N,N-Dimethylformamide

Base Information

• Chemical Name: N,N-Dimethylformamide
• CAS No.: 68-12-2
• Deprecated CAS: 114057-15-7,15175-63-0,15175-77-6,33513-42-7,15175-63-0,15175-77-6
• Molecular Formula: C₃H₇NO
• Molecular Weight: 73.0947
• Hs Code.: 2924.10
• European Community (EC) Number: 200-679-5
• ICSC Number: 0457
• NSC Number: 5356
• UN Number: 2265
• UNII: 8696NH0Y2X
• DSSTox Substance ID: DTXSID6020515
• Nikkaji Number: J1.923B
• Wikipedia: Dimethylformamide
• Wikidata: Q409298
• NCI Thesaurus Code: C83974
• Metabolomics Workbench ID: 37910
• ChEMBL ID: CHEMBL268291
• Mol file: 68-12-2.mol

Synonyms:Dimethylformamide;N,N Dimethylformamide;N,N-dimethylformamide

Chemical Property of N,N-Dimethylformamide

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 2.7 mm Hg ( 20 °C)
• Melting Point: -61 °C
• Refractive Index: n20/D 1.430(lit.)
• Boiling Point: 153 °C at 760 mmHg
• PKA: -0.44±0.70(Predicted)
• Flash Point: 57.8 °C
• PSA: 20.31000
• Density: 0.884 g/cm³
• LogP: 0.34030
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: water: miscible
• Water Solubility.: soluble
• XLogP3: -1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 73.052763847
• Heavy Atom Count: 5
• Complexity: 33.9
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

N,N-Dimethylformamide- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 61-20/21-36
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Amides (
• Canonical SMILES: CN(C)C=O
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract. The substance may cause effects on the liver. This may result in tissue lesions. The effects may be delayed. Medical observation is indicated. If swallowed the substance easily enters the airways and could result in aspiration pneumonitis.
• Effects of Long Term Exposure: The substance may have effects on the liver. This may result in impaired functions. Tumours have been detected in experimental animals but may not be relevant to humans. Animal tests show that this substance possibly causes toxic effects upon human reproduction.
• Physical properties: Clear, colorless to light yellow, hygroscopic, mobile liquid with a faint, characteristic, ammonialike odor. An experimentally determined odor threshold concentration of 100 ppmv was reported by Leonardos et al. (1969).
• Uses: N,N-Dimethylformamide (DMF) is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents. Dimethylformamide solutions are used toprocess polymer fibers, films, and surface coatings; to permit easy spinning of acrylic fibers; to produce wire enamels, and as a crystallization medium in the pharmaceutical industry.DMF can also be used for formylation with alkyllithium or Grignard reagents. It is used as a reagent in Bouveault aldehyde synthesis and also in Vilsmeier-Haack reaction. It acts as a catalyst in the synthesis of acyl chlorides. It is used for separating and refining crude from olefin gas. DMF along with methylene chloride acts as a remover of varnish or lacquers. It is also used in the manufacture of adhesives, fibers and films.

Technology Process of N,N-Dimethylformamide

There total 189 articles about N,N-Dimethylformamide 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: 91.0%

N,N-dimethylaminomethylidene-P-phenylphosphine (75471-07-7,79908-23-9,1219922-13-0) + C,N-diphenylnitrone (201024-81-9) → benzylidene phenylamine (538-51-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7)

Guidance literature:

In tetrahydrofuran;

DOI:10.1007/BF00957868

Reference yield: 85.0%

benzyloxy-trimethylsilane (14642-79-6) + (diphenylphosphoryl)(N,N-dimethylamino)chloromethane (1352709-73-9) → N,N-dimethylaminobis(diphenylphosphoryl)methane (23587-60-2) + benzyl chloride (100-44-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7)

Guidance literature:

(diphenylphosphoryl)(N,N-dimethylamino)chloromethane; In chloroform; at 5 ℃; for 18h;

benzyloxy-trimethylsilane; In chloroform; at 5 ℃; for 18h;

DOI:10.1246/bcsj.20110157

Reference yield: 82.0%

carbon dioxide (124-38-9,18923-20-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N,N-dimethyl-formamide (68-12-2,33513-42-7) + carbonic acid dimethyl ester (616-38-6)

Guidance literature:

at 110 ℃; for 15h; under 37503 Torr;

DOI:10.1080/00397910600908744

upstream raw materials:

N,N,N,N,N,N-hexamethylphosphoric triamide

formic acid

N,N-dimethyloxamic acid

hexamethylenetetramine

Downstream raw materials:

1-Nitro-piperazin

furfural

thiophene-2-carbaldehyde

2,3,4,5,6,7-Hexahydro-1H-benzimidazol-2-on

Refernces

• 1、 Cheng, Yujie,Gan, Tao,He, Qian,He, Xiaohui,Ji, Hongbing,Sun, Qingdi,Wang, Pengbo,Zhang, Hao. "N-formylation of amines using phenylsilane and CO2 over ZnO catalyst under mild condition". . . Retrieved 2020/10/27.
• 2、 Zhang, Kai,Zong, Lingbo,Jia, Xiaofei. "Bifunctional Ru-loaded Porous Organic Polymers with Pyridine Functionality: Recyclable Catalysts for N-Formylation of Amines with CO2 and H2". . p. 1335 - 1340. Retrieved 2021/02/05.