Category: 13312-84-0

Karrer, P. published the artcileGlucosides. IX, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Helvetica Chimica Acta (1921), 130-48, database is CAplus.

K has shown (C. A. 13, 1841; 14, 742, 1972) that BrC₆H₇O₅Ac₄ (A) reacts with the Ag salts of α- or o-HO and o-NH₂ acids to form both acetylated glucosides and glucose esters, indicating that the Ag is bound to both the CO₂H and the OH or NH₂ groups by principal and secondary valences. On this assumption, m- and p-HOC₆H₄CO₂Ag should yield tetraacetylglucose esters but no glucoside, since the more distant OH groups would exercize no appreciable effect on the Ag atom. By boiling 25 g. of p-HOC₆H₄CO₂Ag with 41 g. of A in 200 cc. of C₇H₈ for 1.5 mins. and filtering while hot tetracetylglucose p-hydroxybenzoate crystallized from the filtrate on cooling, m. 197°, [α]_D²⁰ -29.76°. On extracting the filtrate with dilute NH₃ and acidifying, a white crystalline precipitate was formed, identical with the above compound No glucoside was found. Similarly, tetraacetylglucose m-hydroxybenzoate was prepared, white needles from EtOH, m. 147°, [α]_D²⁰ -26.61°. The combination between Ag and S in HSCH₂CO₂Ag was apparently too firm, as no reaction with A took place. Instead of using the Ag salt, 17 g. of A in 25 cc. of absolute MeOH were mixed with 2 g. of K in 25 cc. of MeOH, to which 7 g. of HSCH₂CO₂Et had been added. KBr was precipitated and removed after 2 hrs. and the filtrate evaporated in vacuo at 30-40° to remove MeOH. The resinous residue was digested with Ac₂O and AcONa to restore any Ac group split off, treated with cold H₂O to destroy Ac₂O, dissolved in Et₂O, the solution evaporated, and the crude product extracted with hot H₂O. On cooling, long needles of ethyl β-tetraacetyl-d-glucosidoothioglycolate formed, soluble in EtOH, Et₂O, C₆H₆, m. 63°, [α]_D¹⁵ -58.52°. Saturated Ba(OH)₂ converted it into β-d-glucosidothioglycolic acid, m. 148-50°, [α]_D -66.19°. From 20 g. of 2,5-HO(MeO)C₆H₃CO₂Ag and 30 g. of A in 250 cc. of boiling C₇H₈, AgBr was precipitated and removed, and the C₇H₈ solution extracted repeatedly with 50-cc. portions of 1:40 NH₃. The latter was acidified with HCl, after filtering, giving a white crystalline precipitate of β-tetracetyl-d-glucosido-5-methoxygentisinic acid (B), needles from EtOH, m. 172-4°, [α]_D²⁰ -32.13°. From the C₇H₈ after the NH₃ extractions tetracetylglucose 5-methoxygentisinate crystallized on evaporation, needles from EtOH, m. 163°, [α]_D²⁰ -40.2°. Cold saturated Ba(OH)₂ saponified B of β-d-glucosido-5-methoxygentisinic acid (C), fine needles from EtOH, m. 166°, [α]_D²⁰ -39.62°, easily soluble in H₂O, insoluble in Et₂O. Methyl ester of C, by the action of CH₂N₂ in Et₂O on C in concentrated EtOH solution, m. 83°, [α]_D²⁰ -48.52°. The above method applied to 13 g. of Ag p-methylmandelate and 25 g. of A in 125 g. of C₇H₈ gave 16 g. of dl-tetraacetylglucose p-methylmandelate, snow-white needles, m. 155°, while the NH₃ extractions yielded 5 g. of β-d-tetraacetylglucosido-p-methylmandelic acid, small felt-like needles, m. 149-50°. By the action of KCN and concentrated HCl on 50 g. of o-ClC₆H₄CHO at 0°, 55 g. of o-chlorobenzaldehyde cyanohydrin were obtained, and converted into o-chloromandelic acid by saponifying with concentrated HCl. Unchanged aldehyde was separated by extracting the crude product with 10% NaOH, acidifying and crystallizing the acid from C₆H₆, the yield being 18 g., m. 84-5°. The acid was dissolved in EtOH, treated with the equivalent amount of AgNO₃ in H₂O, and NH₄OH added from a buret, giving silver o-chloromandelate. From 15.6 g. of the latter, rubbed in a mortar with A and heated with 100 cc. of C₇H₈, AgBr was precipitated and removed, and the C₇H₈ solution extracted with 0.5% NH₄OH as above, etc., giving β-d-tetraacetylglucosido-o-chloromandelic acid, small white needles from dilute EtOH, m. 182°. Similarly, 8 g. of Ag orsellinate with the equivalent amount of A gave tetraacetylglucose orsellinate, m. 153°, [α]_D¹⁸ -41.75°. Ag quinolcarboxylate (Ag gentisinate) and A yielded tetraacetylglucose quinolcarboxylate, white needles from EtOH, m. 185°, [α]₁₈ -39.82°. Five g. of Ag mandelate and 13.5 g. of acetobromomaltose in 100 cc. of boiling C₇H₈ gave a small yield of heptaacetylmaltosido-dl-mondelic acid, which could not be obtained crystalline, m. 65-85°, insoluble in H₂O, easily soluble in EtOH. Polarization in CHCl₃ gave varying results, [α]_D 9-35°. This compound agrees rather closely with acetylamygdalic acid in m. p. and [α], but is entirely different from acetylcellosidomandelic acid, which is crystalline, m., 179-82°, [α]_D -44°. These facts furnish additional evidence that the sugar of amygdalin is not a cellobiose, but is probably maltose or isomaltose. A study of the influence of various salts, etc., on the rotation of glucosides showed that in 2% solution salicin was affected by H₃BO₃, Na₂B₄O₇ and NaOH, but not by NaCl, KCl, KHC₂O₄, KNO₃, CaCl₂, or H₂C₂O₄. Amygdalin was affected by Na₂B₄O₇, which caused mutarotation, and by NaOH. Menthyl α-glucoside was not affected by any of the above in 0.5% EtOH solution or in 0.5% glycerol solution

Helvetica Chimica Acta 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, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Ikeda, Yoshitsugu published the artcileReactions of acyl peroxides. I. The photochemical decomposition of benzoyl peroxide in glacial acetic acid, Application In Synthesis of 13312-84-0, the publication is Nippon Kagaku Zasshi (1958), 354-8, database is CAplus.

Bz₂O₂ (I) (24.2 g.) in 1 l. HOAc was irradiated by light (2537 A.) 50 hrs. at 20°. At the end of this period, unreacted I was less than 0.5 g., and CO₂, which was removed and absorbed in KOH as it was evolved, was 1.85 g. from 2 runs. Fractional distillation gave 5 g. C₆H₆. (CH₂CO₂H)₂ (2.3 g.) was first obtained from the residue and steam distillation yielded 9.1 g. BzOH and 15.9 g. neutral substance (II). The residue from the steam distillation gave 1.1 g. neutral substance (III), 1.2 g. homophthalic acid (IV), 0.9 g. homoisophthalic acid (V), 1.5 g. homoterephthalic acid (VI), 2.3 g. p-PhC₆H₄CO₂H (VII), and 5.1 g. resinous material. II and III gave 3.8 g. Ph₂, 2.2 g. BzOH, and 1.8 g. PhOH. Thus II and III were mixtures of Ph₂ and BzOPh. Thermal decomposition of I was neglected because the rate was too small. The products were related as follows. I decomposed to BzO• (VIII). VIII decomposed to Ph• and CO₂ and with AcOH produced BzOH and •CH₂CO₂H (IX). Ph• also reacted with AcOH to produce C₆H₆ and IX. IX combined to produce (CH₂CO₂H)₂ and reacted with BzOH to give VI. VIII and IX gave IV, V, and VI, which were also produced from I and IX. The formation of BzOPh and Ph₂ was attributed to induced decomposition of I and to the recombination of VIII and Ph• or Ph• itself because of the accumulation at rather low temperature

Nippon Kagaku Zasshi 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

Buck, Johannes S. published the artcileCatalytic reduction of mandelonitriles, Formula: C8H6ClNO, the publication is Journal of the American Chemical Society (1933), 2593-7, database is CAplus.

In the presence of a slight excess of concentrated HCl, mandelonitriles in EtOH are smoothly reduced catalytically to the corresponding β-phenylethylamine or the β-HO derivative; the reaction is complex and although some of the yields are not satisfactory, the expediency of the method makes it convenient for the preparation of certain amines. The following mandelonitriles were prepared: o-MeO, m. 73°, 65% yield; o-Cl, m. 47° (73%); 2,3-di-MeO, m. 79° (54%); p-MeO, m. 67° (62%); 3,4-di-MeO, m. 103° (78%); p-Cl, m. 43° (81%); carbomethoxy, b₃ 136°, d₄²⁵ 1.1735, n_D²⁵ 1.5000; p-methoxycarbethoxy, b_2-1 170°, d. 1.1683, n 1.5063; o-chlorocarbethoxy, b_1.4 145°, d. 1.2444, n 1.5115. In the reduction those nitriles with o-substituents give the β-hydroxyamine, the others give the amine. The following HCl salts of β-phenylethylamines were prepared: o-methoxy-β-hydroxy, m. 184° (59% yield) (p-nitrobenzoyl derivative, pale yellow, m. 178°); o-chloro-β-hydroxy, m. 197° (41%; p-nitrobenzoyl derivative, m. 194°); 2,3-dimethoxy-β-hydroxy, m. 134° (23.5%; p-nitrobenzoyl derivative, pale yellow, m. 178°); o-Cl, flows 204° (94%; p-nitrobenzoyl derivative, m. 112°); p-dimethylamino, froths 238° (44%; Bz derivative, lemon-yellow, m. 130°); p-MeO, 52% from p-MeOC₆H₄CH:CHCN and 49% from MeO₂CC₆H₄CH:CHCN (p-nitrobenzoyl derivative, pale yellow or bright orange, m. 145°); 3,4-di-MeO, m. 151° (52%; p-nitrobenzoyl derivative, pale lemon, m. 147°); p-Cl, orange, m. 195° (50%; Bz derivative, m. 147°); the p-nitrobenzoyl derivative of the o-MeO derivative, pale yellow, m. 138°.

Journal of the American 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, Formula: C8H6ClNO.

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

DeSantis, Grace published the artcileAn enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives, Related Products of nitriles-buliding-blocks, the publication is Journal of the American Chemical Society (2002), 124(31), 9024-9025, database is CAplus and MEDLINE.

The discovery, from nature, of a large and diverse set of nitrilases is reported. The utility of this nitrilase library for identifying enzymes that catalyze efficient production of valuable hydroxy carboxylic acid derivatives is demonstrated. Unprecedented enantioselectivity and substrate scope are highlighted for 3 newly discovered and distinct nitrilases. For example, a wide array of (R)-mandelic acid derivatives and analogs were produced with high rates, yields, and enantiomeric excesses (95-99% ee). We also have found nitrilases that provide direct access to (S)-phenyllactic acid and other aryllactic acid derivatives, again with high yields and enantioselectivities. Finally, different nitrilases have been discovered that catalyze enantiotopic hydrolysis of 3-hydroxyglutaronitrile to afford either enantiomer of 4-cyano-3-hydroxybutyric acid with high enantiomeric excesses (>95% ee). The 1st enzymes are reported that effect this transformation to furnish the (R)-4-cyano-3-hydroxybutyric acid, which is a precursor to the blockbuster drug Lipitor.

Journal of the American 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, Related Products of nitriles-buliding-blocks.

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

Zhang, Chen-Sheng published the artcileEfficient production of (R)-o-chloromandelic acid by deracemization of o-chloromandelonitrile with a new nitrilase mined from Labrenzia aggregata, Category: nitriles-buliding-blocks, the publication is Applied Microbiology and Biotechnology (2012), 95(1), 91-99, database is CAplus and MEDLINE.

(R)-o-Chloromandelic acid (I) is the key precursor for the synthesis of Clopidogrel, a best-selling cardiovascular drug. Although nitrilases are often used as an efficient tool in the production of α-hydroxy acids, there is no practical nitrilase specifically developed for I. Here, a new nitrilase from L. aggregata (II) was discovered for the 1st time by genomic data mining, which hydrolyzed o-chloromandelonitrile (III) with high enantioselectivity, yielding (R)-o-chloromandelic acid in 96.5% ee. II was overexpressed in Escherichia coli BL21 (DE3), purified, and its catalytic properties were studied. When III was used as the substrate, the V_max and K_m values of II were 2.53 μmol min^-1 mg^-1 protein and 0.39 mM, resp., indicating its high catalytic efficiency. In addition, a study of the substrate spectrum showed that II preferred to hydrolyze arylacetonitriles. To relieve substrate inhibition and to improve the productivity of II, a biphasic system of toluene-water (1:9, volume/volume) was adopted, in which III at 300 mM (apparent concentration, based on total volume) could be transformed by II in 8 h, giving an isolated yield of 94.5%. Thus, the development of II makes it possible to produce I by deracemizing III with a good ee value and high substrate concentration

Applied Microbiology and Biotechnology 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 C2H4ClNO, Category: nitriles-buliding-blocks.

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

He, Yu-Cai published the artcileBiocatalytic synthesis of (R)-(-)-mandelic acid from racemic mandelonitrile by cetyltrimethylammonium bromide-permeabilized cells of Alcaligenes faecalis ECU0401, Synthetic Route of 13312-84-0, the publication is Journal of Industrial Microbiology & Biotechnology (2010), 37(7), 741-750, database is CAplus and MEDLINE.

The nitrilase from Alcaligenes faecalis ECU0401 belongs to the category of arylacetonitrilase, which could hydrolyze 2-chloromandelonitrile, 3,4-dimethoxyphenylacetonitrile, mandelonitrile, and phenylacetonitrile into the corresponding arylacetic acids. To overcome the permeability barrier and prepare whole cell biocatalysts with high activities, permeabilization of Alcaligenes faecalis ECU0401 in relation to nitrilase activity was optimized by using cetyltrimethylammonium bromide (CTAB) as permeabilizing agent. The nitrilase activity from Alcaligenes faecalis ECU0401 increased 4.5-fold when the cells were permeabilized with 0.3% (w/v) CTAB for 20 min at 25°C and pH 6.5. Consequently, almost all the mandelonitrile was consumed and converted to (R)-(-)-mandelic acid with greater than 99.9% enantiomeric excess (e.e.) by the CTAB-permeabilized cells. The permeability barrier has been significantly reduced in the hydrolysis of mandelonitrile by using CTAB-permeabilized cells and a dynamic resolution was successfully achieved, giving a 100% theor. yield of (R)-(-)-mandelic acid. Efficient biocatalyst recycling was achieved as a result of cell immobilization in calcium alginate, with a product-to-biocatalyst ratio of 3.82 g (R)-(-)-mandelic acid g^-1 dry cell weight (dcw) cell after 20 cycles of repeated use.

Journal of Industrial Microbiology & Biotechnology 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, Synthetic Route of 13312-84-0.

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

Chen, Peiran published the artcileKinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Tetrahedron Letters (2014), 55(14), 2290-2294, database is CAplus.

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Tetrahedron 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, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

He, Yu-Cai published the artcileBioproduction of glycolic acid from glycolonitrile with a new bacterial isolate of Alcaligenes sp. ECU0401, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Applied Biochemistry and Biotechnology (2010), 160(5), 1428-1440, database is CAplus and MEDLINE.

Alcaligenes sp. ECU0401 has been isolated from soil samples with high nitrilase activity against glycolonitrile using the enrichment culture technique. The preferred carbon/nitrogen sources and metal ions were sodium acetate, a composite of peptone and yeast extract, and Cu²⁺, resp. Glycolic acid was obtained in a yield of 96.5% after 14 h of biotransformation from a total of 200 mM glycolonitrile in the mode of sequential addition during the cultivation of Alcaligenes sp. ECU0401 in a 5-L jar fermenter. Fifty micromolars of glycolonitrile could be hydrolyzed in a yield of 94.1% by resting cells after 36 h. The microbial nitrilase system could hydrolyze various nitriles with high activity, and no amidase activity and glycolic acid were observed in hydrolyzing glycolamide. It significantly exhibited high enantioselectivity in the hydrolysis of mandelonitrile and 2-chloromandelonitrile (>99.9% e.e._p). Efficient biocatalyst recycling was achieved as a result of immobilization in glutaraldehyde/polyethylenimine cross-linked carrageenan with immobilized cells exhibiting a biocatalyst productivity of 1,042.2 g glycolic acid per g dry cell weight after 29 batch recycles.

Applied Biochemistry and Biotechnology 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, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Li, Zhi published the artcileSeparation of chiral cyanohydrin enantiomers by gas chromatography, Application In Synthesis of 13312-84-0, the publication is Fenxi Huaxue (1997), 25(6), 708-713, database is CAplus.

The enantiomers of 14 cyanohydrins were separated on permethylated β-cyclodextrin column (fused silica, 25 m × 0.22 mm) by derivatization. The acetyl chloride and trifluoroacetic anhydride were used as derivatization reagents. All racemates were separated to baseline with separation factors (α) = 1.02-1.13. The enantiomer excess values of some enantiomers from asym. synthesis samples were determined, and they were identical with those by optical purity and HPLC methods. The separation effect of the two derivatization methods and the separation mechanism of enantiomers are discussed.

Fenxi Huaxue 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

Li, Ying published the artcileSynthesis and cytotoxicity of dihydroartemisinin ethers containing cyanoarylmethyl group, COA of Formula: C8H6ClNO, the publication is Bioorganic & Medicinal Chemistry (2003), 11(6), 977-984, database is CAplus and MEDLINE.

A new type of ether of dihydroartemisinin containing cyano and aryl groups was prepared and tested for cytotoxicity to A549, P388, L1210 and HT29 cells using the MTT assay. Compounds 12k and 12l were the most cytotoxic compounds Compound 13, lacking the peroxy group, showed a 1000-fold less potency than 12l. Similarly, the inactive compound 14 indicated that the position of cyano groups was also important. Flow cytometry data showed that the compounds caused an accumulation of P388 cells in the G₁-phase of the cell cycle.

Bioorganic & 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 C8H6ClNO, COA of Formula: C8H6ClNO.

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