3162-58-1

Basic information

• Product Name: SULFUR TRIOXIDE TRIMETHYLAMINE COMPLEX
• Synonyms: SULPHUR TRIOXIDE-TRIMETHYLAMINE COMPLEX;SULFUR TRIOXIDE TRIMETHYLAMINE;SULFUR TRIOXIDE TRIMETHYLAMINE COMPLEX;SULFUR TRIOXIDE TRIMETHYLAMINEOMPLEX;TRIMETHYLAMINE SULFUR TRIOXIDE;TRIMETHYLAMINE SULFUR TRIOXIDE COMPLEX;TRLIMETHYLAMINE SULPHUR TRIOXIDE COMPLEX;Trimethylamine-sulphur trioxide complex
• CAS NO: 3162-58-1
• Molecular Formula: C₃H₉N*O₃S
• Molecular Weight: 139.17
• EINECS: 221-614-7
• Mol File: 3162-58-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 232 °C (dec.)(lit.)
• Boiling Point: 2.8°Cat760mmHg
• Flash Point: °C
• Appearance: White to off-white/Powder
• Density: g/cm³
• Water Solubility: Soluble in hot water and ethanol. Slightly soluble in dimethyl sulfoxide and methanol. Insoluble in water.
• Sensitive: Moisture Sensitive
• BRN: 3681759
• CAS DataBase Reference: SULFUR TRIOXIDE TRIMETHYLAMINE COMPLEX(CAS DataBase Reference)
• NIST Chemistry Reference: SULFUR TRIOXIDE TRIMETHYLAMINE COMPLEX(3162-58-1)
• EPA Substance Registry System: SULFUR TRIOXIDE TRIMETHYLAMINE COMPLEX(3162-58-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 3-9-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 3162-58-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder. Soluble in hot water, ethanol; soluble with difficulty in cold water and acetone; not dissociated in benzene and chloroform solutions; distinctly different from the isomeric adduct of trimethylamine oxide and sulfur dioxide.

Uses

Different sources of media describe the Uses of 3162-58-1 differently. You can refer to the following data:
1. Reactant for sulfation reactions involving: Synthesis of sulfate-conjugated resveratrol metabolitesChitooligosaccharides used for anti-HIV-1 activityDodecyl thioglycopyranoside used as a surfactant for enantiomeric separationGlycosaminoglycans which facilitate activation of signaling pathways dependent on sulfation patternPolysaccharides as heparan sulfate mimeticsNucleophile for the synthesis of α-tosyloxy ketones
2. Separation of isomers, soil sterilant, catalyst for thermosetting resins.

InChI:InChI=1/C3H9N.O3S/c2*1-4(2)3/h1-3H3;

Synthetic route

trimethylamine (75-50-3) → sulfur trioxide trimethylamine complex (3162-58-1)

Conditions	Yield
With trimethylsilyl N,N-dimesylamidosulfonate In dichloromethane at 0℃;	95%
With chlorosulphuric acid; chloroform

trimethylsilyl N,N-dimesylamidosulfonate (176759-56-1) + trimethylamine (75-50-3) → trimethylsilyldimesylamine (30488-04-1) + sulfur trioxide trimethylamine complex (3162-58-1)

Conditions	Yield
In dichloromethane at 0℃; Product distribution; other Lewis bases;	A n/a B 95%

sulfur trioxide (7446-11-9) + trimethylamine (75-50-3) → sulfur trioxide trimethylamine complex (3162-58-1)

Conditions	Yield
In neat (no solvent) react. of SO3-vapor (dild. with N2 as carrier gas) with dry (CH3)3N-vapor;; crystn.;;
In neat (no solvent) react. of SO3-vapor (dild. with N2 as carrier gas) with dry (CH3)3N-vapor;; crystn.;;

sulfur trioxide trimethylamine complex (3162-58-1) + 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (4132-28-9, 4291-69-4, 6386-24-9, 6564-72-3, 59531-24-7, 69257-52-9, 78184-89-1, 78609-17-3, 78609-18-4, 96553-53-6, 104111-61-7, 131347-08-5, 78609-16-2) → 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl sulfate

Conditions	Yield
In acetonitrile for 48h; Heating;	100%

sulfur trioxide trimethylamine complex (3162-58-1) + C64H72N6O21 → C64H72N6O30S3*3C3H9N

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 72h;	100%

sulfur trioxide trimethylamine complex (3162-58-1) + C64H74N6O21 → C64H74N6O33S4*4C3H9N

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 72h;	100%

C47H55N3O15 + sulfur trioxide trimethylamine complex (3162-58-1) → C47H51N3O27S4(4-)*4Na(1+)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃;	100%

2-(N-benzyloxycarbonyl)aminoethyl 2,3,4-tri-O-(4-methyl)benzoyl-6-O-(2-naphthylmethyl)-β-D-galactopyranosyl-(1→4)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside + sulfur trioxide trimethylamine complex (3162-58-1) → 2-(N-benzyloxycarbonyl)aminoethyl 2,3,4-tri-O-(4-methyl)benzoyl-6-O-(2-naphthylmethyl)-β-D-galactopyranosyl-(1→4)-3-O-benzyl-2-deoxy-2-phthalimido-6-O-sulfo-β-D-glucopyranoside trimethylamine salt

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	100%

C148H152N12O45 + sulfur trioxide trimethylamine complex (3162-58-1) → C148H152N12O57S4*4C3H9N

Conditions	Yield
With N,N-dimethyl-formamide In 1,2-dichloro-ethane at 80℃; for 0.5h; Inert atmosphere;	98.1%

sulfur trioxide trimethylamine complex (3162-58-1) + C71H78N6O21 → C71H78N6O27S2*2C3H9N

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 72h;	96%

2-(N-benzyloxycarbonyl)aminoethyl 2,3,4-tri-O-(4-methylbenzoyl)-6-O-(2-naphthylmethyl)-β-D-galactopyranosyl-(1→4)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→3)-2,4-di-O-(4-methyl)benzoyl-6-O-(2-naphthylmethyl)-β-D-galactopyranosyl-(1→4)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside + sulfur trioxide trimethylamine complex (3162-58-1) → 2-(N-benzyloxycarbonyl)aminoethyl 2,3,4-tri-O-(4-methylbenzoyl)-6-O-(2-naphthylmethyl)-β-D-galactopyranosyl-(1→4)-3-O-benzyl-2-deoxy-2-phthalimido-6-O-sulfo-β-D-glucopyranosyl-(1→3)-2,4-di-O-(4-methyl)benzoyl-6-O-(2-naphthylmethyl)-β-d-galactopyranosyl-(1→4)-3-O-benzyl-2-deoxy-2-phthalimido-6-O-sulfo-β-D-glucopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 26h; Inert atmosphere;	96%

C107H113N9O33 + sulfur trioxide trimethylamine complex (3162-58-1) → C107H113N9O45S4*4C3H9N

Conditions	Yield
With N,N-dimethyl-formamide In 1,2-dichloro-ethane at 90℃; for 0.333333h; Inert atmosphere;	95.2%

4-methylphenyl 6-O-acetyl-2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside (1374561-81-5) + sulfur trioxide trimethylamine complex (3162-58-1) → C29H30O10S2*C3H9N

Conditions	Yield
With N,N-dimethyl-formamide In acetonitrile at 60℃; for 2h; Solvent; Temperature; Reagent/catalyst;	95%

Dipentaerythritol (126-58-9) + sulfur trioxide trimethylamine complex (3162-58-1) → C10H22O25S6*6C3H9N

Conditions	Yield
With N,N-dimethyl-formamide In toluene at 80℃; for 0.833333h; Inert atmosphere;	93.8%

C38H39N3O10 + sulfur trioxide trimethylamine complex (3162-58-1) → C38H39N3O13S*C3H9N

Conditions	Yield
With N,N-dimethyl-formamide In 1,2-dichloro-ethane at 100℃; for 1h; Microwave irradiation;	93.7%

p-nitrophenyl 2-acetamido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-hydroxy-β-D-glucopyranoside + sulfur trioxide trimethylamine complex (3162-58-1) → p-nitrophenyl 2-acetamido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-sulfo-β-D-glucopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 40 - 50℃; for 111h;	92%

p-nitrophenyl 2-acetamido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-hydroxy-β-D-glucopyranoside + sulfur trioxide trimethylamine complex (3162-58-1) → trimethylammonium p-nitrophenyl 2-acetamido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-sulfo-β-D-glucopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 40 - 50℃; for 144h;	92%

7-methoxy-2-naphthyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->3)-(2,4-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (904684-22-6) + sulfur trioxide trimethylamine complex (3162-58-1) → 7-methoxy-2-naphthyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->3)-(2,4-di-O-benzoyl-6-O-sodium sulfonato-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 1h;	91%

sulfur trioxide trimethylamine complex (3162-58-1) + γ-cyclodextrin octa(2,3-dipalmitoyl) ester → octa(6-O-trimethylammonium sulfate) γ-cyclodextrin octa(2,3-dipalmitoyl) ester

Conditions	Yield
In N,N-dimethyl-formamide; toluene at 80℃; for 48h;	90.3%

7-methoxy-2-naphthyl O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside (904684-11-3) + sulfur trioxide trimethylamine complex (3162-58-1) → 7-methoxy-2-naphthyl O-(2,3,4-tri-O-benzoyl-6-O-sodium sulfonato-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 1h;	90%

7-methoxy-2-naphthyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->3)-(2,4-di-O-benzoyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranoside (904684-20-4) + sulfur trioxide trimethylamine complex (3162-58-1) → 7-methoxy-2-naphthyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->3)-(2,4-di-O-benzoyl-6-O-sodium sulfonato-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 1h;	90%

calenduladiol (10070-48-1) + sulfur trioxide trimethylamine complex (3162-58-1) → disodium 3β,16β-dihydroxylup-20(29)-ene disulfate

Conditions	Yield
Stage #1: calenduladiol; sulfur trioxide trimethylamine complex In N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere; Stage #2: With Amberlite CG-120 (Na+ form) In methanol; N,N-dimethyl-formamide Inert atmosphere;	90%

2-(N-benzyloxycarbonyl)aminoethyl 2,3,4-tri-O-(4-methyl)benzoyl-β-D-galactopyranosyl-(1→4)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside + sulfur trioxide trimethylamine complex (3162-58-1) → 2-(N-benzyloxycarbonyl)aminoethyl 2,3,4-tri-O-(4-methyl)benzoyl-6-O-sulfo-β-D-galactopyranosyl-(1→4)-3-O-benzyl-2-deoxy-2-phthalimido-6-O-sulfo-β-D-glucopyranoside bistrimethylamine salt

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	90%

sulfur trioxide trimethylamine complex (3162-58-1) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → C18H17NO8S*C3H9N

Conditions	Yield
With N,N-dimethyl-formamide In ethyl acetate at 80℃; for 0.416667h; Inert atmosphere;	89.1%

7-methoxy-2-naphthyl O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranoside (904684-09-9) + sulfur trioxide trimethylamine complex (3162-58-1) → 7-methoxy-2-naphthyl O-(2,3,4-tri-O-benzoyl-6-O-sodium sulfonato-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 1h;	89%

6-azidohexyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1→3)-(2-acetamido-2-deoxy-β-D-galactopyranoside)-(1→4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1→3)-2-acetamido-2-deoxy-β-D-galactopyranoside + sulfur trioxide trimethylamine complex (3162-58-1) → C71H75N5O40S4(4-)*4C3H9N*4H(1+)

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 48h; Schlenk technique; Inert atmosphere;	89%

sulfur trioxide trimethylamine complex (3162-58-1) + methyl (methyl 3,4-di-O-pivaloyl-α-L-idopyranosyluroate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-6-O-pivaloyl-α-D-glucopyranoside (630129-64-5) → methyl (methyl 2-O-trimethylaminesulfonato-3,4-di-O-pivaloyl-α-L-idopyranosyluroate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-6-O-pivaloyl-α-D-glucopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 60℃;	88%

2-(N-benzyloxycarbonyl)aminoethyl 2,3,4-tri-O-(4-methyl)benzoyl-β-D-galactopyranosyl-(1→4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside + sulfur trioxide trimethylamine complex (3162-58-1) → 2-(N-benzyloxycarbonyl)aminoethyl 2,3,4-tri-O-(4-methyl)benzoyl-6-O-sulfo-β-D-galactopyranosyl-(1→4)-6-O-acetyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside trimethylamine salt

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	88%

sulfur trioxide trimethylamine complex (3162-58-1) + methyl (2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (849101-45-7) → methyl (2-azido-3-O-benzyl-2-deoxy-6-O-trimethylaminesulfonato-α-D-glucopyranosyl)-(1->4)-(methyl 3-O-pivaloyl-2-O-trimethylaminesulfonato-α-L-idopyranosyluronate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-6-O-trimethylaminesulfonato-α-D-glucopyranoside

Conditions	Yield
In N,N-dimethyl-formamide at 60℃;	86%

trifluoroethylamine (753-90-2) + sulfur trioxide trimethylamine complex (3162-58-1) → trimethylammonium (2,2,2-trifluoroethyl)sulfamate

Conditions	Yield
In acetonitrile at 0 - 22℃; for 0.5h; Inert atmosphere;	86%

hexane-1,2,6-triol (106-69-4) + sulfur trioxide trimethylamine complex (3162-58-1) → C6H14O12S3*3C3H9N

Conditions	Yield
With N,N-dimethyl-formamide In 1,2-dichloro-ethane at 80℃; for 0.416667h; Inert atmosphere;	85.8%

Upstream product

• 75-50-3 trimethylamine 
• 176759-56-1 trimethylsilyl N,N-dimesylamidosulfonate 
• 7446-11-9 sulfur trioxide 

Downstream Products

• 75-50-3 trimethylammonium radical cation 
• 3162-58-1 C₃H₈N*O₃S 

Relevant articles and documents

POLYSULFONYLAMINE: TEIL LXXI. EIN MOLEKUEL MIT EINER LANGEN Si(sp3)-O-BINDUNG: SYNTHESE, STRUKTUR UND REAKTIVITAET VON N,N-DIMESYLAMIDOSCHWEFELSAEURETRIMETHYLSILYLESTER

The title compound (MeSO2)2N-SO2-O-SiMe3 (2; m.p. 57 deg C) is obtained by treating (MeSO2)2N-SiMe3 (3) with one equivalent of sulfur trioxide in CH2Cl2 at -20 deg C.The crystal structure of 2 (triclinic, space group P) was established by low-temperature X-ray diffraction.The most interesting feature of the molecular structure is the geometry of the S-O-Si sequence, displaying a very long Si(sp3)-O bond, a short S(sp3)-O bond and a large angle at oxygen (mean values for two independent molecules: Si-O 174.1, S-O 151.1 pm, S-O-Si 134.3 deg).The coordination at nitrogen is trigonal-planar (S-N-S 118.5-121.0 deg, S-N 170.5-173.1 pm). 2 is instantaneously hydrolyzed by excess water to form (MeSO2)2NH, sulfuric acid and (Me3Si)2O.In vacuo at 60 deg C, molten 2 will readily dissociate into its precursors 3 and SO3.It is shown that 2 may react either as an SO3 donor or as a sulfosilylating reagent.Reaction with Lewis bases such as Me3N, pyridine or R2PCl (R = tBu, Ph) proceeds with the formation of the corresponding complexes B*SO3; thermolysis of the isolable phosphane complexes affords the respective phosphane oxides R2(Cl)PO.Sulfosilylation of phenol, cyclohexene or 2,3-dimethyl-2-butene with 2 in CH2Cl2 gives the trimethylsilyl esters of 4-hydroxybenzenesulfonic, cyclohexene-3-sulfonic, or 2,3-dimethyl-1-butene-3-sulfonic acids, respectively.Key words: Trimethylsilyl N,N-dimesylamidosulfonate, synthesis, X-ray structure, long Si(sp3)-O bond, SO3 transfer, sulfosilylation.