[ CAS No. 77395-10-9 ]

Name: 77395-10-9|5-Bromo-7-methylindoline-2,3-dione|95%
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Product Details of [ 77395-10-9 ]

CAS No. :	77395-10-9	MDL No. :	MFCD00463080
Formula :	C₉H₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NPRAKNSGKOICIE-UHFFFAOYSA-N
M.W :	240.05	Pubchem ID :	542843
Synonyms :

Safety of [ 77395-10-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 77395-10-9 ]

* 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 [ 77395-10-9 ]
Downstream synthetic route of [ 77395-10-9 ]

[ 77395-10-9 ] Synthesis Path-Upstream 1~1

1
[ 77395-10-9 ]
[ 206548-13-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dihydrogen peroxide; sodium chloride; sodium hydroxide In water at 0℃; for 1.5 h;	Step 4: 2-amino-5-bromo-3-methylbenzoic acidA mixture of 5-bromo-7-methylindoline-2,3-dione (8 g, 0.033 mol), sodium chloride (4.5 g, 0.09 mol) and sodium hydroxide (3.6 g, 0.09 mol) was dissolved in water (96 mL) with stirring to give a yellow solution. The reaction mixture was cooled to 0°C and to this mixture was added slowly a solution of 30percent hydrogen peroxide (7 mL) and .sodium hydroxide (6.27 g) in 83 mL of water. The reaction mixture was stirred for another 1.5 h at 0°C and then quenched with glacial acetic acid to give a tan precipitate. The solid was filtered, washed thoroughly with cold water and dried under vacuum to afford the title compound (5.8 g, 75percent).^XH NMR (400 MHz, DMSO-d₆) : δ 7.69 (d, J = 2.4 Hz, 1H), 7.26 (s, 1H), 2.0 (s, 3H); ESI-MS : Calculated mass: 228.97; Observed mass: 228.10 [M-H]\

Reference： [1] Journal of Organic Chemistry, 2006, vol. 71, # 16, p. 5921 - 5929
[2] Patent: WO2014/169167, 2014, A1, . Location in patent: Page/Page column 81; 82

[ 77395-10-9 ] Synthesis Path-Downstream 1~34

1
[ 1127-59-9 ]
[ 77395-10-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With bromine; In chloroform; at 20 - 80℃; for 24.25h;	Step 3: 5-bromo-7-methylindoline-2,3-dioneTo a stirred mixture of 7-methylindoline-2,3-dione (7 g, 0.043 mol) in chloroform (700 mL) was added a solution of bromine (2.8 mL, 0.053 mol) in chloroform (100 mL) dropwise over 15 min at room temperature. The reaction mixture was heated at 80C for 24 h and then cooled to 0C, which resulted in precipitation of the product as a red solid. The solid was collected by suction filtration and dried under vacuum to afford the title compound (8 g, 77%).XH NMR (400 MHz, DMSO-d6) : δ 11.20 (s, 1H), 7.64 (d, J = 1.2 Hz, 1H), 7.42 (d, J = 7.2 Hz, 1H), 2.18 (s, 3H); ESI-MS: Calculated mass: 238.96; Observed mass: 238.30 [M-H]".

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929
[2]Patent: WO2014/169167,2014,A1 .Location in patent: Page/Page column 81
[3]Bulletin de la Societe Chimique de France,1946,p. 586,587
[4]Journal of Medicinal Chemistry,2007,vol. 50,p. 21 - 39

2
hydroxyimino-acetic acid-(4-bromo-2-methyl-anilide) [ No CAS ]
[ 77395-10-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1923,vol. <4>33,p. 639

3
[ 77395-10-9 ]
[ 206548-13-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dihydrogen peroxide; sodium chloride; sodium hydroxide; In water; at 0℃; for 1.5h;	Step 4: 2-amino-5-bromo-3-methylbenzoic acidA mixture of 5-bromo-7-methylindoline-2,3-dione (8 g, 0.033 mol), sodium chloride (4.5 g, 0.09 mol) and sodium hydroxide (3.6 g, 0.09 mol) was dissolved in water (96 mL) with stirring to give a yellow solution. The reaction mixture was cooled to 0C and to this mixture was added slowly a solution of 30% hydrogen peroxide (7 mL) and .sodium hydroxide (6.27 g) in 83 mL of water. The reaction mixture was stirred for another 1.5 h at 0C and then quenched with glacial acetic acid to give a tan precipitate. The solid was filtered, washed thoroughly with cold water and dried under vacuum to afford the title compound (5.8 g, 75%).XH NMR (400 MHz, DMSO-d6) : delta 7.69 (d, J = 2.4 Hz, 1H), 7.26 (s, 1H), 2.0 (s, 3H); ESI-MS : Calculated mass: 228.97; Observed mass: 228.10 [M-H]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929
[2]Patent: WO2014/169167,2014,A1 .Location in patent: Page/Page column 81; 82

4
[ 77395-10-9 ]
[ 39561-82-5 ]
C₁₇H₁₁BrClNO₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 21 - 39

5
2-hydroxyimino-<i>N</i>-<i>o</i>-tolyl-acetamide [ No CAS ]
[ 77395-10-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 21 - 39

6
[ 95-53-4 ]
2.5.6.1¹.3¹-pentabromo-4-acetoxy-1.3-dimethyl-benzene [ No CAS ]
[ 77395-10-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 21 - 39
[2]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929

7
(E)-2-(hydroxyimino)-N-(o-tolyl)acetamide [ No CAS ]
[ 77395-10-9 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929
[2]Patent: WO2014/169167,2014,A1

8
[ 77395-10-9 ]
[ 908597-10-4 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929

9
[ 77395-10-9 ]
[ 908597-09-1 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929

10
[ 77395-10-9 ]
dimethyl 4,4'-dibromo-6,6'-dimethyl[1,1'-biphenyl]-2,2'-dicarboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929
[2]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929

11
[ 77395-10-9 ]
[ 908597-02-4 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5921 - 5929

12
[ 583-75-5 ]
[ 77395-10-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1923,vol. <4>33,p. 639
[2]Patent: WO2017/62581,2017,A1
[3]Tetrahedron,2018,vol. 74,p. 1294 - 1306

13
[ 1189051-96-4 ]
[ 77395-10-9 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 7357 - 7363

14
[ 77395-10-9 ]
[ 68014-21-1 ]
[ 1373943-25-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2512 - 2515

15
[ 95-53-4 ]
[ 77395-10-9 ]

Reference： [1]Patent: WO2014/169167,2014,A1
[2]Patent: WO2022/64454,2022,A1

16
[ 77395-10-9 ]
6-bromo-8-methylquinazoline-2,4( 1H,3H)-dione [ No CAS ]