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75-50-3

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75-50-3 Usage

General Description

Trimethylamine is a colorless, flammable gas with a strong, fishy odor. It is a volatile organic compound that is commonly found in seafood, and is also produced by the microbial decomposition of organic matter in water. In addition to its natural sources, trimethylamine is also used in various industrial processes, such as in the production of agricultural chemicals, pharmaceuticals, and rubber chemicals. It is also a byproduct of the production of certain drugs, such as choline and betaine. In addition, trimethylamine is used as an intermediate in the production of certain dyes and surfactants. Due to its strong odor and potential health hazards, trimethylamine is regulated as a hazardous substance by various environmental and occupational health and safety agencies around the world.

Check Digit Verification of cas no

The CAS Registry Mumber 75-50-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 5 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 75-50:
(4*7)+(3*5)+(2*5)+(1*0)=53
53 % 10 = 3
So 75-50-3 is a valid CAS Registry Number.
InChI:InChI=1S/C3H9N/c1-4(2)3/h1-3H3

75-50-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (T0464)  Trimethylamine (ca. 28% in Water, ca. 4.3mol/L)  

  • 75-50-3

  • 25mL

  • 105.00CNY

  • Detail
  • TCI America

  • (T0464)  Trimethylamine (ca. 28% in Water, ca. 4.3mol/L)  

  • 75-50-3

  • 500mL

  • 165.00CNY

  • Detail
  • TCI America

  • (T2268)  Trimethylamine (ca. 25% in Methanol, ca. 3.2mol/L)  

  • 75-50-3

  • 100mL

  • 180.00CNY

  • Detail
  • TCI America

  • (T2268)  Trimethylamine (ca. 25% in Methanol, ca. 3.2mol/L)  

  • 75-50-3

  • 500mL

  • 555.00CNY

  • Detail
  • TCI America

  • (T2704)  Trimethylamine (ca. 13% in Tetrahydrofuran, ca. 2mol/L)  

  • 75-50-3

  • 100mL

  • 190.00CNY

  • Detail
  • TCI America

  • (T2704)  Trimethylamine (ca. 13% in Tetrahydrofuran, ca. 2mol/L)  

  • 75-50-3

  • 500mL

  • 640.00CNY

  • Detail
  • TCI America

  • (T2892)  Trimethylamine (ca. 25% in Ethanol, ca. 3mol/L)  

  • 75-50-3

  • 100mL

  • 490.00CNY

  • Detail
  • TCI America

  • (T2893)  Trimethylamine (ca. 25% in Isopropyl Alcohol, ca. 3mol/L)  

  • 75-50-3

  • 100mL

  • 210.00CNY

  • Detail
  • TCI America

  • (T2893)  Trimethylamine (ca. 25% in Isopropyl Alcohol, ca. 3mol/L)  

  • 75-50-3

  • 500mL

  • 660.00CNY

  • Detail
  • TCI America

  • (T3567)  Trimethylamine (ca. 13% in Acetonitrile, ca. 2mol/L)  

  • 75-50-3

  • 100mL

  • 240.00CNY

  • Detail
  • TCI America

  • (T3567)  Trimethylamine (ca. 13% in Acetonitrile, ca. 2mol/L)  

  • 75-50-3

  • 500mL

  • 890.00CNY

  • Detail
  • Alfa Aesar

  • (H32899)  Trimethylamine, 1M soln. in THF   

  • 75-50-3

  • 100ml

  • 651.0CNY

  • Detail

75-50-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name trimethylamine

1.2 Other means of identification

Product number -
Other names TRIMETHYLAMINE HYDRO

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:75-50-3 SDS

75-50-3Synthetic route

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
With Dimethylphenylsilane; C40H56FeN2Si4(2-) In benzene-d6 at 120℃; for 10h; Reagent/catalyst; Sealed tube; Inert atmosphere;99%
With bis(tetrahydrofuran)calcium di(bis(trimethylsilyl)amide); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 25℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox;99%
With sodium tetrahydroborate; Bis-(2-bromoethyl)selenium dibromide In tetrahydrofuran at 65℃; for 4h; Product distribution; Mechanism; other temperature (25 deg C), other reaction time, also presence od diethyl selenium dibromide; various other tertiary amides investigated;82%
Dimethylphenylsilane
766-77-8

Dimethylphenylsilane

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
With C40H56N2RuSi4 at 120℃; for 5h; Reagent/catalyst; Sealed tube;99%
With bis(1,5-cyclooctadiene)dichloro[1,3-bis(1′-butylbenzimidazol-2′-yliden-3′-yl)benzene]dirhodium(I) In benzene-d6 at 100℃; for 2h; Catalytic behavior; Time; Reagent/catalyst;89%
carbon dioxide
124-38-9

carbon dioxide

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
With aluminium(III) triflate; [Ru(Triphos)(TMM)]; hydrogen; ammonium chloride In 1,4-dioxane; water at 150℃; under 67506.8 Torr; for 24h; Solvent; Temperature; Pressure; Autoclave; Schlenk technique;99%
With octane; hydrogen; ammonium bicarbonate In neat (no solvent) at 250℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Autoclave;65%
With aluminium(III) triflate; [Ru(1,1,1-tris(diphenylphosphinomethyl)ethane)(trimethylenemethane)]; ammonia; hydrogen; bis(trifluoromethanesulfonyl)amide In 1,4-dioxane at 150℃; under 60006 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere; Autoclave;77 %Spectr.
C17H18ClN3O
85598-30-7

C17H18ClN3O

A

5-(4-chlorophenyl)-3-phenyl-1,2,4-oxadiazole
28825-13-0

5-(4-chlorophenyl)-3-phenyl-1,2,4-oxadiazole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
at 215℃; for 0.25h;A 98%
B n/a
triethylsilane
617-86-7

triethylsilane

bis-(dimethylamino)methane
51-80-9

bis-(dimethylamino)methane

A

1,1,1-triethyl-N,N-dimethylsilylamine
3550-35-4

1,1,1-triethyl-N,N-dimethylsilylamine

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
With nickel at 140 - 150℃;A 97%
B n/a
C17H19N3O
85598-29-4

C17H19N3O

A

3,5-diphenyl-1,2,4-oxadiazole
888-71-1

3,5-diphenyl-1,2,4-oxadiazole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
at 210℃; for 0.0833333h;A 97%
B n/a
C18H21N3O
85715-90-8

C18H21N3O

A

3-phenyl-5-(p-tolyl)-1,2,4-oxadiazole
16112-24-6

3-phenyl-5-(p-tolyl)-1,2,4-oxadiazole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
at 210℃; for 0.166667h;A 97%
B n/a
[(E)-4-(Diethoxy-phosphorylsulfanyl)-but-2-enyl]-trimethyl-ammonium; chloride
108546-39-0

[(E)-4-(Diethoxy-phosphorylsulfanyl)-but-2-enyl]-trimethyl-ammonium; chloride

A

ethyl phosphate
1623-14-9

ethyl phosphate

B

ethyl 1,3-butadienyl sulfide
10574-85-3

ethyl 1,3-butadienyl sulfide

C

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
With potassium hydroxide at 110℃; Product distribution; Mechanism;A 85.4%
B 33.3%
C 96.3%
trimethyl-borane; compound with trimethylamine
856617-42-0

trimethyl-borane; compound with trimethylamine

A

trimethylborane
593-90-8

trimethylborane

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
at 111.3°C, 64.5 Torr equilibrium;A 96%
B 96%
at 111.3°C, 64.5 Torr equilibrium;A 96%
B 96%
at 65.8°C, 47.5 Torr equilibrium;A 63.8%
B 63.8%
propylborane; compound with trimethylamine (1:1)

propylborane; compound with trimethylamine (1:1)

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-propyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
115002-30-7

2-propyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In benzene byproducts: H2; by heating at reflux then cooling, adding pentane to the mixture; recrystn. from benzene-pentane;A 95%
B n/a
isobutylborane; compound with trimethylamine (1:1)

isobutylborane; compound with trimethylamine (1:1)

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-isobutyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
114328-55-1

2-isobutyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In benzene byproducts: H2; reflux, then cooling and adding pentane to the mixture; recrystn. from benzene-pentane;A 95%
B n/a
bis-[(diethoxy-methyl-silanyl)-methyl]-methyl-amine
18551-79-6

bis-[(diethoxy-methyl-silanyl)-methyl]-methyl-amine

phenol
108-95-2

phenol

A

methyltriphenoxysilane
3439-97-2

methyltriphenoxysilane

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
for 1.5h; Heating;A 92%
B n/a
sec-butyl-borane; compound with trimethylamine (1:1)

sec-butyl-borane; compound with trimethylamine (1:1)

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-sec-butyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
114328-54-0

2-sec-butyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In benzene byproducts: H2; by heating at reflux, then cooling and adding pentane to the mixture; recrystn. from benzene-pentane;A 92%
B n/a
trimethylamine-1-benzylborane
124287-34-9

trimethylamine-1-benzylborane

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-benzyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
124139-26-0

2-benzyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In benzene byproducts: H2; reflux, cooling then adding pentane to the mixture; crystn. from benzene-pentane;A 92%
B n/a
potassium sulfite

potassium sulfite

A

potassium dithionate

potassium dithionate

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
With (CH3)3NSO3 In further solvent(s) 12°C, hydrogencarbonatalkal. soln.; cooling the mixture with ice;A 92%
B n/a
With (CH3)3NSO3 In further solvent(s) 12°C, hydrogencarbonatalkal. soln.; cooling the mixture with ice;A 92%
B n/a
isopropylborane; compound with trimethylamine (1:1)

isopropylborane; compound with trimethylamine (1:1)

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-isopropyl-2,3-dihydro-1H-1,3,2-benzodiazaborole
125929-63-7

2-isopropyl-2,3-dihydro-1H-1,3,2-benzodiazaborole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In benzene byproducts: H2; by heating at reflux, then cooling and adding pentane to the mixture; recrystn. from benzene-pentane;A 91%
B n/a
C15H37NO6Si2
382156-73-2

C15H37NO6Si2

phenol
108-95-2

phenol

A

tetraphenoxysilane
1174-72-7

tetraphenoxysilane

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
for 1.5h; Heating;A 89%
B n/a
cyclohexylborane; compound with trimethylamine (1:1)

cyclohexylborane; compound with trimethylamine (1:1)

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-cyclohexyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
108484-20-4

2-cyclohexyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In benzene byproducts: H2; by heating at reflux, cooling and adding pentane to the mixture; recrystn. from benzene-pentane;A 89%
B n/a
acetic acid 15-allyl-3-benzyloxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester
1013940-31-2

acetic acid 15-allyl-3-benzyloxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester

A

acetic acid 3-benzyloxy-15-(3-hydroxy-propyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester
1013940-33-4

acetic acid 3-benzyloxy-15-(3-hydroxy-propyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
Stage #1: acetic acid 15-allyl-3-benzyloxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 10 - 20℃; for 4h;
Stage #2: With trimethylamine-N-oxide In tetrahydrofuran; ethanol; diethylene glycol dimethyl ether at 150℃; for 1h;
A 89%
B n/a
C12H15Cl2N3O
85598-33-0

C12H15Cl2N3O

A

5-(2,4-dichloro-phenyl)-3-methyl-[1,2,4]oxadiazole
59562-67-3

5-(2,4-dichloro-phenyl)-3-methyl-[1,2,4]oxadiazole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
at 170℃; for 0.5h;A 88%
B n/a
tetrakis(dimethylamido)titanium(IV)

tetrakis(dimethylamido)titanium(IV)

ZrCl4*2N(CH3)3

ZrCl4*2N(CH3)3

A

ZrCl4Ti(N(CH3)2)4
82089-50-7

ZrCl4Ti(N(CH3)2)4

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In pentane under N2, Ti(NMe2)4 in n-pentane added dropwise to suspn. of ZrCl4*2NMe3 in n-pentane, stirred for 24 h; ppt. collected, washed with n-hexane, dried in vac. for 3 h at room temp.; elem. anal.;A 85.7%
B n/a
bis-[(ethoxy-dimethyl-silanyl)-methyl]-methyl-amine

bis-[(ethoxy-dimethyl-silanyl)-methyl]-methyl-amine

phenol
108-95-2

phenol

A

dimethyl-diphenoxy-silane
3440-02-6

dimethyl-diphenoxy-silane

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
for 1.5h; Heating;A 85%
B n/a
butylborane; compound with trimethylamine (1:1)

butylborane; compound with trimethylamine (1:1)

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-butyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
31748-14-8

2-butyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In benzene byproducts: H2; reflux, then cooling and adding pentane to the mixture; recrystn. from benzene-pentane;A 85%
B n/a
(μ-pyridyl)(μ-hydrido)dirhenium octacarbonyl

(μ-pyridyl)(μ-hydrido)dirhenium octacarbonyl

trimethylamine-N-oxide dihydrate
62637-93-8

trimethylamine-N-oxide dihydrate

A

(μ-hydrido)(μ-pyridyl)(trimethylamine N-oxide)dirhenium heptacarbonyl
84538-00-1

(μ-hydrido)(μ-pyridyl)(trimethylamine N-oxide)dirhenium heptacarbonyl

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
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
trimethylamine-N-oxide
1184-78-7

trimethylamine-N-oxide

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
With C55H43P3Rh(1+)*C32H12BF24(1-); isopropyl alcohol at 80℃; for 24h; Reagent/catalyst; Inert atmosphere;82%
biochemische Reduktion durch gaerende Zucker-Loesungen;
With zinc
methylammonium 1-methylcaffolide
104815-74-9

methylammonium 1-methylcaffolide

A

3,6,8-trimethyl-1-oxa-3,6,8-triaza-spiro[4.4]nonane-2,4,7,9-tetraone
7366-48-5

3,6,8-trimethyl-1-oxa-3,6,8-triaza-spiro[4.4]nonane-2,4,7,9-tetraone

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In diethyl ether for 48h;A 80%
B n/a
ammonium caffolide
104795-02-0

ammonium caffolide

A

3,6,8-trimethyl-1-oxa-3,6,8-triaza-spiro[4.4]nonane-2,4,7,9-tetraone
7366-48-5

3,6,8-trimethyl-1-oxa-3,6,8-triaza-spiro[4.4]nonane-2,4,7,9-tetraone

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In diethyl ether for 48h;A 80%
B n/a
ammonium 1,3-dimethylcaffolide
105116-10-7

ammonium 1,3-dimethylcaffolide

A

3,6,8-trimethyl-1-oxa-3,6,8-triaza-spiro[4.4]nonane-2,4,7,9-tetraone
7366-48-5

3,6,8-trimethyl-1-oxa-3,6,8-triaza-spiro[4.4]nonane-2,4,7,9-tetraone

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In diethyl ether for 48h;A 80%
B n/a
cis-tetracarbonyl(2-ethoxy-2-oxoethyl)(triphenylphosphine)rhenium

cis-tetracarbonyl(2-ethoxy-2-oxoethyl)(triphenylphosphine)rhenium

trimethylamine-N-oxide
1184-78-7

trimethylamine-N-oxide

fac-(MeCN)(OC)3(Ph3)ReCH2COOEt

fac-(MeCN)(OC)3(Ph3)ReCH2COOEt

B

carbon dioxide
124-38-9

carbon dioxide

C

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
A 80%
B n/a
C n/a
hexylborane; compound with trimethylamine (1:1)

hexylborane; compound with trimethylamine (1:1)

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-hexyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole
124138-66-5

2-hexyl-2,3-dihydro-1H-benzo[1,3,2]diazaborole

B

trimethylamine
75-50-3

trimethylamine

Conditions
ConditionsYield
In benzene byproducts: H2; reflux, then cooling and adding pentane to the mixture; recrystn. from benzene-pentane;A 79%
B n/a
4-Methylbenzyl bromide
104-81-4

4-Methylbenzyl bromide

trimethylamine
75-50-3

trimethylamine

(4-methylbenzyl)trimethylammonium bromide
16814-21-4

(4-methylbenzyl)trimethylammonium bromide

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃;100%
In tetrahydrofuran; ethanol at 25℃; for 24h; Inert atmosphere;99%
2-chloroethyl methyl ether
627-42-9

2-chloroethyl methyl ether

trimethylamine
75-50-3

trimethylamine

Choline methyl ether chloride
6340-44-9

Choline methyl ether chloride

Conditions
ConditionsYield
In water; acetonitrile at 140℃; for 5.5h;100%
In ethanol at 180℃; for 2.5h;93%
at 95℃;
1,3-propanesultone
1120-71-4

1,3-propanesultone

trimethylamine
75-50-3

trimethylamine

N-(3-sulfonatopropyl)-N,N,N-trimethylammonium
21865-17-8

N-(3-sulfonatopropyl)-N,N,N-trimethylammonium

Conditions
ConditionsYield
In ethanol; acetone at 0 - 20℃; for 24h;100%
In acetone at 35℃; for 2h;86%
In benzene
dichloromethanesulphonyl chloride
41197-29-9

dichloromethanesulphonyl chloride

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

trimethylamine
75-50-3

trimethylamine

A

trichloromethanesulfinyl chloride
25004-95-9

trichloromethanesulfinyl chloride

B

Trimethylammonium-(methylsulfonyl)methansulfonat
14843-83-5

Trimethylammonium-(methylsulfonyl)methansulfonat

Conditions
ConditionsYield
In tetrahydrofuran at -70℃;A 55%
B 100%
Dimethyl phosphite
868-85-9

Dimethyl phosphite

trimethylamine
75-50-3

trimethylamine

tetramethylammonium methyl hydrogen phosphite

tetramethylammonium methyl hydrogen phosphite

Conditions
ConditionsYield
at 20℃; for 24h;100%
dichloromethanesulphonyl chloride
41197-29-9

dichloromethanesulphonyl chloride

trimethylamine
75-50-3

trimethylamine

trimethylammonium trichloromethanesulfinate
98182-00-4

trimethylammonium trichloromethanesulfinate

Conditions
ConditionsYield
In tetrahydrofuran at -70℃;100%
tert-butyl N-[4-(2-bromoethoxy)-3-methoxybenzyl]carbamate
130972-90-6

tert-butyl N-[4-(2-bromoethoxy)-3-methoxybenzyl]carbamate

trimethylamine
75-50-3

trimethylamine

{2-[4-(tert-Butoxycarbonylamino-methyl)-2-methoxy-phenoxy]-ethyl}-trimethyl-ammonium; bromide

{2-[4-(tert-Butoxycarbonylamino-methyl)-2-methoxy-phenoxy]-ethyl}-trimethyl-ammonium; bromide

Conditions
ConditionsYield
In methanol for 18h; Heating;100%
5,10,15,20-tetrakis(4’-bromomethylphenyl)porphyrin

5,10,15,20-tetrakis(4’-bromomethylphenyl)porphyrin

trimethylamine
75-50-3

trimethylamine

5,10,15,20-tetrakis(α-trimethylammonio-4-methylphenyl)phenylporphyrin tetrabromide

5,10,15,20-tetrakis(α-trimethylammonio-4-methylphenyl)phenylporphyrin tetrabromide

Conditions
ConditionsYield
In ethanol at 80℃; for 14h; Substitution;100%
In ethanol; chloroform Reflux;91%
In ethanol at 80℃; for 14h;49%
Toluene-4-sulfonic acid (2R,4R,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester
258336-21-9

Toluene-4-sulfonic acid (2R,4R,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

trimethylamine
75-50-3

trimethylamine

Toluene-4-sulfonate((2R,4R,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-tetrahydro-furan-2-ylmethyl)-trimethyl-ammonium;

Toluene-4-sulfonate((2R,4R,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-tetrahydro-furan-2-ylmethyl)-trimethyl-ammonium;

Conditions
ConditionsYield
In ethanol at 80℃; for 24h; Substitution;100%
C48H36N4O2Ru

C48H36N4O2Ru

trimethylamine
75-50-3

trimethylamine

(meso-Tetrakis{p-tolyl}porphyrinato)bis(trimethylamine)ruthenium(II)

(meso-Tetrakis{p-tolyl}porphyrinato)bis(trimethylamine)ruthenium(II)

Conditions
ConditionsYield
With water for 1h; Reduction;100%
C44H24Cl4N4O2Ru

C44H24Cl4N4O2Ru

trimethylamine
75-50-3

trimethylamine

(meso-Tetrakis{p-chlorophenyl}porphyrinato)bis(trimethylamine)ruthenium(II)

(meso-Tetrakis{p-chlorophenyl}porphyrinato)bis(trimethylamine)ruthenium(II)

Conditions
ConditionsYield
With water for 1h; Reduction;100%
N-tert-Butyloxycarbonyl-L-glutaminyl-L-threonine 2-bromoethyl ester
287178-85-2

N-tert-Butyloxycarbonyl-L-glutaminyl-L-threonine 2-bromoethyl ester

trimethylamine
75-50-3

trimethylamine

N-tert-Butyloxycarbonyl-L-glutaminyl-L-threonine choline ester bromide

N-tert-Butyloxycarbonyl-L-glutaminyl-L-threonine choline ester bromide

Conditions
ConditionsYield
In acetone at 20℃; for 72h; Alkylation;100%
1-bromo-2,4-hexadecadiyne

1-bromo-2,4-hexadecadiyne

trimethylamine
75-50-3

trimethylamine

2,4-hexadecadiynyltrimethylammonium bromide

2,4-hexadecadiynyltrimethylammonium bromide

Conditions
ConditionsYield
In water at 20℃;100%
2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

trimethylamine
75-50-3

trimethylamine

2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride
34798-95-3

2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;100%
In ethanol; dimethyl sulfoxide at 20℃; for 12h;76%
In dimethyl sulfoxide for 12h;72%
2-(N-acetylanilino)-4-chloromethyl-1,3-selenazole
62707-38-4

2-(N-acetylanilino)-4-chloromethyl-1,3-selenazole

trimethylamine
75-50-3

trimethylamine

[2-(N-acetylanilino)-1,3-selenazol-4-ylmethyl]trimethylammonium chloride

[2-(N-acetylanilino)-1,3-selenazol-4-ylmethyl]trimethylammonium chloride

Conditions
ConditionsYield
In benzene at 20℃; for 2h;100%
2-(N-acetylanilino)-4-iodomethyl-1,3-selenazole
121995-12-8

2-(N-acetylanilino)-4-iodomethyl-1,3-selenazole

trimethylamine
75-50-3

trimethylamine

[2-(N-acetylanilino)-1,3-selenazol-4-ylmethyl]trimethylammonium iodide

[2-(N-acetylanilino)-1,3-selenazol-4-ylmethyl]trimethylammonium iodide

Conditions
ConditionsYield
In benzene at 20℃; for 2h;100%
1,4-anhydro-2,3-O-isopropylidene-5-O-toluene-p-sulphonyl-DL-ribitol
17118-00-2, 30002-85-8, 84773-09-1

1,4-anhydro-2,3-O-isopropylidene-5-O-toluene-p-sulphonyl-DL-ribitol

trimethylamine
75-50-3

trimethylamine

N-(1,4-anhydro-2,3-O-isopropylidene-D,L-ribitol-5-yl)trimethylammonium tosylate

N-(1,4-anhydro-2,3-O-isopropylidene-D,L-ribitol-5-yl)trimethylammonium tosylate

Conditions
ConditionsYield
In ethanol at 70℃; for 0.25h;100%
4,16-bis(6'-bromohexyl)[2.2]paracyclophane

4,16-bis(6'-bromohexyl)[2.2]paracyclophane

trimethylamine
75-50-3

trimethylamine

4,16-bis(6'-(N,N,N-trimethylammonium)hexyl)[2.2]paracyclophane dibromide

4,16-bis(6'-(N,N,N-trimethylammonium)hexyl)[2.2]paracyclophane dibromide

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃; for 24h;100%
1,4-bis(3',5'-bis(6''-bromohexyl)styryl)benzene
854669-58-2

1,4-bis(3',5'-bis(6''-bromohexyl)styryl)benzene

trimethylamine
75-50-3

trimethylamine

1,4-bis(3',5'-bis(6'-(N,N,N-trimethylammonium)hexyl)styryl)benzene tetrabromide

1,4-bis(3',5'-bis(6'-(N,N,N-trimethylammonium)hexyl)styryl)benzene tetrabromide

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃; for 24h;100%
1,4-bis(4'-(N,N-bis(6''-iodohexyl)amino)styryl)benzene

1,4-bis(4'-(N,N-bis(6''-iodohexyl)amino)styryl)benzene

trimethylamine
75-50-3

trimethylamine

1,4-bis(4'-(N,N-bis(6''-(N,N,N-trimethylammonium)hexyl)amino)styryl)benzene tetraiodide

1,4-bis(4'-(N,N-bis(6''-(N,N,N-trimethylammonium)hexyl)amino)styryl)benzene tetraiodide

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃; for 24h;100%
In tetrahydrofuran; water at -78 - 20℃; for 24h;92%
1-(bromomethyl)-2,5-dichloro-4-methylbenzene
868860-21-3

1-(bromomethyl)-2,5-dichloro-4-methylbenzene

trimethylamine
75-50-3

trimethylamine

2,5-dichloro-(4-methylbenzyl)trimethylammonium bromide

2,5-dichloro-(4-methylbenzyl)trimethylammonium bromide

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃;100%
In diethyl ether at 0 - 20℃;
[14C2-1,4]-1,4-dibromobutane
32330-80-6

[14C2-1,4]-1,4-dibromobutane

trimethylamine
75-50-3

trimethylamine

C8(14)C2H26N2(2+)*2Br(1-)

C8(14)C2H26N2(2+)*2Br(1-)

Conditions
ConditionsYield
In ethanol100%
4,4'-bis(bromomethyl)-2,2'-bipyridine
134457-14-0

4,4'-bis(bromomethyl)-2,2'-bipyridine

trimethylamine
75-50-3

trimethylamine

4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine

4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine

Conditions
ConditionsYield
In dichloromethane; water at 20℃; for 24h;100%
In ethanol; water at 20℃; for 1h; Inert atmosphere;100%
In ethanol; water at 20℃; for 1h;
In dichloromethane; water at 20℃; for 24h;
In dichloromethane at 20℃; for 24h;
5,15-bis-[4-(3-bromo-propyloxy)-phenyl]-porphyrin

5,15-bis-[4-(3-bromo-propyloxy)-phenyl]-porphyrin

trimethylamine
75-50-3

trimethylamine

5,15-bis-[4-(3-trimethylammonio-propyloxy)-phenyl]-porphyrin dibromide

5,15-bis-[4-(3-trimethylammonio-propyloxy)-phenyl]-porphyrin dibromide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 50℃; under 750.075 - 1500.15 Torr; for 17h; Autoclave; Industry scale;100%
trimethylaminealane
16842-00-5

trimethylaminealane

trimethylamine
75-50-3

trimethylamine

bis(trimethylamino) alane

bis(trimethylamino) alane

Conditions
ConditionsYield
In not given react. of the Al compd. with an excess of NMe3;100%
6-methylbenzofuran-3-ylmethyl bromide
1187956-06-4

6-methylbenzofuran-3-ylmethyl bromide

trimethylamine
75-50-3

trimethylamine

Br(1-)*C13H18NO(1+)
1187956-09-7

Br(1-)*C13H18NO(1+)

Conditions
ConditionsYield
In tetrahydrofuran; chloroform at 20℃; Inert atmosphere;100%
3-bromomethylbenzofuran
38281-49-1

3-bromomethylbenzofuran

trimethylamine
75-50-3

trimethylamine

Br(1-)*C12H16NO(1+)
1187956-08-6

Br(1-)*C12H16NO(1+)

Conditions
ConditionsYield
In tetrahydrofuran; chloroform at 20℃; Inert atmosphere;100%
Methyl 4-(bromomethyl)benzoate
2417-72-3

Methyl 4-(bromomethyl)benzoate

trimethylamine
75-50-3

trimethylamine

1-(4-(methoxycarbonyl)phenyl)-N,N,N-trimethylmethanammonium bromide
1192363-78-2

1-(4-(methoxycarbonyl)phenyl)-N,N,N-trimethylmethanammonium bromide

Conditions
ConditionsYield
In water; acetonitrile at 80℃; for 15h; Sealed flask;100%
In acetonitrile at 50℃; for 12h;
1-(2,3-dioleyl-5-O-tosyl-α-D-ribofuranosyl)-4-nitroimidazole
1231718-49-2

1-(2,3-dioleyl-5-O-tosyl-α-D-ribofuranosyl)-4-nitroimidazole

trimethylamine
75-50-3

trimethylamine

1-(2,3-dioleyl-5-trimethylammonium-α-D-ribofuranosyl)-4-nitroimidazole tosylate
1231718-52-7

1-(2,3-dioleyl-5-trimethylammonium-α-D-ribofuranosyl)-4-nitroimidazole tosylate

Conditions
ConditionsYield
In tetrahydrofuran; acetonitrile at 50℃; for 48h;100%
1-(2,3-dioleyl-5-O-tosyl-α-D-ribofuranosyl)-5-nitroindole
1231718-39-0

1-(2,3-dioleyl-5-O-tosyl-α-D-ribofuranosyl)-5-nitroindole

trimethylamine
75-50-3

trimethylamine

1-(2,3-dioleyl-5-trimethylammonium-α-D-ribofuranosyl)-5-nitroindole tosylate
1231718-42-5

1-(2,3-dioleyl-5-trimethylammonium-α-D-ribofuranosyl)-5-nitroindole tosylate

Conditions
ConditionsYield
In tetrahydrofuran; acetonitrile at 50℃; for 48h;100%

75-50-3Relevant articles and documents

Aylett, B. J.,Campbell, J. M.

, (1967)

Cahn

, p. 702,704 (1930)

Novel self assembling nanoparticles for the oral administration of fondaparinux: Synthesis, characterization and in vivo evaluation

Ralay-Ranaivo, Bettina,Desma?le, Didier,Bianchini, Elsa P.,Lepeltier, Elise,Bourgaux, Claudie,Borgel, Delphine,Pouget, Thierry,Tranchant, Jean Fran?ois,Couvreur, Patrick,Gref, Ruxandra

, p. 323 - 331 (2014)

Fondaparinux (Fpx) is the anticoagulant of choice in the treatment of short- and medium-term thromboembolic disease. To overcome the low oral bioavailability of Fpx, a new nanoparticulate carrier has been developed. The nanoparticles (NPs) contain squalenyl derivatives, known for their excellent oral bioavailability. They spontaneously self-assemble upon both electrostatic and hydrophobic interactions between the polyanionic Fpx and cationic squalenyl (CSq) derivatives. The preparation conditions were optimized to obtain monodisperse, stable NPs with a mean diameter in the range of 150-200 nm. The encapsulation efficiencies were around 80%. Fpx loadings reached 39 wt.%. According to structural and morphological analysis, Fpx and CSq organized in spherical multilamellar ("onion-type") nanoparticles. Furthermore, in vivo studies in rats suggested that Fpx was well absorbed from the orally administered NPs, which totally dissociated when reaching the blood stream, leading to the release of free Fpx. The Fpx:CSq NPs improved the plasmatic concentration of Fpx in a dose-dependent manner. However, the oral bioavailability of these new NPs remained low (around 0.3%) but of note, the Cmax obtained after oral administration of 50 mg/kg NPs was close to the prophylactic plasma concentration needed to treat venous thromboembolism. Moreover, the oral bioavailability of Fpx could be dramatically increased up to 9% by including the nanoparticles into gastroresistant capsules. This study opens up new perspectives for the oral administration of Fpx and paves the way towards elaborating squalene-based NPs which self assemble without the need of covalently grafting the drug to Sq.

Replica of a fishy enzyme: Structure-function analogue of trimethylamine-n-oxide reductase

Moula, Golam,Bose, Moumita,Sarkar, Sabyasachi

, p. 5316 - 5327 (2013)

Three new complexes, [MoIVO(mnt)(SS)]2- (SS = dimethylethylenedicarboxylate (DMED), toluenedithiolate (tdt), benzenedithiolate (bdt); mnt = maleonitriledithiolate), each possessing two different dithiolene ligands, are synthesized as model of trimethylamine-N-oxide reductase. The asymmetric dithiolene ligands present in these complexes simulate the two different (P and Q) pterin coordinations in the family of DMSO reductase. These complexes reduce trimethylamine-N-oxide ((CH3)3N +-O- or TMANO), the biological substrate of trimethylamine-N-oxide reductase, to trimethylamine ((CH3) 3N), responsible for the fishy smell of dead aquatic animals. The reaction kinetics of trimethylamine-N-oxide reduction by these complexes follow the Michaelis-Menten saturation kinetics. These experimental findings have been rationalized by DFT, TD-DFT level of calculations.

Husemann

, (1875)

Heterogeneous platinum catalysts for direct synthesis of trimethylamine by N-methylation of ammonia and its surrogates with CO2/H2

Toyao, Takashi,Siddiki, S. M. A. Hakim,Ishihara, Keisuke,Kon, Kenichi,Onodera, Wataru,Shimizu, Ken-Ichi

, p. 68 - 70 (2017)

Direct synthesis of trimethylamine through N-methylation of NH3 or its surrogate (NH4HCO3) with both CO2 and H2 has been achieved by employing Pt and MoOx coloaded TiO2 (Pt-MoOx/TiO2). Pt-MoOx/TiO2 was found to be superior to other supported Pt and transition-metal-loaded MoOx/TiO2 catalysts for the trimethylamine synthesis process.

Aylett, B. J.,Campbell, J. M.

, (1969)

Deoxygenation of primary amides to amines with pinacolborane catalyzed by Ca[N(SiMe3)2]2(THF)2

Gong, Mingliang,Guo, Chenjun,Jiang, Linhong,Luo, Yunjie,Yu, Chong

supporting information, p. 1201 - 1206 (2021/05/29)

Deoxygenative reduction of amides is a challenging but favorable synthetic method of accessing amines. In the presence of a catalytic amount of Ca[N(SiMe3)2]2(THF)2, pinacolborane (HBpin) could efficiently reduce a broad scope of amides, primary amides in particular, into corresponding amines. Functional groups and heteroatoms showed good tolerance in this process of transformation, and a plausible reaction mechanism was proposed.

Reduction of Amides to Amines with Pinacolborane Catalyzed by Heterogeneous Lanthanum Catalyst La(CH2C6H4NMe2- o)3@SBA-15

Guo, Chenjun,Zhang, Fangcao,Yu, Chong,Luo, Yunjie

supporting information, p. 13122 - 13135 (2021/08/31)

Hydroboration of amides is a useful synthetic strategy to access the corresponding amines. In this contribution, it was found that the supported lanthanum benzyl material La(CH2C6H4NMe2-o)3@SBA-15 was highly active for the hydroboration of primary, secondary, and tertiary amides to amines with pinacolborane. These reactions selectively produced target amines and showed good tolerance for functional groups such as -NO2, -halogen, and -CN, as well as heteroatoms such as S and O. This reduction procedure exhibited the recyclable and reusable property of heterogeneous catalysts and was applicable to gram-scale synthesis. The reaction mechanisms were proposed based on some control experiments and the previous literature. This is the first example of hydroborative reduction of amides to amines mediated by heterogeneous catalysts.

Electrochemical Reductive N-Methylation with CO2Enabled by a Molecular Catalyst

Rooney, Conor L.,Wu, Yueshen,Tao, Zixu,Wang, Hailiang

supporting information, p. 19983 - 19991 (2021/12/01)

The development of benign methylation reactions utilizing CO2 as a one-carbon building block would enable a more sustainable chemical industry. Electrochemical CO2 reduction has been extensively studied, but its application for reductive methylation reactions remains out of the scope of current electrocatalysis. Here, we report the first electrochemical reductive N-methylation reaction with CO2 and demonstrate its compatibility with amines, hydroxylamines, and hydrazine. Catalyzed by cobalt phthalocyanine molecules supported on carbon nanotubes, the N-methylation reaction proceeds in aqueous media via the chemical condensation of an electrophilic carbon intermediate, proposed to be adsorbed or near-electrode formaldehyde formed from the four-electron reduction of CO2, with nucleophilic nitrogenous reactants and subsequent reduction. By comparing various amines, we discover that the nucleophilicity of the amine reactant is a descriptor for the C-N coupling efficacy. We extend the scope of the reaction to be compatible with cheap and abundant nitro-compounds by developing a cascade reduction process in which CO2 and nitro-compounds are reduced concurrently to yield N-methylamines with high monomethylation selectivity via the overall transfer of 12 electrons and 12 protons.

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