temp.; recrystn. (CH2Cl2/MeOH);	83%

{Fe(CO)3(η4-CH3(CH)4CH3)} (164457-02-7, 52993-12-1, 93482-06-5, 52993-16-5, 12108-38-2) + trimethylamine-N-oxide dihydrate (62637-93-8) + triethyl phosphite (122-52-1) → dicarbonyl{2-5-η-((2E,4E)-hexa-2,4-diene)}(triethoxyphosphine)iron (127454-44-8, 127514-37-8)

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (37-40°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	82%

1,10-Phenanthroline (66-71-7) + tungsten hexacarbonyl (14040-11-0) + trimethylamine-N-oxide dihydrate (62637-93-8) → tetracarbonyl(1,10-phenanthroline)tungsten(0) (14729-20-5)

Conditions	Yield
In benzene N2-atmosphere; stoichiometric amts., room temp.;	81%

tricarbonyl(benzylideneacetone)iron + trimethylamine-N-oxide dihydrate (62637-93-8) + triethyl phosphite (122-52-1) → dicarbonyl{O-4-η-((E)-4-phenylbut-3-en-2-one)}(triethoxyphosphine)iron

Conditions	Yield
In acetonitrile Addn. of phosphorus ligand and iron complex to suspn. of Me3NO*2H2O (MeCN) under inert atmosphere, stirring of mixt. (0°C, 4-18 h) until disappearance of starting material.; Extn. of mixt. with hexane/Et2O, removal of solvent under reduced pressure, chromy. of residue on silica gel with hexane/Et2O as eluent. Pure compound obtained after elimination of solvent.;	80%

(μ3-H)RuCo3(CO)12 + trimethylamine-N-oxide dihydrate (62637-93-8) → HRuCo3(CO)11(N(CH3)3) + RuCo3(CO)12(1-)*(HN(CH3)3)(1+)={RuCo3(CO)12}{HN(CH3)3}

Conditions	Yield
In dichloromethane byproducts: CO2; under N2, using standard Schlenk techniques, addn. of Me3NO to a soln. of complex in CH2Cl2, color changed from deep red to red-brown, stirred for 0.25 h at room temp.; filtered, evapd. in vac., washed with hexane, extd. with toluene, evapd.; elem. anal.;	A 80% B n/a
In dichloromethane byproducts: CO2; under N2, using standard Schlenk techniques, addn. of Me3NO*2H2O to a soln. of complex in CH2Cl2, color changed from deep red to red-brown, stirred for 4 h at room temp., product ratio depended on react. time;

Downstream Products

• 125641-44-3 1-(dimethylamino)-2-(benzylamino)propane 
• 125641-48-7 1-(dimethylamino)-2-((benzylmethyl)amino)propane 
• 107703-38-8 (OC)5Mo(η(1)-bis(diphenylphosphino)methane) 
• 40545-00-4 Cr(CO)5(bis-(diphenylphosphino)-methane) 
• 111112-36-8 tungsten{1-hydroxy-1-imido-2-cyano-4-phenyl-5,5-bis(trifluoromethyl)penta-2,4-dien-3-yl}(carbonyl)2(η-C5H5)*0.25dichloromethane 
• 127432-76-2 (η4-buta-1,3-diene)dicarbonyl(cyclohexyl isocyanide)iron 
• 15748-39-7 (η4-buta-1,3-diene)dicarbonyl(triphenylphosphine)iron 
• 14971-42-7 triphenylphosphinemolybdenumpentacarbonyl 
• 14489-09-9 Mo2(CO)10(μ-1,2-bis(diphenylphosphino)ethane) 
• 14917-12-5 triphenylphosphine chromium pentacarbonyl 
• 40545-09-3 tetracarbonyl-1,3-bis(diphenylphosphino)propane-chromium⁽⁰⁾ 
• 15444-65-2 triphenylphosphine tungsten pentacarbonyl 
• 51371-61-0 Mn₂(CO)9(triphenylphosphine) 
• 15279-67-1 dimanganese octacarbonyl di-(triphenyl phosphine)