Home Cart Sign in  
Chemical Structure| 16793-89-8 Chemical Structure| 16793-89-8

Structure of 16793-89-8

Chemical Structure| 16793-89-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 16793-89-8 ]

CAS No. :16793-89-8
Formula : C8H8BrNO2
M.W : 230.06
SMILES Code : [O-][N+](=O)C1=C(CCBr)C=CC=C1
MDL No. :MFCD06800159
InChI Key :SJLIPOVZERLCNL-UHFFFAOYSA-N
Pubchem ID :12363878

Safety of [ 16793-89-8 ]

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

Application In Synthesis of [ 16793-89-8 ]

* 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 [ 16793-89-8 ]

[ 16793-89-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 16793-89-8 ]
  • [ 151-50-8 ]
  • [ 2001-32-3 ]
  • 2
  • [ 15121-84-3 ]
  • [ 16793-89-8 ]
YieldReaction ConditionsOperation in experiment
81% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; for 0.75h; 1-(2-bromoethyl)-2-nitrobenzene; Triphenylphosphine (6.60 g, 25.2 mmol) was dissolved in dichloromethane (75 ml). Mixture was cooled to 0° C. 2-Nitrophenethyl alcohol (3.0 ml, 21.36 mmol) was added to the mixture drop-wise. A solution of carbon tetrabromide (8.50 g, 25.6 mmol) in 5 mL dichloromethane was added to the reaction mixture drop-wise. Reaction stirred at 0° C. for 45 minutes. Mixture was concentrated by roto-vap. Residue was treated with 100 mL diethyl ether. Solids were filtered off, washed with diethyl ether and discarded. Filtrate was concentrated. Silica gel chromatography on the residue eluting ethyl acetate-hexanes afforded the title compound as yellow oil in 81percent yield. 1H NMR (300 MHz, CHLOROFORM-D) delta ppm 7.97 (d, J=8.05 Hz, 1 H) 7.49-7.68 (m, 1 H) 7.41 (t, J=7.68 Hz, 2 H) 3.66 (t, J=6.77 Hz, 2 H) 3.43 (t, J=7.14 Hz, 2 H).
With phosphorus tribromide; In water; benzene; (1) Preparation of 2-(2-nitrophenyl)ethyl bromide 2.5 ml of <strong>[15121-84-3]2-(2-nitrophenyl)ethanol</strong> and 5.4 ml of PBr3 were stirred and mixed at 0° C. for 30 minutes to carry out reaction, and the resultant reaction mixture was diluted with 30 ml of benzene and the diluted mixture was then poured into 30 ml of water. The separated organic layer was separated, dried over anhydrous sodium sulfate, and then treated under reduced pressure to distill off the solvent, thereby obtaining 3 g of the crude product of 2-(2-nitrophenyl)ethyl bromide.
With phosphorus tribromide; In water; (1) Preparation of 2-(2-nitrophenyl)ethyl bromide (compound 11): First, 2.5 ml of <strong>[15121-84-3]2-(2-nitrophenyl)ethanol</strong> and 5.4 ml of PBr3 were mixed and stirred at 0° C. for 30 minutes to perform reaction therebetween, and the resulting reaction mixture was diluted with 30 ml of benzene and was then poured into 30 ml of water. Afterward, the separated organic layer was collected, dried over anhydrous sodium sulfate, and then treated under reduced pressure to distill off the solvent therefrom, thereby preparing 3 g of a crude product, 2-(2-nitrophenyl)ethyl bromide (compound 11).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; Triphenylphosphine (39.2 g, 0.150 mol) and carbon tetrabromide (49.5 g, 0.150 mol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene (25.0 g, 0.150 mol) in methylene chloride (400 mL) at 0OC. The reaction was stirred overnight and quenched with saturated sodium bicarbonate solution. The methylene chloride phase was washed with saturated brine and dried over magnesium sulfate. The crude product was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Further purification by flash chromatography by (silica gel, 0-10percent ethyl acetate in hexane gradient elution) produced the title compound (27.9 g).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; 1-(2-Bromoethyl)-2-nitrobenzene; To a solution of 1-(2-hydroxyethyl)-2-nitrobenzene (21 ml, 150 mmol) and triphenylphosphine (39.2 g, 150 mmol) in DCM (400 ml) at 0° C. was add CBr4 (49.5 g, 150 mmol) in portions and the reaction mixture was stirred from 0° C. to RT overnight. The reaction mixture was quenched with sat. aq. Na2CO3, the layers were separated and the organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was treated with EtOAc and the precipitated Ph3O was filtered and the solvent removed. This was repeated twice more. Purification by column chromatography (0percent to 10percent EtOAc in Hx) gave an oil that solidified on standing.
With carbon tetrabromide; triphenylphosphine; In dichloromethane; INTERMEDIATE 7 3 -f 4-PiperidinyD- 1 ,3 A5-tetrahydro-2H- 1 ,3 -benzodiazapin-2-one hydrochloride Step A. 2-(2-Bromoetfayl)nitrobenzene; Triphenylphosphine (39.2 g, 0.150 mol) and carbon tetrabromide (49.5 g, 0.150 mol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene (25.0 g, 0.150 mol) in methylene chloride (400 mL) at O0C. The reaction was stirred overnight and quenched EPO <DP n="71"/>with saturated sodium bicarbonate solution. The methylene chloride phase was washed with saturated brine and dried over magnesium sulfate. The crude product was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Further purification by flash chromatography by (silica gel, 0-10percent ethyl acetate in hexane gradient elution) produced the title compound (27.9 g).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; Triphenylphosphine (39.2 g, 0.150 mol) and carbon tetrabromide (49.5 g, 0.150 mol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene (25.0 g, 0.150 mol) in methylene chloride (400 mL) at O0C. The reaction was stirred overnight and quenched with saturated sodium bicarbonate solution. The methylene chloride phase was washed with saturated brine and dried over magnesium sulfate. The crude product was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Further purification by flash chromatography by (silica gel, 0-10percent ethyl acetate in hexane gradient elution) produced the title compound (27.9 g).
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; (i) Triphenylphosphine (2.62 g, 10.0 mmol) and carbon tetrabromide (3.32 g, 10.0 mmol) were added sequentially to a solution of 2-(2-hydroxyethyl)-nitrobenzene(1.41 ml, 10.0 mmol) in dichloromethane (50 ml) at O0C. The reaction was stirred overnight and quenched with saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over anhydrous magnesium sulphate and concentrated in vacuo. The residue was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Purified by flash-silica gel column chromatography, eluting with a 0-100percent gradient of ethyl acetate in hexane to yield 2-(2-Bromoethyl)-nitrobenzene (2.30 g).

  • 3
  • [ 15121-84-3 ]
  • [ 16793-89-8 ]
  • [ 791-28-6 ]
YieldReaction ConditionsOperation in experiment
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0℃; Triphenylphosphine (39.2 g, 0.150 mol) and carbon TETRABROMIDE (49.5 g, 0.150 mol) were added sequentially to a solution of 2- (2-hydroxyethyl)-nitrobenzene (25.0 g, 0.150 mol) in methylene chloride (400 mL) at OOC. The reaction was stirred overnight and quenched with saturated sodium bicarbonate solution. The methylene chloride phase was washed with saturated brine and dried over magnesium sulfate. The crude product was treated with ethyl acetate, and the precipitated triphenylphosphine oxide removed by filtration. Further purification by flash chromatography by (silica gel, 0-10percent ethyl acetate in hexane gradient elution) produced the title compound (27.9 g).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 16793-89-8 ]

Aryls

Chemical Structure| 1806399-96-1

A409859 [1806399-96-1]

1-(3-Bromopropyl)-3-ethyl-2-nitrobenzene

Similarity: 0.91

Chemical Structure| 63307-45-9

A348130 [63307-45-9]

2-(3-Bromopropyl)nitrobenzene

Similarity: 0.91

Chemical Structure| 1805701-50-1

A645516 [1805701-50-1]

1-(3-Bromopropyl)-3-ethyl-4-nitrobenzene

Similarity: 0.91

Chemical Structure| 102878-75-1

A665617 [102878-75-1]

2-Ethyl-4-methyl-1-nitrobenzene

Similarity: 0.91

Chemical Structure| 1803816-85-4

A484802 [1803816-85-4]

1,3-Dimethyl-5-ethyl-4-nitrobenzene

Similarity: 0.91

Bromides

Chemical Structure| 1806399-96-1

A409859 [1806399-96-1]

1-(3-Bromopropyl)-3-ethyl-2-nitrobenzene

Similarity: 0.91

Chemical Structure| 63307-45-9

A348130 [63307-45-9]

2-(3-Bromopropyl)nitrobenzene

Similarity: 0.91

Chemical Structure| 1805701-50-1

A645516 [1805701-50-1]

1-(3-Bromopropyl)-3-ethyl-4-nitrobenzene

Similarity: 0.91

Chemical Structure| 1804184-17-5

A439770 [1804184-17-5]

1-(3-Bromopropyl)-4-ethyl-2-nitrobenzene

Similarity: 0.89

Nitroes

Chemical Structure| 1806399-96-1

A409859 [1806399-96-1]

1-(3-Bromopropyl)-3-ethyl-2-nitrobenzene

Similarity: 0.91

Chemical Structure| 63307-45-9

A348130 [63307-45-9]

2-(3-Bromopropyl)nitrobenzene

Similarity: 0.91

Chemical Structure| 1805701-50-1

A645516 [1805701-50-1]

1-(3-Bromopropyl)-3-ethyl-4-nitrobenzene

Similarity: 0.91

Chemical Structure| 102878-75-1

A665617 [102878-75-1]

2-Ethyl-4-methyl-1-nitrobenzene

Similarity: 0.91

Chemical Structure| 1803816-85-4

A484802 [1803816-85-4]

1,3-Dimethyl-5-ethyl-4-nitrobenzene

Similarity: 0.91