4-(1,3-Dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)-N,N-dimethylaniline TCI D5944

Chemical Identity

Other names: N-DMBI · 4-(2,3-Dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine · 1,3-Dimethyl-2-(4-dimethylaminophenyl)benzimidazolidine · 4-(1,3-Dimethyl-2,3-dihydro-1H-benzoimidazol-2-yl)phenyldime
CAS No.: 302818-73-1
PubChem: CID 759333·SID 468591657
Formula: C17H21N3
Molecular weight: 267.38 g/mol
Purity: >95.0%(T)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 4-(1,3-dimethyl-2H-benzimidazol-2-yl)-N,N-dimethylaniline
SMILES: CN1C(N(C2=CC=CC=C21)C)C3=CC=C(C=C3)N(C)C
InChIKey: AKIIMLCQTGCWQQ-UHFFFAOYSA-N
MDL: MDL00222361

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TCI D5944, 4-(1,3-Dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)-N,N-dimethylaniline, is a benzimidazoline compound — the reduced form of the benzimidazole core carrying an aryl group at the two position and two methyl groups on both nitrogen atoms. In this particular variant, the aryl group is a highly electron-rich N,N-dimethylaniline ring. Compounds of this class are known in the laboratory as organic reducing agents, specifically as hydride donors and electron donors that operate without involving any metal. Their function is to deliver a hydride or an electron to a substrate or to a catalyst, after which they convert into a benzimidazolium cation that is stabilised by the rearomatisation of the heterocyclic core.

The property that makes this material attractive is its combination of substantial reducing power with retained controllability. Release of the hydride from the two position is thermodynamically driven by the recovery of aromaticity in the benzimidazole ring, so the reaction proceeds with a strong driving force. The presence of the dimethylamino group on the aryl ring contributes additional electron density and stabilises the positive charge in the oxidised state, which makes this compound a stronger donor than the corresponding phenyl-substituted benzimidazoline. This tunability through aryl substitution is precisely what allows researchers to select a donor matched to the demands of a given transformation.

In Indonesian laboratories, this reagent is typically encountered in university research groups, institutional chemistry laboratories, and industrial R&D units working on synthetic methodology, organocatalysis, and photoredox chemistry. It is generally purchased in small research quantities rather than in bulk, since a single reaction usually consumes only a modest amount. Because it is supplied as a catalogue research chemical, it is commonly ordered alongside other TCI synthetic reagents for method development work rather than for routine analytical testing.

Related TCI products

Metal-free reduction of organic substrates, where the compound serves as a hydride source that avoids introducing metal residues into the product, simplifying purification for sensitive synthetic targets.
Organocatalytic transformations requiring a stoichiometric reductant, where the benzimidazoline delivers hydride to the catalytic cycle and turns over into a stable benzimidazolium cation without side reactions.
Photoredox and single-electron transfer chemistry, where the electron-rich dimethylamino-substituted ring makes this reagent a strong electron donor suitable for generating radical intermediates under mild conditions.
Synthetic methodology development, in which researchers compare donor strength across a series of substituted benzimidazolines to calibrate the reducing power needed for a particular bond-forming reaction.
Mechanistic and physical organic studies, where the well-defined rearomatisation driving force of hydride release makes the compound a useful probe for examining hydride and electron transfer pathways.

Brand	TCI (Tokyo Chemical Industry)
CAS number	302818-73-1
Molecular formula	—
Purity	—
Category	TCI
Pack sizes	available in research-scale catalogue pack sizes; please confirm the current packing option when ordering
Physical form	—
Storage	store according to the manufacturer's stated conditions on the product label and safety data sheet

Chemical class: 2-aryl-1,3-dimethylbenzimidazoline; organic hydride and electron donor

Store this reagent in its original tightly closed container in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and any oxidising agents, since benzimidazolines are electron-rich species that can be sensitive to oxidation. Amber glass or the manufacturer's supplied packaging is appropriate, and containers should be resealed promptly after each use to limit exposure to air and moisture. Handle in a fume hood using a laboratory coat, chemical-resistant gloves, and safety glasses. Weigh and transfer with clean, dry spatulas to avoid contamination. Always consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials through the laboratory's approved chemical waste route in accordance with applicable regulations.

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