Tag: M.W=150-200

Xie, Yan published the artcileSynthesis of 2-(2-Aryl)ethylbenzoic acid, Computed Properties of 612-13-5, the publication is Zhongguo Yiyao Gongye Zazhi (2012), 43(2), 87-89, database is CAplus.

2-(2-Phenylethyl)benzoic acid or 2-(thiophene-2-ylethyl)benzoic acid was synthesized from o-cyanobenzyl chloride via Wittig-Horner reaction with benzaldehyde or 2-thiopene carboxaldehyde, hydrolysis and then hydrogenation, with the overall yield of about 64% or 60%.

Zhongguo Yiyao Gongye Zazhi published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C3H7NO2, Computed Properties of 612-13-5.

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

Zhou, Wenjun published the artcileSynthesis and characterization of o-cyanostilbenes, Application In Synthesis of 612-13-5, the publication is Huagong Shengchan Yu Jishu (2011), 18(3), 28-31, database is CAplus.

The preparation and characterization of five o-cyanostilbenes from o-cyanobenzyl chloride, tri-Et phosphate, aromatic aldehydes in N,N-DMF via Wittig-Horner reaction with yields ranged from 83.8% to 93.1% were reported. The reported method had the advantages of reliable and high yields, simple operations, cheap and readily available raw materials.

Huagong Shengchan Yu Jishu published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C15H24O2, Application In Synthesis of 612-13-5.

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

Xu, Lu-Feng published the artcileSynthesis of 2-aryloxymethylbenzonitriles from 2-cyanobenzyl chloride, SDS of cas: 612-13-5, the publication is Asian Journal of Chemistry (2012), 24(11), 5329-5331, database is CAplus.

2-[(Aryloxy)methyl]benzonitriles were synthesized from 2-cyanobenzyl chloride and phenols with K₂CO₃ as a base in DMF at 80-110° in good to excellent yields. 2-Cyanobenzyl chloride is a better alternative to the more costly and less atom economical bromo analog or chloro- or bromobenzoate.

Asian Journal of Chemistry published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C5H5N3S, SDS of cas: 612-13-5.

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

Chen, Zhen published the artcileUse of a Traceless Activating and Directing Group for the Construction of Trifluoromethylpyrazoles: One-Pot Transformation of Nitroolefins and Trifluorodiazoethane, Quality Control of 5153-73-1, the publication is Angewandte Chemie, International Edition (2017), 56(16), 4569-4574, database is CAplus and MEDLINE.

We disclose an efficient one-pot transformation of trifluorodiazoethane and higher perfluorinated homologues with various nitroolefins. This method takes advantage of the nitro group as a traceless activating and directing group (TADG) that is released in the aromatization step to produce 4-substituted 3-perfluoroalkyl pyrazoles with complete regioselectivity [e.g, trans-β-nitrostyrene + CF₃CHN₂ → pyrazole I (89%) in presence of Ag₂O and Na₃PO₄]. The potential of this method is further demonstrated by the synthesis of penthiopyrad. Safety: 2,2,2-trifluorodiazoethane is potentially explosive.

Angewandte Chemie, International Edition published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.

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

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

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

Kapustin, A. I. published the artcileSimultaneous application of 2M-4XM (Tropotox) and superphosphate in clover cultivation, HPLC of Formula: 3336-34-3, the publication is Khim. v Sel’sk. Khoz. (1965), 3(11), 41-4, database is CAplus.

Herbicidal activity of Tropotox (I) in combination with superphosphate was studied on a 2-year-old cultivation of pink clover. The soil on the lot was soddy podzolic, sandy-silty clay, containing 4% of humus, 6 mg. of P and, 16 mg. of K/100 g. of soil, 75% saturated with alk. materials, pH 5.6. I at 4 kg./ha. was most effective against dicotyledonous perennials, e.g. yellow thistle and bindweed (reduced to half the control amount). Combination of I (4 kg./ha.) and superphosphate (10 kg./ha. of P₂O₅) was even more effective, killing 85% of the above weeds. I was also effective against dicotyledonous annuals, but in combination with superphosphate its effectiveness dropped. During the first 5-10 days after application of I, the growth of clover was slightly suppressed, but it then continued in a normal manner. I at 4 kg./ha. alone and in mixture with 10 kg. superphosphate/ha. does not affect the quality of clover seeds. At large doses of I (6 kg./ha.), the seed were impaired.

Khim. v Sel’sk. Khoz. published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, HPLC of Formula: 3336-34-3.

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

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

Ni, Jie published the artcileFluorescent brightening agent S-ER, Name: 2-(Chloromethyl)benzonitrile, the publication is Yinran (2014), 40(11), 35-37, database is CAplus.

1,4-Bis (2-cyano-styryl) benzene, a fluorescent whitening agent S-ER is prepared with o-toluene cyanide, tri-Et phosphite and terephthaldehyde as raw materials, and then is applied to polyester fiber dyeing. The whitening agent S-ER has better whitening effect than the conventional whitening agent DT with the amount only 1/10-1/12 of DT.

Yinran published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Name: 2-(Chloromethyl)benzonitrile.

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