Imines & Amidines

Imine and Amidine Intermediates for Biologically Active Nitrogen Heterocycle Synthesis

What is an imine?

An Imine is a compound or functional group with a nitrogen double bond and often an alkyl or aryl functional group or hydrogen. Imine formation results from the reaction of an aldehyde or ketone with a primary amine.

Imines and their derivatives (e.g., Schiff bases) are recognized as key intermediates for the synthesis of nitrogen heterocycles, especially biologically active nitrogen heterocycles such as those involved in alkaloid synthesis. Imines have combined reactivity modes as both electrophiles and nucleophiles and participate in reactions analogous to those of aldehydes and ketones. Imines can undergo hydrolysis to their corresponding amines and carbonyl compounds.

Amidines are dinitrogen analogs of carboxylic acids and esters. They display basicity and biological activity and are used as intermediates in the synthesis of some metallocyclic and heterocyclic complexes. They combine the properties of an azomethine-like C-N double bond with an amide-like C-N single bond having some partial double bond character. Amidines as strong Lewis bases react with boron trihalides to form amidine-mixed boron trihalide adducts.

Use the product table below to browse imines and amidines by product number, chemical structure, molecular formula, purity, price, package size, and availability.

What is a Schiff base reaction?
Schiff bases are aldehyde- or ketone-like compounds that have a nitrogen double bond rather than an oxygen double bond. In a Schiff base reaction, a compound′s oxygen bonds are swapped for nitrogen, making it a Schiff base. These bases are named after Hugo Schiff, who discovered them and developed the Schiff test, a chemical test to detect organic aldehydes. Not all imines are Schiff bases.

Is imine formation reversible?
Yes, imine bonds are formed through an acid-catalyzed hydrolysis reaction that is reversible. This reaction yields an aldehyde or ketone.

Related Resources
Organic building blocks
Schiff reagents for tissue staining

Product #

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Description

Molecular Formula

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F15803 Formamidine acetate salt 99% CH4N2 · C2H4O2
268607 Formamidine hydrochloride 97% CH4N2 · HCl
140198 Formamidoxime 99% CH4N2O
CDS003733 Trifluoroacetamidine AldrichCPR C2H3F3N2
591475 Chloroacetamidine hydrochloride 97% C2H6Cl2N2
159158 Acetamidine hydrochloride 95% C2H6N2 · HCl
17259 2-Aminoacetamidine dihydrobromide ≥80.0% (CE) C2H7N3 · 2HBr
162876 Dichloromethylene-dimethyliminium chloride technical grade C3H6Cl3N
411531 (Bromomethylene)dimethyliminium bromide 95% C3H7Br2N
176516 Malonamamidine hydrochloride 98% C3H7N3O · HCl
483893 N,N-Dimethylmethyleneiminium chloride technical grade, 90% C3H8ClN
214914 N,N-Dimethylmethyleneiminium iodide 98% C3H8IN
CBR01339 Propanimidamide hydrochloride AldrichCPR C3H9ClN2
CDS003615 propionamidine hydrochloride AldrichCPR C3H9ClN2
735647 Cyclopropaneamidine hydrochloride 97% C4H8N2 · HCl
391875 (Dimethylaminomethylene)dimethylammonium chloride 97% C5H13ClN2
289078 Gold’s Reagent 95% C6H16ClN3
CDS005160 3,5-difluoro-benzamidine hydrochloride AldrichCPR C7H7ClF2N2
139327 3-Nitrobenzamidine hydrochloride 95% C7H7N3O2 · HCl
CDS004472 4-fluoro-benzamidine hydrochloride AldrichCPR C7H8ClFN2
CDS005174 3-chlor-benzamidine hydrochloride AldrichCPR C7H8Cl2N2
12072 Benzamidine ≥95.0% C7H8N2
CDS001188 Benzamidoxime AldrichCPR C7H8N2O
857734 3-Aminobenzamidine dihydrochloride 96% C7H9N3 · 2HCl
857661 4-Aminobenzamidine dihydrochloride 98% C7H9N3 · 2HCl
299065 N′-tert-Butyl-N,N-dimethylformamidine 97% C7H16N2
A7300 N-Acetylbenzoquinoneimine C8H7NO2
B24154 N-Benzylidenemethylamine 97% C8H9N
CDS015050 3-fluoro-4-methylbenzamidine hydrochloride AldrichCPR C8H10ClFN2
733571 3-Methoxybenzamidoxime 97% C8H10N2O2
CDS001308 2-(Phenylsulfinyl)acetamidoxime AldrichCPR C8H10N2O2S
CDS008540 2-methyl-benzamidine hydrochloride AldrichCPR C8H11ClN2
CDS004524 4-methylbenzamidine hydrochloride AldrichCPR C8H11ClN2
CDS006449 4-anisamidine hydrochloride AldrichCPR C8H11ClN2O
CDS000528 N-Hydroxyoctanamide AldrichCPR C8H17NO2
CDS016420 2-([imino(phenyl)methyl]amino)acetic acid AldrichCPR C9H10N2O2
420182 N,N′-(2,5-Dimethyl-2,5-cyclohexadiene-1,4-diylidene)biscyanamide 98% C10H8N4
704644 N-(Trimethylsilyl)-4-chlorobenzaldimine 95% C10H14ClNSi
699322 N-Trimethylsilylbenzaldimine 95% C10H15NSi
469637 N-Benzylidene-tert-butylamine 98% C11H15N
CDS002865 Adamantane-1-carboxamidine hydrochloride AldrichCPR C11H19ClN2
119814 Sodium 2,6-dichloroindophenolate hydrate ACS reagent C12H6Cl2NNaO2 · xH2O
CDS016609 4-amino-2-methyl-10h-thieno(2,3-b)(1,5)-benzodiazepine AldrichCPR C12H11N3S
CDS017493 (3-allyl-2-imino-2,3-dihydro-benzoimidazol-1-yl)-acetic acid AldrichCPR C12H13N3O2
713376 tert-Butyl (phenylmethylene)carbamate ≥98.0% C12H15NO2
645117 N-(2-Chlorobenzylidene)-4-fluoroaniline 97% C13H9ClFN
645133 N-(4-Fluorobenzylidene)-4-fluoroaniline 97% C13H9F2N
689971 N-Phenylbenzimidoyl chloride 95% C13H10ClN
565504 Salicylideneaniline 97% C13H11NO
159646 N,N′-Diphenylformamidine 98% C13H12N2
725951 N-Boc-4-methoxybenzylideneamine 97% C13H17NO3
730386 N-(4-Bromobenzylidene)-p-toluenesulfonamide 97% C14H12BrNO2S
645109 N-(4-Methoxybenzylidene)-4-fluoroaniline 97% C14H12FNO
690570 Phenyl-(1-phenylethylidene)amine ≥98.0% C14H13N
680362 N-(4-Methoxybenzylidene)aniline 97% C14H13NO
711802 (E)-N-Benzylidene-4-methylbenzensulfonamide 99% C14H13NO2S
730394 N-Benzylidene-p-toluenesulfonamide 97% C14H13NO2S
CDS004126 N-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)alanine AldrichCPR C14H18N2O2
637599 N-(3,4-Methylenedioxybenzylidene)benzylamine C15H13NO2
649007 3,4-Dimethyl-N-(4-fluorobenzylidene)aniline 97% C15H14FN
902837 4-Methoxy-N-(1-phenylethylidene)benzenamine C15H15NO
645826 N-(4-Methoxybenzylidene)-4-methoxyaniline 97% C15H15NO2
712434 N-(4-Methoxybenzylidene)-4-methylbenzenesulfonamide 97% C15H15NO3S
648965 4-Acetyl-N-(4-methoxybenzylidene)aniline 97% C16H15NO2
236071 N,N′-Bis(salicylidene)ethylenediamine 98% C16H16N2O2
250929 N,N′-Bis(salicylidene)-1,3-propanediamine 99% C17H18N2O2
649015 N,N′-Terephthalylidene-bis(4-fluoroaniline) 97% C20H14F2N2
78166 N-(4-Phenylbenzylidene)benzylamine ≥98.0% (GC) C20H17N
649023 N,N′-Terephthalylidene-bis(4-methoxyaniline) 97% C22H20N2O2
690503 2,3-Bis(2,6-diisopropylphenylimino)butane 98% C28H40N2
CDS000290 Riboflavine tetrabutyrate AldrichCPR C33H44N4O10
779040 (S,S)-N,N′-Bis[2-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine ≥95% (H-NMR) C44H40N2P2