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Chemical Structure| 715-51-5 Chemical Structure| 715-51-5

Structure of 715-51-5

Chemical Structure| 715-51-5

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Product Details of [ 715-51-5 ]

CAS No. :715-51-5
Formula : C14H9Cl
M.W : 212.67
SMILES Code : ClC1=CC=C2C=CC3=C(C=CC=C3)C2=C1
MDL No. :MFCD16251530
InChI Key :BVFJTESUEYBUOL-UHFFFAOYSA-N
Pubchem ID :3013936

Safety of [ 715-51-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 715-51-5 ]

* 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 [ 715-51-5 ]

[ 715-51-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1892-54-2 ]
  • [ 715-51-5 ]
YieldReaction ConditionsOperation in experiment
50% With tert.-butylnitrite; copper dichloride; In acetonitrile; at 0℃; for 1.33333h; General procedure: 3-amino-phenanthrene of 30g (155 mmol), of 36.7g CuBr2 (15 5 mmol) is dissolved in anhydrous acetonitrile 300 ml. Of 40.4ml tert- Butyl nitrile (535 mmol) is added in portions at 0C . The suspension was stirred for an additional hour, then poured into ice-water 400 ml, and stirred for about 20 minutes. The precipitated solid is filtered off with suction, dissolved in dichloromethane, washed several times with water. The organic phase was evaporated in a rotary evaporator is recrystallized from toluene / heptane. A yield of 21.9g (85 mmol) (55% of theory).
Step 3: 3-chlorophenanthreneCuCl2 (21 g) was dried under high vacuum at 115 0C for 90 minutes then cooled down to 65 0C followed by the addition of 250 mL of dry acetonitrile and 26 g of t-butyl nitrite. The 3- phenanthrylamine (25 g) from Step 2 was added over 30 minutes as a solution in 100 mL of acetonitrile. The reaction was stirred 45 minutes at 65 0C, cooled down to room temperature followed by the addition of 1 L of 1 N HCl. The aqueous layer was extracted with methylene chloride and combined organic layers were washed with water, brine, dried over sodium sulphate and volatiles were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using hexane as the eluent to afford a white solid which was recristallized from hexane to produce 14.4 g of 3- chlorophenanthrene as a white solid.
With tert.-butylnitrite; copper dichloride; In acetonitrile; at 65℃; for 1.25h; Step 3; 3-chlorophenanthrene; CuCl2 (21 g) was dried under high vacuum at 115 0C for 90 minutes then cooled down to 65 0C followed by the addition of 250 mL of dry acetonitrile and 26 g of ^-butyl nitrite. The 3- phenanthrylamine (25 g) from Step 2 was added over 30 minutes as a solution in 100 mL of acetonitrile. The reaction was stirred 45 minutes at 65 0C, cooled down to room temperature followed by the addition of 1 L of 1 N HCl. The aqueous layer was extracted with methylene chloride and combined organic layers were washed with water, brine, dried over sodium sulphate and volatiles were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using hexane as the eluent to afford a white solid which was recristallized from hexane to produce 14.4 g of 3- chlorophenanthrene as a white solid.
Step 3 : 3-chlorophenanthreneCuCl2 (21 g) was dried under high vacuum at 115 0C for 90 minutes and then cooled to 65 0C. Dry acetonitrile (250 mL) and ?-butyl nitrite (26 g) were then added, followed by the addition of a solution of 3-phenanthrylamine (25 g) from Step 2 above, in acetonitrile (100 mL) over 30 minutes. The reaction was stirred for 45 minutes at 65 0C, then cooled to room temperature. To the reaction mixture was then added HCl (IN, IL). The aqueous layer was extracted with methylene chloride and the combined organic layers were washed successively with water and brine, dried over Na2SC4 and filtered. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica (100% hexanes) to afford a white solid which was recrystallized from hexane to yield 3- chlorophenanthrene (14.4 g) as a white solid.
With tert.-butylnitrite; copper dichloride; In acetonitrile; at 65℃; for 1.25h; CuCl2 (21 g) was dried under high vacuum at 115 C for 90 minutes then cooled down to 65 C followed by the addition of 250 mL of dry acetonitrile and 26 g of t-butyl nitrite. The 3-phenanthrylamine (25 g) from Step 2 was added over 30 minutes as a solution in 100 mL of acetonitrile. The reaction was stirred 45 minutes at 65 0C, cooled down to room temperature followed by the addition of 1 L of 1 N HCl. The aqueous layer was extracted with methylene chloride and combined organic layers were washed with water, brine, dried over sodium sulphate and volatiles were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using hexane as the eluent to afford a white solid which was recristallized from hexane to produce 14.4 g of 3-chlorophenanthrene as a white solid.

 

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