[ CAS No. 1643-39-6 ] {[proInfo.proName]}

Name: 1643-39-6|2-Amino-4,6-di-tert-butylphenol|98%
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Product Details of [ 1643-39-6 ]

CAS No. :	1643-39-6	MDL No. :	MFCD00173890
Formula :	C₁₄H₂₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IVVMNEWWVJXCLX-UHFFFAOYSA-N
M.W :	221.34	Pubchem ID :	324555
Synonyms :

Safety of [ 1643-39-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1643-39-6 ]

* 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 [ 1643-39-6 ]
Downstream synthetic route of [ 1643-39-6 ]

[ 1643-39-6 ] Synthesis Path-Upstream 1~15

1
[ 52184-29-9 ]
[ 95-83-0 ]
[ 1643-39-6 ]
[ 3864-99-1 ]

Reference： [1] Heterocycles, 1998, vol. 48, # 12, p. 2581 - 2592

2
[ 20039-94-5 ]
[ 1643-39-6 ]

Reference： [1] European Journal of Inorganic Chemistry, 2008, # 14, p. 2278 - 2285
[2] Russian Chemical Bulletin, 1995, vol. 44, # 9, p. 1720 - 1724[3] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1995, # 9, p. 1789 - 1793
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 12, p. 2841 - 2848
[5] Chemistry Letters, 2002, # 3, p. 358 - 359
[6] Patent: US2010/168094, 2010, A1, . Location in patent: Page/Page column 72; 73
[7] Organometallics, 2013, vol. 32, # 24, p. 7460 - 7469
[8] Journal of the American Chemical Society, 2014, vol. 136, # 33, p. 11574 - 11577
[9] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 0517
[10] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1319 - 1332
[11] Organometallics, 2017, vol. 36, # 10, p. 1936 - 1945

3
[ 3383-21-9 ]
[ 1643-39-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 6, p. 1179 - 1182
[2] Dalton Transactions, 2012, vol. 41, # 39, p. 11980 - 11983
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 5850 - 5865
[4] Journal of Organometallic Chemistry, 2000, vol. 614-615, p. 283 - 293
[5] Russian Journal of Organic Chemistry, 2006, vol. 42, # 11, p. 1653 - 1661
[6] Russian Chemical Bulletin, 1995, vol. 44, # 9, p. 1720 - 1724[7] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1995, # 9, p. 1789 - 1793
[8] J. Gen. Chem. USSR (Engl. Transl.), 1986, vol. 56, p. 765 - 768[9] Zhurnal Obshchei Khimii, 1986, vol. 56, # 4, p. 869 - 872
[10] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 362 - 372
[11] Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2375 - 2385

4
[ 96-76-4 ]
[ 1643-39-6 ]

Reference： [1] Tetrahedron Asymmetry, 2006, vol. 17, # 24, p. 3351 - 3357
[2] Tetrahedron Letters, 1988, vol. 29, # 8, p. 851 - 852
[3] Chemistry Letters, 2002, # 3, p. 358 - 359
[4] Organometallics, 2013, vol. 32, # 24, p. 7460 - 7469
[5] Journal of the American Chemical Society, 2014, vol. 136, # 33, p. 11574 - 11577
[6] Patent: US2015/231142, 2015, A1,
[7] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1319 - 1332
[8] Organometallics, 2017, vol. 36, # 10, p. 1936 - 1945

5
[ 20039-94-5 ]
[ 1643-39-6 ]

Reference： [1] Patent: US2011/98311, 2011, A1,

6
[ 1188-01-8 ]
[ 3383-21-9 ]
[ 3997-91-9 ]
[ 1643-39-6 ]

Reference： [1] Molecules, 2005, vol. 10, # 3, p. 760 - 770

7
[ 615-82-7 ]
[ 3383-21-9 ]
[ 1643-39-6 ]

Reference： [1] Molecules, 2005, vol. 10, # 3, p. 760 - 770

8
[ 52749-93-6 ]
[ 1643-39-6 ]
[ 76439-86-6 ]

Reference： [1] Heterocycles, 1980, vol. 14, # 9, p. 1259 - 1264
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 12, p. 2841 - 2848

9
[ 3383-21-9 ]
[ 201023-39-4 ]
[ 1643-39-6 ]

Reference： [1] Molecules, 2005, vol. 10, # 3, p. 760 - 770

10
[ 325463-16-9 ]
[ 1643-39-6 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1986, vol. 56, p. 765 - 768[2] Zhurnal Obshchei Khimii, 1986, vol. 56, # 4, p. 869 - 872

11
[ 873055-54-0 ]
[ 1643-39-6 ]

Reference： [1] Patent: US2015/231142, 2015, A1,

12
[ 52184-14-2 ]
[ 1643-39-6 ]
[ 95-54-5 ]
[ 3846-71-7 ]

Reference： [1] Heterocycles, 1998, vol. 48, # 12, p. 2581 - 2592

13
[ 52184-29-9 ]
[ 95-83-0 ]
[ 1643-39-6 ]
[ 3864-99-1 ]

Reference： [1] Heterocycles, 1998, vol. 48, # 12, p. 2581 - 2592

14
[ 52749-93-6 ]
[ 55429-04-4 ]
[ 1643-39-6 ]
[ 76439-79-7 ]

Reference： [1] Heterocycles, 1980, vol. 14, # 9, p. 1259 - 1264
[2] Heterocycles, 1980, vol. 14, # 9, p. 1259 - 1264
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 12, p. 2841 - 2848

15
[ 52184-14-2 ]
[ 1643-39-6 ]
[ 95-54-5 ]
[ 3846-71-7 ]

Reference： [1] Heterocycles, 1998, vol. 48, # 12, p. 2581 - 2592

[ 1643-39-6 ] Synthesis Path-Downstream 1~66

1
[ 1643-39-6 ]
[ 55429-04-4 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 5994 - 5998
[2]Chemische Berichte,1968,vol. 101,p. 262 - 271

2
[ 96-76-4 ]
[ 1643-39-6 ]

Reference： [1]Tetrahedron Asymmetry,2006,vol. 17,p. 3351 - 3357
[2]Tetrahedron Letters,1988,vol. 29,p. 851 - 852
[3]Chemistry Letters,2002,p. 358 - 359
[4]Organometallics,2013,vol. 32,p. 7460 - 7469
[5]Journal of the American Chemical Society,2014,vol. 136,p. 11574 - 11577
[6]Patent: US2015/231142,2015,A1
[7]Inorganic Chemistry,2017,vol. 56,p. 1319 - 1332
[8]Organometallics,2017,vol. 36,p. 1936 - 1945

3
[ 90-02-8 ]
[ 1643-39-6 ]
[ 103661-06-9 ]

Reference： [1]Russian Journal of Organic Chemistry,1995,vol. 31,p. 645 - 650
    Zhurnal Organicheskoi Khimii,1995,vol. 31,p. 699 - 704
[2]Journal of general chemistry of the USSR,1986,vol. 56,p. 765 - 768
    Zhurnal Obshchei Khimii,1986,vol. 56,p. 869 - 872
[3]Doklady Chemistry,1986,vol. 288,p. 184 - 186
    Dokl. Akad. Nauk SSSR Ser. Khim.,1986,vol. 288,p. 1117 - 1120

4
[ 605-70-9 ]
[ 1643-39-6 ]
Naphthalene-1,4-dicarboxylic acid bis-[(3,5-di-tert-butyl-2-hydroxy-phenyl)-amide] [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1982,p. 1423 - 1433

5
C₁₂⁽¹³⁾CH₁₃Br₂P [ No CAS ]
[ 1643-39-6 ]
[ 77358-25-9 ]

Reference： [1]Chemische Berichte,1981,vol. 114,p. 447 - 455

6
[ 20039-94-5 ]
[ 1643-39-6 ]

Yield	Reaction Conditions	Operation in experiment
	With stannous chloride dihydrate; ethanol; at 100℃; for 0.5h;Microwave irradiation;	A solution of 2,4-di-tert-butyl-6-nitro-phenol (27 mg, 0.11 mmol) and SnCl2.2H2O (121 mg, 0.54 mmol) in EtOH (1.0 mL) was heated in microwave oven at 100 C. for 30 min. The mixture was diluted with EtOAc and water, basified with sat. NaHCO3 and filtered through Celite. The organic layer was separated and dried over Na2SO4. Solvent was removed by evaporation to provide 6-amino-2,4-di-tert-butyl-phenol (C-8), which was used without further purification. HPLC ret. time 2.74 min, 10-99% CH3CN, 5 min run; ESI-MS 222.5 m/z (MH+)
	With tin(II) chloride dihdyrate; In ethanol; at 100℃; for 0.5h;Microwave irradiation;	A solution of 2,4-di-tert-butyl-6-nitro-phenol (27 mg, 0.11 mmol) and SnCl2.2H2O (121 mg, 0.54 mmol) in EtOH (1.0 mL) was heated in microwave oven at 100 C. for 30 min. The mixture was diluted with EtOAc and water, basified with sat. NaHCO3 and filtered through Celite. The organic layer was separated and dried over Na2SO4. Solvent was removed by evaporation to provide 6-amino-2,4-di-tert-butyl-phenol (C-8), which was used without further purification. HPLC ret. time 2.74 min, 10-99% CH3CN, 5 min run; ESI-MS 222.5 m/z (MH+).

Reference： [1]European Journal of Inorganic Chemistry,2008,p. 2278 - 2285
[2]Russian Chemical Bulletin,1995,vol. 44,p. 1720 - 1724
Izvestiya Akademi Nauk, Seriya Khimicheskaya,1995,p. 1789 - 1793
[3]Journal of the Chemical Society. Perkin transactions I,1982,p. 2841 - 2848
[4]Chemistry Letters,2002,p. 358 - 359
[5]Patent: US2010/168094,2010,A1 .Location in patent: Page/Page column 72; 73
[6]Organometallics,2013,vol. 32,p. 7460 - 7469
[7]Journal of the American Chemical Society,2014,vol. 136,p. 11574 - 11577
[8]Patent: US2015/231142,2015,A1 .Location in patent: Paragraph 0517
[9]Inorganic Chemistry,2017,vol. 56,p. 1319 - 1332
[10]Organometallics,2017,vol. 36,p. 1936 - 1945

7
[ 108-24-7 ]
[ 1643-39-6 ]
[ 60043-08-5 ]

Reference： [1]Pharmaceutical Chemistry Journal,2002,vol. 36,p. 410 - 412
[2]Journal of Organometallic Chemistry,2007,vol. 692,p. 5549 - 5554
[3]Journal of the Chemical Society. Perkin transactions I,1982,p. 2841 - 2848
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2420 - 2423

9
[ 3383-21-9 ]
[ 1643-39-6 ]
[ 55429-04-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 3,5-di-tert-butyl-o-benzoquinone; 2-amino-4,6-di-tertbutylphenol In pyridine; methanol for 2h; Reflux; Stage #2: With potassium hydroxide; potassium hexacyanoferrate(III) In diethyl ether; water	Synthesis of redox-active phenox-imQ was carriedout using an original procedure which is a modificationof published earlier [27]. 4,6-Di-tert-butyl-oaminophenol(3.50 g, 15.8 mmol) [28] and 3,5-di-tertbutyl-o-benzoquinone (3.47 g, 15.8 mmol) wereplaced in a flask with a stirrer and dissolved in methanol(50 mL). After dissolution the reaction mixtureturned intensively violet. Pyridine (5 mL) was addedto the resulting solution, and the reaction mixture wasrefluxed with an air reflux condenser for 2 h. The reactionafforded a mixture of the oxidized and reducedforms of phenox-imQ. The dropwise addition of waterto the reaction mixture resulted in the precipitation ofa dark blue substance. The dry residue was dissolved inEt2O, and the solution was transferred to a separatingfunnel. A saturated aqueous solution of K3Fe(CN)6(20 g) and KOH (1 g) was added to the obtained mixture.The resulting reaction mixture was vigorouslyshaken. The oxidation process was monitored by thinlayerchromatography (TLC) using a hexane-ethylacetate (1 : 30) system as an eluent. The disappearanceof one of two blue spots on the chromatogram servedas the indication of the reaction end. The obtainedproduct was crystallized from hexane at -18°. Theformed dark blue crystals of phenox-imQ weredecanted from the mother liquor. The yield was 5.26 g(78%). The spectroscopic data of the synthesizedcompound correspond to the published data [27, 29].
	With ammonia; water 1.) MeOH; Yield given. Multistep reaction;

Reference： [1]Arsenyeva, K. V.; Chegerev, M. G.; Cherkasov, A. V.; Piskunov, A. V. [Russian Journal of Coordination Chemistry, 2020, vol. 46, # 11, p. 746 - 755][Koord. Khim., 2020, vol. 46, # 11, p. 672 - 681,10]
[2]Vol'eva, V. B.; Prokof'eva, T. I.; Prokof'ev, A. I.; Belostotskaya, I. S.; Komissarova, N. L.; Ershov, V. V. [Russian Chemical Bulletin, 1995, vol. 44, # 9, p. 1720 - 1724][Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1995, # 9, p. 1789 - 1793]

10
[ 1643-39-6 ]
[ 3383-21-9 ]

Reference： [1]Chemistry Letters,1996,p. 819 - 820
[2]Inorganic Chemistry,2015,vol. 54,p. 1720 - 1727

11
[ 52184-14-2 ]
[ 1643-39-6 ]
[ 95-54-5 ]
[ 3846-71-7 ]

Reference： [1]Heterocycles,1998,vol. 48,p. 2581 - 2592

12
[ 52184-29-9 ]
[ 95-83-0 ]
[ 1643-39-6 ]
[ 3864-99-1 ]

Yield	Reaction Conditions	Operation in experiment
88 % Chromat.	With 2-bromo-2-nitropropane; zinc In methanol; dichloromethane for 4h; Ambient temperature;

Reference： [1]Kim, Byeong Hyo; Lee, Yoon Seok; Kwon, Woong; Jin, Youngoo; Tak, Jung Ae; Jun, Young Moo; Baik, Woonphil; Lee, Byung Min [Heterocycles, 1998, vol. 48, # 12, p. 2581 - 2592]

13
2,4-di-tert-butyl-6-(5-chloro-2-nitro-phenylazo)-phenol [ No CAS ]
[ 95-83-0 ]
[ 1643-39-6 ]
[ 3864-99-1 ]

Yield	Reaction Conditions	Operation in experiment
79 % Chromat.	With 2-bromo-2-nitropropane; zinc In methanol; dichloromethane for 3.5h; Ambient temperature;

Reference： [1]Kim, Byeong Hyo; Lee, Yoon Seok; Kwon, Woong; Jin, Youngoo; Tak, Jung Ae; Jun, Young Moo; Baik, Woonphil; Lee, Byung Min [Heterocycles, 1998, vol. 48, # 12, p. 2581 - 2592]

14
[ 1643-39-6 ]
(5aS,11aS)-2-Chloro-4-isothiocyanato-6-oxo-6,11,11a,12-tetrahydro-benzo[b]xanthene-5a-carboxylic acid ethyl ester [ No CAS ]
2-chloro-4-[3-(3,5-di-tert-butyl-2-hydroxy-phenyl)-thioureido]-6-oxo-6,11,11a,12-tetrahydro-benzo[b]xanthene-5a-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 5853 - 5856

15
[ 79-37-8 ]
[ 1643-39-6 ]
[ 36931-29-0 ]

Reference： [1]European Journal of Inorganic Chemistry,2003,p. 1768 - 1777

16
[ 79-03-8 ]
[ 1643-39-6 ]
4,6-di-(tert-butyl)-2-(N-propanoylamino)phenol [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,2002,vol. 36,p. 410 - 412
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2420 - 2423

17
[ 98-88-4 ]
[ 1643-39-6 ]
4,6-di-(tert-butyl)-2-(N-benzoylamino)phenol [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,2002,vol. 36,p. 410 - 412

18
[ 1643-39-6 ]
[ 141-75-3 ]
4,6-di-(tert-butyl)-2-(N-butanoylamino)phenol [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,2002,vol. 36,p. 410 - 412
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2420 - 2423

19
[ 1643-39-6 ]
[ 79-04-9 ]
4,6-di-(tert-butyl)-2-(N-chloroacetylamino)phenol [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,2002,vol. 36,p. 410 - 412

20
[ 71381-91-4 ]
[ 1643-39-6 ]
4,6-di-(tert-butyl)-2-[N-[2-(4-isobutylphenyl)propanoyl]amino]phenol [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,2002,vol. 36,p. 410 - 412

21
[ 1080-44-0 ]
[ 1643-39-6 ]
N-(p-toluenesulfonyl)-glycine-3,5-di-tert-butyl-2-phenolamide [ No CAS ]