Category: 13312-84-0

Franzen, H. published the artcileAction of cyanides on aldehydes and ketones, HPLC of Formula: 13312-84-0, the publication is Journal fuer Praktische Chemie (Leipzig) (1914), 293-306, database is CAplus.

cf. C. A., 7, 775. The crystalline metallic derivatives previously obtained by shaking cyanides of the alk. earths in H₂O with AcCH₂CO₂Et, BzCH₂CO₂Et, and Ac₂CH₂ are not metallic derivatives of cyanohydrins as then supposed, but metallic salts of the diketones and ketonic esters. The Ca, Sr, Ba and Mg salts of AcCH₂CO₂Et were prepared and the constitution of the Ca salt of mandelonitrile, Ca[OCH(CN)Ph]₂, was proven by its conversion into the Bz derivative, by shaking the Ca salt in Et₂O with BzCl. o-Calcium chloromandelonitrile was obtained in 62% yield from CaO, HCN and o-ClC₆H₄CHO, light yellow powder. The calcium, strontium and magnesium salts of Ac₂CH₂ were obtained in the form of needles from alc. From P-MeC₆H₄CHO was obtained, in 63% yield, calcium p-methylmandelonsirile in the form of orange-yellow crystals, which gave an intense blue coloration with concentrate H₂SO₄. p-Calcium methoxymandelonitrile was prepared from anisaldehyde. The labile, crystalline compound obtained by Kohn (Monalsh., 20, 903) by the action of HCHO on Ca(CN)₂, is shown to have the constitution Ca[OCH(CaOH)CN]₂.AcH forms a similar compound, crystallization powder. KCN and AcH yielded alanine and α-iminodipropionic acid.

Journal fuer Praktische Chemie (Leipzig) 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

Mehta, K. J. published the artcilePreparation and antimicrobial activity of p-chloro-p’-(α-carbamoylbenzylamino)diphenyl sulfones and 3-amino-2-aryl-5-p-chlorophenylsulfonylindoles, Quality Control of 13312-84-0, the publication is Acta Ciencia Indica, Chemistry (1985), 11(3), 187-90, database is CAplus.

4-ClC₆H₄SO₂C₆H₄NHCHRR¹ (I, R = Ph, 2-HOC₆H₄, 3-HOC₆H₄, 4-HOC₆H₄, MeOC₆H₄, 2-ClC₆H₄, 4-ClC₆H₄, 3,4-MeO(HO)C₆H₃, PhCH:CH, 4-O₂NC₆H₄, 2-furyl; R¹ = cyano) were prepared by treating RCH(OH)CN with 4-ClC₆H₄SO₂C₆H₄NH₂-4. Treatment of I (R¹ = cyano) with H₂SO₄ for 2 days gave I (R¹ = CONH₂) whereas after 7 days the indoles II were obtained. I (R¹ = CONH₂) have bactericidal activity against Staphylococcus aureus and Escherichia coli (no data).

Acta Ciencia Indica, 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, Quality Control of 13312-84-0.

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

Juhl, Martin published the artcileCO₂-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions, Category: nitriles-buliding-blocks, the publication is Chemistry – A European Journal (2021), 27(1), 228-232, database is CAplus and MEDLINE.

Use of carbon dioxide/carbon disulfide to accelerate cyanohydrin RR¹COHCN [R = cyclohexyl, Ph, 2-furyl, etc.; R¹ = H, CO₂H] and R²CHOC(S)SMeCN [R² = 4-FC₆H₄, (CH₂)₂Ph] syntheses starting from alkyl- and aryl aldehydes under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN were reported. Under inert atm., the reaction was essentially not operative due to the unfavored equilibrium The utility of CO₂-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani-Fischer synthesis under neutral conditions. This protocol offered an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atm. pressure of CO².

Chemistry – A European Journal 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, Category: nitriles-buliding-blocks.

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

Parekh, Hansa published the artcilePreparation and resolution of (+-)-p-(α-cyanoarylamino)benzoic acid, Synthetic Route of 13312-84-0, the publication is Indian Journal of Chemistry (1973), 11(5), 501-3, database is CAplus.

α-Amino nitriles (±)-RCH(CN)NHC6H4COOH-p [(±)I:R = Ph, o-ClC6H4, p-MeOC6H4] were prepared by condensing an aldehyde cyanhydrin with p-aminobenzoic acid. The resolution of (±)(I) into optical isomers was accomplished through fractional crystallization of the brucine salts to give the resp. (-)-nitriles. With (±)-I (R = p-MeOC6H4), the (+)-nitrile was also obtained. The introduction of Cl in the Ph nucleus at the ortho-position enhanced the optical activity, while the MeO group at the paraposition decreased the optical activity.

Indian Journal of 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, Synthetic Route of 13312-84-0.

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

Zhang, Zhi-Jun published the artcileSignificant enhancement of (R)-mandelic acid production by relieving substrate inhibition of recombinant nitrilase in toluene-water biphasic system, Computed Properties of 13312-84-0, the publication is Journal of Biotechnology (2011), 152(1-2), 24-29, database is CAplus and MEDLINE.

The enantioselective hydrolysis of mandelonitrile with whole cells of a recombinant Escherichia coli expressing nitrilase activity was severely inhibited by the substrate at high concentrations (>300 mM), which resulted in a low yield of the target product (R)-(-)-mandelic acid. To relieve the substrate inhibition and to enhance the (R)-(-)-mandelic acid productivity, eight water-organic solvent biphasic systems were attempted in this work. Toluene was found to be the most suitable solvent as the organic phase among the solvents tested. Various parameters were systematically examined and optimized in shake flasks. The phase volume ratio, buffer pH and reaction temperature were shown to be sensitive parameters affecting both the yield and the enantiopurity of product in the biphasic system. Under the optimized conditions, significant enhancement of substrate tolerance from 200 mM to 500 mM and average productivity from 179.6 g L^-1 d^-1 to 352.6 g L^-1 d^-1 were achieved. Subsequently, the biocatalytic hydrolysis of mandelonitrile was successfully carried out in a stirred reactor (2-L scale) by repeated use of the calcium alginate entrapped cells for 5 batches, affording 110.7 g (R)-(-)-mandelic acid in 98.0% ee (enantiomeric excess) and a specific production of 13.8 g (mandelic acid) g^-1 (cell), resp.

Journal of 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 C14H26O2, Computed Properties of 13312-84-0.

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

Moon, Lomary S. published the artcileChiral Solvating Agents for Cyanohydrins and Carboxylic Acids, SDS of cas: 13312-84-0, the publication is Journal of Organic Chemistry (2010), 75(16), 5487-5498, database is CAplus and MEDLINE.

A structure as simple as an ion pair of (R)- or (S)-mandelate and dimethylamminopyridinium ions possesses structural features that are sufficient for NMR enantiodiscrimination of cyanohydrins. Also, ¹H NMR data of cyanohydrins of known configuration obtained in the presence of the mandelate-dimethylaminopyridinium ion pair point to the existence of a correlation between chem. shifts and absolute configuration of cyanohydrins. Mandelate-DMAPH⁺ ion pair and mandelonitrile form a 1:1 complex with an association constant of 338 M^-1 (ΔG⁰, -3.4 kcal/mol) for the (R)-mandelonitrile/(R)-mandelate-DMAPH⁺ and 139 M^-1 (ΔG⁰, -2.9 kcal/mol) for the (R)-mandelonitrile/(S)-mandelate-DMAPH⁺ complex. To understand the origin of enantiodiscrimination, the geometry optimization and energy minimization of the models of ternary complexes of (S)-mandelonitrile/(R)-mandelate/DMAPH⁺ and (S)-mandelonitrile/(S)-mandelate/DMAPH⁺ complexes was performed using DFT methodol. (B3LYP) with the 6-31+G(d) basis set in Gaussian 3.0. Further, anal. of optimized mol. model obtained from theor. studies suggested that (i) DMAP may be replaced with other amines, (ii) the hydroxyl group of mandelic acid is not necessary for stabilization of ternary complex and may be replaced with other groups such as Me, (iii) the ion pair should form a stable ternary complex with any hydrogen-bond donor, provided its OH bond is sufficiently polarized, and (iv) α-H of racemic mandelic acid should also get resolved with optically pure mandelonitrile. These inferences were exptl. verified, which not only validated the proposed model but also led to development of a new chiral solvating agent for determination of ee of carboxylic acids and absolute configuration of aryl but not alkyl carboxylic acids.

Journal of Organic 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, SDS of cas: 13312-84-0.

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

Ooi, T. published the artcileZr(OBu^t)₄ as an effective promoter for the Meerwein-Ponndorf-Verley alkynylation and cyanation of aldehydes: development of a new asymmetric cyanohydrin synthesis, COA of Formula: C8H6ClNO, the publication is Tetrahedron (2001), 57(5), 867-873, database is CAplus.

Zr(OBu^t)₄ can serve as an effective promoter for the Meerwein-Ponndorf-Verley alkynylation of aldehydes and also facilitate MPV type cyanide transfer to aldehyde carbonyls with com. available acetone cyanohydrin under mild conditions. Based on this finding, a new procedure for asym. cyanohydrin synthesis has been developed employing (4R,5R)-2,2-dimethyl-α,α,α’,α’-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL, I) as a chiral ligand. For instance, sequential treatment of a CH₂Cl₂ solution of I (1 equiv) with Zr(OBu^t)₄ (1 equiv) and acetone cyanohydrin (2 equiv) at room temperature for 1 h, and subsequent reaction with 3-phenylpropanal at -40° for 7.5 h resulted in formation of the corresponding cyanohydrin in 63% isolated yield with 85% ee. The scope and limitations of this method have been clarified with various aldehydes as substrates.

Tetrahedron 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

Campbell, Neil published the artcilePreparation of the halophenylacetic acids, Quality Control of 13312-84-0, the publication is Journal of the Chemical Society (1948), 1251-5, database is CAplus.

Gränacher’s synthesis (C.A. 16, 3898; 17, 2424) has been applied to the preparation of XC₆H₄CH₂CO₂H; the method depends on a satisfactory preparation of rhodanine (I), which is discussed. The yield of I depends upon the yield of H₂NCSSNH₄ (II) in the 1st stage of the reaction; the yield of II, as compared with that of CS(SNH₄)₂ (III), is a function of the NH₃ concentration which, in turn, is dependent on the temperature The more concentrated the NH₃ solution, the greater is the yield of III; the best yield of II is obtained at 10-15°; the yield of I from II is 44%. When the temperature is kept below 0%, III is the main product. Methods of distinguishing between II and III are given. Mol. quantities of aldehyde and I in AcOH (5 cc. per g. aldehyde), refluxed 0.5 h. with fused AcONa (twice the weight of I), give the following benzylidenerhodanines (IV): ο-Cl, pale yellow, m. 192°, 97% (Andreasch, C.A. 22, 3410, gives 169°); m-Cl, pale yellow, m. 233°, 93%; p-Cl, yellow, m. 231-2°, 93%; ο-Br, orange, m. 183.5°, 80%; m-Br, yellow, m. 238°, 90%; p-Br, yellow, m. 237-8°, 84%. IV were transformed into β-phenyl-α-thiopyruvic acids (V) by heating with 8 cc. 8% NaOH (per g. IV) at 50-5° until a clear or nearly clear solution resulted, cooling in an ice-salt bath, and acidifying rapidly with 3 N HCl; the crude acid in cold EtOH is precipitated with 1-2 volumes cold H₂O and recrystallized from MeOH, petr. ether, etc.; however, the crude acids were used in the next step. ο-Cl, m. 134-5°, 72% (A. gives 119-20°); m-Cl, straw-colored, m. 134°, 84%; p-Cl, yellow, m. 169-71°, 84% [a byproduct is probably α,α’-dithiobis(m-chlorocinnamic acid), yellow, m. 221-2°]; ο-Br, lemon-yellow, m. 142-3°, 70%; m-Br, pale yellow, m. 133-4°, 81%; p-Br, m. 165-80°, 75% (could not be purified further). α-Isonitroso-β-(halophenyl)propionic acids (VI) were prepared from V by refluxing (about 0.5 h.) in alc. containing 3 mols. NH₂OH (until H₂S evolution ceases); the crude acid is precipitated from dilute NaOH solution with concentrated HCl. ο-Cl, m. 156°, 83%; m-Cl, m. 149° (decomposition), 100%; p-Cl, m. 170° (decomposition) (1 sample m. 182°), 100%; ο-Br, m. 150° (decomposition), 100%; m-Br, m. 151°, 93%; p-Br, m. 173°, 85% (yields are of crude products). VI, refluxed 10 min. with Ac₂O (4 cc. per g. VI), the Ac₂O removed in vacuo, and the residue extracted with ether, give the (halophenyl)acetonitriles (VII): ο-Cl, b₁₁ 123-5°, 64%; m-Cl, b₁₀ 134-6°, 55%; p-Cl, b₁₂ 137-9°, m. 31-2°, 80%; ο-Br, b₁₃, 140-1°, 88%; m-Br, b₁₀ 145-7°, m. 27-8°, 70%; p-Br, b_10-12 152-6°, m. 48°, 72%. The over-all yields of the VII from the aldehydes were: ο-, m-, and p-Cl, 57, 47, 62%; ο-, m-, and p-Br, 49, 44, 38%; further losses, sometimes considerable, occur in the next step. VII were hydrolyzed by boiling with 60% H₂SO₄ or, preferably, with 20% EtOH-KOH, giving RC₆H₄CH₂CO₂H (R given): ο-Cl, m. 93-5° (p-nitrobenzyl ester, m. 70-1°); m-Cl, m. 77° (p-nitrobenzyl ester, m. 74-5°; p-toluidide, m. 138°); p-Cl, m. 104-6° (p-nitrobenzyl ester, m. 117°); ο-Br, m. 104-5° (p-nitrobenzyl ester, m. 74-5°; p-toluidide, m. 183-4°; anilide, m. 153-4°); m-Br, m. 102-3° (p-nitrobenzyl ester, m. 75-6°; p-toluidide, m. 135°); p-Br, m. 113-15° (p-nitrobenzyl ester, m. 128-9°; anilide, m. 174-6°; p-toluidide, m. 203°). The results show that this method leaves much to be desired. The crystalline compound from 20 g. p-BrC₆H₄CHO, 80 cc. NaHSO₃, and 5 cc. EtOH, stirred 2 h. with 10 g. KCN in 20 cc. H₂O, gives 12.5 g. p-bromomandelonitrile, m. 78-9°; 11 g. and 46 cc. HI (d. 1.94), refluxed 1 h. give 1.5 g. p-BrC₆H₄CH₂CO₂H; an unknown compound, m. 126-7°, is a byproduct. ο-ClC₆H₄CHO, through ο-ClC₆H₄CH(OH)CN, yields the benzoate (no properties given); refluxing with Pt black in tetralin did not give ο-ClC₆H₄CH₂CN. p-MeOC₆H₄CH₂CN was obtained in 39% yield (yield of intermediate benzoate 74 and 92% in 2 experiments). Other methods were tried without much success. A mixture of ο- and p-BrC₆H₄CH₂CO₂H could not be separated by fractional distillation of the acid chlorides or Et esters; chromatog. separation of the anilides, p-toluidides, and 2-naphthalides was only partially successful (they fluoresce in C₆H₆ but not on the Al₂O₃ column). α-(ο-Bromophenyl)aceto-2-naphthalide, m. 188-9°; p-isomer, m. 203-4°. α-Phenylaceto-2-naphthalide m. 162-3°. In the preparation of the naphthalides by heating the acids with 2-C₁₀H₇NH₂, (2-C₁₀H₇)₂NH is obtained, the catalyst presumably being the halo acid. 2-C₁₀H₇NH₂ and PhNH₂ give 2-C₁₀H₇NHPh, and p-MeC₆H₄NH₂ gives 2-C₁₀H₇NHC₆H₄Me-p, but ο- or m-ClC₆H₄NH₂ gives only (2-C₁₀H₇)₂NH. 2-C₁₀H₇NH₂ and its derivatives are more strongly adsorbed than the corresponding 1-derivatives

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, Quality Control of 13312-84-0.

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

Liu, Tang-Lin published the artcileCyano-borrowing: titanium-catalyzed direct amination of cyanohydrins with amines and enantioselective examples, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(4), 651-654, database is CAplus and MEDLINE.

In the presence of Ti(Oi-Pr)₄, aldehyde and ketone cyanohydrins underwent amination reactions with amines such as 4-methoxyaniline to yield α-aminonitriles. Aryl, aryl alkyl, and dialkyl ketones and aryl and alkyl aldehyde cyanohydrins underwent amination. Reaction of aldehyde cyanohydrins with 4-methoxyaniline in the presence of Ti(Oi-Pr)₄, (S)-BINOL, and quinine yielded nonracemic (S)-α-aminonitriles in 31-88% ee. The reaction mechanism was studied; the reaction is proposed to occur by elimination of cyanide from the cyanohydrin followed by imine formation and addition of cyanide to the imine (“cyanide borrowing”) rather than by loss of a proton, imine formation, and reduction (“hydrogen borrowing”).

Chemical Communications (Cambridge, United Kingdom) 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

Li, Qing-Hua published the artcileTitanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia, Formula: C8H6ClNO, the publication is Organic Letters (2019), 21(20), 8429-8433, database is CAplus and MEDLINE.

Herein, the direct amination of cyanohydrins with the partner of ammonia for the synthesis of N-unprotected α-aminonitriles H₂NC(R¹)(R²)CN (R¹ = Ph, 4-FC₆H₄, 2-thienyl, etc.; R² = H, Me, Et; -R¹R²– = -(CH₂)₄-) is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesized with moderate to high yields under mild reaction conditions.

Organic 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, Formula: C8H6ClNO.

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