Sodium Methoxide

Base Information

• Chemical Name: Sodium Methoxide
• CAS No.: 124-41-4
• Deprecated CAS: 27419-20-1,879636-47-2,1633026-84-2,879636-47-2
• Molecular Formula: CH3NaO
• Molecular Weight: 54.024
• Hs Code.: 2905.19 Oral rat LD50: 2037 mg/kg
• European Community (EC) Number: 204-699-5
• ICSC Number: 0771
• UN Number: 1431
• UNII: IG663U5EMC
• DSSTox Substance ID: DTXSID8027030
• Nikkaji Number: J2.934C
• Wikipedia: Sodium methoxide,Sodium_methoxide
• Wikidata: Q414384
• Mol file: 124-41-4.mol

Synonyms:Alcohol, Methyl;Alcohol, Wood;Carbinol;Methanol;Methoxide, Sodium;Methyl Alcohol;Sodium Methoxide;Wood Alcohol

Chemical Property of Sodium Methoxide

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 50 mm Hg ( 20 °C)
• Melting Point: -98 °C
• Refractive Index: 1.3700
• Boiling Point: 48.1 °C at 760 mmHg
• PKA: 15.17[at 20 ℃]
• Flash Point: 11.1 °C
• PSA: 23.06000
• Density: 0.97 g/mL at 20 °C
• LogP: 0.04670
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with ethanol, methanol, fats and esters.Immiscible with
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 54.00815900
• Heavy Atom Count: 3
• Complexity: 4.8
• Transport DOT Label: Spontaneously Combustible Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Sodium methoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T,C
• Hazard Codes: F,T,C
• Statements: 11-23/24/25-34-39/23/24/25-36/38-14-36/37/38-22-10
• Safety Statements: 8-16-26-43-45-7-36/37-7/8-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metal Alkoxides
• Canonical SMILES: C[O-].[Na+]
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema, but only after initial corrosive effects on eyes and/or airways have become manifest.
• Uses: 1. Sodium methoxide can be used as alkaline condensing agent and catalyst in organic synthesis. It can be used to synthesize perfumes, dyes and the like. It is also the raw material of vitamin B1, A and sulfadiazine. 2. It can be used as condensing agent in organic synthesis and catalyst in edible oil process. It is also the important raw material to synthesize sulfadiazine, sulfamethoxazole, sulfa synergist and the like. 3. It is the main raw material used for medicine, pesticide. It is also used in dyes and chemical fiber industry.4. Fatty transesterification catalyst. It can change the fat structure so that it is suitable for margarine. It must be removed in the final food.5. It is mainly used as condensing agent, strong alkaline catalyst and methoxy agent. It can be used for the preparation of vitamin B1 and A, sulfadiazine and other drugs. And little can be used in the production of pesticides. It can also be used as the catalyst for processing edible fats and oils (especially processing lard). It can also be used as analytical reagent.6. It is widely used in perfumes, dyes and other industries. It is mainly used as condensing agent, strong alkaline catalyst and methoxy agent for the preparation of vitamin B1 and A, sulfadiazine and other drugs. Little can be used in the production of pesticides. It can also be used as the catalyst for processing edible fats and oils (especially processing lard). It can also be used as analytical reagent.7. It can be used as condensing agent in organic synthesis. Sodium methoxide is mainly used as a condensation agent, a strong alkaline catalyst and a methoxylating agent for the production of vitamin B1 and A, sulfadiazine and other drugs, and in small quantities for the production of pesticides. It is also used as a catalyst for treatment ofedible fats and oils, as an intermediate inmany synthetic reactions, to prepare sodiumcellulosate; and as a reagent in chemicalanalysis.
• Production method: 1. Xylene (water content < 0.05) and metallic sodium are added into reaction vessel. Heat the reaction vessel to 130～140℃, keep for 1h and stop heating. After rapid stirring for 1h, use cooling water to 50℃. Then start to dropwise add anhydrous methanol (water content < 0.1%), and appropriately add dry xylene. The dropping rate depends on the flow rate of methanol and the release of hydrogen. After the dropwise addition finishes, heat it under reflux for 4h and cool to room temperature to obtain sodium methanolate slurry. Xylene can be recovered by vacuum distillation and then dried in vacuo for 4h. Sodium methanolate can be obtained by nitrogen cooling. The yield is over 90%. Sodium methanolate can also be prepared by the continuous reaction and dehydration of sodium hydroxide with methanol at 85～100℃. 2. It can be obtained by the reaction of sodium hydroxide and methanol in benzene.

Technology Process of Sodium Methoxide

There total 46 articles about Sodium Methoxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 35.0%

methanol (67-56-1) + 3-Vinylbicyclobutane-1-carbonitrile (51934-08-8) → sodium methylate (124-41-4) + 3-(2-Methoxyethylidene)cyclobutane-1-carbonitrile (91597-63-6) + Z-3-vinyl-3-methoxycyclobutane-1-carbonitrile (91597-62-5)

Guidance literature:

With perchloric acid; at 20 ℃; for 5h; Yields of byproduct given;

Reference yield:

Trimethylmethoxysilane (1825-61-2) → Hexamethyldisiloxane (107-46-0) + sodium methylate (124-41-4) + sodium trimethylsilanolate (18027-10-6)

Guidance literature:

With sodium hydroxide; at 0 - 35 ℃; for 0.05h;

DOI:10.1002/hc.20280

Reference yield:

Natrium-1-cyan-2-methoxy-3.5-dinitro-2H-cyclohexadienylid → 3,5-dinitrobenzonitrile (4110-35-4) + sodium methylate (124-41-4)

Guidance literature:

In methanol; dimethyl sulfoxide; at 25 ℃; Equilibrium constant;

DOI:10.1021/jo00971a002

upstream raw materials:

diazomethane

Methyl formate

2-(carboxymethyl)-4-methoxybenzoic acid

methanol

Downstream raw materials:

methyl 2,3,4-tri-O-benzoyl-β-D-ribopyranoside

(2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol

methyl 3,6-anhydro-β-D-glucopyranoside

methyl-(2,3-anhydro-β-D-allopyranoside)

Refernces

• 1、 Fendler,E.J. et al.. "-". . p. 812 - 819. Retrieved 1972.
• 2、 Hu, Jianshu,Zhu, Wei,Meng, Hu,Liu, Ying,Wang, Xin,Hu, Chun. "Identification of 1, 4-Dihydrothieno[3', 2':5, 6]thiopyrano [4, 3-c]pyrazole derivatives as human 5-lipooxygenase inhibitors". . p. 642 - 647. Retrieved 2014.
• 3、 Dalloul, Hany M. M.,El-Nwairy, Khaled A.,Shorafa, Ali Z.,Abu Samaha, Ahmed S.. "Synthesis and antimicrobial activities evaluation of some new thiadiazinone and thiadiazepinone derivatives bearing sulfonamide moiety". . p. 288 - 293. Retrieved 2018.
• 4、 Klesiewicz, Karolina,Karczewska, Elzbieta,Budak, Alicja,Marona, Henryk,Szkaradek, Natalia. "Anti-Helicobacter pylori activity of some newly synthesized derivatives of xanthone". . p. 825 - 834. Retrieved 2016.
• 5、 Juan, Ao,Sun, Hao,Qiao, Jinghui,Guo, Jinbao. "Near-infrared light-controlled circularly polarized luminescence of self-organized emissive helical superstructures assisted by upconversion nanoparticles". . p. 13649 - 13652. Retrieved 2020.
• 6、 Zhu, You-Quan,Zhang, Jin,Yuan, Yan-Wei,Xie, Li-Fen,Xu, Hai-Zhen,Zou, Xiao-Mao,Yang, Hua-Zheng. "Synthesis and herbicidal activities of novel 3-(α-hydroxymethylene) pyrrolidine-2,4-dione derivatives containing a cyclopropane moiety". . p. 202 - 205. Retrieved 2013.
• 7、 Goto, Mitsuki,Nakashima, Yuta,Nanjo, Masato. "Synthesis and structure of hypercoordinated germanate complexes with naphthalene-2,3-dialkoxide ligands". . . Retrieved 2021.
• 8、 Smith, Aaron C.,Kung, Daniel W.,Shavnya, Andre,Brandt, Thomas A.,Dent, Philip D.,Genung, Nathan E.,Cabral, Shawn,Panteleev, Jane,Herr, Michael,Yip, Ka Ning,Aspnes, Gary E.,Conn, Edward L.,Dowling, Matthew S.,Edmonds, David J.,Edmonds, Ian D.,Fernando, Dilinie P.,Herrinton, Paul M.,Keene, Nandell F.,Lavergne, Sophie Y.,Li, Qifang,Polivkova, Jana,Rose, Colin R.,Thuma, Benjamin A.,Vetelino, Michael G.,Wang, Guoqiang,Weaver, John D.,Widlicka, Daniel W.,Price Wiglesworth, Kristin E.,Xiao, Jun,Zahn, Todd,Zhang, Yingxin. "Evolution of the Synthesis of AMPK Activators for the Treatment of Diabetic Nephropathy: From Three Preclinical Candidates to the Investigational New Drug PF-06409577". . p. 681 - 696. Retrieved 2018.
• 9、 Grazia Martina, Maria,Vicenti, Ilaria,Bauer, Lisa,Crespan, Emmanuele,Rango, Enrico,Boccuto, Adele,Olivieri, Noemi,Incerti, Matteo,Zwaagstra, Marleen,Allodi, Marika,Bertoni, Simona,Dreassi, Elena,Zazzi, Maurizio,van Kuppeveld, Frank J. M.,Maga, Giovanni,Radi, Marco. "Bithiazole Inhibitors of Phosphatidylinositol 4-Kinase (PI4KIIIβ) as Broad-Spectrum Antivirals Blocking the Replication of SARS-CoV-2, Zika Virus, and Human Rhinoviruses". supporting information. p. 3548 - 3552. Retrieved 2021/09/09.