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D34108

Sigma-Aldrich

Dibenzylamine

97%

Synonym(s):

(N-Benzylaminomethyl)benzene, Bibenzylamine, DBA, Dibenzylamine (8CI), N,N-Dibenzylamine, N-(Phenylmethyl)benzenemethanamine, N-Benzyl-1-phenylmethanamine, N-Benzylbenzylamine

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About This Item

Linear Formula:
(C6H5CH2)2NH
CAS Number:
103-49-1
Molecular Weight:
197.28
Beilstein/REAXYS Number:
909664
EC Number:
203-117-7
MDL number:
MFCD00004770
UNSPSC Code:
12352100
PubChem Substance ID:
24893752
NACRES:
NA.22

Quality Level

200

assay

97%

form

liquid

refractive index

n20/D 1.574 (lit.)

bp

300 °C (lit.)

mp

−26 °C (lit.)

density

1.026 g/mL at 25 °C (lit.)

SMILES string

C(NCc1ccccc1)c2ccccc2

InChI

1S/C14H15N/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2

InChI key

BWLUMTFWVZZZND-UHFFFAOYSA-N

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General description

Dibenzylamine is mainly used in the production of rubber accelerators, which play a key role in the vulcanization process. It is used as a precursor in the nitrosative cleavage of tertiary amines, aiding in various chemical reactions. It also serves as an intermediate in the synthesis of palladium complexes.

Application


  • Environmental monitoring in shale gas wastewater: Dibenzylamine was identified among the hazardous substances in shale gas wastewater, with research characterizing its concentration and distribution in the Upper Yangtze River, contributing to improved environmental management practices (Tang et al., 2024).

  • Advancements in organic synthesis: Dibenzylamine was used in a novel synthetic strategy for (L)-Monomethyl Tyrosine via bulky ′forced-traceless′ regioselective Pd-catalyzed C(sp(2))-H activation, showcasing its utility in pharmaceutical compound development (Illuminati et al., 2023).

  • Application in crystallography: The crystal structure of di-benzyl-ammonium was elucidated, providing insights into molecular interactions and potential applications in material science and drug design (Traoré et al., 2023).

  • Utilization in green chemistry: Dibenzylamine facilitated a green approach towards Triazole forming reactions, aiming to develop anticancer drugs by minimizing environmental impact and enhancing reaction efficiency (Rastogi et al., 2023).


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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1C

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

289.4 °F - closed cup

flash_point_c

143 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR6283
MKBV9999V
MKBK8317V
MKBG7546V
MKBF0522V

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Palladium-Assisted Formation of Carbon- Carbon Bonds. 8.1 Synthesis and Reactivity toward Internal Alkynes, Carbon Monoxide, and Isocyanides of Orthopalladated Dibenzylamine Complexes
Vicente et al.
Organometallics, 18, 2683-2693 (1999)
Thermal decomposition of the rubber vulcanization agent, zinc dibenzyldithiocarbamate, and its potential role in nitrosamine formation in hams processed in elastic nettings
Helmick et al.
Journal of Agricultural and Food Chemistry, 42, 2541-2544 (1994)
Jong M Rho et al.
Epilepsia, 43(4), 358-361 (2002-04-16)
To investigate whether ketone bodies are directly anticonvulsant. We tested the effects of acetoacetate (ACA), acetone, and both stereoisomers, D-(-)- and L-(+), of beta-hydroxybutyrate (BHB) on sensory-evoked seizures in Frings audiogenic seizure-susceptible mice. We found that these ketone bodies, with
M Manoach et al.
Heart and vessels, 2(1), 36-40 (1986-01-01)
In previous studies, we showed that dibenzepin HCl (D) and other tricyclic antidepressants (TCAD), given either before or during occlusion of the left anterior descending artery (LAD), decreased the incidence of ventricular fibrillation (VF) following occlusion and reperfusion. Moreover, once
B Doepner et al.
Naunyn-Schmiedeberg's archives of pharmacology, 364(1), 9-13 (2001-08-04)
Ventricular myocytes of the mouse ventricle were voltage clamped with a patch-clamp technique in the whole-cell configuration. At depolarizing voltage pulses, these myocytes develop a large voltage-dependent K+ outward current. Application of the drug dibenzylamine (DBA) to the bath solution
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