[ CAS No. 586-96-9 ] {[proInfo.proName]}

Name: 586-96-9|Nitrosobenzene|98%
Brand: Ambeed
SKU: A195460
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Quality Control of [ 586-96-9 ]

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Product Details of [ 586-96-9 ]

CAS No. :	586-96-9	MDL No. :	MFCD00002059
Formula :	C₆H₅NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NLRKCXQQSUWLCH-UHFFFAOYSA-N
M.W :	107.11	Pubchem ID :	11473
Synonyms :

Safety of [ 586-96-9 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P363-P405-P501	UN#:	2811
Hazard Statements:	H301-H312-H332	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 586-96-9 ]

* 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.

Upstream synthesis route of [ 586-96-9 ]
Downstream synthetic route of [ 586-96-9 ]

[ 586-96-9 ] Synthesis Path-Upstream 1~14

1
[ 57310-43-7 ]
[ 586-96-9 ]
[ 76567-67-4 ]
[ 1682-20-8 ]

Reference： [1] Journal of Fluorine Chemistry, 1985, vol. 28, p. 325

2
[ 64-17-5 ]
[ 623-11-0 ]
[ 815627-04-4 ]
[ 586-96-9 ]
[ 93-98-1 ]
[ 1877-75-4 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1937, vol. <2> 148, p. 126,133

3
[ 586-96-9 ]
[ 26260-02-6 ]

Reference： [1] Journal of the American Chemical Society, 2014, vol. 136, # 8, p. 2978 - 2981

4
[ 106-47-8 ]
[ 586-96-9 ]
[ 63069-48-7 ]
[ 4340-77-6 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 16, p. 3150 - 3156

5
[ 106-47-8 ]
[ 586-96-9 ]
[ 63069-48-7 ]
[ 4340-77-6 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 16, p. 3150 - 3156

6
[ 100-52-7 ]
[ 586-96-9 ]
[ 304-88-1 ]

Yield	Reaction Conditions	Operation in experiment
50 %Chromat.	With potassium <i>tert</i>-butylate In dichloromethane at 20℃; for 0.166667 h;	In studies using different imidazolium and triazolium salts, it was observed that sterically less hindered triazolium salts provided higher yields of the product (Table 1) .Reaction with catalyst concentrations as low as 0.125 mol percent was observed.Table 1. Reaction Conditions for the Preparation of
95 %Chromat.	With potassium <i>tert</i>-butylate In dichloromethane at 20℃; for 0.166667 h;	In studies using different imidazolium and triazolium salts, it was observed that sterically less hindered triazolium salts provided higher yields of the product (Table 1) .Reaction with catalyst concentrations as low as 0.125 mol percent was observed.Table 1. Reaction Conditions for the Preparation of
85 %Chromat.	With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.166667 h;	In studies using different imidazolium and triazolium salts, it was observed that sterically less hindered triazolium salts provided higher yields of the product (Table 1) .Reaction with catalyst concentrations as low as 0.125 mol percent was observed.Table 1. Reaction Conditions for the Preparation of

96 - 99 %Chromat.

With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.166667 h;

In studies using different imidazolium and triazolium salts, it was observed that sterically less hindered triazolium salts provided higher yields of the product (Table 1) .Reaction with catalyst concentrations as low as 0.125 mol percent was observed.Table 1. Reaction Conditions for the Preparation of

Reference： [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 624 - 629
[2] Patent: WO2008/115153, 2008, A1, . Location in patent: Page/Page column 27-28
[3] Patent: WO2008/115153, 2008, A1, . Location in patent: Page/Page column 41-42
[4] Patent: WO2008/115153, 2008, A1, . Location in patent: Page/Page column 41-42
[5] Patent: WO2008/115153, 2008, A1, . Location in patent: Page/Page column 41-42
[6] Patent: WO2008/115153, 2008, A1, . Location in patent: Page/Page column 41-42
[7] Patent: WO2008/115153, 2008, A1, . Location in patent: Page/Page column 41-42
[8] Patent: WO2008/115153, 2008, A1, . Location in patent: Page/Page column 41-42; 43
[9] Chemistry - An Asian Journal, 2013, vol. 8, # 12, p. 2965 - 2969

7
[ 201024-81-9 ]
[ 304-88-1 ]
[ 100-52-7 ]
[ 586-96-9 ]

Reference： [1] Tetrahedron, 1983, vol. 39, # 22, p. 3833 - 3842

8
[ 586-96-9 ]
[ 611-73-4 ]
[ 304-88-1 ]

Reference： [1] Journal of Organic Chemistry, 1989, vol. 54, # 18, p. 4449 - 4453

9
[ 119-53-9 ]
[ 586-96-9 ]
[ 5928-67-6 ]
[ 304-88-1 ]

Reference： [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 624 - 629

10
[ 7664-93-9 ]
[ 932-98-9 ]
[ 64-19-7 ]
[ 586-96-9 ]
[ 13065-93-5 ]

Reference： [1] Patent: US1900426, 1929, ,
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 456,457
[3] Patent: DE512722, 1929, ,

11
[ 586-96-9 ]
[ 23699-65-2 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 6, p. 1667 - 1671

12
[ 586-96-9 ]
[ 128942-88-1 ]

Reference： [1] Organic Letters, 2002, vol. 4, # 5, p. 699 - 701

13
[ 586-96-9 ]
[ 92623-83-1 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 3, p. 412 - 415

14
[ 586-96-9 ]
[ 37968-69-7 ]
[ 945016-63-7 ]

Reference： [1] Tetrahedron, 2010, vol. 66, # 6, p. 1280 - 1288

[ 586-96-9 ] Synthesis Path-Downstream 1~88

1
[ 35486-42-1 ]
[ 586-96-9 ]
3,5-dibromo-2-(phenyl-<i>trans</i>)-azo-pyridine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1953,p. 1281,1285

2
[ 19056-41-8 ]
[ 586-96-9 ]
(E)-1-(3-bromo-4-methoxyphenyl)-2-phenyldiazene [ No CAS ]

Reference： [1]Journal of the Chemical Society,1928,p. 2935

3
[ 2589-57-3 ]
[ 586-96-9 ]
[ 856637-53-1 ]

Reference： [1]Journal of the Chemical Society,1958,p. 2056

4
[ 153-78-6 ]
[ 586-96-9 ]
[ 858259-22-0 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 3010,3013

5
[ 14543-43-2 ]
[ 586-96-9 ]
triphenodioxazine-2,9-dicarbonitrile [ No CAS ]

Reference： [1]Chemische Berichte,1897,vol. 30,p. 991

6
[ 2589-57-3 ]
[ 586-96-9 ]
[ 108-88-3 ]
[ 856637-53-1 ]

Reference： [1]Journal of the Chemical Society,1958,p. 2056

7
[ 586-96-9 ]
[ 17220-38-1 ]
[ 53454-70-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1974,vol. 47,p. 1493 - 1495

8
[ 57310-43-7 ]
[ 586-96-9 ]
[ 76567-67-4 ]
[ 1682-20-8 ]
2,3,5,6-tetrafluoro-4-(phenyl-ONN-azoxy)pyridine [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1985,vol. 28,p. 325

9
[ 42726-73-8 ]
[ 586-96-9 ]
[ 97985-80-3 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1985,vol. 21,p. 642 - 648
Zhurnal Organicheskoi Khimii,1985,vol. 21,p. 709 - 715

10
[ 106-49-0 ]
[ 586-96-9 ]
[ 501-60-0 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3684 - 3690

11
[ 30095-98-8 ]
[ 586-96-9 ]
(E)-methyl (2-nitrophenyl)(phenylimino) acetate [ No CAS ]
(Z)-methyl (2-nitrophenyl)(phenylimino) acetate [ No CAS ]
[ 251982-40-8 ]

Reference： [1]Acta Chemica Scandinavica,1999,vol. 53,p. 814 - 823
[2]Acta Chemica Scandinavica,1999,vol. 53,p. 814 - 823

12
[ 7664-93-9 ]
[ 932-98-9 ]
[ 64-19-7 ]
[ 586-96-9 ]
[ 13065-93-5 ]

Reference： [1]Patent: US1900426,1929,

13
[ 55533-24-9 ]
[ 586-96-9 ]
[ 906734-92-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid; at 20℃; for 12h;	Nitrosobenzene (346 mg, 3.23 mmol, 1 eq) and and 4-aminophenylalanine (500 mg, 1.78 mmol, 1.1 eq) were added to acetic acid (15 mL) and the mixture was stirred at room temperature for 12 h. The solution was diluted with water, extracted with DCM, dried over MgSO4 and the solvent evaporated under reduced pressure. Purification by flash chromatography (20% EtOAc:Hexane) gave 8a (537 mg, 82%) as an orange foam. 1H NMR (500 MHz, CDCl3) delta 7.90 (d, J = 7.3 Hz, 2H, 2xArH), 7.87 (d, J = 8.3 Hz, 2H, 2xArH), 7.53-7.44 (m, 3H, 3xArH), 7.34 (d, J = 8.2 Hz, 2H, 2xArH), 4.98 (d, J = 7.1 Hz, 1H, NH), 4.66 (dd, J = 12.8, 6.8 Hz, 1H, Tyr-a-H), 3.30 (dd, J = 13.7, 5.1 Hz, 1H, Tyr-b-CHH), 3.17 (dd, J = 13.7, 6.0 Hz, 1H, Tyr-b-CHH) and 1.43 (s, 9H, C(CH3)3) ppm. 13C NMR (126 MHz, CDCl3) delta 176.1, 155.5, 152.8, 151.9, 139.4, 131.1, 130.3, 129.2, 123.1, 123.0, 80.6, 54.4, 38.0 and 28.4 ppm. HRMS (ESI) calcd for C20H23NaN3O4 (M+Na)+ 392.1586, found 392.1584. IR (ATR) : 2981 (O-H), 1710 and 1653 (C=O) and 1512 (N=O) cm-1.Nitrosobenzene (346 mg, 3.23 mmol, 1 eq) and and 4-aminophenylalanine (500 mg, 1.78 mmol, 1.1 eq) were added to acetic acid (15 mL) and the mixture was stirred at room temperature for 12 h. The solution was diluted with water, extracted with DCM, dried over MgSO4 and the solvent evaporated under reduced pressure. Purification by flash chromatography (20% EtOAc:Hexane) gave 8a (537 mg, 82%) as an orange foam. 1H NMR (500 MHz, CDCl3) delta 7.90 (d, J = 7.3 Hz, 2H, 2xArH), 7.87 (d, J = 8.3 Hz, 2H, 2xArH), 7.53-7.44 (m, 3H, 3xArH), 7.34 (d, J = 8.2 Hz, 2H, 2xArH), 4.98 (d, J = 7.1 Hz, 1H, NH), 4.66 (dd, J = 12.8, 6.8 Hz, 1H, Tyr-a-H), 3.30 (dd, J = 13.7, 5.1 Hz, 1H, Tyr-b-CHH), 3.17 (dd, J = 13.7, 6.0 Hz, 1H, Tyr-b-CHH) and 1.43 (s, 9H, C(CH3)3) ppm. 13C NMR (126 MHz, CDCl3) delta 176.1, 155.5, 152.8, 151.9, 139.4, 131.1, 130.3, 129.2, 123.1, 123.0, 80.6, 54.4, 38.0 and 28.4 ppm. HRMS (ESI) calcd for C20H23NaN3O4 (M+Na)+ 392.1586, found 392.1584. IR (ATR) : 2981 (O-H), 1710 and 1653 (C=O) and 1512 (N=O) cm-1.

Reference： [1]Chemical Communications,2016,vol. 52,p. 3143 - 3146
[2]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5050 - 5054
[3]Chemical Communications,2017,vol. 53,p. 9348 - 9351
[4]Journal of the American Chemical Society,2006,vol. 128,p. 388 - 389

14
[ 586-96-9 ]
[ 776-41-0 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 699 - 701

15
[ 586-96-9 ]
<Co(acac)2OH>2 [ No CAS ]
[ 776-41-0 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 699 - 701

16
[ 33538-83-9 ]
[ 586-96-9 ]
(R)-2-(hydroxy(phenyl)amino)-3-(2-methoxyphenyl)propan-1-ol [ No CAS ]
[ 960622-64-4 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 8054 - 8056

17
[ 33538-83-9 ]
[ 586-96-9 ]
[ 1017233-92-9 ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 8054 - 8056

18
[ 1273-82-1 ]
[ 586-96-9 ]
FeC₁₀H₉NNOC₆H₅ [ No CAS ]
phenylazoferrocene [ No CAS ]

Reference： [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1964,p. 184 - 185
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1964,p. 197 - 199
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.5.1, page 171 - 175
[3]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1964,p. 184 - 185
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1964,p. 197 - 199
[4]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.6.6, page 222 - 229

19
[ 1273-82-1 ]
[ 586-96-9 ]
phenylazoferrocene [ No CAS ]

20
[ 1273-82-1 ]
[ 586-96-9 ]
azoferrocene [ No CAS ]
FeC₁₀H₉NNOC₆H₅ [ No CAS ]

21
[ 50982-12-2 ]
[ 586-96-9 ]
Ru⁽²⁺⁾*2Cl^(1-)*C₈H₁₂*2C₆H₅NO=RuCl₂(C₈H₁₂)(C₆H₅NO)2 [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1984,vol. 277,p. 417 - 422

22
[ 52784-31-3 ]
[ 586-96-9 ]
[ 1286795-64-9 ]
5-hydroxy-1,4-diphenylpyrrolidin-2-one [ No CAS ]

Reference： [1]Synlett,2011,p. 89 - 93

23
[ 52784-31-3 ]
[ 586-96-9 ]
[ 1286795-64-9 ]
5-hydroxy-1,4-diphenylpyrrolidin-2-one [ No CAS ]
5-hydroxy-1,4-diphenylpyrrolidin-2-one [ No CAS ]

Reference： [1]Synlett,2011,p. 89 - 93

24
[ 586-96-9 ]
[ 105752-11-2 ]
4-iodo-3-(phenylazo)pyridine [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 4217 - 4222

25
[ 586-96-9 ]
[ 105752-11-2 ]
3-azophenyl-4,4'-bipyridine [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 4217 - 4222

26
[ 586-96-9 ]
[ 80058-84-0 ]
C₁₈H₂₁BrN₂ [ No CAS ]
[ 1315282-46-2 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 6415 - 6418

27
[ 34801-09-7 ]
[ 586-96-9 ]
[ 1346157-82-1 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 9826 - 9834

28
[ 55533-24-9 ]
[ 586-96-9 ]
(S)-2-tert-Butoxycarbonylamino-3-(4-phenylazo-phenyl)-propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 20℃; for 16h;	The unnatural amino acid was prepared according to literature conditions.1 To flame dried round bottom was added 4-Amino-N-(tert-butoxycarbonyl)-L-phenylalanine (1.007 g, 3.59 mmol, 1 equiv.) and glacialacetic acid (200ml). Nitrosobenzene (579 mg, 540 mmol, 1.5 equiv.), was thenadded and the reaction was stirred for 16 hours then quenched with water. Theproduct was extracted with ethyl acetate (3 x 20 mL), and the organic layer wasthen back-extracted with brine (2 x 30mL). The organic layer was isolated, dried with MgSO4, filtered, and solvent was removed by rotatory evaporation. Theorange solid was purified via flash chromatography with a 9:1 DCM/Methanol eluent. The product was concentrated and dissolved in Dioxane (4 mL), and cooled in anice bath. To the solution, 4N HCl (2 mL) was added and stirred for 3 hours. Thesolvent was removed in vacuo toafford the deprotected azobenzene amino acid as an orange solid in a 61percent yield (2.19mmol).

Reference： [1]Chemical Communications,2012,vol. 48,p. 8796 - 8798
[2]Chemistry - A European Journal,2013,vol. 19,p. 8861 - 8874
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 470 - 473

29
[ 33631-09-3 ]
[ 586-96-9 ]
[ 1418921-56-8 ]
[ 1418921-58-0 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 16358 - 16368

30
[ 586-96-9 ]
[ 105752-11-2 ]
[ 1291057-14-1 ]
[ 1418921-50-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 16358 - 16368

31
[ 373-88-6 ]
[ 586-96-9 ]
[ 614-47-1 ]
(2,5-diphenyl-3-(trifluoromethyl)isoxazolidin-4-yl)(phenyl)methanone [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

32
[ 373-88-6 ]
[ 586-96-9 ]
[ 1896-62-4 ]
1-(2,5-diphenyl-3-(trifluoromethyl)isoxazolidin-4-yl)ethan-1-one [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

33
[ 50396-96-8 ]
[ 373-88-6 ]
[ 586-96-9 ]
1-(5-methyl-2-phenyl-3-(trifluoromethyl)isoxazolidin-4-yl)propan-1-one [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

34
[ 95152-22-0 ]
[ 373-88-6 ]
[ 586-96-9 ]
N-(4-methoxyphenyl)-5-methyl-2-phenyl-3-(trifluoromethyl)isoxazolidine-4-carboxamide [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

35
[ 373-88-6 ]
[ 624-48-6 ]
[ 586-96-9 ]
dimethyl 2-phenyl-3-(trifluoromethyl)isoxazolidine-4,5-dicarboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

36
[ 373-88-6 ]
[ 624-48-6 ]
[ 586-96-9 ]
dimethyl 3-(trifluoromethyl)cyclopropane-1,2-dicarboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

37
[ 24393-53-1 ]
[ 373-88-6 ]
[ 586-96-9 ]
ethyl 5-(4-bromophenyl)-2-phenyl-3-(trifluoromethyl)isoxazolidine-4-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

38
[ 373-88-6 ]
[ 586-96-9 ]
[ 623-70-1 ]
ethyl 5-methyl-2-phenyl-3-(trifluoromethyl)isoxazolidine-4-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

39
[ 373-88-6 ]
[ 586-96-9 ]
[ 623-91-6 ]
diethyl 2-phenyl-3-(trifluoromethyl)isoxazolidine-4,5-dicarboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

40
[ 37746-78-4 ]
[ 373-88-6 ]
[ 586-96-9 ]
ethyl 5-(bromomethyl)-2-phenyl-3-(trifluoromethyl)isoxazolidine-4-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

41
[ 373-88-6 ]
[ 497-23-4 ]
[ 586-96-9 ]
2-phenyl-3-(trifluoromethyl)tetrahydrofuro[3,4-d]isoxazol-4(2H)-one [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

42
[ 373-88-6 ]
[ 586-96-9 ]
[ 624-49-7 ]
dimethyl 2-phenyl-3-(trifluoromethyl)isoxazolidine-4,5-dicarboxylate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3166 - 3169

43
[ 60532-63-0 ]
[ 586-96-9 ]
[ 1582774-32-0 ]

Reference： [1]Journal of Materials Chemistry A,2014,vol. 2,p. 13831 - 13834

44
[ 21857-45-4 ]
[ 586-96-9 ]
5-methoxy-N-phenyl-1H-indol-1-amine [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 13056 - 13058

45
[ 135865-78-0 ]
[ 586-96-9 ]
C₂₀H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With L-proline; In acetonitrile; at -10℃;	General procedure: To a stirred precooled (?10 °C) MeCN (25 mL) solution of beta-amino aldehydes 6a?f (17 mmol) and nitrosobenzene (13.6mmol) was added L-proline (0.039 g, 20 molpercent). The reactionmixture was allowed to stir at the same temperature for 20 hfollowed by the addition of MeOH (10 mL) and NaBH4 (25mmol) to the reaction mixture, which was stirred for further 10min. After addition of phosphate buffer, the resulting mixturewas extracted with EtOAc (3 × 30 mL), the combined organicphases were dried over anhydrous Na2SO4 and concentrated togive the crude aminooxy alcohol, which was directly taken upfor the next step without purification. To a MeOH (25 mL) solutionof the above crude aminooxy alcohol was addedCu(OAc)2·H2O (2.6 mmol) at 25 °C, and the reaction mixture wasallowed to stir for 10 h at that temperature. After addition ofphosphate buffer, the resulting mixture was extracted withCHCl3 (3 × 30 mL), and the combined organic phases were driedover anhydrous Na2SO4 and concentrated to give the crudeproduct, which was then purified by column chromatographyover silica gel using PE?EtOAc to give 3-amino-1,2-alkane diols1a?f.

Reference： [1]Synlett,2015,vol. 26,p. 355 - 358

46
[ 135865-78-0 ]
[ 586-96-9 ]
C₂₀H₂₄N₂O₄ [ No CAS ]

Reference： [1]Synlett,2015,vol. 26,p. 355 - 358

47
[ 60532-63-0 ]
[ 586-96-9 ]
C₄₉H₃₆N₈ [ No CAS ]

Reference： [1]Nature Chemistry,2015,vol. 7,p. 634 - 640

48
[ 7462-74-0 ]
[ 586-96-9 ]
C₁₄H₂₁N₃O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 11614 - 11617

49
[ 21573-10-4 ]
[ 586-96-9 ]
C₃₀H₃₂N₂O₇ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 13253 - 13257
Angew. Chem.,2015,vol. 127,p. 13451 - 13455,5

50
[ 21573-10-4 ]
[ 586-96-9 ]
C₁₃H₁₃NO₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 13253 - 13257
Angew. Chem.,2015,vol. 127,p. 13451 - 13455,5

51
[ 21573-10-4 ]
[ 1446877-16-2 ]
[ 586-96-9 ]
C₃₀H₃₂N₂O₇ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 13253 - 13257
Angew. Chem.,2015,vol. 127,p. 13451 - 13455,5

52
[ 38762-41-3 ]
[ 586-96-9 ]
(E)-2-[(4-bromo-2-chlorophenyl)diazenyl]phenol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 1850 - 1857

53
[ 38762-41-3 ]
[ 586-96-9 ]
(E)-1-(4-bromo-2-chlorophenyl)-2-phenyldiazene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 1850 - 1857

54
[ 1639-31-2 ]
[ 586-96-9 ]
1-phenyl-2-(3,4,5-trimethylphenyl)diazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With acetic acid; at 20℃;Cooling;	General procedure: To the solution of the relevant 4-alkyl aniline derivative in glacial acetic acid (0.05 ? 0.1 mol/L) is slowly added an equimolar amount of the respective nitrosobenzene at 20°C under water cooling. The reaction mixture is then stirred at room temperature until full conversion of the starting materials. Depending on the substitution pattern of the aniline derivative the coupling reaction takes hours to days until completion. The acetic acid is subsequently removed under reduced pressure. The residual crude product is adsorbed on silica gel and purified by column chromatography (usual solvent mixtures consist of 0.5 ? 5 vol percent diethyl ether in petrol ether). Solid diazenes are recrystallized afterwards.

Reference： [1]Tetrahedron,2016,vol. 72,p. 3151 - 3161

55
[ 80936-82-9 ]
[ 586-96-9 ]
1-(4-(methoxymethyl)phenyl)-2-phenyldiazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With acetic acid; at 20℃;Cooling;	General procedure: To the solution of the relevant 4-alkyl aniline derivative in glacial acetic acid (0.05 - 0.1 mol/L) is slowly added an equimolar amount of the respective nitrosobenzene at 20C under water cooling. The reaction mixture is then stirred at room temperature until full conversion of the starting materials. Depending on the substitution pattern of the aniline derivative the coupling reaction takes hours to days until completion. The acetic acid is subsequently removed under reduced pressure. The residual crude product is adsorbed on silica gel and purified by column chromatography (usual solvent mixtures consist of 0.5 - 5 vol% diethyl ether in petrol ether). Solid diazenes are recrystallized afterwards.

Reference： [1]Tetrahedron,2016,vol. 72,p. 3151 - 3161

56
[ 42014-60-8 ]
[ 586-96-9 ]
1-(4-tert-butyl-2,6-dimethylphenyl)-2-phenyldiazene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With acetic acid; at 20℃;Cooling;	General procedure: To the solution of the relevant 4-alkyl aniline derivative in glacial acetic acid (0.05 - 0.1 mol/L) is slowly added an equimolar amount of the respective nitrosobenzene at 20C under water cooling. The reaction mixture is then stirred at room temperature until full conversion of the starting materials. Depending on the substitution pattern of the aniline derivative the coupling reaction takes hours to days until completion. The acetic acid is subsequently removed under reduced pressure. The residual crude product is adsorbed on silica gel and purified by column chromatography (usual solvent mixtures consist of 0.5 - 5 vol% diethyl ether in petrol ether). Solid diazenes are recrystallized afterwards.

Reference： [1]Tetrahedron,2016,vol. 72,p. 3151 - 3161

57
[ 34743-49-2 ]
[ 586-96-9 ]
[ 150370-06-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 9912 - 9918

58
[ 34743-49-2 ]
[ 586-96-9 ]
5-methoxy-7-methyl-2-phenyl-2H-indazole [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 9912 - 9918

59
[ 74896-24-5 ]
[ 586-96-9 ]
3,5-dimethyl-4-(phenyldiazenyl)benzonitrile [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 9912 - 9918

60
[ 74896-24-5 ]
[ 586-96-9 ]
7-methyl-2-phenyl-2H-indazole-5-carbonitrile [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 9912 - 9918

61
[ 49607-51-4 ]
[ 586-96-9 ]
(E)-1-methyl-3-(phenyldiazenyl)-1H-1,2,4-triazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 1261 - 1274

62
[ 5779-93-1 ]
[ 586-96-9 ]
1,2-dimethylacridine [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 6263 - 6266

63
[ 68176-57-8 ]
[ 586-96-9 ]
C₁₆H₁₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In toluene; at 60℃; for 21h;Inert atmosphere;	General procedure: A solution of amine (1.00 equiv) in toluene (7 mL/mmol) was degassed with a nitrogen stream for 15 min. Then, the nitroso compound (1.00 equiv) and acetic acid (4.00 equiv) were added. The mixture was stirred at 60 °C for 21 h. The residue was purified by flash column chromatography (SiO2, hexane/EtOAc, 7:1), followed by distillation under vacuum to afford corresponding 2-(phenyldiazenyl) aniline.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3875 - 3878

64
[ 118062-05-8 ]
[ 586-96-9 ]
2,3,4-trimethoxy-N-phenylaniline [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1667 - 1671

65
[ 87199-14-2 ]
[ 586-96-9 ]
[ 53044-24-9 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1667 - 1671

66
[ 586-96-9 ]
[ 221006-70-8 ]
2,6-dimethoxy-N-phenylpyridin-3-amine [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1667 - 1671

67
[ 586-96-9 ]
[ 3469-20-3 ]

Reference： [1]Synthesis,2018,vol. 50,p. 1728 - 1736

68
[ 137436-76-1 ]
[ 4062-60-6 ]
[ 586-96-9 ]
C₁₆H₂₉CuN₃O⁽¹⁺⁾*F₆Sb^(1-) [ No CAS ]