4-Bromo-2,6-dimethylbenzenamine
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4-Bromo-2,6-dimethylbenzenamine
structure -
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CAS No:
24596-19-8
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Formula:
C8H10BrN
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Chemical Name:
4-Bromo-2,6-dimethylbenzenamine
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Synonyms:
Benzenamine,4-bromo-2,6-dimethyl-;2,6-Xylidine,4-bromo-;4-Bromo-2,6-dimethylbenzenamine;4-Bromo-2,6-dimethylaniline;2,6-Dimethyl-4-bromoaniline;4-Bromo-2,6-xylidine;NSC 227944;4-Bromo-2,6-dimethylphenylamine
- Categories:
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CAS No:
4-Bromo-2,6-dimethylbenzenamine Basic Attributes
200.08
200.08
1936300
246-337-9
227944
DTXSID40179345
2921430090
Characteristics
26
2.7
Clear yellow to orange to amber Liquid
1.4±0.1 g/cm3
47 °C
120 °C @ Press: 0.22 Torr
>230 °F
1.597
0.0134mmHg at 25°C
Safety Information
6.1
UN2811/6.1/III
3
38-43-36/37/38-20/21/22
36/37-36/37/39-26
Xi,Xn
Harmful
P261-P342 + P311
H315-H334
|Danger|H302 (16.67%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P285, P301+P312, P302+P352, P304+P312, P304+P340, P304+P341, P305+P351+P338, P312, P314, P321, P322, P330, P332+P313, P337+P313, P342+P311, P362, P363, and P501|Aggregated GHS information provided by 48 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-Bromo-2,6-dimethylbenzenamine Use and Manufacturing
General procedure: 1-Methoxy-3, 5-dimethylbenzene(100mg, 0.73 mmol), N-Bromosuccinimide (NBS, 260 mg, 1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reaction was monitored by TLC/General procedure: 1-Methoxy-3, 5-dimethylbenzene (100mg, 0.73 mmol), N-Bromosuccinimide (NBS, 260 mg, 1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reactionwas monitored by TLC/21.3 ml (66.1 g, 0.413 mol) of bromine were added dropwise, while vigorously stirring, over ca. 20 minutes to a solution of 50.0 g (0.413 mol) of 2, 6-dimethylanilme in 1200 cm4-Bromo-2, 6-dimethylaniline 2) 250 g of 2, 6-dimethylaniline (5) and3L N, N- dimethylformamide solution was added to 5L three reaction flask, 1 L of 246 g N-bromosuccinimide was slowly added dropwise at about 0 ° CN, N-dimethylformamide, and the mixture was stirred at room temperature for 2 hours.The reaction mixture was introduced into 30 L of water, extracted with 3 L of ethyl acetate twice, The organic phase was washed with 2 L saturated brine, dried over anhydrous sodium sulfate, filtered, Dried to afford 350 g of 2, 6-dimethyl-4-bromoaniline (6) as a yellow solid.350 g of product (6), 268 g of potassium acetate, 364 g of bis (pinacolato) diboron, 50 g of [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloride and 4L of 1, 4-bis Oxygen ring, 400mL water was added 5L three-necked flask, nitrogen protection, heating to 80 ° C continued stirring 15h. After the temperature was lowered to room temperature, the mixture was filtered and spin-dried to obtain 414 g of a brown solid borate (7); 332 g of the product (6), 414 g of the product (7), 667 g of cesium carbonate and 50 g of [1, 1'- Yl) ferrocene] palladium dichloride, 4L 1, 4-dioxane was added to a 5L three-necked flask and heated to 75 ° C under a nitrogen atmosphere for 16 hours. After the temperature was lowered to room temperature, it was filtered and the filtrate was washed with 2 L of water, dried over anhydrous sodium sulfate, filtered and spun dry. Recrystallization from 2 L ethyl acetate: petroleum ether = 1: 4 (volume ratio) solution gave the 210 g white crystals of 2, 2 ', 6, 6'-tetramethylbiphenylenediamine (8).General procedure: A reaction tube was charged with the 2-aryloxypropanamide (1.0 mmol), potassium hydroxide (112 mg, 2.0 mmol), DMSO (3 mL) and 1, 3-Dimethyl-3, 4, 5, 6-tetrahydro-2(1H)-pyrimidinone (DMPU 1 mL).The mixture was heated at 140 C for 3-16 h. The reaction was monitored by TLC. After the reaction period, the reaction mixture was cooled, diluted with saturated brine and extracted with dichloromethane
Computed Properties
Molecular Weight:200.08
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:198.99966
Monoisotopic Mass:198.99966
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:104
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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