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372-09-8

372-09-8

Identification

  • Product Name:Cyanoacetic acid

  • CAS Number: 372-09-8

  • EINECS:206-743-9

  • Molecular Weight:85.0623

  • Molecular Formula: C3H3NO2

  • HS Code:2926 90 70

  • Mol File:372-09-8.mol

Synonyms:Aceticacid, cyano- (6CI,8CI,9CI);2-Cyanoacetic acid;Malonic mononitrile;Monocyanoacetic acid;NSC 5571;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes:C

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH314 Causes severe skin burns and eye damage H332 Harmful if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Contact irritates eyes and may irritate skin. (USCG, 1999)

  • Fire-fighting measures: Suitable extinguishing media ... Water ... effective in controlling fire; however, resulting liquid ... extremely corrosive ... Special Hazards of Combustion Products: Toxic oxides of nitrogen and toxic and flammable acetonitrile vapors may form in fire. (USCG, 1999) 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. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Stop or control the leak, if this can be done without undue risk. Absorb in noncombustible material for proper 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. Protect against physical damage. Separate from other storage ... /Store/ away from any area where fire hazard may be acute. Outside or detached storage is preferred ...

  • 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

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  • Manufacture/Brand:TRC
  • Product Description:Cyanoacetic Acid
  • Packaging:250 g
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Cyanoacetic Acid >98.0%(T)
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  • Product Description:Cyanoacetic Acid >98.0%(T)
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  • Product Description:Cyanoacetic acid for synthesis. CAS 372-09-8, chemical formula NCCH COOH., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Cyanoacetic acid for synthesis
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  • Product Description:Cyanoacetic acid for synthesis
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Relevant articles and documentsAll total 54 Articles be found

Electrocarboxylation of chloroacetonitrile mediated by electrogenerated cobalt(I) phenanthroline

Fabre,Reynes

, p. 1360 - 1362 (2010)

The electrocarboxylation of chloroacetonitrile mediated by [Co(II)(phen)3]2+ has been investigated. Cyclic voltammetry studies of [Co(II)(phen)3]2+ have shown that [Co(I)(phen)3]+, an 18 electron complex, activates chloroacetonitrile by an oxidative addition through the loss of a phenanthroline ligand to give [RCo(III)(phen)2Cl]+. The unstable one-electron-reduced complex underwent Co-C bond cleavage. In carbon dioxide saturated solution, CO2 insertion proceeds after reduction of the alkylcobalt complex. A catalytic current is observed which corresponds to the electrocarboxylation of chloroacetonitrile into cyanoacetic acid. Electrolyses confirmed the process and gave faradic yield of 62% in cyanoacetic acid at potentials that are about 0.3 V less cathodic than the one required for Ni(salen).

Hydrogen peroxide oxidation of 2-cyanoethanol catalyzed by metal complexes

Veghini,Shul'pina,Strelkova,Shul'pin

, p. 167 - 170 (2006)

Oxidation of 2-cyanoethanol, a relatively inert primary alcohol, with several systems (both homogeneous and heterogenized) based on transition metal complexes was studied. The oxidation was performed under homogeneous conditions with 35% hydrogen peroxide upon catalysis by the chlorides FeCl3 or OsCl3. The best result was obtained upon the oxidation catalyzed by OsCl3 at 70°C for 3 h in the absence of solvent: the total yield of the corresponding aldehyde and cyanoacetic acid reached 90%, and the turnover number was 1500. The systems [LMnIV(O)3Mn IVL]n(X)m-oxalic acid (where L = 1,4,7-trimethyl-1,4,7-triazacyclononane) also catalyze oxidation of 2-cyanoethanol with yields of 50-70% either under homogeneous conditions (X = PF- 6, n = 1, and m = 2) or with the use of the catalyst in the heterogenized form (as insoluble heteropoly acid salt), where X = W 12SiO4- 40, n = 2, and m = 1. Nauka/Interperiodica 2006.

5-Oxyacetic Acid Modification Destabilizes Double Helical Stem Structures and Favors Anionic Watson–Crick like cmo5U-G Base Pairs

Strebitzer, Elisabeth,Rangadurai, Atul,Plangger, Raphael,Kremser, Johannes,Juen, Michael Andreas,Tollinger, Martin,Al-Hashimi, Hashim M.,Kreutz, Christoph

, p. 18903 - 18906 (2018)

Watson–Crick like G-U mismatches with tautomeric Genol or Uenol bases can evade fidelity checkpoints and thereby contribute to translational errors. The 5-oxyacetic acid uridine (cmo5U) modification is a base modification at the wobble position on tRNAs and is presumed to expand the decoding capability of tRNA at this position by forming Watson–Crick like cmo5Uenol-G mismatches. A detailed investigation on the influence of the cmo5U modification on structural and dynamic features of RNA was carried out by using solution NMR spectroscopy and UV melting curve analysis. The introduction of a stable isotope labeled variant of the cmo5U modifier allowed the application of relaxation dispersion NMR to probe the potentially formed Watson–Crick like cmo5Uenol-G base pair. Surprisingly, we find that at neutral pH, the modification promotes transient formation of anionic Watson–Crick like cmo5U?-G, and not enolic base pairs. Our results suggest that recoding is mediated by an anionic Watson–Crick like species, as well as bring an interesting aspect of naturally occurring RNA modifications into focus—the fine tuning of nucleobase properties leading to modulation of the RNA structural landscape by adoption of alternative base pairing patterns.

Kinetics of the Deamination of Amides by Nitrous Acid

Al-Mallah, Khawla,Stedman, Geoffrey

, p. 670 - 671 (1998)

The kinetic profile of the rate constant for the nitrous acid-amide reaction in sulfuric acid as a function of acidity for a range of aliphatic and aromatic primary amides has been interpreted in terms of the HNO2/NO+ and the amide/ amide · H+ equilibria.

Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters

Ruan, Shixiang,Ruan, Jiancheng,Chen, Xinzhi,Zhou, Shaodong

, (2020/12/09)

The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.

Surface active ionic liquid assisted metal-free electrocatalytic-carboxylation in aqueous phase: A sustainable approach for CO2utilization paired with electro-detoxification of halocarbons

Bhat, Khursheed Ahmad,Bhat, Mohsin Ahmad,Bhat, Sajad Ahmad,Ingole, Pravin P.,Manzoor Bhat, Zahid,Pandit, Sarwar Ahmad,Rather, Mudasir Ahmad,Rehman, Shakeel U.,Sofi, Feroz Ahmad,Thotiyl, Musthafa Ottakam

, p. 9992 - 10005 (2021/12/24)

Electrocarboxylation of halocarbons is a promising green synthetic strategy for capture, fixation and utilization of CO2 for the synthesis of high-added-value industrial compounds. However, the unparalleled kinetic/thermodynamic stability and solubility concerns of CO2 and halocarbons warrant the use of appropriate (often precious metal based) electrocatalytic electrodes and environmentally non-green solvent systems to drive this otherwise kinetically slow electrochemical process. Herein we demonstrate that owing to their unique solubility and excellent electrocatalytic properties, the aqueous micellar solutions of imidazolium-based surface active ionic liquids (SAILs) can be used for the efficient and selective electrocatalytic-carboxylation of halocarbons to produce carboxylic acids. Specifically, we present results from our detailed electrochemical investigations regarding the electroreductive cleavage of the C-X bond and electrocarboxylation of 9-bromoanthracene (9-BAN) and chloroacetonitrile (CAN) in buffered (pH 7, phosphate buffer) micellar solutions of 1-dodecyl-3-methyl-imidazolium chloride ([DDMIM][Cl]). We demonstrate that the unique ability of [DDMIM][Cl] micelles to stabilize the electrogenerated reactive intermediates facilitates a novel reaction pathway that ensures selective and efficient electrocatalytic-reductive carboxylation of 9-BAN and CAN. The presented results clearly establish that besides allowing for the electrocarboxylation of halocarbons in aqueous green electrolytes, the use of SAILs ensures electrochemical fixation of CO2 at practically low cost current and potential conditions imposed over metal free, economically viable and electrochemically robust carbon electrodes. The use of SAILs is reported to improve the faradaic efficiency (~95%) and reduce the chances of undesired side product reactions which continue to be a major concern in the state of art electro-carboxylation processes. The presented approach we opine offers a promising avenue toward design of eco-green pathways in the direction of CO2 fixation and electro-organic synthesis of a diverse range of value-added products from water insoluble halocarbons (toxic pollutants) in aqueous media.

Study on the degradation mechanism and pathway of benzene dye intermediate 4-methoxy-2-nitroaniline: Via multiple methods in Fenton oxidation process

Guo, Ying,Xue, Qiang,Cui, Kangping,Zhang, Jia,Wang, Hui,Zhang, Huanzhen,Yuan, Fang,Chen, Honghan

, p. 10764 - 10775 (2018/03/26)

Benzene dye intermediate (BDI) 4-methoxy-2-nitroaniline (4M2NA) wastewater has caused significant environmental concern due to its strong toxicity and potential carcinogenic effects. Reports concerning the degradation of 4M2NA by advanced oxidation process are limited. In this study, 4M2NA degradation by Fenton oxidation has been studied to obtain more insights into the reaction mechanism involved in the oxidation of 4M2NA. Results showed that when the 4M2NA (100 mg L-1) was completely decomposed, the TOC removal efficiency was only 30.70-31.54%, suggesting that some by-products highly recalcitrant to the Fenton oxidation were produced. UV-Vis spectra analysis based on Gauss peak fitting, HPLC analysis combined with two-dimensional correlation spectroscopy and GC-MS detection were carried out to clarify the degradation mechanism and pathway of 4M2NA. A total of nineteen reaction intermediates were identified and two possible degradation pathways were illustrated. Theoretical TOC calculated based on the concentration of oxalic acid, acetic acid, formic acid, and 4M2NA in the degradation process was nearly 94.41-97.11% of the measured TOC, indicating that the oxalic acid, acetic acid and formic acid were the main products. Finally, the predominant degradation pathway was proposed. These results could provide significant information to better understand the degradation mechanism of 4M2NA.

Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources

Nauth, Alexander M.,Konrad, Tim,Papadopulu, Zaneta,Vierengel, Nina,Lipp, Benjamin,Opatz, Till

supporting information, p. 4217 - 4223 (2018/09/29)

In cyanation reactions, the cyanide source is often directly added to the reaction mixture, which restricts the choice of conditions. The spatial separation of cyanide release and consumption offers higher flexibility instead. Such a setting was used for the cyanation of iminium ions with a variety of different easy-to-handle HCN sources such as hexacyanoferrate, acetonitrile or α-amino acids. The latter substrates were first converted to their corresponding nitriles through oxidative decarboxylation. While glycine directly furnishes HCN in the oxidation step, the aliphatic nitriles derived from α-substituted amino acids can be further converted into the corresponding cyanohydrins in an oxidative C-H functionalization. Mn(OAc)2 was found to catalyze the efficient release of HCN from these cyanohydrins or from acetone cyanohydrin under acidic conditions and, in combination with the two previous transformations, permits the use of protein biomass as a non-toxic source of HCN.

Process route upstream and downstream products

Process route

p-nitrophenyl cyanoacetate
80256-92-4

p-nitrophenyl cyanoacetate

cyanoacetic acid
372-09-8

cyanoacetic acid

Conditions
Conditions Yield
With pH = 7.0; In water; at 28.7 ℃; under 750.06 Torr; Mechanism; Rate constant; Thermodynamic data; pressure-dependence of rates of elimination; activation parameters for hydrolysis: ΔV(excit.), ΔS(excit.), EA(excit.); var. reaction conditions (pH, pressure);
water
7732-18-5

water

2-cyano-3-phenylacrylic acid
1011-92-3

2-cyano-3-phenylacrylic acid

benzaldehyde
100-52-7

benzaldehyde

cyanoacetic acid
372-09-8

cyanoacetic acid

Conditions
Conditions Yield
at 170 - 180 ℃;
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

N-(aminocarbonyl)-2-cyano-acetamide
1448-98-2

N-(aminocarbonyl)-2-cyano-acetamide

cyanoacetic acid
372-09-8

cyanoacetic acid

urea
57-13-6

urea

Conditions
Conditions Yield
3-Hydroxypropionitrile
109-78-4

3-Hydroxypropionitrile

cyanoacetaldehyde
6162-76-1

cyanoacetaldehyde

cyanoacetic acid
372-09-8

cyanoacetic acid

Conditions
Conditions Yield
In sulfuric acid; Yield given. Yields of byproduct given; anodic oxidation at Pt or PbO2;
3-Hydroxypropionitrile
109-78-4

3-Hydroxypropionitrile

cyanoacetaldehyde
6162-76-1

cyanoacetaldehyde

cyanoacetic acid
372-09-8

cyanoacetic acid

Conditions
Conditions Yield
With [2,2]bipyridinyl; osmium (III) chloride; dihydrogen peroxide; In acetonitrile; at 70 ℃; for 4h; Further Variations:; Reagents; Temperatures; Solvents; Product distribution;
Cyanessigsaeure-o-nitrophenylester
22065-72-1

Cyanessigsaeure-o-nitrophenylester

cyanoacetic acid
372-09-8

cyanoacetic acid

2-hydroxynitrobenzene
88-75-5,78813-12-4

2-hydroxynitrobenzene

Conditions
Conditions Yield
With pH = 4.75; In water; at 30.2 ℃; under 750.06 Torr; Mechanism; Rate constant; Thermodynamic data; pressure-dependence of rates of elimination; activation parameters for hydrolysis: ΔV(excit.), ΔS(excit.), EA(excit.); var. reaction conditions (temp, pH, pressure);
4-methoxy-2-nitroaniline
96-96-8

4-methoxy-2-nitroaniline

hydrogen azide
7782-79-8

hydrogen azide

ethyl isopropyl ketone
565-69-5

ethyl isopropyl ketone

n-hexan-3-one
589-38-8

n-hexan-3-one

but-3-enamide
28446-58-4

but-3-enamide

(2E,4Z)-3-methoxyhexa-2,4-dienedinitrile
1789-46-4

(2E,4Z)-3-methoxyhexa-2,4-dienedinitrile

acetic acid
64-19-7,77671-22-8

acetic acid

cyanoacetic acid
372-09-8

cyanoacetic acid

Methacrylamide
79-39-0

Methacrylamide

ethyl cyanate
627-48-5

ethyl cyanate

Conditions
Conditions Yield
With ferrous(II) sulfate heptahydrate; dihydrogen peroxide; at 25 ℃; for 0.0833333h; pH=6.12; pH-value; Kinetics;
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

cyanoacetic acid
372-09-8

cyanoacetic acid

Conditions
Conditions Yield
With water; nitric acid; at 95 - 100 ℃; for 4h;
72%
With water; nitric acid; at 60 ℃;
With hydrogenchloride; for 1.5h; Heating;
With potassium hydroxide; potassium dihydrogenphosphate; potassium carbonate; In water; acetonitrile; at 30 ℃; Kinetics; Mechanism; var. cyanoacetate esters;
With water; toluene-4-sulfonic acid; for 10h; Concentration; Time; Reagent/catalyst; Reflux; Heating; Dean-Stark;
With hydrogenchloride; In water; at 100 ℃; for 1.5h;
sodium cyanide
773837-37-9

sodium cyanide

chloroacetic acid
79-11-8

chloroacetic acid

cyanoacetic acid
372-09-8

cyanoacetic acid

Conditions
Conditions Yield
chloroacetic acid; With sodium carbonate; In water; pH=6.5 - 7;
sodium cyanide; In water; at 50 - 105 ℃;
With hydrogenchloride; In water;
sodium cyanide
773837-37-9

sodium cyanide

sodium monochloroacetic acid
3926-62-3

sodium monochloroacetic acid

cyanoacetic acid
372-09-8

cyanoacetic acid

Conditions
Conditions Yield
With hydrogenchloride; In water; at 85 - 105 ℃; Concentration;

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