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(4-BROMOBENZYL)METHYLAMINE

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Products Intro: Product Name:(4-BROMOBENZYL)METHYLAMINE
CAS:699-03-6
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Products Intro: Product Name:N-Methyl-4-bromobenzylamine
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CAS:699-03-6
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(4-BROMOBENZYL)METHYLAMINE manufacturers

(4-BROMOBENZYL)METHYLAMINE Basic information
Product Name:(4-BROMOBENZYL)METHYLAMINE
Synonyms:4-BROMO-N-METHYLBENZYLAMINE;(4-BROMOBENZYL)METHYLAMINE;(4-Bromobenzyl)methylamine95%;N-Methyl-4-bromobenzylamine;874-73-7 (Hydrochloride);Aids107181;Aids-107181;Benzenemethanamine, 4-bromo-N-methyl-
CAS:699-03-6
MF:C8H10BrN
MW:200.08
EINECS:
Product Categories:amine| alkyl bromide;Amines and Anilines
Mol File:699-03-6.mol
(4-BROMOBENZYL)METHYLAMINE Structure
(4-BROMOBENZYL)METHYLAMINE Chemical Properties
Boiling point 218-219 °C(lit.)
density 1.00 g/mL at 25 °C(lit.)
refractive index n20/D 1.5650(lit.)
Fp >230 °F
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka9.52±0.10(Predicted)
AppearanceColorless to light yellow Liquid
Sensitive Air Sensitive
InChIKeyURFJXIULELMVHV-UHFFFAOYSA-N
CAS DataBase Reference699-03-6
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 36
WGK Germany 2
MSDS Information
ProviderLanguage
SigmaAldrich English
(4-BROMOBENZYL)METHYLAMINE Usage And Synthesis
Synthesis
4-Bromobenzaldehyde

1122-91-4

Methylamine

74-89-5

(4-BROMOBENZYL)METHYLAMINE

699-03-6

General procedure for the synthesis of N-methyl-4-bromobenzylamine: In an autoclave, 4-bromobenzaldehyde (2.08 g, 11.55 mmol) was mixed with a methanolic solution of 2 M methylamine (25 mL, 33.44 mmol) and the reaction was stirred at 65 °C for 4 hours. After completion of the reaction, cooled to room temperature, sodium borohydride (633 mg, 16.72 mmol) was added in batches. Stirring was continued for 30 minutes at room temperature, followed by vacuum concentration. The residue was dissolved in ethyl acetate (30 mL) and the organic layer was washed with saturated aqueous sodium bicarbonate. The aqueous phase was adjusted to pH 13 with a few drops of 1 N sodium hydroxide solution and then extracted twice with ethyl acetate. The organic extracts were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give N-methyl-4-bromobenzylamine as a colorless oil (2.04 g, 91% yield), which was used directly in the next step of the reaction.LC-MS analysis (Analytical Condition A, Zorbax SB-AQ columns, Acidic conditions): retention time t R = 0.61 min; [M + H]+ = 241.06 (acetonitrile adduct).

References[1] Patent: WO2010/58353, 2010, A1. Location in patent: Page/Page column 77-78
[2] Patent: US2011/224210, 2011, A1. Location in patent: Page/Page column 54
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 78, # 1-4, p. 141 - 152
[4] Organic Letters, 2014, vol. 16, # 2, p. 358 - 361
Tag:(4-BROMOBENZYL)METHYLAMINE(699-03-6) Related Product Information
STATIL 3,4,5,6-TETRABROMOPHTHALIMIDE 4-Bromo-3,5-dihydroxy-N-methylbenzamide (3-BROMOBENZYL)METHYLAMINE,(3-Bromobenzyl)methylamine95% (4-BROMOBENZYL)DIMETHYLAMINE Halofuginone Lactate (2-Bromobenzyl)methylamine95%,(2-BROMOBENZYL)METHYLAMINE 4-Bromobenzylamine 4-bromo-N-(4-methylphenyl)benzamide 4-BROMO-N,N-DIISOPROPYLBENZYLAMINE, 95 N-(4-BROMO-2-METHOXYBENZYL)-4-(TRIFLUOROMETHOXY)ANILINE 4,5,6,7-TETRABROMO-2-(OXIRAN-2-YLMETHYL)ISOINDOLINE-1,3-DIONE N-(4-BROMO-2-METHOXYBENZYL)-5-FLUORO-2-METHYLANILINE 2-(4-BROMOPHENYL)-5,5-DIMETHYL-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID 5-ACETYL-3-(4-BROMOBENZYL)-1-(4-CHLOROPHENYL)-2,4(1H,3H)-PYRIMIDINEDIONE TIMTEC-BB SBB006035 N,N'-(methylenedi-p-phenylene)bis[3,4,5,6,-tetrabromophthalimide] N-(2,3-DIMETHYL-5-OXO-1-PHENYL(3-PYRAZOLIN-4-YL))(3,4,5-TRIBROMOPHENYL)FORMAMIDE

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