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N-Methylformamide

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

N-Methylformamide Properties

Melting point:
-3.2 °C
Boiling point:
199 °C
Density 
1.011 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.432(lit.)
Flash point:
>230 °F
solubility 
soluble in water, chloroform, alcohols, acetone, ethylacetate but not in diethyl ether and petroleum ether
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
Formamide, N-methyl-(123-39-7)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H312 Harmful in contact with skin Acute toxicity,dermal Category 4 Warning P280,P302+P352, P312, P322, P363,P501
H360 May damage fertility or the unborn child Reproductive toxicity Category 1A, 1B Danger
Precautionary statements:
P201 Obtain special instructions before use.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P405 Store locked up.

N-Methylformamide price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 473936 N-Methylformamide 99% 123-39-7 1l $96.6 2018-11-13 Buy
Sigma-Aldrich 473936 N-Methylformamide 99% 123-39-7 2.5l $196 2018-11-13 Buy
TCI Chemical F0059 N-Methylformamide >99.0%(GC) 123-39-7 25g $14 2018-11-22 Buy
TCI Chemical F0059 N-Methylformamide >99.0%(GC) 123-39-7 500g $43 2018-11-22 Buy
Alfa Aesar L03908 N-Methylformamide, 99% 123-39-7 50g $20.1 2018-11-13 Buy

N-Methylformamide Chemical Properties,Uses,Production

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

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

Uses

Solvent.

Definition

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

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).

General Description

Clear colorless liquid with a slight amine odor.

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


N-Methylformamide Suppliers

Global( 196)Suppliers
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View Lastest Price from N-Methylformamide manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-05-20 N-methylformamide
123-39-7
US $10.00 / KG 1KG 99.9% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
2018-07-25 N-Methylformamide
123-39-7
US $3030.00 / KG 50KG 99% 20T career henan chemical co
2018-04-03 N-methyl formamide
123-39-7
US $3.00 / KG 200KG 99.9%min. 8000 tons per year Hefei TNJ Chemical Industry Co.,Ltd.

N-Methylformamide Spectrum


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