Category: 13312-84-0

Loudon, J. D. published the artcileElimination of sulfinate from sulfonic esters, HPLC of Formula: 13312-84-0, the publication is Journal of the Chemical Society (1959), 1780-2, database is CAplus.

In a typical experiment, 1.4 g. 2-ClC₆H₄CHO, 1.9 g. 4-MeC₆H₄SO₂Cl, 2 cc. dioxane, and 4 cc. H₂O, at 5° treated with 0.66 g. KCN, the mixture stirred 1 h., the solid filtered off, dissolved in 5 cc. 2:2:1 Me₂CO-EtOH-H₂O, filtered, and the filtrate treated with 3 g. ice gave 78% 2-ClC₆H₄CH(CN)OSO₂C₆H₄Me-4 (I), m. 86° (EtOH). In similar fashion were prepared the following RCH(CN)OSO₂C₆H₄Me-4 derivatives (R, % yield, and m.p. given): Ph(Ia), 72, 60°; 2-BrC₆H₄, 75, 104°; 3-MeOC₆H₄, 55, 52°: 2-O₂NC₆H₄(II), 72, 111°; 2,4-Cl₂C₆H₃, 72, 78°; 2,5-Cl(O₂N)C₆H₃, 70, 118°. PhCH(CN)OSO₂C₆H₃Cl₂-2,5, -, 102°, and 4-ClC₆H₄CH(CN)OSO₂C₆H₃Cl₂ -2,5, -, 86°, were also prepared II (1.66 g.) in 10 cc. EtOH kept 0.25 h. with 0.12 g. Na in 2 cc. EtOH, concentrated in vacuo, and the residual material extracted with C₆H₆ left 0.77 g. 4-MeC₆H₄SO₂Na(III) and the C₆H₆ solution chromatographed on alumina gave 0.68 g. O₂NC₆H₄CO₂Et (IV), m. 30°. All the above compounds gave good yields of the corresponding Na sulfinate. When the NaOEt in the experiment with I was replaced by NaCH(CO₂Et)₂, the products were III, IV, and 2-O₂NC₆H₄CH(CN)SO₂C₆H₄Me-4(V), m. 167°. I (1.5 g.) and 5 cc. Et₃N 0.5 h. at 100° gave 2-ClC₆H₄CH(CN)SO₂C₆H₄Me-4(VI), m. 112°, and 2-ClC₆H₄CO₂Et. PhSO₂NPh(CH₂Bz) (0.73 g.) in 10 cc. EtOH and 0.046 g. Na in 3 cc. EtOH as above gave III and BzCO₂Et (identified by reaction with ο-C₆H₄(NH₂)₂ as 2-phenylquinoxaline). Ia (2.87 g.), 20 cc. MeOH, and 1.53 g. NaBr refluxed 1 h. and concentrated gave 70% PhCH(CN)Br, b₁₅ 137-9°, m. 29°. I (0.32 g.), 0.13 g. 4-MeC₆H₄SH, and 0.04 g. NaOH in 8 cc. 4:1 EtOH-H₂O refluxed 0.5 h. gave 85% 2-ClC₆H₄CH(CN)SC₆H₄Me-4. I (0.32 g.) and 0.27 g. III in 5 cc. EtOH refluxed 48 h. gave VI. I (1.6 g.) and 2 cc. anhydrous C₅H₅N at 0° gave the pyridinium derivative (VII), m. 101° (C₆H₆-petr. ether); VII and 5N NaOH gave the betaine, dark red crystals, m. 138° (EtOH). I (0.32 g.) 3 cc. AcOH, 0.05 cc. concentrated H₂SO₄, and 0.15 g. 10% Pd on C absorbed 3 mol equivalents H in 3 h. to give 60% 2-ClC₆-H₄CH₂CH₂NH₂; picrate m. 186° (C₆H₆). CH₂N₂ (approx. 10 g.) in 50 mL. Et₂O and 15.5 g. PhCH₂COCl in 50 cc. Et₂O kept several hrs. and 17 g. powd. 4-MeC₆H₄SO₃H added gave after 12 h. at 20° PhCH₂COCH₂OSO₂C₆H₄Me-4, m. 63° (EtOH).

Journal of the Chemical Society published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, HPLC of Formula: 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Rucka, Lenka published the artcileExpression control of nitrile hydratase and amidase genes in Rhodococcus erythropolis and substrate specificities of the enzymes, Related Products of nitriles-buliding-blocks, the publication is Antonie van Leeuwenhoek (2014), 105(6), 1179-1190, database is CAplus and MEDLINE.

Bacterial amidases and nitrile hydratases can be used for the synthesis of various intermediates and products in the chem. and pharmaceutical industries and for the bioremediation of toxic pollutants. The aim of this study was to analyze the expression of the amidase and nitrile hydratase genes of Rhodococcus erythropolis and test the stereospecific nitrile hydratase and amidase activities on chiral cyanohydrins. The nucleotide sequences of the gene clusters containing the oxd (aldoxime dehydratase), ami (amidase), nha1, nha2 (subunits of the nitrile hydratase), nhr1, nhr2, nhr3 and nhr4 (putative regulatory proteins) genes of two R. erythropolis strains, A4 and CCM2595, were determined All genes of both of the clusters are transcribed in the same direction. RT-PCR anal., primer extension and promoter fusions with the gfp reporter gene showed that the ami, nha1 and nha2 genes of R. erythropolis A4 form an operon transcribed from the Pami promoter and an internal Pnha promoter. The activity of Pami was found to be weakly induced when the cells grew in the presence of acetonitrile, whereas the Pnha promoter was moderately induced by both the acetonitrile or acetamide used instead of the inorganic nitrogen source. However, R. erythropolis A4 cells showed no increase in amidase and nitrile hydratase activities in the presence of acetamide or acetonitrile in the medium. R. erythropolis A4 nitrile hydratase and amidase were found to be effective at hydrolyzing cyanohydrins and 2-hydroxyamides, resp.

Antonie van Leeuwenhoek published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Bischoff, Francois P. published the artcileDesign and synthesis of a novel series of cyanoindole derivatives as potent γ-secretase modulators, Application In Synthesis of 13312-84-0, the publication is Bioorganic & Medicinal Chemistry Letters (2019), 29(14), 1737-1745, database is CAplus and MEDLINE.

The discovery, design and synthesis of a new series of GSMs is described. The classical imidazole heterocycle has been replaced by a cyano group attached to an indole nucleus. The exploration of this series has led to compound 26-S (I) which combined high in vitro and in vivo potency with an acceptable drug-like profile.

Bioorganic & Medicinal Chemistry Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Application In Synthesis of 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Alagoz, Dilek published the artcilePurification, immobilization and characterization of (R)-hydroxynitrile lyase from Prunus amygdalus turcomanica seeds and their applicability for synthesis of enantiopure cyanohydrins, SDS of cas: 13312-84-0, the publication is Journal of Molecular Catalysis B: Enzymatic (2014), 40-46, database is CAplus.

A hydroxynitrile lyase (HNL) was purified from wild almond seeds (Prunus amygdalus turcomanica Lincz.) for the first time. Native and subunit mol. masses of the HNL were determined as 100 and 25 kDa, resp. indicating that the enzyme is a homotetramer. The purified enzyme was immobilized onto Eupergit CM and Eupergit C 250 L supports and their lyase and carboligation (synthetic) activities were characterized in terms of optimal pH, temperature and kinetic parameters. While the optimal pH of the free HNL for the lyase activity was 6.0, it was 5.5 for both of the immobilized HNLs. Optimal temperature was determined as 25 °C for all HNL preparations For mandelonitrile cleavage, the apparent K_m – V_max values were 0.38 mM – 197.0 U mg protein^-1 for the free HNL, 1.30 mM – 26.0 U mg protein^-1 for HNL immobilized onto Eupergit CM (HNL-Eup CM) and 0.95 mM – 17.5 U mg protein^-1 for HNL immobilized onto Eupergit C 250 L (HNL-Eup C 250 L), resp. For the carboligation activity, the optimal pH was measured as 4.0 and optimal temperature was determined as 5 °C for all of the HNL preparations For mandelonitrile synthesis, the apparent K_m – V_max values were 14.0 mM – 2.70 U mg protein^-1 for the free HNL, 41.0 mM – 0.49 U mg protein^-1 for HNL-Eup CM and 38.0 mM – 0.54 U mg protein^-1 for HNL-Eup C 250 L, resp. All of the HNL preparations were employed for the synthesis of mandelonitrile, 2-chloromandelonitrile, 3,4-dihydroxymandelonitrile and 2-hydroxy-4-Ph butyronitrile in a biphasic tert-Bu Me ether-citrate buffer (pH 4.0) medium. The results showed that the immobilized HNL preparations were better than the free HNL in the synthesis of abovementioned cyanohydrins except 2-chloromandelonitrile with higher yields and enantiopurities.

Journal of Molecular Catalysis B: Enzymatic published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, SDS of cas: 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Rafiee, E. published the artcileCobalt polyoxometalate, [CoW₁₂O₄₀]^5-, as a new reusable catalyst for addition of trimethylsilyl cyanide to carbonyl compounds, Quality Control of 13312-84-0, the publication is Bulletin of the Korean Chemical Society (2005), 26(10), 1585-1587, database is CAplus.

A series of cyanohydrin trimethylsilyl ethers have been prepared via cyanosilylation of various carbonyl compounds with trimethylsilyl cyanide. The reaction was catalyzed with potassium dodecatungstocobaltate trihydrate which was found to be a convenient and reusable catalyst.

Bulletin of the Korean Chemical Society published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Quality Control of 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ooi, Takashi published the artcileZr(OtBu)₄ as a new promoter for the Meerwein-Ponndorf-Verley alkynylation and cyanation of aldehydes, Product Details of C8H6ClNO, the publication is Synlett (2000), 69-70, database is CAplus.

Zr(OCMe₃)₄ can serve as an effective promoter for the Meerwein-Ponndorf-Verley alkynylation of aldehydes, and it was found to be particularly attractive in the Meerwein-Ponndorf-Verley cyanation.

Synlett published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Product Details of C8H6ClNO.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Castro, E. A. published the artcileStructure and reactivity of arylcyanohydrins, Related Products of nitriles-buliding-blocks, the publication is Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie (1974), 29(3-4), 209-12, database is CAplus.

The relation between structure and reactivity was examined for 18 RCH(OH)CN (I, R = substituted phenyl) by CNDO/2 calculation of the stability of I (dissociation constant for I �RCHO + HCN) and of at. energy terms.

Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Xue, Ya-Ping published the artcileDesign of Nitrilases with Superior Activity and Enantioselectivity towards Sterically Hindered Nitrile by Protein Engineering, Product Details of C8H6ClNO, the publication is Advanced Synthesis & Catalysis (2015), 357(8), 1741-1750, database is CAplus.

The enantioselective hydrolysis of ortho-chloromandelonitrile with nitrilase is one of the most attractive approaches to prepare (R)-ortho-chloromandelic acid. To date, efforts to develop this nitrilase-mediated process were plagued by either insufficient ee_p (enantiomeric excess of product) or low activity due to the steric hindrance from the ortho-substituted substrate. To improve the nitrilase potential for producing (R)-ortho-chloromandelic acid, an enhancement of both activity and enantioselectivity towards sterically hindered nitriles would be highly desirable. Mol. docking of the (R)-ortho-chloromandelonitrile into the active site of wild-type 2A6 nitrilase (nitA) allowed the identification of proximal nitA active site residues. Several residues (52, 132, 189 and 190) were selected as targets for single and double point mutation to improve nitA activity and enantioselectivity towards ortho-chloromandelonitrile. Targeted mutagenesis yielded several nitA variants with superior activity and enantioselectivity. The best mutant T132A/F189T exhibited a 4.37-fold higher specific activity (7.39 U/mg) towards ortho-chloromandelonitrile than the wild-type nitA. More importantly, the enantioselectivity (E) was improved from 17.34 to >200, resulting in a highly enantiopure product. Mol. docking experiments further support the enhanced activity and enantioselectivity shown exptl. and the structural effects of this amino acid substitution on the active site of nitA are provided. The amino acids at sites 189 and 132 determine the activity and enantioselectivity towards ortho-chloromandelonitrile. With mutant T132A/F189T as a catalyst, a maximum of 450 mM of (R)-ortho-chloromandelic acid was produced with a 90% conversion and >99% ee_p within 3 h. This is the first time that a high productivity of (R)-ortho-chloromandelic acid of up to 671.76 g L^-1 d^-1 using a nitrilase-mediated approach is reported. The engineered T132A/F189T variant represents a promising and competitive biocatalyst for practical application in synthesizing (R)-ortho-chloromandelic acid.

Advanced Synthesis & Catalysis published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C11H15NO2, Product Details of C8H6ClNO.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wu, J.-M. published the artcileSynthesis and cytotoxicity of artemisinin derivatives containing cyanoarylmethyl group, Application In Synthesis of 13312-84-0, the publication is European Journal of Medicinal Chemistry (2001), 36(5), 469-479, database is CAplus and MEDLINE.

A series of 12α-deoxoartemisinyl cyanoarylmethyl dicarboxylates, dicarboxylic acids 12α-deoxoartemisinyl ester cyanoarylmethyl amide, and dicarboxylic acids 12α-deoxoartemisinyl ester N-methylcyanoarylmethyl amide, I (Y = (CH₂)₂, (CH₂)₄, (CH₂)₅, (CH₂)₇; X = O, NH, NMe) showing moderate cytotoxicity against P388 and L1210 cells were prepared They induced the significant accumulation of L1210 and P388 cells in the G1 phase of the cell cycle. This mechanism of action was quite different from that of the majority of cytotoxic compounds used in the chemotherapy of cancer. Compound I possessed better cytotoxicity than the other compounds

European Journal of Medicinal Chemistry published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C9H8BNO2, Application In Synthesis of 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Gvozdyakova, A. published the artcileHydrazides of o-, m-, and p-substituted derivatives of α-hydroxyphenylacetic acid, Quality Control of 13312-84-0, the publication is Acta Facultatis Rerum Naturalium Universitatis Comenianae, Chimia (1966), 9(12), 585-94, database is CAplus.

The following cyanohydrins XC6H4CH(OH)CN (I) were prepared by treating 1.25 moles aldehyde and 1 mole KCN with 1 mole H2SO4 (as a 1:1 solution) at 10-20° (X, m.p. or b.p., and % yield given): H, b12-14 98-102°, 73.4; p-NO2, 197°, 45.0; o-NO2, 213-15°, 41.6; m-NO2, b12 183-7°, 36.4; p-Cl, 198-9°, 66.3; o-Cl, b18-20 165-70°, 62.1; o-OH, 148°, 69.9. The following Et α-hydroxyarylacetates XC6H4CH(OH)CO2Et (II) were prepared by heating 0.015 mole I with 3 ml. absolute EtOH and 3 ml. concentrated H2SO4 (X, m.p. or b.p., and % yield given): H, b12 60-4°, 73.7; p-NO2, 55-6°, 43.3; o-NO2, 134°, 35.2; m-NO2, 38.5°, 27.3; p-Cl, 172-4°, 71.6; o-Cl, b12 88-91°, 81.3; o-OH, 212-14°, 76.4. When 0.03 mole II was heated 4 hrs. with 10 ml. absolute EtOH and 6 ml. 50% H2NNH2.H2O, the product distilled in vacuo and the solid was recrystallized from EtOH, the following XC6H4CH(OH)CONHNH2 were prepared X, m.p., and % yield given): H, 91-2°, 75.9; p-NO2, 223-5°, 53.7; o-NO2, 239°, 37.4; m-NO2, 156-7°, 76.2; p-Cl, 90-2°, 54.05; o-Cl, 174-5°, 71.7; o-OH, 260-2°, 54.3. The hydrazides had no inhibitory effect, even at high concentration, on tubercular bacilli.

Acta Facultatis Rerum Naturalium Universitatis Comenianae, Chimia published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Quality Control of 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts