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593-81-7

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593-81-7 Usage

Chemical Description

Trimethylamine hydrochloride is a salt of trimethylamine, a colorless gas with a fishy odor.

Chemical Properties

white to slightly cream crystalline powder

Uses

Different sources of media describe the Uses of 593-81-7 differently. You can refer to the following data:
1. In the manufacture of quaternary ammonium Compounds; as insect attractant; as warning agent for natural gas.
2. Trimethylamine hydrochloride is used in the manufacture of quaternary ammonium compounds, as insect attractant. It is used as a raw material for the synthesis of choline chloride, quaternary ammonium compounds, ion exchange resins. It acts as cationic starch reagents, phase transfer catalyst, oil field chemicals, warning agent for natural gas and flotation agent.
3. Trimethylamine hydrochloride is a precursor to prepare aluminium chloride- trimethylamine hydrochloride ionic liquid, which is commonly used in electrodeposition of aluminum wires. It is also used in the synthesis of trimethylamine gallane, trimethylamine-borane and azido-bridged perovskite-type metal-organic frameworks (MOFs).

Definition

ChEBI: A hydrochloride salt formed by reaction of equimolar amounts of trimethylamine and hydrogen chloride.

Flammability and Explosibility

Nonflammable

Purification Methods

The salt crystallises from CHCl3, EtOH or n-propanol, and is dried under vacuum. It also crystallises from *benzene/MeOH, MeOH/diethyl ether and is dried under vacuum over paraffin wax and H2SO4. It is kept over P2O5 as it is hygroscopic.[Beilstein 4 H 262, 4 I 419, 4 IV 138.]

Check Digit Verification of cas no

The CAS Registry Mumber 593-81-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 3 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 593-81:
(5*5)+(4*9)+(3*3)+(2*8)+(1*1)=87
87 % 10 = 7
So 593-81-7 is a valid CAS Registry Number.
InChI:InChI=1/C3H9N.ClH/c1-4(2)3;/h1-3H3;1H

593-81-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (L04718)  Trimethylamine hydrochloride, 98%   

  • 593-81-7

  • 50g

  • 165.0CNY

  • Detail
  • Alfa Aesar

  • (L04718)  Trimethylamine hydrochloride, 98%   

  • 593-81-7

  • 250g

  • 496.0CNY

  • Detail
  • Aldrich

  • (T72761)  Trimethylaminehydrochloride  98%

  • 593-81-7

  • T72761-25G

  • 153.27CNY

  • Detail
  • Aldrich

  • (T72761)  Trimethylaminehydrochloride  98%

  • 593-81-7

  • T72761-100G

  • 314.73CNY

  • Detail
  • Aldrich

  • (T72761)  Trimethylaminehydrochloride  98%

  • 593-81-7

  • T72761-500G

  • 981.63CNY

  • Detail
  • Vetec

  • (V900705)  Trimethylaminehydrochloride  Vetec reagent grade, 98%

  • 593-81-7

  • V900705-500G

  • 150.64CNY

  • Detail

593-81-7SDS

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 hydrochloride

1.2 Other means of identification

Product number -
Other names Methanamine, N,N-dimethyl-, hydrochloride

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:593-81-7 SDS

593-81-7Synthetic route

trimethylamine-N-oxide
1184-78-7

trimethylamine-N-oxide

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

N,N-dimethyl-formamide

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
for 24h; Ambient temperature;A 97%
B 98%
trimethylamine-N-oxide
1184-78-7

trimethylamine-N-oxide

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

A

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 24h; Ambient temperature;A 97%
B 98%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide dimethyl acetal With [1,4-bis(diphenylphosphino)butane](1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen In methanol at 25℃; under 30003 Torr; Autoclave;
Stage #2: With hydrogenchloride In methanol; water Reagent/catalyst;
96%
formaldehyd
50-00-0

formaldehyd

dimethyl amine
124-40-3

dimethyl amine

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
With oxalic acid at 100 - 120℃; Eschweiler-Clarke methylation;84%
methanol
67-56-1

methanol

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
Stage #1: methanol With ammonium hydroxide; Ag/TiO2 at 25℃; for 10h; UV-irradiation;
Stage #2: With hydrogenchloride In water
80%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran for 24h; Ambient temperature;72%
Stage #1: N,N-dimethyl-formamide With tris(bis(trimethylsilyl)amido)lanthanum(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene at 25℃; for 1h; Inert atmosphere; Glovebox;
Stage #2: With hydrogenchloride In methanol at 0℃;
50%
Stage #1: N,N-dimethyl-formamide With tris((4,4-dimethyl-2-oxazolinyl)phenylborate) MgMe; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Stage #2: With hydrogenchloride
18%
cyclopropanesulfonyl-1-d chloride
146475-62-9

cyclopropanesulfonyl-1-d chloride

isopropyl alcohol
67-63-0

isopropyl alcohol

trimethylamine
75-50-3

trimethylamine

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

propan-2-yl cyclopropanesulfonate
146475-51-6

propan-2-yl cyclopropanesulfonate

C

N,N-dimethylcyclopropanesulfonamide-1-d

N,N-dimethylcyclopropanesulfonamide-1-d

Conditions
ConditionsYield
In dichloromethane at 25℃; for 36h;A n/a
B 11.7%
C 27.4%
N,N-dimethoxyamine
88470-26-2

N,N-dimethoxyamine

trimethylamine
75-50-3

trimethylamine

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

tetramethlyammonium chloride
75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
With tert-butylhypochlorite In diethyl ether 1) -78 deg C, 0.5 h, 2) -8 deg C, 24 h;A 15.7%
B 22.8%
Cl2B-N(CH3)2*N(CH3)3

Cl2B-N(CH3)2*N(CH3)3

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

A

Bis(trimethylsilyl)aminochlorodimethylaminoboran
32882-72-7

Bis(trimethylsilyl)aminochlorodimethylaminoboran

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
In benzene stirring for 1 week in dry benzene; sepn. of trimethylamine hydrochloride and benzene;A 16%
B n/a
In benzene stirring for 1 week in dry benzene; sepn. of trimethylamine hydrochloride and benzene;A 16%
B n/a
toluene
108-88-3

toluene

methyl 3-chloropropionate
6001-87-2

methyl 3-chloropropionate

trimethylamine
75-50-3

trimethylamine

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

(2-methoxycarbonylethyl)trimethylammonium chloride
16332-33-5

(2-methoxycarbonylethyl)trimethylammonium chloride

Conditions
ConditionsYield
at -5℃;
methanol
67-56-1

methanol

methyl 3-chloropropionate
6001-87-2

methyl 3-chloropropionate

trimethylamine
75-50-3

trimethylamine

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

(2-methoxycarbonylethyl)trimethylammonium chloride
16332-33-5

(2-methoxycarbonylethyl)trimethylammonium chloride

Conditions
ConditionsYield
at -5℃;
diethyl ether
60-29-7

diethyl ether

methyl 3-chloropropionate
6001-87-2

methyl 3-chloropropionate

trimethylamine
75-50-3

trimethylamine

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

(2-methoxycarbonylethyl)trimethylammonium chloride
16332-33-5

(2-methoxycarbonylethyl)trimethylammonium chloride

Conditions
ConditionsYield
at -5℃;
3-Chloropropionitrile
542-76-7

3-Chloropropionitrile

ethanol
64-17-5

ethanol

trimethylamine
75-50-3

trimethylamine

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

acrylonitrile
107-13-1

acrylonitrile

piperidine
110-89-4

piperidine

trimethyl-(3-oxo-3-phenyl-propenyl)-ammonium; chloride
120225-40-3

trimethyl-(3-oxo-3-phenyl-propenyl)-ammonium; chloride

A

1-phenyl-3-(piperidin-1-yl)prop-2-en-1-one
4452-12-4

1-phenyl-3-(piperidin-1-yl)prop-2-en-1-one

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant;
piperidine
110-89-4

piperidine

trans-β-(p-nitrophenylsulfinyl)vinyltrimethylammonium chloride
120225-39-0

trans-β-(p-nitrophenylsulfinyl)vinyltrimethylammonium chloride

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

p-nitrophenyl β-piperidylaminovinyl sulfoxide

p-nitrophenyl β-piperidylaminovinyl sulfoxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; Rate constant; further solvent;
piperidine
110-89-4

piperidine

trans-β-(p-nitrophenylsulfonyl)-vinyltrimethylammonium chloride
110065-18-4

trans-β-(p-nitrophenylsulfonyl)-vinyltrimethylammonium chloride

A

β-piperidyl aminovinyl sulfone
107415-63-4

β-piperidyl aminovinyl sulfone

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant;
methanol
67-56-1

methanol

benzyltrimethylammonium chloride
56-93-9

benzyltrimethylammonium chloride

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

C

toluene
108-88-3

toluene

D

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
at 30℃; for 2h; Irradiation; Further byproducts given;A 77 % Chromat.
B 32 % Chromat.
C 27 % Chromat.
D 45 % Chromat.
With water at 30℃; for 2h; Irradiation; Further byproducts given;A 77 % Chromat.
B 10 % Chromat.
C 27 % Chromat.
D 45 % Chromat.
at 30℃; for 2h; Irradiation; Further byproducts given;A 77 % Chromat.
B 10 % Chromat.
C 27 % Chromat.
D 45 % Chromat.
methanol
67-56-1

methanol

(3,5-dimethoxybenzyl)trimethylammonium chloride
26050-72-6

(3,5-dimethoxybenzyl)trimethylammonium chloride

A

1,3-dimethoxy-5-methylbenzene
4179-19-5

1,3-dimethoxy-5-methylbenzene

B

1-methylmethoxy-3,5-dimethoxybenzene
73569-69-4

1-methylmethoxy-3,5-dimethoxybenzene

C

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

D

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
at 30℃; for 2h; Irradiation;A 46 % Chromat.
B 12 % Chromat.
C 23 % Chromat.
D 77 % Chromat.
benzyltrimethylammonium chloride
56-93-9

benzyltrimethylammonium chloride

A

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

C

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

D

toluene
108-88-3

toluene

E

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With water In water at 30℃; for 2h; Mechanism; Irradiation; 253.7 nm;A 23 % Chromat.
B 77 % Chromat.
C 10 % Chromat.
D 27 % Chromat.
E 45 % Chromat.
benzyltrimethylammonium chloride
56-93-9

benzyltrimethylammonium chloride

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

C

toluene
108-88-3

toluene

D

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With water at 30℃; for 2h; Irradiation; Further byproducts given;A 77 % Chromat.
B 10 % Chromat.
C 27 % Chromat.
D 45 % Chromat.
vinylsulfonyl chloride
6608-47-5

vinylsulfonyl chloride

trimethylamine
75-50-3

trimethylamine

A

2-(N,N,N-trimethylamino)ethanesulfonate
7465-57-8

2-(N,N,N-trimethylamino)ethanesulfonate

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

C

Ethenesulfonic acid; compound with trimethyl-amine
58928-02-2

Ethenesulfonic acid; compound with trimethyl-amine

Conditions
ConditionsYield
With potassium chloride; water In 1,2-dimethoxyethane at 1℃; Rate constant; Product distribution;
trans-1-propene-1-sulfonyl chloride
98821-29-5

trans-1-propene-1-sulfonyl chloride

trimethylamine
75-50-3

trimethylamine

A

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B

C6H15NO3S
94129-00-7

C6H15NO3S

C

(E)-Propene-1-sulfonic acid; compound with trimethyl-amine

(E)-Propene-1-sulfonic acid; compound with trimethyl-amine

Conditions
ConditionsYield
With potassium chloride; water In 1,2-dimethoxyethane at 1℃; Rate constant; Product distribution;
formaldehyd
50-00-0

formaldehyd

ammonium chloride

ammonium chloride

A

formic acid
64-18-6

formic acid

B

carbon dioxide
124-38-9

carbon dioxide

C

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

D

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

hydroxymethyl-trimethyl-ammonium; chloride
29124-44-5

hydroxymethyl-trimethyl-ammonium; chloride

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

water
7732-18-5

water

hydroxymethyl-trimethyl-ammonium; chloride
29124-44-5

hydroxymethyl-trimethyl-ammonium; chloride

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
at 25℃; Geschwindigkeit der Zersetzung in Abhaengigkeit vom pH;
water
7732-18-5

water

ethoxycarbonyl-trimethyl-ammonium; chloride

ethoxycarbonyl-trimethyl-ammonium; chloride

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

polyoxymethylene

polyoxymethylene

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
With ammonium chloride at 120 - 170℃; analog lassen sich andere Ammoniumsalze anwenden;
ethanol
64-17-5

ethanol

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

platinum black

platinum black

A

cyclohexane
110-82-7

cyclohexane

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

Conditions
ConditionsYield
at 20 - 25℃; under 1520 - 2280 Torr; Hydrogenation;
water
7732-18-5

water

ethylsulfanylcarbonyl-trimethyl-ammonium; chloride

ethylsulfanylcarbonyl-trimethyl-ammonium; chloride

A

carbon dioxide
124-38-9

carbon dioxide

B

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

C

ethanethiol
75-08-1

ethanethiol

oxirane
75-21-8

oxirane

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

choline chloride
67-48-1

choline chloride

Conditions
ConditionsYield
With sodium hydroxide at 24.9℃; Thermodynamic data; ΔrH1;100%
With sodium hydroxide at 24.9℃;100%
trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

triphenylbismuthane
603-33-8

triphenylbismuthane

bismuth(III) chloride
7787-60-2

bismuth(III) chloride

Conditions
ConditionsYield
byproducts: benzene; heating (CH3)3NHCl with triphenyl bismuth at 130°C (also in presence of ethanol);;100%
byproducts: benzene; heating (CH3)3NHCl with triphenyl bismuth at 130°C (also in presence of ethanol);;100%
Hf(C5(CH3)5)2(CH2CH(CH3)CH2)
105931-10-0

Hf(C5(CH3)5)2(CH2CH(CH3)CH2)

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

(Hf(C5(CH3)5)2(CH2CH(CH3)2))Cl
156278-76-1

(Hf(C5(CH3)5)2(CH2CH(CH3)2))Cl

Conditions
ConditionsYield
In dichloromethane-d2 to Hf-compd. and (HNMe3)Cl CD2Cl2 is vacuum transferred at -78°C(N2); tube is allowed to warm to 23°C and to stand with occasional shaking for 4 h;100%
tris(trimethylsilylmethyl)gallium
72708-53-3

tris(trimethylsilylmethyl)gallium

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

A

tetramethylsilane
75-76-3

tetramethylsilane

B

Ga(3+)*2CH2Si(CH3)3(1-)*Cl(1-)*N(CH3)3=Ga(CH2Si(CH3)3)2Cl*N(CH3)3
72709-13-8

Ga(3+)*2CH2Si(CH3)3(1-)*Cl(1-)*N(CH3)3=Ga(CH2Si(CH3)3)2Cl*N(CH3)3

Conditions
ConditionsYield
In benzene under N2 or Ar mixt. in stoich. quantity stirred at room temp. for 2 h; volatile components removed by vac. distn., crude product sublimed at 32°C; elem. anal.;A 100%
B 98.5%
1,2-dicarba-closo-dodecaborane(12)
16872-09-6

1,2-dicarba-closo-dodecaborane(12)

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

B9H11C2(2-)*2(CH3)3NH(1+)=[(CH3)3NH]2[B9H11C2]

B9H11C2(2-)*2(CH3)3NH(1+)=[(CH3)3NH]2[B9H11C2]

Conditions
ConditionsYield
With KOH In ethanol; water B compd. (34.7 mmol) added to EtOH soln. of KOH (104 mmol), refluxed for4 h (TLC control), evapd., dissolved (H2O), excess Me3NHCl added; ppt. filtered off, dried;100%
trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

tetramethlyammonium chloride
75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;99%
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;
dimethyl η5-cyclopentadienyl η5-pentamethylcyclopentadienyl zirconium
81476-76-8

dimethyl η5-cyclopentadienyl η5-pentamethylcyclopentadienyl zirconium

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

[Zr(η5-cyclopentadienyl)(η5-pentamethylcyclopentadienyl)(CH3)Cl]

[Zr(η5-cyclopentadienyl)(η5-pentamethylcyclopentadienyl)(CH3)Cl]

Conditions
ConditionsYield
In tetrahydrofuran stirring 4 days at room temp., evapn.; extn. (toluene), filtration, evapn., purity: 95% (NMR), analytically pure material obtained by repeated recrystn. (toluene/hexanes), elem. anal.;99%
In tetrahydrofuran
[U(N(CH2CH2NSiMe2But)2(CH2CH2NSiMeButCH2))]
249284-51-3

[U(N(CH2CH2NSiMe2But)2(CH2CH2NSiMeButCH2))]

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

U[N(CH2CH2NSi(CH3)2(C(CH3)3))3]Cl
183054-80-0

U[N(CH2CH2NSi(CH3)2(C(CH3)3))3]Cl

Conditions
ConditionsYield
In not given99%
8,8'-μ-methylcarboniodioxy-bis(1,2-dicarbollido)-3-cobalt(1-)ate
31422-93-2

8,8'-μ-methylcarboniodioxy-bis(1,2-dicarbollido)-3-cobalt(1-)ate

water
7732-18-5

water

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

trimethyl ammonium 8,8'-dihydroxy-bis(1,2-dicarbollido)-3-cobalt(1-)ate

trimethyl ammonium 8,8'-dihydroxy-bis(1,2-dicarbollido)-3-cobalt(1-)ate

Conditions
ConditionsYield
With HCl In ethanol; water byproducts: CH3COOH; concd. HCl was added to suspn. of Co complex in aq. EtOH at 80°C;mixt. was shaken within ca. 30 min; Me3N*HCl in H2O was added; cooled overnight; septd.; crystd. at 80°C from MeCN by slow addition of CHCl3; cooled overnight; elem. anal.;99%
lithium aluminium tetrahydride
16853-85-3

lithium aluminium tetrahydride

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

trimethylamine
75-50-3

trimethylamine

bis(trimethylamine)alane
17211-58-4, 50981-97-0, 60934-33-0

bis(trimethylamine)alane

Conditions
ConditionsYield
In diethyl ether under N2 or Ar; LiAlH4 and Me3NHCl cooled to -78°C; Et2O added; stirred; warmed to room temp.; 1 h; solvent removed in vac.; NMe3 gas condensed; stirred for 20 min; sublimed at 50°C into flask at -78°C;98%
cesium carba-closo-dodecaborate

cesium carba-closo-dodecaborate

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

CB11Cl12(1-)*C3H9N*H(1+)

CB11Cl12(1-)*C3H9N*H(1+)

Conditions
ConditionsYield
Stage #1: cesium carba-closo-dodecaborate With antimonypentachloride at 180℃; for 168h; Inert atmosphere;
Stage #2: trimethylamine hydrochloride In water-d2
98%
formaldehyd
50-00-0

formaldehyd

C4H24B22N2(2-)*2Cs(1+)

C4H24B22N2(2-)*2Cs(1+)

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

C5H25B22N2(1-)*C3H9N*H(1+)

C5H25B22N2(1-)*C3H9N*H(1+)

Conditions
ConditionsYield
Stage #1: formaldehyd With hydrogenchloride In 1,4-dioxane for 0.333333h; Inert atmosphere;
Stage #2: C4H24B22N2(2-)*2Cs(1+) In 1,4-dioxane; ethyl acetate for 3h; Inert atmosphere;
Stage #3: trimethylamine hydrochloride In 1,4-dioxane; water; ethyl acetate Inert atmosphere;
98%
di-μ-chlorobis[chloro(N,N'-bis-(2,6-(diisopropyl)phenyl)imidazol-2-ylidene)palladium]

di-μ-chlorobis[chloro(N,N'-bis-(2,6-(diisopropyl)phenyl)imidazol-2-ylidene)palladium]

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

C27H36Cl3N2Pd(1-)*C3H9N*H(1+)

C27H36Cl3N2Pd(1-)*C3H9N*H(1+)

Conditions
ConditionsYield
In chloroform at 50℃; for 15h;98%
1.2H4N2*C5H19B9NS(1-)*H(1+)

1.2H4N2*C5H19B9NS(1-)*H(1+)

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

C3H9N*C5H19B9NS(1-)*H(1+)

C3H9N*C5H19B9NS(1-)*H(1+)

Conditions
ConditionsYield
In water97%
C4H24B22N2(2-)*2Cs(1+)

C4H24B22N2(2-)*2Cs(1+)

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

C4H24B22N2(1-)*C3H9N*H(1+)

C4H24B22N2(1-)*C3H9N*H(1+)

Conditions
ConditionsYield
In water Inert atmosphere;97%
C4H24B22N2(2-)*2Cs(1+)

C4H24B22N2(2-)*2Cs(1+)

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

2C3H9N*C4H24B22N2(2-)*2H(1+)

2C3H9N*C4H24B22N2(2-)*2H(1+)

Conditions
ConditionsYield
In water Solvent;97%
1,2-diphenyl-3-fluoro-1,2-closo-dodecacarborane
634196-69-3

1,2-diphenyl-3-fluoro-1,2-closo-dodecacarborane

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

[HN(CH3)3][3-fluoro-7,8-diphenyl-7,8-nido-undecacarborane]

[HN(CH3)3][3-fluoro-7,8-diphenyl-7,8-nido-undecacarborane]

Conditions
ConditionsYield
With KOH; CO2 In ethanol N2, a soln. of B compd. refluxed with KOH for 72 h, treated wit CO2, volatiles removed (vac.), dissolved (H2O), a soln. of N compd. (excess) added; ppt. extrd. (CH2Cl2), dried (MgSO4), evapd., recrystd. (CH2Cl2); elem. anal.;96.1%
dipotassium 7-(2-carboxybenzoylaminoethyl)-7,8-dicarba-nido-undecaborate(10)

dipotassium 7-(2-carboxybenzoylaminoethyl)-7,8-dicarba-nido-undecaborate(10)

water
7732-18-5

water

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

bis(trimethylammonium) 7-(2-carboxybenzoylaminoethyl)-7,8-dicarba-nido-undecaborate(10) monohydrate

bis(trimethylammonium) 7-(2-carboxybenzoylaminoethyl)-7,8-dicarba-nido-undecaborate(10) monohydrate

Conditions
ConditionsYield
In not given cation metathesis react. of B compd. and Me3NHCl; recrystd. from water-EtOH: elem. anal.;96%
1,2-(C6H5CH2)2-1,2-C2B10H10
24034-98-8

1,2-(C6H5CH2)2-1,2-C2B10H10

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

[Me3NH][7,8-(C6H5CH2)2-nido-7,8-C2B9H10]

[Me3NH][7,8-(C6H5CH2)2-nido-7,8-C2B9H10]

Conditions
ConditionsYield
With KOH; HCl In methanol; water N2-atmosphere; stirring (0°C to room temp., 30 min), refluxing (overnight), evapn. H2O and HCl addn., pptn. on Me3NHCl addn.; filtering, washing (H2O), drying (vac.);96%
2-(2-trimethylsilylethynyl)-3,4-(o-carborano)-2,5-dihydrofuran

2-(2-trimethylsilylethynyl)-3,4-(o-carborano)-2,5-dihydrofuran

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

2-ethynyl-3,4-(dodecahydro-nido-undecadicarbaborato)-2,5-dihydrofuran*trimethylammonium

2-ethynyl-3,4-(dodecahydro-nido-undecadicarbaborato)-2,5-dihydrofuran*trimethylammonium

Conditions
ConditionsYield
Stage #1: 2-(2-trimethylsilylethynyl)-3,4-(o-carborano)-2,5-dihydrofuran With sodium hydroxide In methanol for 1h; Reflux;
Stage #2: trimethylamine hydrochloride With hydrogenchloride In water
96%
potassium titanyl oxalate

potassium titanyl oxalate

10K(1+)*P2W17O61(10-)*99H2O = K10P2W17O61*99H2O

10K(1+)*P2W17O61(10-)*99H2O = K10P2W17O61*99H2O

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

TiOP2W17O61(8-)*8(CH3)3NH(1+) = ((CH3)3NH)8TiOP2W17O61

TiOP2W17O61(8-)*8(CH3)3NH(1+) = ((CH3)3NH)8TiOP2W17O61

Conditions
ConditionsYield
In water a soln. of W-compound in NaOAc buffer (pH 5.25) was treated with Ti-compound at 65°C; stirred for 10 min; addn. of Me3NHCl at 25°C; precipitate washed (water), dried;;95%
(Me3NH)(1-H-CB9Cl9)

(Me3NH)(1-H-CB9Cl9)

benzyl bromide
100-39-0

benzyl bromide

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

(Me3NH)(1-C6H5CH2-CB9Cl9)

(Me3NH)(1-C6H5CH2-CB9Cl9)

Conditions
ConditionsYield
With n-BuLi; NaOH In tetrahydrofuran; diethyl ether; water byproducts: Me3N; to THF soln. (Me3NH)(1-H-CB9Cl9) was slowly added n-BuLi in hexane at 0°C, mixt. was stirred at room temp. for 4 h and refluxed for 4 h,Me3N was removed, THF soln. PhCH2Br was added at 0°C, soln. was stirred for 4 h at room temp. and; refluxed overnight, solvent was removed, residue was treated with 5 % aq. NaOH, extd. with Et2O and treated with aq. Me3NHCl;95%
1.2-dicarba-closo-dodecaborano-tetrahydrofurane
19610-39-0

1.2-dicarba-closo-dodecaborano-tetrahydrofurane

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

[Me3NH][μ-7,8-CH2OCH2-7,8-C2B9H10]

[Me3NH][μ-7,8-CH2OCH2-7,8-C2B9H10]

Conditions
ConditionsYield
With KOH In ethanol (N2); KOH added to a soln. of B compd., refluxed overnight; solvent-removed, dissolved in H2O, pptd. ((CH3)3NHCl), filtered, washed (H2O), dried (vac.); elem. anal.;95%
C4H17B9NS(1-)*1.4H4N2*H(1+)

C4H17B9NS(1-)*1.4H4N2*H(1+)

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

C4H17B9NS(1-)*C3H9N*H(1+)

C4H17B9NS(1-)*C3H9N*H(1+)

Conditions
ConditionsYield
In water95%
1,12-dibromododecane
3344-70-5

1,12-dibromododecane

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

N,N,N,N',N',N'-hexamethyldodecane-1,12-diammonium dibromide
1674-82-4

N,N,N,N',N',N'-hexamethyldodecane-1,12-diammonium dibromide

Conditions
ConditionsYield
With sodium hydroxide In methanol for 12h; Heating / reflux;94%
1-Me2NCH2CH2-1,2-C2B10H11
802892-30-4

1-Me2NCH2CH2-1,2-C2B10H11

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

7-Me2N(H)CH2CH2-7,8-C2B9H11

7-Me2N(H)CH2CH2-7,8-C2B9H11

Conditions
ConditionsYield
With KOH In water (N2); addn. of methanol to a mixt. of boron compd. and KOH with stirringat 0°C, warming to room temp., stirring for 30 min, reflux overn ight, evapn., addn. of water, addn. of aq. ammonium salt; filtration, washing ppt. with water, n-hexane, drying in vac., recrystn.(ethanol); elem. anal.;94%
[Me3NH][1-H-CB11Cl11]

[Me3NH][1-H-CB11Cl11]

trimethylamine hydrochloride
593-81-7

trimethylamine hydrochloride

ethyl iodide
75-03-6

ethyl iodide

Me3NH[EthylCB11Cl11]

Me3NH[EthylCB11Cl11]

Conditions
ConditionsYield
With tert-butoxide In tert-butyl alcohol a soln. of B-contg. compd. in tert-butanol was treated with KOBu(t) (3.5equivs.) for 30 min at 30°C; the volatiles were removed; the res idue was redissolved in tert-butanol and treated with EtI (7 equivs.) at30°C for 1 h; the volatiles were removed, the residue dissolved in H2O; addn. of concd. HCl (2 drops) and Me3NHCl (2.5 equivs.); mass- and (11)B NMR spectra studies;94%

593-81-7Relevant articles and documents

Migration of methyl groups between aliphatic amines in water

Callahan, Brian P.,Wolfenden, Richard

, p. 310 - 311 (2003)

Glycine undergoes spontaneous decarboxylation in dilute aqueous solution at elevated temperatures to form methylamine. During that process, we noticed the appearance of dimethylamine and trimethylamine in smaller amounts that increased gradually with time. These observations suggested the existence of disproportionation reactions of methylamines in water, for which there appears to be no direct precedent in the literature. Every member of the methylamine series is found to yield other members of the methylamine series. When the total concentration of amine was held constant and the rate of reaction was examined as a function of changing pH using the amine itself as the buffer, the initial rate of appearance of the products was found to reach a maximum when the conjugate acid and the conjugate base were present at equivalent concentrations. Near this equivalence point, the rate of reaction varied with pH as expected for a second-order reaction between the protonated and the unprotonated species. Under similar conditions, methyl groups were also found to migrate between the nitrogen atoms of N,N-dimethyl-1,3-propanediamine in a first-order process. With dimethylamine as a common acceptor, tetramethylammonium ion at ambient temperature. Copyright

Manganese-Catalyzed Hydroborations with Broad Scope

Ghosh, Pradip,Jacobi von Wangelin, Axel

supporting information, p. 16035 - 16043 (2021/06/16)

Reductive transformations of easily available oxidized matter are at the heart of synthetic manipulation and chemical valorization. The applications of catalytic hydrofunctionalization benefit from the use of liquid reducing agents and operationally facile setups. Metal-catalyzed hydroborations provide a highly prolific platform for reductive valorizations of stable C=X electrophiles. Here, we report an especially facile, broad-scope reduction of various functions including carbonyls, carboxylates, pyridines, carbodiimides, and carbonates under very mild conditions with the inexpensive pre-catalyst Mn(hmds)2. The reaction could be successfully applied to depolymerizations.

La[N(sime3)2]3-catalyzed deoxygenative reduction of amides with pinacolborane. scope and mechanism

Barger, Christopher J.,Dicken, Rachel D.,Weidner, Victoria L.,Motta, Alessandro,Lohr, Tracy L.,Marks, Tobin J.

supporting information, p. 8019 - 8028 (2020/05/27)

Tris[N,N-bis(trimethylsilyl)amide]lanthanum (LaNTMS) is an efficient and selective homogeneous catalyst for the deoxygenative reduction of tertiary and secondary amides with pinacolborane (HBpin) at mild temperatures (25-60 °C). The reaction, which yields amines and O(Bpin)2, tolerates nitro, halide, and amino functional groups well, and this amide reduction is completely selective, with the exclusion of both competing inter- and intramolecular alkene/alkyne hydroboration. Kinetic studies indicate that amide reduction obeys an unusual mixed-order rate law which is proposed to originate from saturation of the catalyst complex with HBpin. Kinetic and thermodynamic studies, isotopic labeling, and DFT calculations using energetic span analysis suggest the role of a [(Me3Si)2N]2La-OCHR(NR′2)[HBpin] active catalyst, and hydride transfer is proposed to be ligand-centered. These results add to the growing list of transformations that commercially available LaNTMS is competent to catalyze, further underscoring the value and versatility of lanthanide complexes in homogeneous catalysis.

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