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426318

Sigma-Aldrich

Tetramethylammonium hydroxide solution

ACS reagent

Synonym(s):

N,N,N-trimethyl-methanaminium hydroxide, TMAH, TMAOH

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About This Item

Linear Formula:
(CH3)4N(OH)
CAS Number:
75-59-2
Molecular Weight:
91.15
Beilstein:
3558708
MDL number:
MFCD00008280
UNSPSC Code:
12352100
PubChem Substance ID:
24866695
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

form

liquid

concentration

1.0 M±0.02 M in H2O

ign. residue

≤5 ppm

color

APHA: ≤10

refractive index

n20/D 1.3497

bp

100 °C

density

1.005 g/mL at 25 °C

anion traces

chloride (Cl-): ≤0.03%

cation traces

K: ≤2 ppm
Na: ≤2 ppm

SMILES string

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

InChI

1S/C4H12N.H2O/c1-5(2,3)4;/h1-4H3;1H2/q+1;/p-1

InChI key

WGTYBPLFGIVFAS-UHFFFAOYSA-M

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Application

Tetramethylammonium hydroxide solution can be used as:
  • A reagent in the organocatalyzed photoinduced Birch reduction of arenes to 1,4-cyclohexadienes.
  • A catalyst to synthesize 1,2-dihydro-1-arylnaphtho-oxazine-3-one derivatives via one-pot three-component condensation reaction of 2-naphthol, aromatic aldehydes, and urea.
  • A peptizing agent for magnetite nanoparticles to promote repulsive stabilization forces.
  • A template in the hydrothermal synthesis of hierarchical zeolite T aggregates with different sizes.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B - STOT RE 2 Dermal - STOT SE 2

Target Organs

Central nervous system, Liver,thymus

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW5220
MKCV2454
MKCS1253
MKCQ2224
MKCN0479

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Tetraethylammonium hydroxide solution ~1.0 M (CH3CH2)4NOH in H2O, electrochemical grade

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Tetraethylammonium hydroxide solution

Lulu Xie et al.
Science (New York, N.Y.), 342(6156), 373-377 (2013-10-19)
The conservation of sleep across all animal species suggests that sleep serves a vital function. We here report that sleep has a critical function in ensuring metabolic homeostasis. Using real-time assessments of tetramethylammonium diffusion and two-photon imaging in live mice
L Lemée et al.
Bioresource technology, 117, 234-241 (2012-05-24)
Lignocellulosic biomass was submitted to a biological pretreatment prior to a catalytic hydroliquefaction in order to produce biofuel. The biodegradation process was conducted over 3 months in a reactor under controlled conditions. During the biodegradation process the organic matter was
N Kodiah Beyeh et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(18), 5552-5557 (2012-04-11)
The non-covalent interactions of different upper-rim-substituted C(2)-resorcinarenes with tetramethylammonium salts were analyzed in the gas phase in an Electrospray Ionization Fourier-transform ion-cyclotron-resonance (ESI-FTICR) mass spectrometer and by (1)H NMR titrations. The order of binding strengths of the hosts towards the
M R Faria et al.
International journal of pharmaceutics, 446(1-2), 183-190 (2013-02-21)
This work assesses the characteristics of magnetoliposomes of soybean phosphatidylcholine (SPC):cholesterol (Chol) loaded with superparamagnetic iron oxide nanoparticles (IONPs) stabilized with tetramethylammonium hydroxide (TMAOH) and their capacity to enhance magnetic resonance imaging (MRI) contrast. Magnetoliposomes of SPC were used for
Nadia Nabil Haj-Yasein et al.
Glia, 60(6), 867-874 (2012-03-16)
Little is known about the physiological roles of aquaporin-4 (AQP4) in the central nervous system. AQP4 water channels are concentrated in endfeet membranes of astrocytes but also localize to the fine astrocytic processes that abut central synapses. Based on its
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