Formamide solution is an organic compound with the molecular formula of CH3NO. It is a colorless transparent liquid with a slight ammonia smell. Soluble in ether and chlorine containing solvents, slightly soluble in benzene, and miscible with water, methanol, ethanol, acetic acid, acetone, dioxane, ethylene glycol, phenol and lower esters. It can dissolve casein, but not albumin. It can also dissolve casein, glucose, corn protein, gelatin, animal glue, resin, starch, lignin, acetate fiber, nylon and some inorganic salts, chlorides of copper, lead, zinc, tin, cobalt, iron, aluminum and nickel, some sulfates and nitrates. It is a raw material for synthetic medicine, spices, dyes, etc., and can also be used as a solvent for synthetic fiber spinning, plastic processing, and the production of ligncasein ink.
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Chemical Formula |
CH3NO |
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Exact Mass |
45 |
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Molecular Weight |
45 |
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m/z |
45 (100.0%), 46 (1.1%) |
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Elemental Analysis |
C, 26.67; H, 6.71; N, 31.10; O, 35.52 |
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Formamide, with the molecular formula CH3NO, is a colorless and transparent liquid with a slight ammonia odor. It is an important raw material for the synthesis of pharmaceuticals, fragrances, dyes, and can also be widely used as a solvent in multiple fields.
Organic synthesis field
Solvent:
Formamide, as a polar solvent, is used in organic synthesis to dissolve various organic compounds and promote the progress of reactions. For example, in some organic reactions, formamide can act as a solvent to help reactants better contact and react, increasing reaction rate and yield.
Other reactions:
Formamide can generate hydrogen cyanide through catalysts at high temperatures, which is used to synthesize imidazole (for treating trichomoniasis), pyrimidine (for treating parasitic diseases), and 1,3,5-triazine.
Formamide is also used in the production of caffeine, theobromine, tea alkaloids, etc.
Reaction intermediates:
Formamide is an important intermediate in many organic reactions, participating in various substitution, addition, and condensation reactions. The specific examples are as follows:
Ring reaction:
The intermediate 4,6-dihydroxypyrimidine of vitamin B ₁ (adenine phosphate) is obtained by cyclization of formamide with diethyl malonate.
Formamide is cyclized with ortho aminobenzoic acid to obtain the intermediate quinazolone-4 of the antiarrhythmic drug Changluolin.
Formamide is cyclized with 3-amino-4-ethoxycarbonylpyrazole to obtain the xanthine oxidase inhibitor allopurinol.
Formamide is cyclized with diethylamine tetraacetic acid to obtain the anticancer drug ethyleneimine.
The intermediate of sulfonamide drugs, 5-methoxy-4,6-dihydroxypyrimidine disodium, was obtained by cyclization of formamide with methoxyethyl malonate.
Medical field
Drug synthesis:
Formamide is an important raw material for synthesizing various drugs, with specific examples as follows:
Sulfonamide drugs:
Sulfamethoxazole (sulfamethoxazole) is a medium acting sulfonamide drug with a wide spectrum of antibacterial properties and strong antibacterial effects. It is mainly used for the treatment of respiratory and urinary system infections. During its synthesis, the intermediate 4,6-dihydroxymethoxypyrimidine is synthesized by cyclization of methoxymalonyl and formamide in sodium methoxide.
vitamin:
Vitamin B ₁ (adenine phosphate) has a stimulating effect on white blood cell proliferation and can be used to treat leukopenia caused by various reasons. In the process of synthesizing vitamin B ₁ from diethyl malonate, formamide is used as the main raw material for the first and fifth cyclization reactions.
Vitamin B (pyridoxine hydrochloride) is an important coenzyme in amino acid metabolism, used to prevent and treat central nervous system symptoms of isoniazid and the side effects of peripheral neuropathy. In the α - oxazole pathway for synthesizing vitamin B from pyruvic acid, formamide is used as a formylation reagent.
Hypolipidemic drugs:
Dextran sulfate (sodium salt) (DS Na for short) is used as a new drug for lowering blood lipids and preventing arteriosclerosis caused by high blood lipids. The drug is produced using the formamide chlorosulfonic acid method.
Allopurinol:
Allopurinol is used clinically to treat various diseases with primary or secondary serum uric acid elevation, such as gout, acute or chronic leukemia, polycythemia vera, etc. In the three-step reaction of synthesizing allopurinol from hexyl cyanoacetate, formamide is used as an intermediate material in the third cyclization reaction.
Other medications:
Imine-154 (ethylenediamine tetraacetylimine) has obvious inhibitory effect on a variety of experimental tumors. It has a certain alleviating effect on gastric cancer, breast cancer, reticular cell sarcoma, and has a good therapeutic effect on psoriasis.
Drug solvent:
Formamide can be used as a drug solvent to improve the solubility and stability of drugs. For example, formamide is often used as a solvent in the crystallization process of penicillin and dihydrostreptomycin sulfate.
Formamide is one of the raw materials for the production of sulfonamide drugs, vitamin B, lipid-lowering drugs, allopurinol, new drugs for psoriasis, and other drugs.
Sulfonamide drugs such as sulfamethoxazole. Also known as Xinnuoming or Xinmingsu, the English name SMZ is a medium acting sulfonamide drug with a wide spectrum of antibacterial properties and strong antibacterial effects. It is mainly used for the treatment of respiratory and urinary system infections. In the synthesis of SMZ, the intermediate 4,6-dihydroxymethoxypyrimidine is synthesized by cyclization of methoxymalonyl and formamide in sodium methoxide.
Synthesis of vitamin B4. Vitamin B, also known as adenosine monophosphate or 6-kryptopurine phosphate, has a stimulating effect on white blood cell proliferation and can be used to treat leukopenia caused by various reasons, especially for leukopenia caused by tumor chemotherapy. In the process of synthesizing B from diethyl malonate, formamide is used as the main raw material for the first and fifth cyclization reactions.
Synthesis of vitamin B6. Vitamin B6, also known as pyridoxine hydrochloride, is a coenzyme of important enzymes such as transaminase and amino acid decarboxylase in kryptote metabolism. Used for the prevention and treatment of central nervous system symptoms of isoniazid and the side effects of peripheral neuropathy, as well as for vomiting, seborrheic dermatitis, pellagra caused by pregnancy, radiation sickness, or anticancer drugs, and vitamin deficiency caused by long-term oral broad-spectrum antibiotics. Formamide is used as a formylation reagent in the oxazole route of vitamin synthesis from propionic acid.
Synthesis of allopurinol. Allopurinol, also known as 4-hydroxypyrazole (3,4, d) pyrimidine, is clinically used to treat various diseases with primary or secondary serum and urine hyperintensities, such as gout, acute or chronic leukopenia, polycythemia vera, multiple myeloma, and other malignant tumors. Hyperuricemia caused by massive cell necrosis during chemotherapy or radiation therapy can prevent and treat uric acid nephropathy. In the three-step reaction of synthesizing allopurinol from hexyl cyanoacetate, formamide is used as an intermediate material in the third cyclization reaction.
Synthesis of lipid-lowering drug Ds~Na. Dextran sulfate (sodium salt) (DS Na for short) is a new drug used for lowering blood lipids and preventing arteriosclerosis caused by high blood lipids. The drug is produced using the formamide chlorosulfonic acid method.
Imine (CRF-154) was prepared. Also known as ethylenediamine tetraacetamide. According to reports, the drug has a significant inhibitory effect on various experimental tumors; Clinical preliminary observation shows that the drug has a certain alleviating effect on gastric cancer, breast cancer and reticulosarcoma. In addition, the drug also has good therapeutic effects on psoriasis. In the four step reaction process of synthesizing ethylenediamine tetraacetamide from chloroacetic acid, formamide is used as an intermediate raw material in the ring stage reaction.
Pesticide field
Pesticide intermediates:
Formamide can be used to synthesize certain pesticide intermediates, which can be further reacted to prepare pesticide products such as insecticides and herbicides. For example, Chlorfenapyr is a highly effective broad-spectrum insecticide, and formamide may be used as an intermediate or solvent in its synthesis process.
Pesticide additives:
Formamide can be used as a pesticide additive to improve the performance of pesticides, such as enhancing their permeability and stability.
Dye field
Dye synthesis:
Formamide can be used in the synthesis of dyes to help improve their color and fastness. Some organic dyes require formamide as a solvent or reaction intermediate during the synthesis process.
Plastic plasticizer:
Formamide can be used as a plastic plasticizer to improve the flexibility and processability of plastics. In foamed plastic products, formamide as a plasticizer makes foam floor mats more expansive and soft.
Electronic field
Electronic materials:
Formamide has certain applications in electronic materials, such as as as a solvent or additive in the synthesis process of semiconductor materials, liquid crystal materials, etc. Although there are few specific application cases, its potential in the electronics industry is gradually being valued.
Textile additives:
Formamide can be used in the dyeing and printing processes of textiles as a solvent for dyes or pigments, helping to improve the dyeing performance and hand feel of textiles. In addition, formamide can also be used as a softener in the fiber industry and animal glue.
Other uses
Paper processing agent: Formamide can be used as a paper processing agent to improve the performance of paper.
Petroleum drilling and construction industry coagulant: Formamide is used as a coagulant in the petroleum drilling and construction industry to improve construction efficiency.
Casting carburizing and nitriding agent: Formamide is used as a carburizing and nitriding agent in the casting industry to improve the performance of castings.
Analytical reagent: In the laboratory, formamide can be used as an analytical reagent to determine the amino acid content in rice.
Method 1
Methyl formate is formed from carbon monoxide and methanol in the presence of sodium methoxide. Methyl formate is re ammonolyzed to form formamide under the reaction conditions of 80-100 ℃ and 0.2-0.6 MPa. This method has few problems.
Method 2
First, formic acid and methanol undergo esterification reaction to generate methyl formate, then ammonolysis to generate formamide, and then rectification to separate methanol and impurities to obtain the finished product. This method has been phased out due to its high cost.
Method 3
Formamide is directly synthesized from carbon monoxide and ammonia under the catalysis of sodium methoxide under high pressure (10-30MPa) and 80-100 ℃.
Method 4
Formic acid and urea method.
Method 5
Ammonium formate is produced by the reaction of formic acid and ammonia. Heating ammonium formate to dehydrate to obtain formamide.
Formamide's role in science and industry is evolving, driven by sustainability and technological advancements:
Advanced Material Synthesis: Formamide's ability to stabilize metal nanoparticles makes it valuable in catalysis. For example, formamide-reduced gold nanoparticles exhibit high activity in CO oxidation reactions.
Nanotechnology: Formamide solutions are used to synthesize carbon nanotubes and graphene oxide by acting as a carbon source or stabilizing agent.
Energy Storage: Formamide-based electrolytes in supercapacitors show promise due to their high ionic conductivity and wide electrochemical window.
Biodegradable Polymers: Formamide derivatives are being incorporated into polyesters and polyamides to enhance biodegradability without compromising mechanical properties.
AI-Driven Formulation Optimization: Machine learning models are being trained to predict formamide solution behaviors in complex reactions, reducing trial-and-error in drug discovery and material science.
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