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ChemicalBook--->CAS DataBase List--->67344-77-8

67344-77-8

67344-77-8 Structure

67344-77-8 Structure
IdentificationBack Directory
[Name]

(3-BROMOBENZYL)METHYLAMINE
[CAS]

67344-77-8
[Synonyms]

67344-77-8
(3-BROMOBENZYL)METHY
3-BROMO-N-METHYLAMINE
(3-BROMOBENZYL)METHYLAMINE
3-BROMO-N-METHYLBENZYLAMINE
N-Methyl-3-bromobenzylamine
(3-Bromobenzyl)methylamine95%
(3-Bromobenzyl)Methylamine 95%
(3-BroMophenyl)-N-MethylMethanaMine
Benzenemethanamine, 3-bromo-N-methyl-
1-(3-BroMophenyl)-N-MethylMethanaMine
N-Methyl-3-bromobenzylamine Hydrochloride
[Molecular Formula]

C8H10BrN
[MDL Number]

MFCD04507522
[MOL File]

67344-77-8.mol
[Molecular Weight]

200.08
Chemical PropertiesBack Directory
[Boiling point ]

231-232 °C(lit.)
[density ]

1.461 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
[form ]

liquid
[pka]

9.32±0.10(Predicted)
[color ]

colourless
[Sensitive ]

Air Sensitive
[InChIKey]

QCEANFBGRBLXHN-UHFFFAOYSA-N
[CAS DataBase Reference]

67344-77-8
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[Safety Statements ]

36
[WGK Germany ]

2
[HS Code ]

2921490060
Hazard InformationBack Directory
[Uses]

(3-Bromobenzyl)methylamine is a useful intermediate used in the preparation of 2,4-diamino-6-(benzylmethylamino)quinazolines with antimalarial and antitumor activities.
[Synthesis]

3-Bromobenzaldehyde

3132-99-8

Methylamine

74-89-5

(3-BROMOBENZYL)METHYLAMINE

67344-77-8

Step B: At room temperature, 3-bromobenzaldehyde (47.5 mL, 0.4 mol) was dissolved in methanol (460 mL), followed by the addition of an aqueous solution of methylamine (35 mL, 0.4 mol, 40 wt% solution). The reaction mixture was cooled to 0 °C and sodium borohydride (22 g, 0.6 mol) was added in batches. The reaction mixture was kept stirred at 0 °C for 3.5 h and then gradually warmed up to room temperature. After completion of the reaction, the mixture was concentrated under reduced pressure and subsequently partitioned with dichloromethane and water. The aqueous layer was separated and washed with dichloromethane (3×). The organic phases were combined and washed sequentially with saturated sodium bicarbonate solution and brine, then dried over anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure to afford the target product N-methyl-3-bromobenzylamine (76 g, 81%) as a clear oil. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.48 (d, J = 1.5 Hz, 1H), 7.40-7.37 (m, 1H), 7.24-7.16 (m, 2H), 3.73 (s, 2H), 2.45 (s, 3H).

[References]

[1] Patent: US2007/21408, 2007, A1. Location in patent: Page/Page column 94; 103
[2] Journal of Medicinal Chemistry, 1981, vol. 24, # 2, p. 140 - 145
[3] Patent: WO2009/149258, 2009, A2. Location in patent: Page/Page column 21; 48
[4] Patent: US2014/275101, 2014, A1. Location in patent: Paragraph 0072; 0145; 0146
[5] Patent: WO2015/127559, 2015, A1. Location in patent: Page/Page column 55; 56
Spectrum DetailBack Directory
[Spectrum Detail]

(3-BROMOBENZYL)METHYLAMINE(67344-77-8)1HNMR
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10269-01-9 39959-54-1 611-75-6 87-10-5 131707-23-8 90151-50-1

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