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Cas Database

60-35-5

60-35-5

Identification

  • Product Name:Acetamide

  • CAS Number: 60-35-5

  • EINECS:200-473-5

  • Molecular Weight:59.0678

  • Molecular Formula: C2H5NO

  • HS Code:2924.10 Oral rat LD50: 7000 mg/kg

  • Mol File:60-35-5.mol

Synonyms:Aceticacid amide;Acetimidic acid;Ethanamide;Ethanimidic acid;Methanecarboxamide;NSC 25945;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H351 Suspected of causing cancer

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Refer for medical attention . SYMPTOMS: Exposure to this compound may cause irritation to the eyes, skin and mucous membranes. ACUTE/CHRONIC HAZARDS: This chemical may cause skin and eye irritation and corneal damage. If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. When this chemical has been swallowed, get medical attention. ... If this chemical has been inhaled, remove from exposure and transfer promptly to a medical facility.

  • Fire-fighting measures: Suitable extinguishing media Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical, or carbon dioxide. The flash point of this chemical has not been determined, but it is probably combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: P2 filter respirator for harmful particles. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Dry. Well closed.Keep container tightly closed in a dry and well-ventilated place. Moisture sensitive.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:Acetamide
  • Packaging:50g
  • Price:$ 150
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Acetamide >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Acetamide >98.0%(GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acetamide ≥99.0% (GC)
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  • Product Description:Acetamide ~99% (GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acetamide for synthesis
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  • Product Description:Acetamide analytical standard
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  • Manufacture/Brand:Sigma-Aldrich
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acetamide Acetamide for synthesis. CAS No. 60-35-5, EC Number 200-473-5., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Acetamide sublimed, 99%
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Relevant articles and documentsAll total 332 Articles be found

The 3rd degree of biomimetism: Associating the cavity effect, ZnII coordination and internal base assistance for guest binding and activation

Parrot,Collin,Bruylants,Reinaud

, p. 5479 - 5487 (2018)

The synthesis and characterization of a resorcinarene-based tetra(imidazole) ligand is reported. The properties of the corresponding ZnII complex are studied in depth, notably by NMR spectroscopy. In MeCN, acid-base titration reveals that one out of the four imidazole arms is hemi-labile and can be selectively protonated, thereby opening a coordination site in the exo position. Quite remarkably, the 4th imidazole arm promotes binding of an acidic molecule (a carboxylic acid, a β-diketone or acetamide), by acting as an internal base, which allows guest binding as an anion to the metal center in the endo position. Most importantly, the presence of this labile imidazole arm makes the ZnII complex active for the catalyzed hydration of acetonitrile. It is proposed that it acts as a general base for activating a water molecule in the vicinity of the metal center during its nucleophilic attack to the endo-bound MeCN substrate. This system presents a unique degree of biomimetism when considering zinc enzymes: a pocket for guest binding, a similar first coordination sphere, a coordination site available for water activation in the cis position relative to the substrate and finally an internal imidazole residue that plays the role of a general base.

Kretchmer,Daly

, p. 192,194,195 (1976)

Swift, E. H.,Butler, E. A.

, p. 146 - 153 (1956)

Formation of singlet molecular oxygen by the Radziszewski reaction between acetonitrile and hydrogen peroxide in the absence and presence of ketones

Brauer, Hans-Dieter,Eilers, Beate,Lange, Andreas

, p. 1288 - 1295 (2002)

Measurements of the infrared phosphorescence of singlet molecular oxygen (1O2) at 1270 nm have been used to demonstrate the formation of 1O2 by the Radziszewski reaction between acetonitrile and hydrogen peroxide. The kinetics of the Radziszewski reaction either alone or in the presence of ketones have been studied by this technique. The rate-determining step of the 1O2 formation of the reaction in the absence of ketones was found to be independent of both the concentration of acetonitrile and that of hydrogen peroxide. The kinetic data, the results of the volumetric measurements of the oxygen liberated and the results of the determination of the amount of 1O2 generated by the reaction are consistent with the assumption that the reaction between acetonitrile and hydrogen peroxide occurs via the heterolytic decomposition of the intermediate, peroxyacetimidic acid (PAIA), forming 1 mol acetamide and 0.5 mol 1O2 according to the stoichiometric equation: CH3CN + H2O2 → CH3C(=O)NH2 + 0.5 1O2. The rate constant of the heterolytic decomposition of PAIA was determined to be k8 = 1.2 × 10-3 dm3 mol-1 s-1 at T = 30°C. From the measurements at different pH values in the range 9.1 a(PAIA) value was estimated to be 11.1 at T = 30°C. The investigation of the reaction between acetonitrile and hydrogen peroxide by using N,N-dimethyl-4-oxopiperidinium nitrate as catalyst, has unequivocally shown that the rate of 1O2 formation is considerably enhanced by this ketone. For the ketone-catalysed decomposition of PAIA a rate law can be derived showing a first order dependence on the concentration of acetonitrile and hydrogen peroxide at a given pH. In accordance with the observed rate law are the results with acetonitrile in 50% acetone containing a tenfold excess of hydrogen peroxide at pH 8.2 and T = 60°C.

Measurement and calculation of the rate constant for the reaction of isopropyl isocyanate with hydroxyl radical

Parker, James K.,Espada-Jallad, Cyntia,Parker, Claudia L.,Witt, John D.

, p. 187 - 197 (2009)

The rate constant for the gas-phase reaction of hydroxyl radical with isopropyl isocyanate (IIC) has been measured, relative to toluene, in the T =287-321 K range at atmospheric pressure in air. Ultraviolet photolysis of methyl nitrite served as the sourc

House , J. E. Jr.,Dunlap, Denise D.

, p. 113 - 116 (1981)

-

Paul

, (1937)

-

French,Wrightsman

, p. 50 (1938)

EXAFS/FTIR Characterization and Selective Hydration of Acetonitrile on Silica-Supported *)4V6O19>

Yamaguchi, Masatsugu,Shido, Takafumi,Ohtani, Hiroko,Isobe, Kiyoshi,Ichikawa, Masaru

, p. 717 - 718 (1995)

Silica-supported *)4V6O19 exhibited high catalytic activities in the gas-phase hydration of acetonitrile towards acetamide at 350-473 K with selectivity of over 97percent and dehydrogenation of 2-propanol to acetone.EXAFS, XPS and FTIR studies suggested that thermal evacuation of silica-supported *)4V6O19> at 473 K led to the removal of the bridged oxygen atoms in the V6O19 framework.The resulting deoxygenated samples enhanced the acetonitrile hydration, while catalyzed the dehydration of 2-propanol to propene besides the dehydrogenation reaction, probably owing to the newly generated Lewis acid site.

Watanabe,Sakai

, p. 8,9,14 (1966)

Karrer,Haab

, p. 950,956 (1949)

Hydrolysis of N-(1-Aminoalkyl)amides

Loudon, G. Marc,Jacob, James

, p. 377 - 378 (1980)

The hydrolysis of the title compounds involves the expulsion of an amide anion as a leaving group at basic pH, and probably an amide enol (imidoacid) as a leaving group at acidic pH.

Catalytic hydration of benzonitrile and acetonitrile using nickel(0)

Crestani, Marco G.,Arevalo, Alma,Garcia, Juventino J.

, p. 732 - 742 (2006)

The homogeneous catalytic hydration of benzo- and acetonitrile under thermal conditions was achieved using nickel(0) compounds of the type [(dippe)Ni(η2-NCR)] with R = phenyl or methyl (compounds 1 and 2, respectively), as the specific starting intermediates. Alternatively, the complexes may be prepared in situ by direct reaction of the precursor [(dippe)NiH]2 (3) with the respective nitrile. Hydration appears to occur homogeneously, as tested by mercury drop experiments, producing benzamide and acetamide, respectively. Addition of Bu4NI did not lead to catalysis inhibition, suggesting the prevalence of Ni(0) intermediates during catalysis. Hydration using analogous complexes of 3, such as [(dtbpe)NiH] 2 (4) and [(dcype)NiH]2 (5) was also addressed.

Hitch,Gilbert

, p. 1780 (1913)

Unmasking the Action of Phosphinous Acid Ligands in Nitrile Hydration Reactions Catalyzed by Arene-Ruthenium(II) Complexes

Tomás-Mendivil, Eder,Cadierno, Victorio,Menéndez, María I.,L?pez, Ram?n

, p. 16874 - 16886 (2015)

The catalytic hydration of benzonitrile and acetonitrile has been studied by employing different arene-ruthenium(II) complexes with phosphinous (PR2OH) and phosphorous acid (P(OR)2OH) ligands as catalysts. Marked differences in activity were found, depending on the nature of both the P-donor and η6-coordinated arene ligand. Faster transformations were always observed with the phosphinous acids. DFT computations unveiled the intriguing mechanism of acetonitrile hydration catalyzed by these arene-ruthenium(II) complexes. The process starts with attack on the nitrile carbon atom of the hydroxyl group of the P-donor ligand instead of on a solvent water molecule, as previously suggested. The experimental results presented herein for acetonitrile and benzonitrile hydration catalyzed by different arene-ruthenium(II) complexes could be rationalized in terms of such a mechanism.

Hydrolysis of Acetonitrile, Catalyzed by Octaacetatotetraplatinum(II). - High Reactivity of Coordination Sites Trans to the Pt-Pt Bond -

Yamaguchi, Tadashi,Adachi, Hisako,Ito, Tasuku,Sasaki, Yoichi

, p. 3116 - 3118 (1994)

The platinum(II) cluster, , catalyzes the hydrolysis of acetonitrile to acetamide in acetonitrile-water mixtures.Typical turnover number was 104 mol h-1 at 80 deg C.The catalyst was slowly deactivated by the accumulation of the less active acetamide-substituted species, as well as by its decomposition.

Hydration of Aliphatic Nitriles Catalyzed by an Osmium Polyhydride: Evidence for an Alternative Mechanism

Babón, Juan C.,Esteruelas, Miguel A.,López, Ana M.,O?ate, Enrique

, p. 7284 - 7296 (2021/05/29)

The hexahydride OsH6(PiPr3)2 competently catalyzes the hydration of aliphatic nitriles to amides. The main metal species under the catalytic conditions are the trihydride osmium(IV) amidate derivatives OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2, which have been isolated and fully characterized for R = iPr and tBu. The rate of hydration is proportional to the concentrations of the catalyst precursor, nitrile, and water. When these experimental findings and density functional theory calculations are combined, the mechanism of catalysis has been established. Complexes OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2 dissociate the carbonyl group of the chelate to afford κ1-N-amidate derivatives, which coordinate the nitrile. The subsequent attack of an external water molecule to both the C(sp) atom of the nitrile and the N atom of the amidate affords the amide and regenerates the κ1-N-amidate catalysts. The attack is concerted and takes place through a cyclic six-membered transition state, which involves Cnitrile···O-H···Namidate interactions. Before the attack, the free carbonyl group of the κ1-N-amidate ligand fixes the water molecule in the vicinity of the C(sp) atom of the nitrile.

Manganese-Pincer-Catalyzed Nitrile Hydration, α-Deuteration, and α-Deuterated Amide Formation via Metal Ligand Cooperation

Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Milstein, David,Zhou, Quan-Quan,Zou, You-Quan

, p. 10239 - 10245 (2021/08/24)

A simple and efficient system for the hydration and α-deuteration of nitriles to form amides, α-deuterated nitriles, and α-deuterated amides catalyzed by a single pincer complex of the earth-abundant manganese capable of metal-ligand cooperation is reported. The reaction is selective and tolerates a wide range of functional groups, giving the corresponding amides in moderate to good yields. Changing the solvent from tert-butanol to toluene and using D2O results in formation of α-deuterated nitriles in high selectivity. Moreover, α-deuterated amides can be obtained in one step directly from nitriles and D2O in THF. Preliminary mechanistic studies suggest the transformations contributing toward activation of the nitriles via a metal-ligand cooperative pathway, generating the manganese ketimido and enamido pincer complexes as the key intermediates for further transformations.

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Han, Buxing,Ke, Zhengang,Li, Ruipeng,Liu, Zhimin,Tang, Minhao,Wang, Yuepeng,Zeng, Wei,Zhang, Fengtao,Zhao, Yanfei

supporting information, p. 9870 - 9875 (2021/12/27)

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

Half-Sandwich Iridium Complexes Based on β-Ketoamino Ligands: Preparation, Structure, and Catalytic Activity in Amide Synthesis

Wang, Yang,Guo, Wen,Guan, Ai-Lin,Liu, Shuang,Yao, Zi-Jian

, p. 11514 - 11520 (2021/07/31)

A series of β-ketoamino-based N,O-chelate half-sandwich iridium complexes with the general formula [Cp*IrClL] have been prepared in good yields. These air-insensitive iridium complexes showed desirable catalytic activity in an amide preparation under mild conditions. A number of amides with diverse substituted groups were furnished in a one-pot reaction with good-to-excellent yields through an amidation reaction of NH2OH·HCl with aldehydes in the presence of these iridium(III) precursors. The excellent catalytic activity, mild reaction conditions, and broad substrate scope gave this type of iridium catalyst potential for use in industry. All of the obtained iridium complexes were well characterized by different spectroscopy techniques. The exact molecular structure of complex 3 has been confirmed by single-crystal X-ray analysis.

Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with H2O2

Adrio, Javier,Amarante, Giovanni Wilson,Granato, álisson Silva

, p. 13817 - 13823 (2021/10/01)

An environmentally benign protocol for the generation of nitrones from benzylic secondary amines via catalyst-free oxidation of secondary amines using H2O2 in MeOH or CH3CN is described. This methodology provides a selective access to a variety of C-aryl nitrones in yields of 60 to 93%. Several studies have been performed to shed light on the reaction mechanism and the role of the solvent.

Process route upstream and downstream products

Process route

N-(2,2-Dichloro-1-hydroxy-3-oxo-3-phenyl-propyl)-acetamide
184970-72-7

N-(2,2-Dichloro-1-hydroxy-3-oxo-3-phenyl-propyl)-acetamide

acetamide
60-35-5

acetamide

2,2-dichloroacetophenone
2648-61-5

2,2-dichloroacetophenone

Conditions
Conditions Yield
With sodium hydroxide; In ethanol; for 12h; Ambient temperature;
60%
methanol
67-56-1

methanol

vinyl acetate
108-05-4,9003-20-7

vinyl acetate

ammonia
7664-41-7

ammonia

acetamide
60-35-5

acetamide

2-ethyl-5-methylpyridine
18113-81-0

2-ethyl-5-methylpyridine

Conditions
Conditions Yield
at 130 ℃;
hydrazine hydrate
7803-57-8,79785-97-0

hydrazine hydrate

N-bromoacetamide
79-15-2

N-bromoacetamide

acetamide
60-35-5

acetamide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
acetonitrile
75-05-8,26809-02-9

acetonitrile

Benzaldoxime
932-90-1

Benzaldoxime

acetamide
60-35-5

acetamide

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
With indium(III) nitrate; at 100 ℃; for 18h;
89%
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

benzyl acetimidate
90609-60-2

benzyl acetimidate

acetamide
60-35-5

acetamide

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
at 65 ℃; Rate constant;
at 50 ℃; Rate constant;
at 60 ℃; Rate constant;
1-acetyl-3-benzylthiourea
81467-37-0

1-acetyl-3-benzylthiourea

acetamide
60-35-5

acetamide

Benzyl isothiocyanate
622-78-6

Benzyl isothiocyanate

acetyl isothiocyanate
13250-46-9

acetyl isothiocyanate

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
bei der Destillation;
Conditions
Conditions Yield
With sodium hydroxide; at 30 ℃; Mechanism; Thermodynamic data; activation energy, ΔG(excit.);
2-acetyl-5-methyl-3-oxo-hexanoic acid methyl ester
57594-16-8

2-acetyl-5-methyl-3-oxo-hexanoic acid methyl ester

ammonia
7664-41-7

ammonia

acetamide
60-35-5

acetamide

methyl 5-methyl-3-oxohexanoate
30414-55-2

methyl 5-methyl-3-oxohexanoate

Conditions
Conditions Yield
Isobutyl bromide
78-77-3

Isobutyl bromide

acetonitrile
75-05-8,26809-02-9

acetonitrile

acetamide
60-35-5

acetamide

N-tert-butylacetamide
762-84-5

N-tert-butylacetamide

N-(2-butyl)ethanamide
1189-05-5

N-(2-butyl)ethanamide

N-isobutylacetamide
1540-94-9

N-isobutylacetamide

Conditions
Conditions Yield
With lithium perchlorate; (anodic oxidation);
(S)-2-phenylglycine
2935-35-5

(S)-2-phenylglycine

acetamide
60-35-5

acetamide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With N-bromoacetamide; In water; for 24h; Rate constant; Thermodynamic data; Mechanism; acidic or alkaline medium, several organic acid catalysators;

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  • Hangzhou Dingyan Chem Co., Ltd
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  • Main Products:95
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  • Chemwill Asia Co., Ltd.
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  • Amadis Chemical Co., Ltd.
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  • Shaanxi BLOOM TECH Co.,Ltd
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