Merck
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164992

Sigma-Aldrich

Sodium methoxide

reagent grade, 95%, powder

Synonym(s):
Sodium methylate
Linear Formula:
NaOCH3
CAS Number:
Molecular Weight:
54.02
Beilstein:
3592982
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

reagent grade

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 may be used as an alkali catalyst for the production of fatty acid methyl esters (biodiesel) from vegetable oils via transesterification.
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).

Packaging

2 kg in steel can
5 g in glass bottle
100, 500 g in steel can
1 kg in glass bottle

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 2

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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)
A review on biodiesel production using catalyzed transesterification
Leung DYC, et al
Applied Energy, 87(4), 1083-1095 (2010)
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
Harita Rao et al.
Nature protocols, 7(6), 1097-1112 (2012-05-12)
This protocol describes the detailed experimental procedure for the synthesis of an azide-modified uridine triphosphate analog and its effective incorporation into an oligoribonucleotide by in vitro transcription reactions. Furthermore, procedures for labeling azide-modified oligoribonucleotides post-transcriptionally with biophysical probes by copper(I)-catalyzed

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