[ CAS No. 1122-12-9 ] {[proInfo.proName]}

Name: 1122-12-9|3,4-Dibromofuran-2,5-dione|97%
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Quality Control of [ 1122-12-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1122-12-9 ]

Product Details of [ 1122-12-9 ]

CAS No. :	1122-12-9	MDL No. :	MFCD00030673
Formula :	C₄Br₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GEKJEMDSKURVLI-UHFFFAOYSA-N
M.W :	255.85	Pubchem ID :	70727
Synonyms :

Calculated chemistry of [ 1122-12-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	35.98
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.08
Log Po/w (XLOGP3) :	1.68
Log Po/w (WLOGP) :	1.07
Log Po/w (MLOGP) :	0.96
Log Po/w (SILICOS-IT) :	2.0
Consensus Log Po/w :	1.36

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.838 mg/ml ; 0.00328 mol/l
Class :	Soluble
Log S (Ali) :	-2.21
Solubility :	1.59 mg/ml ; 0.00623 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.19
Solubility :	1.67 mg/ml ; 0.00652 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.44

Safety of [ 1122-12-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1122-12-9 ]

* 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 [ 1122-12-9 ]
Downstream synthetic route of [ 1122-12-9 ]

[ 1122-12-9 ] Synthesis Path-Upstream 1~11

1
[ 1122-12-9 ]
[ 1122-10-7 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 19, p. 4585 - 4593

2
[ 1122-12-9 ]
[ 57-13-6 ]
[ 1122-10-7 ]

Reference： [1] American Chemical Journal, 1896, vol. 18, p. 336
[2] Helvetica Chimica Acta, 1920, vol. 3, p. 506

3
[ 108-31-6 ]
[ 1122-12-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	at 120℃; for 16 h; Sealed tube	Synthesis of 3,4-Dibromomaleic anhydride: A mixture of maleic anhydride (2.0 g, 20.39 mmol), aluminum chloride (40.8 mg, 0.3 mmol), and bromine (2.1 ml, 40.78 mmol), was heated at 120 °C for 16 h in sealed tube. After that, it was allowed to coolroom temperature and the reaction mixture was added to ethyl acetate. The ethylacetate solution was filtered and the filtrate was evaporated. To the resulting reddishsolid, 100 nil CHC13 was added and filtered. The filtrate was evaporated to get off-white (yellow) solid in 87percent yield. 13C NMR(CDC13) ö(ppm): 131.8, 159.0.
83%	at 160℃; for 20 h; Sealed tube	Under an inert atmosphere, a mixture of maleic anhydride (1.50 g, 15.3 mmol), A1C13 (0.30 g, 0.21 mmol) and Br2 (1.57 mL, 30.6 mmol) was heated at 160 °C in a sealed ampule for 20 h. Upon cooling to room temperature the reaction mixture was carefully opened to air, EtOAc was added the solid filtered off and repeatedly washed with further EtOAc. The filtrate was finally concentrated in vacuo to give the title compound (1) as a yellow solid (3.25 g, 12.8 mmol, 83percent). m.p. 107-110°C; v_max (cm^"1) 1769, 1706, 1590; 6_C (CDC1₃, 125 MHz) 164.4 (s), 125.9 (s); HRMS (CI) calculated for C₄0₃Br₂ [M]⁺ 253.82087, observed: 253.82082.
78%	at 160℃; for 16 h; Inert atmosphere; Sealed tube	Under an inert atmosphere, a solution of maleic anhydride(1.50 g, 15.3 mmol, 1 eq), aluminium trichloride (300 mg,0.21 mmol, cat.) and bromine (4.95 g, 30.6 mmol, 2 eq) was heated at 160° C. in a sealed ampule (note—blast shield) for 16 h. Upon cooling to 21° C. the reaction mixture was stirred for a further 24 h and careffilly opened to ait EtOAc was added and the solid filtered off and repeatedly washed with thrther EtOAc. The filtrate was finally concentrated in vacuo to give the title compound was a yellow solid which was used without thrther purification (3.05 g, 11.9 mmol, 78percent yield).m.p 107-110° C.; ‘3CNMR(15OMHz, CD3OD) ö 163.33 (s),125.28 (s); IR (MeOH) 1769, 1706, 1590 cm’; HRMS (CI) calcd for C40313r2 [M]253.82087, 253.82082 observed.

Reference： [1] Tetrahedron, 2005, vol. 61, # 19, p. 4585 - 4593
[2] Journal of Materials Chemistry B, 2015, vol. 3, # 16, p. 3195 - 3200
[3] Journal of Materials Chemistry A, 2015, vol. 3, # 21, p. 11607 - 11614
[4] Chemistry - A European Journal, 2014, vol. 20, # 11, p. 3077 - 3083
[5] Patent: WO2015/140792, 2015, A1, . Location in patent: Page/Page column 32; 33
[6] Chemical Communications, 2013, vol. 49, # 74, p. 8187 - 8189
[7] Patent: WO2013/121175, 2013, A1, . Location in patent: Page/Page column 36; 37
[8] Patent: US9295729, 2016, B2, . Location in patent: Page/Page column 62
[9] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2646 - 2655
[10] Journal of the American Chemical Society, 2012, vol. 134, # 3, p. 1847 - 1852
[11] European Journal of Medicinal Chemistry, 1988, vol. 23, # 1, p. 91 - 96
[12] Australian Journal of Chemistry, 2001, vol. 54, # 2, p. 117 - 126
[13] Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 254 - 263
[14] Patent: WO2014/85545, 2014, A1, . Location in patent: Page/Page column 59

4
[ 108-30-5 ]
[ 1122-12-9 ]

Reference： [1] Tetrahedron, 2008, vol. 64, # 19, p. 4347 - 4353
[2] Journal of the Chemical Society, 1930, p. 1733,1739

5
[ 608-37-7 ]
[ 1122-12-9 ]

Reference： [1] Chemische Berichte, 1880, vol. 13, p. 734[2] American Chemical Journal, 1881, vol. 3, p. 47
[3] Chemische Berichte, 1910, vol. 43, p. 1278
[4] Journal of the American Chemical Society, 1930, vol. 52, p. 3423,3435
[5] Journal of the American Chemical Society, 1930, vol. 52, p. 3423,3435
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 45 - 52
[7] Australian Journal of Chemistry, 1987, vol. 40, # 6, p. 1137 - 1144
[8] Chemische Berichte, 1880, vol. 13, p. 734[9] American Chemical Journal, 1881, vol. 3, p. 47
[10] Australian Journal of Chemistry, 2001, vol. 54, # 2, p. 117 - 126
[11] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1359 - 1366

6
[ 32460-09-6 ]
[ 1122-12-9 ]

Reference： [1] Australian Journal of Chemistry, 1987, vol. 40, # 6, p. 1137 - 1144
[2] Australian Journal of Chemistry, 1987, vol. 40, # 6, p. 1137 - 1144

7
[ 55052-06-7 ]
[ 1122-12-9 ]

Reference： [1] Chemische Berichte, 1905, vol. 38, p. 2594

8
[ 5926-51-2 ]
[ 1122-12-9 ]

Reference： [1] Zhurnal Obshchei Khimii, 1954, vol. 24, p. 1216,1219; engl. Ausg. S. 1205, 1206

9
[ 543-20-4 ]
[ 1122-12-9 ]

Reference： [1] Chem. Zentralbl., 1900, vol. 71, # I, p. 404

10
[ 55052-06-7 ]
[ 1122-12-9 ]
[ 64-17-5 ]

Reference： [1] Chemische Berichte, 1905, vol. 38, p. 2594

11
[ 108-30-5 ]
[ 7726-95-6 ]
[ 5470-44-0 ]
[ 1122-12-9 ]

Reference： [1] Journal of the Chemical Society, 1930, p. 1733,1739

[ 1122-12-9 ] Synthesis Path-Downstream 1~88

2
[ 5926-51-2 ]
[ 1122-12-9 ]

Reference： [1]Zhurnal Obshchei Khimii,1954,vol. 24,p. 1216,1219; engl. Ausg. S. 1205, 1206

4
[ 67-56-1 ]
[ 1122-12-9 ]
[ 1114-20-1 ]

Reference： [1]Chemische Berichte,1905,vol. 38,p. 2594

5
[ 917-64-6 ]
[ 1122-12-9 ]
3,4-dibromo-5,5-dimethyl-5H-furan-2-one [ No CAS ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 1278

6
[ 1122-12-9 ]
[ 571-60-8 ]
[ 99562-95-5 ]

Reference： [1]Chemische Berichte,1950,vol. 83,p. 178,180

7
[ 1122-12-9 ]
[ 64-17-5 ]
[ 55052-06-7 ]
[ 13677-32-2 ]

Reference： [1]Helvetica Chimica Acta,1920,vol. 3,p. 506

8
[ 1122-12-9 ]
[ 120-12-7 ]
11,12-dibromo-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid-anhydride [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1931,vol. 486,p. 217,225
Justus Liebigs Annalen der Chemie,1932,vol. 498,p. 7,9,11

9
[ 1122-12-9 ]
[ 542-92-7 ]
[ 33140-59-9 ]

Reference： [1]Australian Journal of Chemistry,2001,vol. 54,p. 117 - 126
[2]Justus Liebigs Annalen der Chemie,1930,vol. 478,p. 137,149
Justus Liebigs Annalen der Chemie,1931,vol. 490,p. 236,241

10
[ 1122-12-9 ]
[ 1165952-91-9 ]
2exo,3exo-dibromo-bicyclo[2.2.2]oct-5-ene-2endo,3endo-dicarboxylic acid-anhydride [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1930,vol. 478,p. 137,149
Justus Liebigs Annalen der Chemie,1931,vol. 490,p. 236,241

11
[ 1122-12-9 ]
[ 62-53-3 ]
3-anilino-4-bromo-1-phenyl-pyrrole-2,5-dione [ No CAS ]

Reference： [1]Chemische Berichte,1905,vol. 38,p. 2594

12
[ 1122-12-9 ]
[ 62-53-3 ]
dianilino-maleic acid-anhydride [ No CAS ]

Reference： [1]Chemische Berichte,1905,vol. 38,p. 3598
[2]Chemische Berichte,1905,vol. 38,p. 2594

13
[ 1122-12-9 ]
[ 123-31-9 ]
[ 51847-26-8 ]

Reference： [1]Chemische Berichte,1950,vol. 83,p. 178,180

14
[ 1122-12-9 ]
[ 150-78-7 ]
[ 51847-26-8 ]

Reference： [1]Canadian Journal of Chemistry,1974,vol. 52,p. 838 - 842
[2]Canadian Journal of Chemistry,1974,vol. 52,p. 838 - 842

15
[ 1122-12-9 ]
[ 108-67-8 ]
2,3-dibromo-4-oxo-4-(2.4.6-trimethyl-phenyl)-cis-crotonic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1930,vol. 52,p. 3423,3435

16
[ 1122-12-9 ]
[ 71-43-2 ]
[ 85653-69-6 ]

Reference： [1]Journal of the American Chemical Society,1930,vol. 52,p. 3423,3435

17
[ 1122-12-9 ]
[ 15111-21-4 ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 1278

18
[ 1122-12-9 ]
[ 6958-60-7 ]

Reference： [1]Zhurnal Obshchei Khimii,1954,vol. 24,p. 1216,1219; engl. Ausg. S. 1205, 1206
[2]Helvetica Chimica Acta,1920,vol. 3,p. 506

19
[ 55052-06-7 ]
[ 1122-12-9 ]

Reference： [1]Chemische Berichte,1905,vol. 38,p. 2594

20
[ 55052-06-7 ]
[ 1122-12-9 ]
[ 64-17-5 ]

Reference： [1]Chemische Berichte,1905,vol. 38,p. 2594

21
[ 608-37-7 ]
[ 1122-12-9 ]

Reference： [1]Chemische Berichte,1880,vol. 13,p. 734
American Chemical Journal,1881,vol. 3,p. 47
[2]Chemische Berichte,1910,vol. 43,p. 1278
[3]Journal of the American Chemical Society,1930,vol. 52,p. 3423,3435
[4]Journal of the American Chemical Society,1930,vol. 52,p. 3423,3435
[5]Journal of the Chemical Society. Perkin transactions I,1985,p. 45 - 52
[6]Australian Journal of Chemistry,1987,vol. 40,p. 1137 - 1144
[7]Chemische Berichte,1880,vol. 13,p. 734
American Chemical Journal,1881,vol. 3,p. 47
[8]Australian Journal of Chemistry,2001,vol. 54,p. 117 - 126
[9]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1359 - 1366

22
[ 543-20-4 ]
[ 1122-12-9 ]

Reference： [1]Chemisches Zentralblatt,1900,vol. 71,p. 404

23
[ 1122-12-9 ]
[ 874-14-6 ]
[ 52695-25-7 ]

Reference： [1]Chemische Berichte,1974,vol. 107,p. 1265 - 1270

24
[ 1122-12-9 ]
[ 64-17-5 ]
[ 55052-06-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1974,p. 2092 - 2095

25
[ 1122-12-9 ]
[ 100-51-6 ]
[ 55052-04-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1974,p. 2092 - 2095

26
[ 108-31-6 ]
[ 1122-12-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With aluminum (III) chloride; bromine; at 120℃; for 16h;Sealed tube;	Synthesis of 3,4-Dibromomaleic anhydride: A mixture of maleic anhydride (2.0 g, 20.39 mmol), aluminum chloride (40.8 mg, 0.3 mmol), and bromine (2.1 ml, 40.78 mmol), was heated at 120 °C for 16 h in sealed tube. After that, it was allowed to coolroom temperature and the reaction mixture was added to ethyl acetate. The ethylacetate solution was filtered and the filtrate was evaporated. To the resulting reddishsolid, 100 nil CHC13 was added and filtered. The filtrate was evaporated to get off-white (yellow) solid in 87percent yield. 13C NMR(CDC13) oe(ppm): 131.8, 159.0.
83%	With aluminum (III) chloride; bromine; at 160℃; for 20h;Sealed tube;	Under an inert atmosphere, a mixture of maleic anhydride (1.50 g, 15.3 mmol), A1C13 (0.30 g, 0.21 mmol) and Br2 (1.57 mL, 30.6 mmol) was heated at 160 °C in a sealed ampule for 20 h. Upon cooling to room temperature the reaction mixture was carefully opened to air, EtOAc was added the solid filtered off and repeatedly washed with further EtOAc. The filtrate was finally concentrated in vacuo to give the title compound (1) as a yellow solid (3.25 g, 12.8 mmol, 83percent). m.p. 107-110°C; vmax (cm"1) 1769, 1706, 1590; 6C (CDC13, 125 MHz) 164.4 (s), 125.9 (s); HRMS (CI) calculated for C403Br2 [M]+ 253.82087, observed: 253.82082.
78%	With aluminum (III) chloride; bromine; at 160℃; for 16h;Inert atmosphere; Sealed tube;	Under an inert atmosphere, a solution of maleic anhydride(1.50 g, 15.3 mmol, 1 eq), aluminium trichloride (300 mg,0.21 mmol, cat.) and bromine (4.95 g, 30.6 mmol, 2 eq) was heated at 160° C. in a sealed ampule (note?blast shield) for 16 h. Upon cooling to 21° C. the reaction mixture was stirred for a further 24 h and careffilly opened to ait EtOAc was added and the solid filtered off and repeatedly washed with thrther EtOAc. The filtrate was finally concentrated in vacuo to give the title compound was a yellow solid which was used without thrther purification (3.05 g, 11.9 mmol, 78percent yield).m.p 107-110° C.; ?3CNMR(15OMHz, CD3OD) oe 163.33 (s),125.28 (s); IR (MeOH) 1769, 1706, 1590 cm?; HRMS (CI) calcd for C40313r2 [M]253.82087, 253.82082 observed.

With aluminum (III) chloride; bromine; at 120℃; for 16h;Sealed tube;

Maleic anhydride (2.0 g, 20 mmol), aluminum(III) chloride (68 mg, 0.51 mmol) and bromine (2.1 mL, 41 mmol) were placed in a sealed reaction vessel and heated to 120 °C for 16 h. After cooling to RT, the reaction was diluted with EtOAc (30 mL) and filtered. The filtrate was then concentrated in vacuo to yield the crude product, 3,4-dibromofuran-2,5-dione, as an orange solid which was used in the next step without further purification. The 3,4-dibromofuran-2,5- dione (1.0 g, 3.9 mmol) was placed in a round-bottomed flask and dissolved in glacial acetic acid (10 mL) at RT. 3.4-Dichloroaniline (0.70 g, 4.3 mmol) was added at RT and then the reaction was heated at reflux for 3 h (120 - 130 °C). The reaction was then cooled to RT and volatiles were removed in vacuo. The crude product was recrystallized from MeOH to yield the title compound as a reddish-brown solid (1.3 g, 80percent). 1H-NMR (400 MHz, DMSO-d6): delta 7.80 (d, J = 8.6 Hz, 1H), 7.69 (d, J = 1.6 Hz, 1H), 7.42 (dd, J = 1.8 Hz, 6.8 Hz, 1H). 13C- NMR (100 MHz, DMSO-d6): delta 162.9, 131.3, 131.2, 131.1 , 129.9, 128.7, 127.3.

Reference： [1]Tetrahedron,2005,vol. 61,p. 4585 - 4593
[2]Journal of Materials Chemistry B,2015,vol. 3,p. 3195 - 3200
[3]Journal of Materials Chemistry A,2015,vol. 3,p. 11607 - 11614
[4]Chemistry - A European Journal,2014,vol. 20,p. 3077 - 3083
[5]Patent: WO2015/140792,2015,A1 .Location in patent: Page/Page column 32; 33
[6]Chemical Communications,2013,vol. 49,p. 8187 - 8189
[7]Patent: WO2013/121175,2013,A1 .Location in patent: Page/Page column 36; 37
[8]Patent: US9295729,2016,B2 .Location in patent: Page/Page column 62
[9]Journal of Organic Chemistry,1998,vol. 63,p. 2646 - 2655
[10]Journal of the American Chemical Society,2012,vol. 134,p. 1847 - 1852
[11]European Journal of Medicinal Chemistry,1988,vol. 23,p. 91 - 96
[12]Australian Journal of Chemistry,2001,vol. 54,p. 117 - 126
[13]Journal of Medicinal Chemistry,2013,vol. 56,p. 254 - 263
[14]Patent: WO2014/85545,2014,A1 .Location in patent: Page/Page column 59

27
[ 32460-09-6 ]
[ 1122-12-9 ]

Reference： [1]Australian Journal of Chemistry,1987,vol. 40,p. 1137 - 1144
[2]Australian Journal of Chemistry,1987,vol. 40,p. 1137 - 1144

28
[ 67-56-1 ]
[ 1122-12-9 ]
[ 2207-27-4 ]
(1R,2R,3S,6S,7S)-2,3-Dibromo-1,7,8,9-tetrachloro-6-methoxy-4-oxo-5-oxa-tricyclo[4.3.0.0^3,7]non-8-ene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 721 - 724

29
[ 1122-12-9 ]
[ 2207-27-4 ]
2,6-Dibromo-1,7,8,9-tetrachloro-10,10-dimethoxy-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1985,p. 1589 - 1590

30
[ 1122-12-9 ]
[ 80027-18-5 ]

Reference： [1]Journal of Fluorine Chemistry,1981,vol. 18,p. 223 - 242

31
[ 1122-12-9 ]
[ 123-01-3 ]
(Z)-2,3-Dibromo-4-(4-dodecyl-phenyl)-4-oxo-but-2-enoic acid [ No CAS ]

Reference： [1]Pharmazie,1999,vol. 54,p. 93 - 98

32
[ 1122-12-9 ]
[ 1459-09-2 ]
(Z)-2,3-Dibromo-4-(4-hexadecyl-phenyl)-4-oxo-but-2-enoic acid [ No CAS ]

Reference： [1]Pharmazie,1999,vol. 54,p. 93 - 98

33
[ 1122-12-9 ]
[ 1459-10-5 ]
3,4-Dibromo-5-hydroxy-5-(4-tetradecyl-phenyl)-5H-furan-2-one [ No CAS ]

Reference： [1]Pharmazie,1999,vol. 54,p. 93 - 98

34
[ 1122-12-9 ]
[ 4445-07-2 ]
(Z)-2,3-Dibromo-4-(4-octadecyl-phenyl)-4-oxo-but-2-enoic acid [ No CAS ]

Reference： [1]Pharmazie,1999,vol. 54,p. 93 - 98

35
[ 1122-12-9 ]
[ 7662-83-1 ]
[ 205128-49-0 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 2646 - 2655

36
[ 1122-12-9 ]
[ 2393-23-9 ]
[ 205128-48-9 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 4585 - 4593
[2]Journal of Organic Chemistry,1998,vol. 63,p. 2646 - 2655

37
[ 1122-12-9 ]
[ 104-84-7 ]
3,4-Dibromo-1-(4-methyl-benzyl)-pyrrole-2,5-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 2646 - 2655

38
[ 1122-12-9 ]
[ 80-62-6 ]
[ 221534-96-9 ]
[ 251459-82-2 ]
3,4-dichloro-5-(2-oxo-propylidene)-5H-furan-2-one [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1999,vol. 33,p. 18 - 21

41
[ 108-30-5 ]
[ 7726-95-6 ]
[ 5470-44-0 ]
[ 1122-12-9 ]

Reference： [1]Journal of the Chemical Society,1930,p. 1733,1739

42
[ 1122-12-9 ]
[ 67-64-1 ]
sodium iodide [ No CAS ]
[ 15111-21-4 ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 1278

43
[ 7726-95-6 ]
[ 543-20-4 ]
iron [ No CAS ]
[ 1122-12-9 ]

Reference： [1]Chemisches Zentralblatt,1900,vol. 71,p. 404

44
[ 1122-12-9 ]
malonic acid diethyl ester ( potassium-compound ) [ No CAS ]
3,4-dibromo-2-oxo-but-3-ene-1,1,4-tricarboxylic acid-1,1-diethyl ester [ No CAS ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 1278

45
[ 1122-12-9 ]
hydrazine hydrate [ No CAS ]
dibromo-maleic acid monohydrazide; hydrazine salt [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1920,vol. 3,p. 506
[2]Helvetica Chimica Acta,1920,vol. 3,p. 506

46
[ 1122-12-9 ]
[ 64-04-0 ]
[ 92751-35-4 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 4585 - 4593

47
[ 1122-12-9 ]
[ 62-53-3 ]
[ 65833-14-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With acetic acid; at 20 - 130℃; for 4.5h;	Reference Example 16 Preparation of N-Phenyldibromomaleimide Aniline (72 muL, 0.788 mmol) was added to a solution of <strong>[1122-12-9]dibromomaleic anhydride</strong> (200 mg, 0.788 mmol) in AcOH (10 mL). The mixture was stirred for 3 h at RT and at 130° C. for 90 mins. After cooling, the mixture was concentrated to dryness and traces of AcOH removed by azeotrope with toluene. The tan residue was purified using silica flash chromatography (5percent EtOAc/95percent petroleum ether) to yield the desired compound as a pale yellow solid (166 mg, 60percent). deltaH (600 MHz, CDCl3) 7.48 (m, 2H, ArH), 7.41 (tt, 1H, J=7.4 and 1.1 Hz, ArH), 7.33 (m, 2H, ArH); deltaC (150 MHz, CDCl3) 163.0, 131.0, 130.0, 129.5, 128.8, 126.2.
57%	With acetic acid; In acetic acid; at 20 - 130℃; for 4.5h;	N-phenyl-dibromomaleimide (2)::-o<strong>[1122-12-9]2,3-dibromo-maleic anhydride</strong> 1 (0.50 g, 1.97 mmol) was dissolved in AcOH (25 mL) and aniline (0.180 mL, 1.97 mmol) was added. The mixture was stirred at room temperature for 3 h and then at 130 °C for 90 mm. Then the mixture was concentrated to dryness and traces of AcOH were removed by repetitive addition and concentration of toluene. The crude residue was purified by flash chromatography to give the title compound as a pale yellow solid (0.37 g, 1.12 mmol, 57percent).Rf 0.35 (10percent EtOAc/petroleum ether); m.p. 136-138°C; Vmax (cm?) 3058, 1727, 1715,1646, 1610, 1598, 1501, 1382, 1265, 1113;oeH(CDC13,500IVIHz)7.48-747(2H,m,An]), 7.44-7.40 (1H, m, An]), 7. 33 (2H, d, J= 7.2 Hz, An]); oec (CDC13, 150 MHz)163.0, 132.8, 130.8, 129.5, 128.8, 126.2; HR11S (El) calculated for C10H5O2NBr2328.86816, observed 328.86854.

Reference： [1]Tetrahedron,2005,vol. 61,p. 4585 - 4593
[2]Patent: US9295729,2016,B2 .Location in patent: Page/Page column 58
[3]Chemical Communications,2013,vol. 49,p. 8187 - 8189
[4]Patent: WO2013/121175,2013,A1 .Location in patent: Page/Page column 37
[5]Chemical Communications,2014,vol. 50,p. 7139 - 7142

48
[ 1122-12-9 ]
[ 100-46-9 ]
[ 91026-00-5 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 4585 - 4593
[2]Tetrahedron,2008,vol. 64,p. 4347 - 4353
[3]Journal of Materials Chemistry B,2015,vol. 3,p. 3195 - 3200

49
[ 1122-12-9 ]
fluoresceinamine [ No CAS ]
N-fluoresceindibromomaleimide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 1960 - 1965

50
(3aSR,4SR,9bSR)-4-(2'-furyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline [ No CAS ]
[ 1122-12-9 ]
(3aSR,9aRS,10SR,11SR,13aSR,13bSR,13cSR)-9a,10-dibromo-11,13a-epoxy-9-oxo-1,2,9,9a,10,11,13b,13c-octahydro-3aH-furo[3,2-c]isoindolo[2,1-a]quinoline-10-carboxylic acid [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2010,vol. 46,p. 1192 - 1206

51
[ 1122-12-9 ]
[ 100-01-6 ]
[ 65833-16-1 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 3122 - 3130
[2]European Journal of Organic Chemistry,2013,p. 1041 - 1045

52
(2-methyl-5-phenylthiophen-3-yl)boronic acid [ No CAS ]
[ 1122-12-9 ]
[ 1345041-61-3 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 10954 - 10956

53
[ 1122-12-9 ]
[ 255042-71-8 ]
[ 1353567-37-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 1847 - 1852

54
[ 62281-07-6 ]
[ 1122-12-9 ]
[ 1301741-17-2 ]

Reference： [1]Macromolecules,2011,vol. 44,p. 4213 - 4221

55
[ 1122-12-9 ]
[ 124-22-1 ]
3,4-dibromo-1-dodecylpyrrole-2,5-dione [ No CAS ]

Reference： [1]Macromolecules,2011,vol. 44,p. 4213 - 4221

56
[ 1122-12-9 ]
[ 4439-56-9 ]
7,7a-dibromo-1-oxo-2-phenyl-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carboxylic acid [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2012,vol. 48,p. 505 - 513
Khimiya Geterotsiklicheskikh Soedinenii,2012,vol. 48,p. 538 - 548,11

57
[ 1122-12-9 ]
[ 95-76-1 ]
[ 1417162-43-6 ]

Yield	Reaction Conditions	Operation in experiment
1.3 g	With acetic acid; at 120 - 130℃; for 3h;	Maleic anhydride (2.0 g, 20 mmol), aluminum(III) chloride (68 mg, 0.51 mmol) and bromine (2.1 mL, 41 mmol) were placed in a sealed reaction vessel and heated to 120 °C for 16 h. After cooling to RT, the reaction was diluted with EtOAc (30 mL) and filtered. The filtrate was then concentrated in vacuo to yield the crude product, <strong>[1122-12-9]3,4-dibromofuran-2,5-dione</strong>, as an orange solid which was used in the next step without further purification. The 3,4-dibromofuran-2,5- dione (1.0 g, 3.9 mmol) was placed in a round-bottomed flask and dissolved in glacial acetic acid (10 mL) at RT. 3.4-Dichloroaniline (0.70 g, 4.3 mmol) was added at RT and then the reaction was heated at reflux for 3 h (120 - 130 °C). The reaction was then cooled to RT and volatiles were removed in vacuo. The crude product was recrystallized from MeOH to yield the title compound as a reddish-brown solid (1.3 g, 80percent). 1H-NMR (400 MHz, DMSO-d6): delta 7.80 (d, J = 8.6 Hz, 1H), 7.69 (d, J = 1.6 Hz, 1H), 7.42 (dd, J = 1.8 Hz, 6.8 Hz, 1H). 13C- NMR (100 MHz, DMSO-d6): delta 162.9, 131.3, 131.2, 131.1 , 129.9, 128.7, 127.3.

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 254 - 263
[2]Patent: WO2014/85545,2014,A1 .Location in patent: Page/Page column 59

58
[ 1122-12-9 ]
[ 2687-43-6 ]
[ 1426960-57-7 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 1041 - 1045

59
(2SR,4SR)-2-(2'-furyl)-4-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
[ 1122-12-9 ]
6,6a,9,10,10a,11-hexahydro-5-(N-pyrrolidine-2-one)-10,10a-dibromo-11-oxo-5H-6b,9-epoxyisoindolo[2,1-a]quinoline-10-carboxylic acid [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2013,vol. 50,p. E18-E38

60
[ 1122-12-9 ]
[ 106792-38-5 ]
4-bromo-2,5-dihydro-3-(5-tert-butyldimethylsilyloxy-1H-indol-3-yl)-1H-pyrrole-2,5-dione [ No CAS ]