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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:
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.

Signal Word

Danger

Hazard Statements

H228,H251,H290,H302,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 2: Flammable solids
Flammable solid
Hazardous rank III

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

164992-BULK:
164992-100G:
164992-2KG:
164992-10KG:
164992-500G:
164992-250G:
164992-1KG:
164992-5G:
164992-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3686
STBL1037
STBL4806
MKCT0508
STBL1239

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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
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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