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(2-Bromobenzyl)methylamine

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(2-Bromobenzyl)methylamine Basic information
Product Name:(2-Bromobenzyl)methylamine
Synonyms:(2-Bromobenzyl)methylamine95%;N-Methyl-2-bromobenzylamine;2-Bromo-N-methyl-Benzenemethanamine;(2-BROMOBENZYL)METHY;2-Bromo-N-methylbenzylamine 97%;Benzenemethanamine, 2-bromo-N-methyl-;SKL295;2-Bromo-N-methylbenzylamine
CAS:698-19-1
MF:C8H10BrN
MW:200.08
EINECS:
Product Categories:Polyamines
Mol File:698-19-1.mol
(2-Bromobenzyl)methylamine Structure
(2-Bromobenzyl)methylamine Chemical Properties
Boiling point 71-74 °C2 mm Hg(lit.)
density 1.358 g/mL at 25 °C(lit.)
refractive index n20/D 1.5670(lit.)
Fp 220 °F
storage temp. Keep in dark place,Inert atmosphere,Room temperature
form Viscous Liquid
pka9.14±0.10(Predicted)
AppearanceColorless to light yellow Liquid
Sensitive Air Sensitive
InChI1S/C8H10BrN/c1-10-6-7-4-2-3-5-8(7)9/h2-5,10H,6H2,1H3
InChIKeyTUADRPBKJHMHDH-UHFFFAOYSA-N
SMILESCNCc1ccccc1Br
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 36
WGK Germany 2
HazardClass 8
Storage Class10 - Combustible liquids
Hazard ClassificationsAcute Tox. 4 Oral
Aquatic Chronic 3
MSDS Information
ProviderLanguage
SigmaAldrich English
(2-Bromobenzyl)methylamine Usage And Synthesis
Synthesis
2-Bromobenzaldehyde

6630-33-7

(2-BROMOBENZYL)METHYLAMINE

698-19-1

Preparation of Example (Compound 22a): 29.4 g of o-bromobenzaldehyde and 81 mL of 40% aqueous methylamine were mixed with 238 mL of tetrahydrofuran (THF). At room temperature, 19 g of sodium borohydride (NaBH4) was added in batches over 25 minutes. The reaction mixture was stirred overnight at room temperature and then concentrated using a rotary evaporator. The residue was stirred into ice water and the aqueous phase was extracted twice with ether. The combined ether phases were concentrated by evaporation under reduced pressure. The product was purified by silica gel column chromatography using ethyl acetate or ethyl acetate/methanol (4:1) as eluent to give 18.5 g of N-methyl-2-bromobenzylamine (22a) in yellow liquid form. Yield: 58%.

References[1] Patent: US6232468, 2001, B1
[2] Tetrahedron, 2003, vol. 59, # 40, p. 8049 - 8056
(2-Bromobenzyl)methylamine Preparation Products And Raw materials
Raw materialsMethylamine-->2-Bromobenzylamine-->2-Bromobenzaldehyde-->2-Bromobenzyl bromide-->Sodium borohydride-->Tetrahydrofuran-->Methanol
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