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N-Methylformamide

Product Name
N-Methylformamide
CAS No.
123-39-7
Chemical Name
N-Methylformamide
Synonyms
x188;X 188;ek7011;EK 7011;nsc3051;HCONHCH3;NSC 3051;Methylformamide;Formylmethylamine;n-methyl-formamid
CBNumber
CB9109065
Molecular Formula
C2H5NO
Formula Weight
59.07
MOL File
123-39-7.mol
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N-Methylformamide Property

Melting point:
-4 °C (lit.)
Boiling point:
198-199 °C (lit.)
Density 
1.011 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.432(lit.)
Flash point:
>230 °F
storage temp. 
Sealed in dry,Room Temperature
solubility 
soluble in water, chloroform, alcohols, acetone, ethylacetate but not in diethyl ether and petroleum ether
pka
16.48±0.23(Predicted)
form 
Liquid
color 
Clear colorless
Relative polarity
6.2
Water Solubility 
miscible
Merck 
14,6076
BRN 
1098352
InChIKey
ATHHXGZTWNVVOU-UHFFFAOYSA-N
CAS DataBase Reference
123-39-7(CAS DataBase Reference)
NIST Chemistry Reference
Formamide, N-methyl-(123-39-7)
EPA Substance Registry System
N-Methylformamide (123-39-7)
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Safety

Hazard Codes 
T
Risk Statements 
61-21-R61-R21
Safety Statements 
53-45-S53-S45
WGK Germany 
1
RTECS 
LQ3000000
TSCA 
Yes
PackingGroup 
II
HS Code 
29241990
Hazardous Substances Data
123-39-7(Hazardous Substances Data)
Toxicity
LD50 in mice (mg/kg): 2300 i.p.; 2600 orally; 1580 i.v.; 2700 i.m. (Langdon)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H312Harmful in contact with skin

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
473936
Product name
N-Methylformamide
Purity
99%
Packaging
1l
Price
$107
Updated
2021/12/16
Sigma-Aldrich
Product number
473936
Product name
N-Methylformamide
Purity
99%
Packaging
2.5l
Price
$213
Updated
2021/12/16
Sigma-Aldrich
Product number
473936
Product name
N-Methylformamide
Purity
99%
Packaging
100ml
Price
$30
Updated
2021/03/22
Sigma-Aldrich
Product number
473936
Product name
N-Methylformamide
Purity
99%
Packaging
250ml
Price
$59.9
Updated
2021/03/22
TCI Chemical
Product number
F0059
Product name
N-Methylformamide
Purity
>99.0%(GC)
Packaging
25g
Price
$14
Updated
2021/12/16
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N-Methylformamide Chemical Properties,Usage,Production

Acquired resistance

N-methylformamide is a clear colorless liquid with a slight amine odor. It is a water-soluble organic solvent. As an adjuvant antineoplastic agent, N-methylformamide depletes cellular glutathione, a key molecule involved in the antioxidation of reactive oxygen species (ROS) and other free radicals, thereby enhancing ionizing radiation-induced DNA cross-linking in and terminal differentiation of tumor cells. (NCI04)

Uses

N-Methylformamide is used in amidation or transamidation chemical reactions where formamide is insufficient.

Uses

N-Methylformamide is used to prepare methyl isocyanate. It is used as an extraction solvent for aromatic hydrocarbons and acts as a ligand in coordination chemistry. It is employed as a solvent in oil refineries and in aluminum electrolytic capacitors. Further, it is used as a reagent in organic synthesis. In addition to this, it is used as an investigational anticancer drug and an intermediate in the production of some pharmaceutical compounds.

Production Methods

N-Methylformamide (NMF) can be synthesized by: (1) reacting methylamine, carbon monoxide, methanol and a small amount of potassium acetate at 250 atm and 160°C; (2) heating methylamine with carbon monoxide and some sodium ethoxide in ethanol at 150 atm; (3) treating methylformate with methylamine and methanol; (4) reacting hexamethylenetetramine with formamide and hydrogen in the presence of Raney nickel at 130-145°C (Beilstein's Handbuch, 1977).

Definition

ChEBI: A member of the class of formamides having a N-methyl substituent.

General Description

N-Methylformamide (NMF), a formamide derivative, is widely employed as an organic solvent. NMF molecule contains C=O and N-H groups, so it can act as a proton donor and acceptor. Due to its important physical properties such as high dielectric constant, high solubility, low conductivity and amphiprotic nature, it is suitable for use as a separation medium in capillary electrophoresis studies.
NMF is closely related to other formamides, notably formamide and dimethylformamide (DMF). However, industrial use and production of NMF are far less than for either of these other formamides. DMF is favored over NMF as a solvent due to its greater stability. Annual production of NMF can be assumed to be significantly less than the production of either formamide (100,000 tons) or DMF (500,000 tons).

Air & Water Reactions

Water soluble.

Reactivity Profile

N-Methylformamide is incompatible with benzene sulfonyl chloride. N-Methylformamide is also incompatible with strong oxidizing agents, acids, bases and acid chlorides. N-Methylformamide may react with chlorine, bromine, nitrates, nitric acid, triethylaluminum, potassium permanganate, chromic acid, chromic anhydride, chromium trioxide, borohydrides, hydrides, thionyl chloride, metallic sodium, phosphorus trioxide, diborane, (octafluoroisobutyrate + sodium nitrite) and (perchloryl fluoride + potassium methyl 4,4-dinitrobutyrate).

Health Hazard

As NMF is an investigational anticancer drug, a number of clinical trials have been conducted with this chemical. The first clinical evaluation was initiated in 1956 (Laird Myers et al 1956). Five patients were treated with NMF; all but one patient received the drug orally. The dose ranged from 0.1 g to 4 g per day for 2-36 days. All patients showed symptoms of toxicity - chiefly anorexia, nausea, and vomiting. Hepatic damage as measured by liver function tests was seen in all patients at total doses between 80-870 mg/kg. The liver damage appeared to be reversible with cessation of treatment. Autopsy examination of the liver of one patient showed irregular lobular disorganization, some large hepatocytes and areas of liver regeneration. McVie et al (1984) administered NMF i.v. and orally to 19 patients at a starting dose of 300 mg/m2/day for 5 days. Treatment cycles were repeated every 2 weeks and doses were escalated to 1200 mg/m2/day for 5 days. Ettinger et al (1985) treated 35 patients with NMF i.v. at doses ranging from 125-3125 mg/m2 weekly every 6 weeks. The principal toxic effects of NMF were general malaise, nausea, vomiting and anorexia. Biochemical disturbances included reversible elevation of serum levels of transaminases in several patients. The occurrence of raised serum enzyme levels did not seem to be related to the dose. Other toxic symptoms were peripheral neuropathy and alcohol intolerance in a few patients
Eisenhauer et al (1986) conducted a phase 2 clinical trial which was terminated early because of NMF-induced hepatic and gastrointestinal toxicity.

Fire Hazard

N-Methylformamide is combustible.

Industrial uses

NMF possesses excellent solvent properties that are similar to those of dimethylformamide. However, NMF appears to be much less important as an industrial solvent than dimethylformamide.

Safety Profile

Moderately toxic by ingestion, intraperitoneal, intravenous, intramuscular, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. An eye irritant. A very dangerous fire hazard when exposed to heat or flame. Violent reaction with benzene sulfonyl chloride. When heated to decomposition it emits toxic fumes of NOx.

Metabolism

In mice, NMF is metabolized mainly to carbon dioxide, which is exhaled with the breath, and to methylamine, which is excreted with the urine (Kestell et al 1985). Of the radioactivity injected with [14C]formyl-NMF (400 mg/kg), 39% was exhaled as carbon dioxide. The amount of the drug excreted unchanged in the urine in mice was only 26% (Brindley et al 1982) and 15% of the dose was metabolized to methylamine (Kestell et al 1985). A mercapturate, N-acetyl-S-(Nmethylcarbamoyl)cysteine was identified as a major metabolite of NMF in the urine of mice, rats and patients (Kestell et al 1986). Formation of this novel metabolite involves oxidation of the formyl moiety and subsequent conjugation with glutathione (Threadgill et al 1987). On GLC analysis of the urine of mice which had received NMF, small amounts of formamide were also detected (Brindley et al 1982). Some evidence suggests that this metabolite was actually N-Hydroxy-methylformamide, the immediate product of N-methyl C-hydroxyla-tion of NMF, and not formamide (Kestell et al 1985). A^Hydroxymethylformamide, like N-hydroxymethyl-N-methylformamide, the principal metabolite of dimethylformamide, is thermally labile and breaks down to give formamide and formaldehyde; but it is stable in aqueous solution. In alkaline solution N-hydroxymethylformamide undergoes facile hydrolysis (Cooksey et al 1983). Only 14% of the radioactivity injected with [14C]methyl-NMF was exhaled as labeled carbon dioxide (Kestell et al 1985). Formate was not a urinary metabolite of NMF in mice (Kestell et al 1985).
When [14C]methyl-NMF (400 mg/kg) was injected i.p. in mice and drug plasma concentrations were determined during the first 24 h, the plasma concentration of radioactivity versus time curve was superimposable on the curve obtained by measuring unmetabolized NMF by GLC (Brindley et al 1982). Therefore, the metabolites of NMF appear to be rapidly eliminated from the blood into the urine. Radioactivity in the plasma was measurable for 8 days post NMF administration, but NMF was not detectable by GLC beyond 24 h after injection (Brindley et al 1982). The areas under the plasma concentration versus time curves after i.p., i.v. and oral administration of NMF in mice were found to be very similar (Brindley et al 1982). Similarly, the bioavailability of NMF was high in patients in a phase I clinical trial (Brindley et al 1983).
Contrary to an earlier report which claimed that NMF was biotransformed to formaldehyde by a rat liver homogenate (Barnes and Ranta, 1972), recent findings have shown that NMF does not undergo appreciable metabolism in vitro. Neither formaldehyde (or a formaldehyde precursor) could be detected as a metabolite of NMF in liver preparations or hepatocytes, nor was metabolism measurable as observed by the disappearance of substrate (Gescher et al 1982). However, NMF labeled with [14C] either in the methyl or the formyl moiety was metabolized by mouse liver microsomes in the presence of NADPH to a species which was bound covalently to microsomal protein. This covalent binding in vitro was abolished in the presence of glutathione (Pearson et al 1987a). Drug-derived radioactivity was incorporated into or bound to hepatic proteins also when [14C]NMF was administered to mice (Pearson et al 1987a). Intraperitoneal injection of NMF (200 mg/kg) in mice caused depletion of the liver glutathione pools by 79% 2 h after administration (Pearson et al 1987b). Incubation of isolated mouse hepatocytes with 7 mM NMF, which was the peak plasma concentration achieved after administration of 400 mg/kg in mice (Brindley et al 1982), led to a significant decrease in intracellular glutathione levels without an increase in glutathione disulfide (Whitby et al 1984b). Similarly, concentrations of NMF in the 0.1 M range caused glutathione depletion in cultures of human colon carcinoma cells (Cordeiro and Savarese, 1984, Cordeiro and Savarese, 1986). This depletion was accompanied by inhibition of cell growth.

Purification Methods

Dry it over molecular sieves for 2days, then distil it under reduced pressure through a column packed with glass helices. Fractionally crystallise it by partial freezing and the solid portion is distilled in a vacuum. [Beilstein 4 IV 170.]

N-Methylformamide Preparation Products And Raw materials

Raw materials

Preparation Products

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N-Methylformamide Suppliers

TCI AMERICA
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+1-800-423-8616 / +1-503-283-1681
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hebei crovell biotech Co,.LTD
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Alfa Aesar
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021-67582001/03/05
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View Lastest Price from N-Methylformamide manufacturers

Wuhan Mulei New Material Technology Co. Ltd
Product
N-Methylformamide / NMF 123-39-7
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99.9%
Supply Ability
100000kg per month
Release date
2021-04-02
Wuhan Aoliqisi New Material Technology Co., Ltd.
Product
N-Methylformamide 123-39-7
Price
US $1.00/g
Min. Order
1000g
Purity
99%
Supply Ability
20ton/month
Release date
2021-07-08
Shanxi Naipu Import and Export Co.,Ltd
Product
Methyl Formamide 123-39-7
Price
US $100.00/KG
Min. Order
1KG
Purity
99
Supply Ability
5tons
Release date
2021-08-16

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