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Chemical Structure| 4392-24-9 Chemical Structure| 4392-24-9
Chemical Structure| 4392-24-9

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CAS No.: 4392-24-9

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Product Details of 3-Phenyl-2-propenyl bromide

CAS No. :4392-24-9
Formula : C9H9Br
M.W : 197.07
SMILES Code : BrCC=CC1=CC=CC=C1
MDL No. :MFCD00000245
InChI Key :RUROFEVDCUGKHD-QPJJXVBHSA-N
Pubchem ID :5357478

Safety of 3-Phenyl-2-propenyl bromide

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:Ⅱ

Application In Synthesis of 3-Phenyl-2-propenyl bromide

* 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 [ 4392-24-9 ]

[ 4392-24-9 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 3743-22-4 ]
  • [ 4392-24-9 ]
  • [ 79833-17-3 ]
  • 2
  • [ 96145-98-1 ]
  • [ 4392-24-9 ]
  • 1-Phenyl-5-((E)-3-phenyl-allyloxy)-3-trifluoromethyl-1H-pyrazole [ No CAS ]
  • 3
  • [ 65651-80-1 ]
  • [ 4392-24-9 ]
  • [ 4105-92-4 ]
  • [ 86576-75-2 ]
  • [ 86576-76-3 ]
  • 4
  • [ 88088-95-3 ]
  • [ 4392-24-9 ]
  • [ 130759-76-1 ]
  • 5
  • [ 6940-80-3 ]
  • [ 4392-24-9 ]
  • [ 221876-43-3 ]
  • 6
  • [ 6374-91-0 ]
  • [ 4392-24-9 ]
  • C17H11Br2NO2 [ No CAS ]
  • 7
  • [ 40492-52-2 ]
  • [ 4392-24-9 ]
  • [ 108-95-2 ]
  • 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hexane; ethyl acetate; mineral oil; benzene; EXAMPLE 1 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran Sodium hydride (0.40 g; 10 mM; 60% in mineral oil) was washed twice with hexane under nitrogen. The sodium hydride was suspended in 15 ml of benzene and <strong>[40492-52-2]5-hydroxy-2,3-dihydrobenzofuran</strong> (1.00 g; 7.37 mM) was added in 20 ml of benzene in one portion. The suspension was stirred at room temperature for 1.5 hours giving a pale blue suspension. Cinnamyl bromide (freshly distilled; b.p.=76-8 at 0.2 torr; 1.58 g; 8.0 mM) was added in 15 ml of benzene. The reaction was then heated to reflux for 3.5 hours. After cooling the reaction mixture was poured into 1N aqueous hydrochloric acid, partitioned and back extracted with ether. The combined organic layers were dried over magnesium sulfate, filtered, and stripped to a brown oil. The crude reaction product was flash chromatographed with 600 ml of 20% ethyl acetate in hexane on a 30 mm by 6" column of silica gel. This chromatography gave a mixture of product and starting phenol which were separated by chromatography on one cartridge in the Waters Prep 500 with 2 gallons of 20% ethyl acetate in hexane and four recycles with peak shaving techniques. The resulting semipurified product was crystallized from benzene/hexane to 0.516 g (28% yield). of 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran. NMR (CDCl3): delta7.0-7.3 (m; 4H); 6.16-6.62 (m; 4H); 4.43 (s; 1H); 4.40 (t (8 Hz); 2H); 3.40 (d(5 Hz); 2H); 3.03 (t(8 Hz); 2H). IR: 3700, 2920, 1610, 1490, 1425, 1140, 981, 870 cm-1 (CHCl3). MS: 252 (M+) (68%); 161 (34%); 148 (100%); 91 (36%).
In hexane; ethyl acetate; mineral oil; benzene; EXAMPLE 1 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran Sodium hydride (0.40 g; 10 mM; 60% in mineral oil) was washed twice with hexane under nitrogen. The sodium hydride was suspended in 15 ml of benzene and <strong>[40492-52-2]5-hydroxy-2,3-dihydrobenzofuran</strong> (1.00 g; 7.37 mM) was added in 20 ml of benzene in one portion. The suspension was stirred at room temperature for 1.5 hours giving a pale blue suspension. Cinnamyl bromide (freshly distilled; b.p.=76-8 at 0.2 torr; 1.58 g; 8.0 mM) was added in 15 ml of benzene. The reaction was then heated to reflux for 3.5 hours. After cooling the reaction mixture was poured into 1N aqueous hydrochloric acid, partitioned and back extracted with ether. The combined organic layers were dried over magnesium sulfate, filtered, and stripped to a brown oil. The crude reaction product was flash chromatographed with 600 ml of 20% ethyl acetate in hexane on a 30 mm by 6" column of silica gel. This chromatography gave a mixture of product and starting phenol which were separated by chromatography on one cartridge in the Waters Prep 500 with 2 gallons of 20% ethyl acetate in hexane and four recycles with peak shaving techniques. The resulting semipurified product was crystallized from benzene/hexane to 0.516 g (28% yield).of 6-cinnamyl-2,3-dihydro-5-hydroxybenzofuran.
  • 8
  • [ 253-72-5 ]
  • [ 4392-24-9 ]
  • 5,6,7,8-tetrahydro-6-cinnamyl-1,6-naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; EXAMPLE 7 Preparation of 5,6,7,8-tetrahydro-6-cinnamyl-<strong>[253-72-5]1,6-naphthyridine</strong> (Compound No. 58) A solution of <strong>[253-72-5]1,6-naphthyridine</strong> (13.0 g, 0.1 mol) and cinnamyl bromide (23.6 g, 0.12 mol) in acetonitrile (100 ml) was stirred overnight at room temperature. The precipitated crystals were separated by filtration and washed with a small quantity of ether.
  • 9
  • [ 117976-90-6 ]
  • [ 4392-24-9 ]
  • [ 1052003-57-2 ]
  • 10
  • [ 570-02-5 ]
  • [ 4392-24-9 ]
  • [ 147729-67-7 ]
  • 11
  • [ 771-15-3 ]
  • [ 4392-24-9 ]
  • 2-bromo-1-[((2E)-3-phenyl-2-propen-1-yl)oxy]naphthalene [ No CAS ]
  • 12
  • [ 13781-53-8 ]
  • [ 6120-82-7 ]
  • [ 4392-24-9 ]
  • 2-(4-(dimethylamino)phenyl)-5-styryl-3-(3-thienyl)thiophene-4-amine [ No CAS ]
  • 13
  • [ 63874-95-3 ]
  • [ 4392-24-9 ]
  • (E/Z)-1-benzyl-4-(3-phenyl(2-propenyl))oxy-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% General procedure: General procedure: To a solution of 4-formyl-1H-1-tritylprazole (8a) (94.6 mg, 0.28 mmol) inCH2Cl2 (6 mL) was added 70% mCPBA (131.8 mg, 0.53 mmol) at 0 C, with stirring. After 5 h,saturated NaHCO3 aq (10 mL) was added to quench the reaction mixture. The mixture was extractedwith CH2Cl2 3 times. Combined organic layer was dried over MgSO4, filtered, and condensedunder reduced pressure to give a crude formate. To an acetone solution of the crude formate (6 mL),20% NaOH aq (4 mL) was added, then the mixture was heated under reflux for 1 h, then crotyl bromide(48 L, 0.42 mmol) was added to the cooled mixture. After stirring for 3 h, saturated NH4Cl aq wasadded to the reaction mixture to quench, the mixture was condensed under reduced pressure, extractedwith CH2Cl2 for 3 times. The combined CH2Cl2 layer was dried over MgSO4, filtered, and condensedunder reduced pressure to give a crude residue, which was purified with flash column chromatography(EtOAc:Hexane = 1:10) to give 4-(2-butenyl)oxy-1H-1-tritylpyrazole (1e) (54.5 mg, 51%).
 

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