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Chemical Structure| 874-27-1 Chemical Structure| 874-27-1

Structure of 874-27-1

Chemical Structure| 874-27-1

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Product Details of [ 874-27-1 ]

CAS No. :874-27-1
Formula : C8H7ClO
M.W : 154.59
SMILES Code : O=CC1=CC=CC(Cl)=C1C
MDL No. :MFCD11047716
InChI Key :WMDHVKYUOKHNQK-UHFFFAOYSA-N
Pubchem ID :13162662

Safety of [ 874-27-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 874-27-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 874-27-1 ]

[ 874-27-1 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 141-82-2 ]
  • [ 874-27-1 ]
  • [ 879-51-6 ]
  • 2
  • [ 75-17-2 ]
  • [ 87-60-5 ]
  • [ 874-27-1 ]
  • 3
  • [ 874-27-1 ]
  • [ 90369-75-8 ]
  • 4
  • [ 54454-12-5 ]
  • [ 874-27-1 ]
YieldReaction ConditionsOperation in experiment
69% With hydrogenchloride; In dichloromethane; A. 3-Chloro-2-methylbenzaldehyde To 3-chloro-2-methylbenzonitrile (5 g, 33 mmol) in dichloromethane (150 mL) at -78 C. was added DiBAL (1M in dichloromethane, 41 mL). The reaction mixture was stirred at -78 C. for 2 h then quenched with methanol. The mixture was warmed to 0 C and HCl (10%) was added. The ice-water bath was removed and the mixture was stirred at room temperature for 10 min. The two phases were separated and aqueous phase was extracted with dichloromethane. Combined dichloromethane was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (5% ethyl acetate/hexane) gave 3-chloro-2-methylbenzaldehyde (3.5 g, 69%). 1H NMR (300 MHz, CDCl3) delta 2.64 (s, 3H), 7.21-7.26 (m, 1H), 7.50-7.53(m, 1H), 7.63-7.66 (m, 1H), 10.20 (s, 1H)
  • 5
  • [ 587-04-2 ]
  • [ 74-88-4 ]
  • [ 874-27-1 ]
  • 6
  • [ 118-69-4 ]
  • [ 874-27-1 ]
  • 8
  • [ 874-27-1 ]
  • [ 90369-76-9 ]
  • 16
  • [ 874-27-1 ]
  • [ 90369-87-2 ]
  • 19
  • [ 874-27-1 ]
  • [ 90388-41-3 ]
  • 28
  • [ 874-27-1 ]
  • [ 90133-70-3 ]
  • 32
  • [ 874-27-1 ]
  • [ 942-17-6 ]
  • 33
  • [ 874-27-1 ]
  • 5-Chlor-4-methyl-indan [ No CAS ]
  • 34
  • [ 874-27-1 ]
  • [ 942-18-7 ]
  • 35
  • [ 874-27-1 ]
  • [ 879-50-5 ]
  • 36
  • [ 874-27-1 ]
  • [ 1008-13-5 ]
  • 37
  • [ 874-27-1 ]
  • 5-Isopropenyl-4-methyl-indan [ No CAS ]
  • 38
  • [ 874-27-1 ]
  • 4-Methyl-indan-5-carbonitrile [ No CAS ]
  • 39
  • [ 874-27-1 ]
  • 2-(4-Methyl-indan-5-yl)-propan-2-ol [ No CAS ]
  • 40
  • [ 874-27-1 ]
  • 4-Methyl-indan-5-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
These aldehydes and ketones are set forth for exemplification and are not to be construed as limiting the scope of this invention. benzaldehyde, ... 1,1-biphenyl-4-carboxaldehyde, 2-naphthylaldehyde, 6-methoxy-2-naphthaldehyde, 1,1-biphenylacetaldehyde, 2-methyl-3-chlorobenzaldehyde, 4-trifluoromethylbenzaldehyde, and benzene acetaldehyde, 4-pyridylaldehyde, 2,4-difluorobenzaldehyde, ...
  • 42
  • [ 874-27-1 ]
  • [ 1779-49-3 ]
  • 3-chloro-2-methylstyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; hexane; PREPARATION 1 (Witting reaction) Methyltriphenylphosphonium bromide (6.9 g, 0.019M) was suspended in dry tetrahydrofuran (100 ml) at -40 C. under an atmosphere of dry nitrogen. n-Butyllithium (13.5 ml. of a 1.55M solution in hexane, 0.021M) was added dropwise during 10 minutes and the mixture was stirred at -40 C. for 30 minutes. <strong>[874-27-1]3-Chloro-2-methylbenzaldehyde</strong> (3.0 g, 0.019M) in dry tetrahydrofuran (10 mls) was then added. The mixture was maintained at -40 C. for 30 minutes and then allowed to warm to room temperature. Hexane (150 ml) was added and the mixture was filtered. The hexane was evaporated to give crude 3-chloro-2-methylstyrene which was used directly without further purification.
  • 43
  • [ 874-27-1 ]
  • [ 6921-34-2 ]
  • [ 1188271-84-2 ]
YieldReaction ConditionsOperation in experiment
60% With hydrogenchloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; B. 1-(3-Chloro-2-methylphenyl)-2-phenylethanamine To <strong>[874-27-1]3-chloro-2-methylbenzaldehyde</strong> (2.85 g, 18.5 mmol) in THF (5 mL) at 0 C. was added lithium bis(trimethylsilyl)amide (1M in THF, 22.2 mL). The ice-water bath was removed and the reaction mixture was stirred from 0 C. to room temperature for 2 h. The reaction mixture was then cooled back to 0 C. and benzylmagnesium chloride (1M in THF, 22.2 mL) was added. The reaction mixture was stirred from 0 C. to room temperature for 1 h then quenched with NH4Cl (Sat.), extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated. HCl (1.25M in methanol) was added until a pH of 2. Methanol was removed to give yellow solid. To the solid was added dichloromethane. The suspension was filtered and washed with dichloromethane to yield white solid. The white solid was dissolved in methanol, basified with NaOH (1N) and extracted with ethyl acetate. Combined ethyl acetate was washed with brine, dried over sodium sulfate and concentrated to produce 1-(3-chloro-2-methylphenyl)-2-phenylethanamine (22.73 g, 60%) as a light yellow oil. 1H NMR (300 MHz, CDCl3) delta 2.37 (s, 3H), 2.67-2.75 (m, 1H), 2.95-3.01 (m, 1H), 4.46-4.50 (m, 1H), 7.17-7.19 (m, 3H), 7.24-7.33(m, 4H), 7.46-7.49 (m, 1H).
  • 44
  • [ 64380-53-6 ]
  • [ 874-27-1 ]
  • 45
  • [ 1400692-86-5 ]
  • [ 874-27-1 ]
  • 46
  • [ 587-04-2 ]
  • [ 874-27-1 ]
  • 47
  • [ 1816-92-8 ]
  • [ 874-27-1 ]
  • methyl (Z)-2-azido-3-(3-chloro-2-methylphenyl)prop-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With methanol; sodium methylate; at -20 - 20℃; for 11.0h;Inert atmosphere; Step 3 - Methyl (Z)-2-azido-3-(3-chloro-2-methylphenyl) prop-2-enoate (0827) [00486] To a solution of sodium methoxide (2.34 g, 43.2 mmol) in methanol (140 mL) was added <strong>[874-27-1]3-chloro-2-methyl-benzaldehyde</strong> (5.80 g, 43.3 mmol) and methyl 2-azidoacetate (16.8 g, 129 mmol,) dropwise at -20 C under nitrogen. The mixture was stirred at 20 C for 11 hours. On completion, the mixture was poured into ice-water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic phase was washed with saturated brine (2 x 100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate = 500:1 to 5:1) to give the title compound. 1H NMR (300MHz, CDCl3) delta = 8.98 (br. s., 1H), 7.37 - 7.10 (m, 3H), 3.98 (s, 3H), 2.60 (s, 3H).
  • 48
  • [ 90369-75-8 ]
  • [ 874-27-1 ]
YieldReaction ConditionsOperation in experiment
With manganese(IV) oxide; In dichloromethane; at 20 - 40℃; for 12.0h;Inert atmosphere; Step 2 - 3-Chloro-2-methyl-benzaldehyde (0825) [00485] To a solution of (3-chloro-2-methyl-phenyl)methanol (400 mg, 2.55 mmol) in dichloromethane (20 mL) was added manganese dioxide (2.22 g, 25.5 mmol) in one portion at 20 C under nitrogen. The mixture was stirred at 30-40 C for 12 hours. On completion, the mixture was filtered and concentrated, the residue was purified by silica gel chromatography (petroleum ether:ethyl acetate = 500:1 to 200:1) to give the title compound.1H NMR (400MHz, CDCl3) delta = 10.28 (s, 1H), 7.73 - 7.71 (d, J = 7.6 Hz, 1H), 7.61 - 7.60 (d, J = 6.8 Hz, 1H), 7.33 - 7.29 (m, 1H), 2.72 (s, 3H).
  • 50
  • [ 874-27-1 ]
  • methyl 5-chloro-4-methyl-1H-indole-2-carboxylate [ No CAS ]
  • 51
  • [ 874-27-1 ]
  • methyl 5-chloro-1,4-dimethyl-1H-indole-2-carboxylate [ No CAS ]
  • 52
  • [ 874-27-1 ]
  • 5-chloro-1,4-dimethyl-1H-indole-2-carboxylic acid [ No CAS ]
  • 53
  • [ 874-27-1 ]
  • 5-chloro-1,4-dimethyl-N-[4-(pyrimidin-2-ylsulfamoyl)phenyl]indole-2-carboxamide [ No CAS ]
  • 54
  • [ 874-27-1 ]
  • 5-chloro-1,4-dimethyl-indole-2-carbonyl chloride [ No CAS ]
 

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Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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