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Cas Database

100007-62-3

100007-62-3

Identification

  • Product Name:Cyclohexaneacetonitrile, a-hydroxy-, (R)-

  • CAS Number: 100007-62-3

  • EINECS:

  • Molecular Weight:139.197

  • Molecular Formula:C8H13NO

  • HS Code:

  • Mol File:100007-62-3.mol

Synonyms:2-cyclohexyl-2-hydroxyethanenitrile;2-cyclohexyl-2-hydroxyacetonitrile;cyclohexyl-hydroxy-acetonitrile;

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin 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.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 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. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for 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. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • 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

Supplier and reference price

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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:(R)-2-HYDROXY-2-CYCLOHEXYLACETONITRILE 95.00%
  • Packaging:5MG
  • Price:$ 497.08
  • Delivery:In stock
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Relevant articles and documentsAll total 83 Articles be found

Nickel-Catalyzed, Reductive C(sp3)?Si Cross-Coupling of α-Cyano Alkyl Electrophiles and Chlorosilanes

Oestreich, Martin,Zhang, Liangliang

supporting information, p. 18587 - 18590 (2021/07/25)

A nickel/zinc-catalyzed cross-electrophile coupling of alkyl electrophiles activated by an α-cyano group and chlorosilanes is reported. Elemental zinc is the stoichiometric reductant in this reductive coupling process. By this, a C(sp3)?Si bond can be formed starting from two electrophilic reactants whereas previous methods rely on the combination of carbon nucleophiles and silicon electrophiles or vice versa.

Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)

-

Paragraph 0414-0415, (2020/01/12)

The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n=0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)

Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines

Cheng, Jiang-Tao,Dong, Xiao-Yang,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Juan,Liu, Xin-Yuan,Luan, Cheng,Wang, Fu-Li,Wang, Li-Lei,Yang, Ning-Yuan,Zhang, Yu-Feng

supporting information, p. 15413 - 15419 (2021/09/30)

α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Juhl, Martin,Petersen, Allan R.,Lee, Ji-Woong

supporting information, p. 228 - 232 (2020/11/30)

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is 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 offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.

A High-Throughput Screening Method for the Directed Evolution of Hydroxynitrile Lyase towards Cyanohydrin Synthesis

Zheng, Yu-Cong,Ding, Liang-Yi,Jia, Qiao,Lin, Zuming,Hong, Ran,Yu, Hui-Lei,Xu, Jian-He

, p. 996 - 1000 (2021/01/15)

Chiral cyanohydrins are useful intermediates in the pharmaceutical and agricultural industries. In nature, hydroxynitrile lyases (HNLs) are a kind of elegant tool for enantioselective hydrocyanation of carbonyl compounds. However, currently available methods for demonstrating hydrocyanation are still stalled at precise, but low-throughput, GC or HPLC analyses. Herein, we report a chromogenic high-throughput screening (HTS) method that is feasible for the cyanohydrin synthesis reaction. This method was highly anti-interference and sensitive, and could be used to directly profile the substrate scope of HNLs either in cell-free extract or fermentation clear broth. This HTS method was also validated by generating new variants of PcHNL5 that presented higher catalytic efficiency and stronger acidic tolerance in variant libraries.

Process route upstream and downstream products

Process route

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

C<sub>13</sub>H<sub>26</sub>O<sub>2</sub>Si
26565-45-7

C13H26O2Si

2-cyclohexyl-2-hydroxyacetonitrile
100007-62-3,107485-34-7,4354-47-6

2-cyclohexyl-2-hydroxyacetonitrile

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With indium (III) iodide; 1,1,3,3-Tetramethyldisiloxane;Indichloromethane;at 20 ℃; for 1h;
Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

2-cyclohexyl-2-hydroxyacetonitrile
100007-62-3,107485-34-7,4354-47-6

2-cyclohexyl-2-hydroxyacetonitrile

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: indium (III) iodide / dichloromethane / 0.05 h / 20 °C
2: indium (III) iodide; 1,1,3,3-Tetramethyldisiloxane / dichloromethane / 1 h / 20 °C
With indium (III) iodide; 1,1,3,3-Tetramethyldisiloxane;Indichloromethane;
2-hydroxy-2,2-diphenylacetonitrile
4746-48-9

2-hydroxy-2,2-diphenylacetonitrile

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

benzophenone
119-61-9

benzophenone

2-cyclohexyl-2-hydroxyacetonitrile
100007-62-3,107485-34-7,4354-47-6

2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
With dibutyldimethoxytin;Indiethyl ether;at 20 ℃; for 20h; Inert atmosphere;
87%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

2-cyclohexyl-2-hydroxyacetonitrile
100007-62-3,107485-34-7,4354-47-6

2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
With P(i-PrNCH2CH2)N;Intetrahydrofuran;at 0 ℃; for 2h;
99%
With tris(pentafluorophenyl)borate;Indichloromethane;at 20 ℃; for 0.333333h; Inert atmosphere;
95%
With tin(IV) chloride; N-(cyclohexylmethylene)aniline;Invarious solvent(s);at -78 ℃;
91%
With potassium carbonate;Indiethyl ether;at 20 ℃;
91%
With potassium carbonate;Indiethyl ether;at 20 ℃;
91%
P(MeNMCH2CH2)3N;Intetrahydrofuran;at 0 ℃; for 2h;
90%
trimethylsilyl cyanide; cyclohexanecarbaldehyde;With 6,6'-bis(methylaminosulfonyl)-7,7'-dihydroxy-8,8'-biquinolyl;Intoluene;at 0 - 20 ℃; for 1.25h; Inert atmosphere;
With hydrogenchloride;Inwater; ethyl acetate; toluene;at 20 ℃; for 1.5h; Inert atmosphere;
86%
With dichlorotitanium 1-polystyrene-oxy-propane-2,3-dioxide;Indichloromethane;at 20 ℃; for 20h;
82%
With potassium tert-butylate; 1,3-bis(mesityl)imidazolium chloride;Intetrahydrofuran;at 20 ℃; for 2h; Schlenk technique; Inert atmosphere;
70%
trimethylsilyl cyanide; cyclohexanecarbaldehyde;With titanium(IV) isopropylate;Indichloromethane;at 0 - 20 ℃; for 4h;
With hydrogenchloride;Intetrahydrofuran; dichloromethane; water;at 0 ℃;
65%
With hydrogenchloride; bismuth(III) chloride;Yield given. Multistep reaction; 1.) 1,2-dichloroethane, RT, 20 min, 2.) MeOH;
((2,6-bis(N-cyclohexyl)imino)phenyl)aquoplatinum(II);Indichloromethane;at 20 ℃; for 24h;
With hydrogenchloride;
cyclohexanecarbaldehyde;With copper(II) bis(trifluoromethanesulfonate);Indichloromethane;at 20 ℃; for 0.25h;
trimethylsilyl cyanide;Indichloromethane;at 20 ℃; for 18h;
trimethylsilyl cyanide; cyclohexanecarbaldehyde;Intetrahydrofuran;for 0.0833333h; Schlenk technique; Inert atmosphere;
With potassium tert-butylate;Intetrahydrofuran;at 20 ℃; Schlenk technique; Inert atmosphere;
potassium cyanide

potassium cyanide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

2-cyclohexyl-2-hydroxyacetonitrile
100007-62-3,107485-34-7,4354-47-6

2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
cyclohexanecarbaldehyde;With sodium hydrogensulfite;Inwater;at 25 ℃; for 1h;
potassium cyanide;Inwater;at 0 - 25 ℃;
99%
With carbon dioxide;Inethanol;at 20 ℃; for 18h; under 760.051 Torr; Sealed tube;
94%
With acetic acid;Indiethyl ether;at 5 - 20 ℃; for 18h;
With sodium hydrogensulfite;Inwater; ethyl acetate;at 40 ℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

(R)-2-cyclohexyl-2-hydroxyacetonitrile
4354-47-6,107485-34-7,100007-62-3

(R)-2-cyclohexyl-2-hydroxyacetonitrile

(S)-2-cyclohexyl-2-hydroxyacetonitrile
4354-47-6,100007-62-3,107485-34-7

(S)-2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
With titanium(IV) dichlorodiisopropylate; (4R-trans)-2-methyl-2-phenyl-α,α,α',α'-tetraphenyl-1,3-dioxolan-4,5-dimethanol;Intoluene;at -65 ℃; for 48h; Title compound not separated from byproducts;
77%
With chiral titanium reagent;Intoluene;at -65 ℃; for 48h; Yield given. Yields of byproduct given;
With (S)-2--3-methyl-1-butanol titanium tetraisopropoxide;Indichloromethane;at -80 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With titanium(IV) isopropylate; (S)-valinol; 3-tert-butyl-2-hydroxybenzaldehyde;Indichloromethane;at -78 ℃; for 36h; Yield given. Title compound not separated from byproducts;
With hydrogenchloride; (S)-2-(N-3-tert-butylsalicylidene)amino-3-methyl-1-butanol; titanium(IV) isopropylate;Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) dichloromethane, -80 deg C, 12 h; 2.) water, ethyl acetate, room temp., 6 h;
With titanium(IV) isopropylate; sulfoximine (R)-3; hydrogen fluoride;Yield given. Multistep reaction; 1.) CH2Cl2, -50 deg C, 20 h, 2.) water, 30 min, RT;
With titanium(IV) isopropylate; hydrogen fluoride; (R)-S-2-hydroxyphenyl S-methyl sulfoximine;Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) dichloromethane, -50 deg C, 20-24 h, 2.) 30 min, room temperature;
With ytterbium(III) chloride; 2,6-bis[4′-isopropyloxazolin-2′-yl]pyridine;Inacetonitrile;for 2h; Yield given; Yields of byproduct given; Ambient temperature;
trimethylsilyl cyanide; cyclohexanecarbaldehyde;With chiral oxazaborolidinium bistriflimidate; Triphenylphosphine oxide;Intoluene;at 0 ℃; for 40h;
With hydrogenchloride;Inethyl acetate; toluene;for 2h; Title compound not separated from byproducts;
trimethylsilyl cyanide; cyclohexanecarbaldehyde;With titanium(IV) isopropylate; 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol;Indichloromethane;at -20 ℃; for 48h; Inert atmosphere;
With hydrogenchloride; water;Indichloromethane; ethyl acetate;at 20 ℃; for 12h; optical yield given as %ee; enantioselective reaction;
With C27H34NO6V; tetrabutyl ammonium fluoride;Inacetonitrile;at -20 ℃; for 24h; optical yield given as %ee; enantioselective reaction;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

(R)-2-cyclohexyl-2-hydroxyacetonitrile
4354-47-6,107485-34-7,100007-62-3

(R)-2-cyclohexyl-2-hydroxyacetonitrile

(S)-2-cyclohexyl-2-hydroxyacetonitrile
4354-47-6,100007-62-3,107485-34-7

(S)-2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
With titanium(IV) dichlorodiisopropylate; (4R-trans)-2-methyl-2-phenyl-α,α,α',α'-tetraphenyl-1,3-dioxolan-4,5-dimethanol;Intoluene;at -65 ℃; for 48h; Title compound not separated from byproducts;
77%
With chiral titanium reagent;Intoluene;at -65 ℃; for 48h; Yield given. Yields of byproduct given;
With (S)-2--3-methyl-1-butanol titanium tetraisopropoxide;Indichloromethane;at -80 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With titanium(IV) isopropylate; (S)-valinol; 3-tert-butyl-2-hydroxybenzaldehyde;Indichloromethane;at -78 ℃; for 36h; Yield given. Title compound not separated from byproducts;
With hydrogenchloride; (S)-2-(N-3-tert-butylsalicylidene)amino-3-methyl-1-butanol; titanium(IV) isopropylate;Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) dichloromethane, -80 deg C, 12 h; 2.) water, ethyl acetate, room temp., 6 h;
With titanium(IV) isopropylate; sulfoximine (R)-3; hydrogen fluoride;Yield given. Multistep reaction; 1.) CH2Cl2, -50 deg C, 20 h, 2.) water, 30 min, RT;
With titanium(IV) isopropylate; hydrogen fluoride; (R)-S-2-hydroxyphenyl S-methyl sulfoximine;Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) dichloromethane, -50 deg C, 20-24 h, 2.) 30 min, room temperature;
With ytterbium(III) chloride; 2,6-bis[4′-isopropyloxazolin-2′-yl]pyridine;Inacetonitrile;for 2h; Yield given; Yields of byproduct given; Ambient temperature;
trimethylsilyl cyanide; cyclohexanecarbaldehyde;With chiral oxazaborolidinium bistriflimidate; Triphenylphosphine oxide;Intoluene;at 0 ℃; for 40h;
With hydrogenchloride;Inethyl acetate; toluene;for 2h; Title compound not separated from byproducts;
trimethylsilyl cyanide; cyclohexanecarbaldehyde;With titanium(IV) isopropylate; 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol;Indichloromethane;at -20 ℃; for 48h; Inert atmosphere;
With hydrogenchloride; water;Indichloromethane; ethyl acetate;at 20 ℃; for 12h; optical yield given as %ee; enantioselective reaction;
With C27H34NO6V; tetrabutyl ammonium fluoride;Inacetonitrile;at -20 ℃; for 24h; optical yield given as %ee; enantioselective reaction;
sodium cyanide
773837-37-9

sodium cyanide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

2-cyclohexyl-2-hydroxyacetonitrile
100007-62-3,107485-34-7,4354-47-6

2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
cyclohexanecarbaldehyde;With sodium hydrogen sulfite;Inwater;at 20 ℃; for 1h;
sodium cyanide;Inwater;at 0 - 25 ℃; for 16h;
38%
cyclohexanecarbaldehyde;With sodium hydrogensulfite;Indiethyl ether; water;at 20 ℃; for 2h;
sodium cyanide;Indiethyl ether; water;at 20 ℃;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

(S)-2-cyclohexyl-2-hydroxyacetonitrile
4354-47-6,100007-62-3,107485-34-7

(S)-2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
trimethylsilyl cyanide; cyclohexanecarbaldehyde;With 4 A molecular sieve; titanium(IV) isopropylate; (1R,2R)-N,N'-bis[(1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylcarbonyl]-1,2-diphenylethylenediamine;Indichloromethane;at -78 ℃;
With hydrogenchloride;Indichloromethane;for 6h; Further stages.;
90%
2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

(R)-2-cyclohexyl-2-hydroxyacetonitrile
4354-47-6,107485-34-7,100007-62-3

(R)-2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
With acetate buffer;Indiethyl ether;at 23 ℃; for 10h; oxynitrilase;
72%
oxynitrilase;
68%

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