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164992

Sigma-Aldrich

Sodium methoxide

reagent grade, 95%, powder

Synonym(s):

Sodium methylate

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About This Item

Linear Formula:
NaOCH3
CAS Number:
124-41-4
Molecular Weight:
54.02
Beilstein/REAXYS Number:
3592982
EC Number:
204-699-5
MDL number:
MFCD00012179
UNSPSC Code:
12352100
PubChem Substance ID:
24850111
NACRES:
NA.21

grade

reagent grade

Quality Level

200

vapor density

1.1 (vs air)

vapor pressure

50 mmHg ( 20 °C)

assay

95%

form

powder

autoignition temp.

851 °F

expl. lim.

36 %

SMILES string

[Na+].C[O-]

InChI

1S/CH3O.Na/c1-2;/h1H3;/q-1;+1

InChI key

WQDUMFSSJAZKTM-UHFFFAOYSA-N

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General description

Sodium methoxide is a sodium alkoxide. Its reaction with unactivated aryl bromides in the presence of copper catalyst under various reaction conditions has been studied. It reacts with aryl halides in the presence of a palladium catalyst in DMF to afford arenes.

Application

Sodium methoxide has been used in the preparation of 5-(3-azidopropyl) uridine. It may be used in the synthesis of methyl 2-cyano-lup-3-hydroxy-2-en-28-oate (CN-BA), a 2-cyano derivative of betulinic acid (BA).
Sodium methoxide may be used as an alkali catalyst for the production of fatty acid methyl esters (biodiesel) from vegetable oils via transesterification.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Flam. Sol. 1 - Met. Corr. 1 - Self-heat. 1 - Skin Corr. 1A

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 2

flash_point_f

91.4 °F - closed cup

flash_point_c

33 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6353
STBK0995
MKCQ2601
STBK4122
MKCP0907

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A review on biodiesel production using catalyzed transesterification
Leung DYC, et al
Applied Energy, 87(4), 1083-1095 (2010)
Production of biodiesel through optimized alkaline-catalyzed transesterification of rapeseed oil.
Rashid U and Anwar F
Fuel: The Science and Technology of Fuel and Energy, 87(3), 265-273 (2008)
Palladium hydrides in organic synthesis. Reduction of aryl halides by sodium methoxide catalyzed by tetrakis (triphenylphosphine) palladium.
Zask A and Helquist P.
The Journal of Organic Chemistry, 43(8), 1619-1620 (1978)
Sudhakar Chintharlapalli et al.
Carcinogenesis, 28(11), 2337-2346 (2007-08-29)
Betulinic acid (BA) is a phytochemical triterpenoid acid from bark extracts and is cytotoxic to cancer cells and tumors. We modified the A-ring of BA to give a 2-cyano-1-en-3-one moiety and the effects of the 2-cyano-lup-1-en-3-oxo-20-oic acid (CN-BA), 2-cyano derivative
The copper catalysed reaction of sodium methoxide with aryl bromides. A mechanistic study leading to a facile synthesis of anisole derivatives.
Aalten HL, et al.
Tetrahedron, 45(17), 5565-5578 (1989)
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