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75-12-7

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Identification

Name
Formamide
CAS
75-12-7
Synonyms
AKOS BBS-00004264
AMIDE C1
CARBAMALDEHYDE
FORMAMIDE
FORMAMIDE, DEIONIZED
FORMIC ACID AMIDE
FORMIC AMIDE
METHANAMIDE
Amid kyseliny mravenci
amidkyselinymravenci
Formamid
Formimidic acid
formimidicacid
Formylamide
HCONH2
methanoicacid,amide
FORMAMIDE HDPE
Formamide Methanamide
Formamide, MB Grade (1.12017)
Formamide, Molecular Biology Grade Methanamide, Molecular Biology Grade
EINECS(EC#)
200-842-0
Molecular Formula
CH3NO
MDL Number
MFCD00007941
Molecular Weight
45.04
MOL File
75-12-7.mol

Chemical Properties

Appearance
Clear, colorless liquid
Appearance
Formamide is a colorless, viscous liquid. Faint ammonia-like odor.
Melting point 
2-3 °C(lit.)

mp 
2-3 °C(lit.)

Boiling point 
210 °C(lit.)

bp 
210 °C(lit.)

density 
1.134 g/mL at 25 °C(lit.)

vapor density 
1.55 (vs air)

vapor pressure 
0.08 mm Hg ( 20 °C)

refractive index 
n20/D 1.447(lit.)

Fp 
310 °F

storage temp. 
2-8°C

solubility 
H2O: 10 M at 20 °C, clear, colorless

form 
liquid

pka
16.50±0.50(Predicted)
Specific Gravity
1.138 (20/20℃)
color 
clear, colorless

PH Range
7.1 at 23 g/l
Relative polarity
7.3
PH
8-10 (200g/l, H2O, 20℃)
Odor
Odorless
explosive limit
2.7-19.0%(V)
Water Solubility 
miscible
Sensitive 
Hygroscopic
λmax
λ: 275 nm Amax: 1.00
λ: 280 nm Amax: 0.20
λ: 300 nm Amax: 0.05
λ: 360 nm Amax: 0.02
λ: 400 nm Amax: 0.01
Merck 
14,4237
BRN 
505995
InChIKey
ZHNUHDYFZUAESO-UHFFFAOYSA-N
CAS DataBase Reference
75-12-7(CAS DataBase Reference)
NIST Chemistry Reference
Formamide(75-12-7)
EPA Substance Registry System
75-12-7(EPA Substance)

Safety Data

Hazard Codes 
T
Risk Statements 
R61:May cause harm to the unborn child.
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
Safety Statements 
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
WGK Germany 
1
RTECS 
LQ0525000


10
Autoignition Temperature
932 °F
TSCA 
Yes
HS Code 
29241900
HS Code 
29309070
Safety Profile
Poison by skin contact and subcutaneous routes. Moderately toxic by ingestion, intraperitoneal, and intramuscular routes. An irritant to skin, eyes, and mucous membranes. Experimental teratogenic and reproductive effects. An eye irritant. Mutation data reported. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. Incompatible with 12, pyridine,SO3. When heated to decomposition it emits toxic fumes of NOx. Has exploded while in storage.
Hazardous Substances Data
75-12-7(Hazardous Substances Data)
Toxicity
LD50 in mice, rats (g/kg): 4.6, 5.7 i.p. (Pham-Huu-Chanh)

Raw materials And Preparation Products

Raw materials
Ammonia-->Sodium formate-->Methyl formate
Preparation Products
alpha-d-Glucopyranoside, beta-d-fructofuranosyl, octadecanoate -->7-(((2-Amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((5-(carboxymethyl)-4-methyl-2-thiazolyl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid-->5-METHYL-2-PYRROL-1-YL-THIOPHENE-3-CARBOXYLIC ACID-->Zidovudine-->2,4-Dimethoxybenzylamine-->(4-OXO-6,7-DIHYDRO-4H,5H-CYCLOPENTA[4,5]THIENO-[2,3-D]PYRIMIDIN-3-YL)-ACETIC ACID-->6-METHYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE-->4-Amino-6-methoxypyrimidine-->CAFENSTROLE-->4-CHLORO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDINE-->5-Ethyl-6-methylthieno[2,3-d]pyrimidin-4(3H)-one ,97%-->5-METHYL-4-OXO-3,4-DIHYDRO-THIENO[2,3-D]PYRIMIDINE-6-CARBOXYLIC ACID-->7-METHYLADENINE-->5-(4-METHOXY-PHENYL)-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE-->6-ethylthieno[2,3-d]pyrimidin-4(3H)-one-->6-PHENYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE-->2,6-Dithiopurine-->6-TERT-BUTYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE-->3,4-DIHYDRO-4-OXOQUINAZOLINE-7-CARBOXYLIC ACID-->6-ISO-PROPYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE-->5-(4-Phenyl-phenyl)thieno[2,3-d]pyrimidin-4(3H)-one ,97%-->5-Ethoxy-4-methyloxazole-->ETHYL 5-METHYL-4-OXO-3,4-DIHYDROTHIENO[2,3-D]-PYRIMIDINE-6-CARBOXYLATE-->5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE-->5-(4-HEXYLOXY-[1,2,5]THIADIAZOL-3-YL)-1-METHYL-1,2,3,6-TETRAHYDRO-PYRIDINE-->6-Iodoquinazolin-4-one-->PEPLOMYCIN-->5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]-PYRIMIDIN-4-ONE-->1,2,3,5-TETRAHYDRO-8-THIA-5,7-DIAZA-CYCLOPENTA[A]INDENE-4-ONE-->2-THIOPHENECARBOXAMIDE-->3,5-DIMETHYL-3H-IMIDAZOLE-4-CARBOXYLIC ACID ETHYL ESTER-->4-CHLORO-8-FLUORO-5H-PYRIMIDO[5,4-B]INDOLE-->VESNARINONE-->4-Methyl-5-thiazolylethyl acetate-->methyl 3,4-dihydro-4-oxoquinazoline-7-carboxylate-->Ivermectin

Hazard Information

General Description
A colorless liquid with a faint odor of ammonia. Denser than water. Freezing point 36°F.
Reactivity Profile
FORMAMIDE(75-12-7) is incompatible with strong oxidizers, acids and bases. Sensitive to light. Reacts with water very slowly at room temperature, but rate is accelerated by acids and bases at elevated temperatures. Incompatible with iodine, pyridine and sulfur trioxide. Reacts explosively with furfuryl alcohol, H2O2, Tl(NO3)3.H2O, nitromethane and P2O5. An effective solvent: dissolves casein, glucose, tannins, starch, lignin, polyvinyl alcohol, cellulose acetate, nylon, the chlorides of copper, lead, zinc, tin, cobalt, iron, aluminum and nickel, the acetates of the alkali metals, some inorganic sulfates and nitrates. Attacks copper and brass .
Air & Water Reactions
Hygroscopic. Water soluble.
Hazard
Toxic material. Toxic by skin absorption.
Health Hazard
INHALATION: A moderate irritant to mucous membranes. EYES: Moderately irritating to the eyes. SKIN: A mild to moderate irritant to the skin.
Potential Exposure
Formamide is a powerful solvent. It is also used as an intermediate in pharmaceutical manufacture.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, includ ing resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
Shipping
UN2810 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Incompatibilities
Forms hydrocyanic acid with water solutions. Hygroscopic (absorbs moisture from air). Incompatible with nonoxidizing mineral acids; strong acids; ammonia, cresols, iodine, isocyanates, oleum, phenols, pyr idine, sulfur trioxide; oxidizers, iodine, pyridine. Formamide decomposes on heating @ 180℃ forming ammonia, water, carbon monoxide and hydrogen cyanide. Attacks metals, such as aluminum, iron, copper, brass, lead, and natural rubber. Thermal decomposition may release deadly hydrogen cyanide. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithio carbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur).
Waste Disposal
Dissolve in a combustible solvent and dispose by burning in a furnace equipped with an alkali scrubber for the exit gases.
Definition
ChEBI: The simplest monocarboxylic acid amide, obtained by formal condensation of formic acid with ammonia. The parent of the class of formaldehydes.
Production Methods
Formamide is produced commercially by two processes (Eberling 1980). In a direct synthesis, ammonia and carbon monoxide react at 100-300 atm and 80-100°C in methanolic sodium methoxide. In the second, a two-stage synthesis, carbon monoxide and methanol form methylformate in the presence of sodium methoxide. The methylformate is treated with liquid or gaseous ammonia at 2-6 atm and 80-100°C.
Agricultural Uses
Fonnamide is an organic compound containing the amide group -CONH2. It is made from formic acid or its ester with ammonia. It is also made from ammonia and carbon monoxide.
Formamide is used in making liquid fertilizers for foliar application of nitrogen. For example, a mixture of formamide, urea and ammonium nitrate is used as a solution fertilizer and has a salt-out temperature of 0°C. It contains more than 35% nitrogen, unlike the aqueous formulations of urea, and ammonium nitrate, which have 32 % nitrogen.Formamide is a good solvent for many organic compounds.
Industrial uses
Formamide is used in the large scale production of formic acid by reaction with inorganic acids, as an intermediate in the chemical industry, as a solvent in the processing of plastics, and as a solvent in felt-tip pens (Eberling 1980).
Environmental Fate
If released to air, formamide will exist solely as a vapor in the ambient atmosphere. Vapor-phase formamide will be degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals. The half-life for this reaction in air is estimated to be 8.0 days. If released to soil, formamide is expected to have very high mobility. Volatilization from moist soil surfaces is not expected to be an important fate process. If released into water, formamide is not expected to adsorb to suspended solids and sediment. Several biodegradation screening studies have observed significant biodegradation of formamide, which suggests that biodegradation may be important. Volatilization from water surfaces is not expected to be an important fate process based upon this compound’s estimated Henry’s law constant.
Metabolism
There are only very few reports on the metabolic fate of formamide in the literature. Halsey (1898) found that formamide gave rise to as much urinary formate in the dog as did formic acid, and assumed complete hydrolysis of the amide in vivo. In a study by Bray et al (1949) the hypothesis was tested that formamide undergoes metabolic hydrolysis in rabbits. Acidic substances were titrated after extraction by ether, before and after hydrolysis of urine samples. The ether-soluble acid determined in hydrolyzed urine was assumed to reflect the amount of formamide excreted unchanged. The difference between the amount of amide administered and the total amount excreted unchanged was considered to represent amide which was metabolically hydrolyzed. After administration of 2-4 g per rabbit orally, 39% of the dose was recovered unchanged using this method. When formamide was incubated with rabbit liver extracts or liver slices, only very little hydrolysis was detected by this method.
Purification Methods
Formamide is easily hydrolysed by acids and bases. It also reacts with peroxides, acid halides, acid anhydrides, esters and (on heating) alcohols, while strong dehydrating agents convert it to a nitrile. It is very hygroscopic. Commercial material often contains acids and ammonium formate. Vorhoek [J Am Chem Soc 58 2577 1956] added some bromothymol blue to formamide and then neutralised it with NaOH before heating to 80-90o under reduced pressure to distil off ammonia and water. The amide is again neutralised and the process is repeated until the liquid remained neutral on heating. Sodium formate is added, and the formamide is concentrated under reduced pressure at 80-90o. The distillate is again neutralised and redistilled. It is then fractionally crystallised in the absence of CO2 and water by partial freezing. Formamide (specific conductance 2 x 10-7 ohm-1 cm-1) of low water content is dried by passage through a column of 3A molecular sieves, then deionized by treatment with a mixed-bed ion-exchange resin loaded with H+ and HCONH-ions (using sodium formamide in formamide)[Notley & Spiro J Chem Soc (B) 362 1966]. [Beilstein 2 IV 45.]
Toxicity evaluation
The mechanism of toxicity of formamide is not known; the response profile is quite different from the better studied dimethyl derivative.

Material Safety Data Sheet(MSDS)

msds information
Formamide(75-12-7).msds

Questions And Answer

Chemical Properties
It is colorless, odorless and oily liquid with slight ammonia-odor when containing impurities. It has hygroscopicity property. It has a relative molecular mass of 45.04. It has the relative density being 1.1334, the melting point being 2.55 ℃, the boiling point being 210.5 ℃, the refractive index being 1.4475, the flash point being 154 ℃ and the viscosity being 3.76mPa • s (20 ℃). It is insoluble in ether and chlorinated solvents, slightly soluble in benzene and is miscible with water, methanol, ethanol, acetic acid, acetone, dioxane, ethylene glycol, phenol and low grade ester. This product can dissolve the casein but does not dissolve albumin. This product can dissolve casein, dextrose, corn protein, gelatin, glue, resin, starch, lignin, cellulose acetate, nylon, and some inorganic salts: the chloride compounds of copper, lead, zinc, tin, cobalt, iron, aluminum and nickel and also some kinds of sulfates and nitrates. At room temperature, formamide has a low hydrolysis rate. Raising the temperature or the addition of acid, alkali can all accelerate the hydrolysis rate. In the presence of a catalyst, being heated to less than 35 ℃ can decompose and release hydrogen cyanide. Formamide contains two active functional groups, namely the carbonyl and amide groups. It is easy to have chemical reaction to produce a lot of nitrogen-containing heterocyclic compound. Formamide can also react with a mineral acid to generate formic acid and ammonium salt. In the presence of a catalyst, it can react with organic halide or alcohol to form formic esters. This product can also react with β-diketone, β-imino ketone, aliphatic acyloin, arene acyloin as well as heterocyclic acyloin. It can also form complex with cobalt, copper and nickel salts. Formamide, in case of strong dehydrating agent such as phosphorus pentoxide, it can generate hydrogen cyanide. It can react with phosphorus pentasulfide to generate sulfur formamide. Formamide has strong corrosion effect on copper, brass, lead and rubber, therefore the storage and transportation should be paid attention.
The main purposes: formamide can be used as the softener and solvent of animal glue and paper. It can also be used as the solvent of the spinning of the acrylonitrile copolymer, the polymerization of unsaturated amine polymerization and the production of pharmaceuticals as well as the solvent for extraction of grease and the dissolving items mentioned above. As intermediates, it can be applied the synthesis of imidazole, pyrimidine, 1, 3, 5-triazine, caffeine, theophylline and theobromine. Furthermore, it can also be used as the raw material of making dyes, spices, paints, adhesives, textile and paper treatment agent as well as the production of formic acid, dimethyl formamide and so on.
The above information is edited by the chemicalbook of Dai Xiongfeng.
Acute toxicity
The LD50 for rat via stomach is 6.1g/kg and for mice is 3.15g/kg. Acute symptoms is characterized by the injury of the nervous system, accompanied with conjunctivitis and respiratory disorders, straight convulsions and the final death after 3 to 4 days. The threshold concentration for chronic inhalation effects was 6 ± 4mg/m3. For the maximum allowable concentration for operating environment: for United States, the value is 30 mg/m3 (20 ppm) while the value is 3 mg/m3 (vapor, absorbed through the skin) for Soviet Union.
Chemical Properties
It is transparent oily liquid with slight ammonia smell. It has hygroscopic property. It is miscible with water and ethanol, slightly soluble in benzene, chloroform and ether.
Uses
It can be used as the raw material for synthesizing imidazole, pyrimidine, 1, 3, 5-triazine, caffeine as well as the solvents for making spinning of acrylonitrile copolymer and plastic anti-static coating, etc.
Formamide has active reactive and special dissolving capability. It can be used as the raw material for organic synthesis, paper processing agents, softening agent of fiber industry and animal glue as well as being used as the analytical reagent for measuring the amino acid content of rice. In the field of organic synthesis, it has most application in medicine as well as a lot of applications in other fields such as pesticides, dyes, pigments, fragrances and additives. It is also a kind of excellent organic solvent and is mainly applied to the spinning of acrylonitrile copolymers and ion exchange resins and plastics antistatic coating or conductive coating. In addition, it can also be used for separating chlorosilane and purifying grease. Formamide can have various kinds of reactions, in addition to have its three hydrogen atoms participate in the reaction, can also be subject to dehydration, CO removal, the introduction of an amino group, an acyl group and cyclization reaction. Take cyclization as an example, diethyl malonate can have cyclization reaction with formamide to generate the intermediate of vitamin B4, the 4, 6-dihydroxypyrimidine. O-aminobenzoic acid can have cyclization reaction with formamide to generate the quinazolinone-4 which is the intermediate for the synthesis of antiarrhythmic drug phenantrolihne. 3--amino-4-ethoxycarbonyl-pyrazole can have cyclization reaction with formamide to generate the inhibitor of the xanthine oxidase, allopurinol. EDTA can have cyclization reaction with formamide to give anti-cancer drugs ethylenediamine. Methyl ethyl methoxymalonate can have cyclization reaction with formamide to generate the intermediate of sulfonamide drug, 5-methoxy-4, 6-dihydroxy pyrimidine disodium.
It can be used as analytical reagents, solvents and softening agents as well as being used in organic synthesis.
It can be applied to medicine and pesticide industry.
Production method
1. One-Step method: the first step is through the reaction of carbon monoxide and methanol for generating methyl formate in the presence of sodium methoxide. The second step: the methyl formate is further subject to aminolysis for generation of formamide with the reaction conditions being 80-100 ℃ and 0.2-0.6 MPa. This method has relative problems. 2. The method of formic acid; the formic acid first has esterification reaction with methanol to generate methyl formate which undergoes aminolysis to generate formamide with the separation of methanol and impurities through distillation to obtain the final product. Owing to its high cost, this method has been gradually eliminated. 3. One Step method: this is via the reaction of carbon monoxide and ammonia for the direct synthesis of formamide in high pressure (10-30 MPa) and a temperature of 80-100 ℃ with the sodium methylate as the catalyst. 4. The formic acid and urea method. 5. The new method has sodium and ammonium salts for reaction to generate formamide at a certain temperature and pressure. This method has already applied domestic invention patent.
Category
Toxic substances.
Toxicity grading
Poisoning
Acute toxicity
Oral-rat LD50: 5577 mg/kg; Oral-Mouse LD50: 3150 mg/kg.
Irritation data
Eye-rabbit 100 mg severe.
Flammability and hazardous characteristics
Flammable with fire releasing toxic nitric oxide gas.
Storage properties
Warehouse: cold, ventilation, dry.
Extinguishing Media
Carbon dioxide, dry chemical powder.
Professional standards
TWA 15 mg/m³; STEL 45 mg/m3

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