Home Cart Sign in  
Chemical Structure| 38191-34-3 Chemical Structure| 38191-34-3

Structure of 38191-34-3

Chemical Structure| 38191-34-3

*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 [ 38191-34-3 ]

CAS No. :38191-34-3
Formula : C6H6BrNO
M.W : 188.02
SMILES Code : OC1=CC(Br)=CC=C1N
MDL No. :MFCD03095028
Boiling Point : No data available
InChI Key :DRQWUAAWZFIVTF-UHFFFAOYSA-N
Pubchem ID :14320605

Safety of [ 38191-34-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 38191-34-3 ]

* 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 [ 38191-34-3 ]

[ 38191-34-3 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 19932-85-5 ]
  • [ 38191-34-3 ]
  • 2
  • [ 182570-26-9 ]
  • [ 38191-34-3 ]
  • [ 1213262-03-3 ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 3h; To a solution of the 1-1 and -methoxychroman-S-carboxylic acid in DMF were added HATU (1.1 equiv) and DIEA (3 equiv). The resulting mixture was stirred at room temperature for 3h. The solution was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate solution. The organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give bromide 1-2 (95% yield).
  • 3
  • [ 38191-34-3 ]
  • [ 301221-79-4 ]
  • [ 1200576-13-1 ]
YieldReaction ConditionsOperation in experiment
84% INTERMEDIATE B7 foert-Butyl 4-(7-bromo-2H-l,4-benzoxazin-3-yl)piperidine-l-carboxylate To a stirred solution of 2-amino-5-bromophenol (Intermediate B3; 898 mg, 4.78 mmol) in DMF (10 mL) was added K2CO3 (660 mg, 4.78 mmol). After 45 min, a solution of tert- <n="141"/>butyl 4-(bromoacetyl)piperidine-l-carboxylate (Intermediate B6; 1.53 g, ca 5 mmol) in DMF (2 rnL) was added and the mixture was stirred at r.t. overnight. Water was added and the product was extracted with toluene. The organic phase was washed with water and brine, dried and evaporated to give 952 mg of crude title compound (used in Intermediate B8). The aqueous layer was extracted with CHCI3 and the organic layer was concentrated. The residue was purified by flash chromatography on silica using 1percent MeOH/CHCl3 as eluent to give an additional 628 mg of the title compound. Total yield 1.58 g (84percent). Analytical HPLC: purity 83percent (System A); LRESIMS (ESI+) m/z = 339/341 (M+FRBu)+.
  • 4
  • [ 1445-45-0 ]
  • [ 38191-34-3 ]
  • [ 151230-42-1 ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid; for 0.5h;Reflux; To an AcOH (1.521 mul, 0.027 mmol) were added 2-amino-5-bromophenol 23 (500 mg, 2.66 mmol) and 1,1,1-trimethoxyethane (600 mul, 4.79 mmol), then the reaction mixture was refluxed for 30 minutes. To the reaction solution was added water, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by column chromatography to give Compound 24 (481 mg, 85%).Compound 24; 1H-NMR (CDCl3) delta: 2.63 (s, 3H), 7.42 (dd, J=8.62, 2.03 Hz, 1H), 7.51 (d, J=8.62 Hz, 1H), 7.64 (d, J=2.03 Hz, 1H).
  • 5
  • [ 38191-34-3 ]
  • [ 78-39-7 ]
  • [ 151230-42-1 ]
YieldReaction ConditionsOperation in experiment
88.5% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 25.0℃; for 0.166667h; 2-Amino-5-bromophenol (561 mg, 3.00 mmol)Was added to triethyl orthoacetate (656 muL, 3.6 mmol),1,3-Dibromo-5,5-dimethylhydantoin (17.2 mg, 6.00 × 10 -2 mmol) was added,And the mixture was stirred at room temperature for 10 minutes.And extracted with ethyl acetate (50 mL × 2).The organic layer was washed with saturated brine,After dehydration with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/4 (volume ratio)) as an elution solvent,Compound 16 was obtained in a yield of 560 mg (88.5%).
65% With acetic acid; for 0.5h;Reflux; To 2-amino-5- bromophenol ( l .OOg, 5.32 mmol) , acetic acid ((0.006 ml) and triethylorthoacetate ( 1.75 ml, 9.58 mmol) were added and refluxed for 3o min. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate : petroleum ether to afford the title compound as a orange solid ((0.756 g, 65%). -NMR (delta ppm, CDC13, 400 MHz): delta 7.64 (d, 7 = 1.7 Hz, 1 H), 7.51 (d, 7 = 8.4 Hz, 1 H), 7.43 (dd, 7 = 8.4, 1.7 Hz, 1 H), 2.67 (s, 3H).
65% With acetic acid; for 0.5h;Reflux; Intermediate 126 6-bromo-2-methylbenzo[d]oxazole: To 2-amino-5-bromophenol (1.00 g, 5.32 mmol), acetic acid ((0.006 ml) and triethylorthoacetate (1.75 ml, 9.58 mmol) were added and refluxed for 30 min. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate: petroleum ether to afford the title compound as a orange solid ((0.756 g, 65%). 1H-NMR (delta ppm, CDCl3, 400 MHz): delta 7.64 (d, J=1.7 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.43 (dd, J=8.4, 1.7 Hz, 1H), 2.67 (s, 3H).
  • 6
  • [ 38191-34-3 ]
  • [ 1361110-64-6 ]
  • 7
  • [ 19213-72-0 ]
  • [ 38191-34-3 ]
  • [ 19932-85-5 ]
  • 8
  • [ 32315-10-9 ]
  • [ 38191-34-3 ]
  • [ 19932-85-5 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine; In dichloromethane; at 0 - 20℃; [0950] To a solution of XXXV-1 (3 g, 16 mmol) in dry DCM (50 mL) was added TEA (3.2 g, 32 mmol). The reaction mixture was cooled to 0C, triphosgene (1.6 g, 5.3 mmol) was added slowly. The mixture was stuffed overnight at rt, then quenched with water, extracted with DCM (80 mLx3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (PE/EA=10/1) to afford XXXV-2b (2.7g, 79% yield).
  • 9
  • [ 5683-43-2 ]
  • [ 38191-34-3 ]
  • 10
  • [ 127-19-5 ]
  • [ 38191-34-3 ]
  • [ 5676-56-2 ]
YieldReaction ConditionsOperation in experiment
87% With Imidazole hydrochloride; at 160℃; for 8h;Schlenk technique; Green chemistry; General procedure: A tube-type schlenk flask was charged with 1a (0.6g, 5.5 mmol, 1 equiv), imidazolium chloride (0.28g, 1.65 mmol, 0.5equiv) and N,N-dimethylacetamide 5ml was stirred at 160C for 8h. When the reaction was completed. Water (15ml) and ethyl acetate (20ml) were added with stirring to the reaction mixture. The organic layer was extracted and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using PE/EA as eluent togive the corresponding product 2a.
  • 11
  • [ 38191-34-3 ]
  • [ 530-62-1 ]
  • [ 19932-85-5 ]
YieldReaction ConditionsOperation in experiment
90% In tetrahydrofuran; at 70℃; for 2h; To a solution of 2-amino-5-bromo-phenol (4.50 g, 23.9 mmol, CAS38191-34-3) in THF (120 mL) was added CDI (4.66 g, 28.7 mmol). The reaction mixture was stirred at 70 C. for 2 hours. On completion, the reaction mixture was added to water (240 mL) and the mixture was adjusted pH=6-7 with 2.0 M aq.HCl, then ethyl acetate (150 mL) was added. The organic layer was separated and washed with a saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized in toluene (60 mL) to give the title compound (3.75 g, 90% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.58 (d, J=1.6 Hz, 1H), 7.32 (dd, J=1.8, 8.4 Hz, 1H), 7.06 (s, 1H), 7.04-7.01 (m, 1H). LC-MS (ESI+) m/z 216.0 & 214.0 (M+Na)+.
90% In tetrahydrofuran; at 70℃; for 2h;Inert atmosphere; To a solution of 2-amino-5-bromo-phenol (4.50 g, 23.9 mmol, CAS 38191-34-3) in THF (120 mL) was added CDI (4.66 g, 28.7 mmol). The reaction mixture was stirred at 70 C for 2 hours. On completion, the reaction mixture was added to water (240 mL) and the mixture was adjusted pH = 6 ~ 7 with 2.0 M aq.HCl, then ethyl acetate (150 mL) was added. The organic layer was separated and washed with a saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized in toluene (60 mL) to give the title compound (3.75 g, 90% yield) as an off-white solid.1H NMR (400MHz, DMSO-d6) d 7.58 (d, J = 1.6 Hz, 1H), 7.32 (dd, J = 1.8, 8.4 Hz, 1H), 7.06 (s, 1H), 7.04 - 7.01 (m, 1H). LC-MS (ESI+) m/z 216.0 & 214.0 (M + Na)+.
90% In tetrahydrofuran; at 70℃; for 2h; To a solution of 2-amino-5-bromo-phenol (4.50 g, 23.9 mmol, CASNo. 38191-34-3) in THF (120 mL) was added CDI (4.66 g, 28.7 mmol). The reaction mixture was stirred at 70 C for 2 hours. On completion, the reaction mixture was added to water (240 mL) and the mixture was adjusted pH = 6 ~ 7 with 2.0 M aq.HCl, then ethyl acetate (150 mL) was added. The organic layer was separated and washed with a saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized in toluene (60 mL) to give the title compound (3.75 g, 90% yield) as an off-white solid. 1H NMR (400MHz, DMSO-d6) δ 7.58 (d, J= 1.6 Hz, 1H), 7.32 (dd, J = 1.8, 8.4 Hz, 1H), 7.06 (s, 1H), 7.04 - 7.01 (m, 1H). LC-MS (ESI+) m/z 216.0 & 214.0 (M + Na)+.
90% In tetrahydrofuran; at 70℃; for 2h; To a solution of 2-amino-5-bromo-phenol (4.50 g, 23.9 mmol, CASNo. 38191-34-3) in THF (120 mL) was added CDI (4.66 g, 28.7 mmol). The reaction mixture was stirred at 70 C for 2 hours. On completion, the reaction mixture was added to water (240 mL) and the mixture was adjusted pH = 6 ~ 7 with 2.0 M aq.HCl, then ethyl acetate (150 mL) was added. The organic layer was separated and washed with a saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized in toluene (60 mL) to give the title compound (3.75 g, 90% yield) as an off-white solid. 1H NMR (400MHz, DMSO-d6) δ 7.58 (d, J= 1.6 Hz, 1H), 7.32 (dd, J = 1.8, 8.4 Hz, 1H), 7.06 (s, 1H), 7.04 - 7.01 (m, 1H). LC-MS (ESI+) m/z 216.0 & 214.0 (M + Na)+.
48% In N,N-dimethyl-formamide; at 60℃; for 2h; General procedure: 1,10-Carbonyldiimidazole (1.6 mmol) was added to a solution ofthe 2-amino-6-bromophenol (1.0 mol) in DMF (3 mL), and the solutionwas heated to 60 C for 2 h [43]. Then, the reaction mixturewas poured into water (15 mL) and extracted with ethyl acetate(3 15 mL). The organic layer was collected, dried, filtered, andevaporated in vacuo. The residue was recrystallized from ethylacetate to give desired product 2.

  • 12
  • [ 38191-34-3 ]
  • [ 26608-06-0 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 38191-34-3 ]

Aryls

Chemical Structure| 40925-68-6

A463737 [40925-68-6]

2-Amino-4-bromophenol

Similarity: 0.98

Chemical Structure| 1037298-16-0

A146270 [1037298-16-0]

2-Amino-4,5-dibromophenol

Similarity: 0.96

Chemical Structure| 116435-77-9

A110975 [116435-77-9]

2-Amino-3-bromophenol

Similarity: 0.91

Chemical Structure| 28165-50-6

A167777 [28165-50-6]

2-Amino-6-bromophenol

Similarity: 0.91

Chemical Structure| 59557-91-4

A126730 [59557-91-4]

4-Bromo-2-methoxyaniline

Similarity: 0.90

Bromides

Chemical Structure| 40925-68-6

A463737 [40925-68-6]

2-Amino-4-bromophenol

Similarity: 0.98

Chemical Structure| 1037298-16-0

A146270 [1037298-16-0]

2-Amino-4,5-dibromophenol

Similarity: 0.96

Chemical Structure| 116435-77-9

A110975 [116435-77-9]

2-Amino-3-bromophenol

Similarity: 0.91

Chemical Structure| 28165-50-6

A167777 [28165-50-6]

2-Amino-6-bromophenol

Similarity: 0.91

Chemical Structure| 59557-91-4

A126730 [59557-91-4]

4-Bromo-2-methoxyaniline

Similarity: 0.90

Amines

Chemical Structure| 40925-68-6

A463737 [40925-68-6]

2-Amino-4-bromophenol

Similarity: 0.98

Chemical Structure| 1037298-16-0

A146270 [1037298-16-0]

2-Amino-4,5-dibromophenol

Similarity: 0.96

Chemical Structure| 116435-77-9

A110975 [116435-77-9]

2-Amino-3-bromophenol

Similarity: 0.91

Chemical Structure| 28165-50-6

A167777 [28165-50-6]

2-Amino-6-bromophenol

Similarity: 0.91

Chemical Structure| 59557-91-4

A126730 [59557-91-4]

4-Bromo-2-methoxyaniline

Similarity: 0.90