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4-Dimethylaminopyridine suppliers in China
Cas No: 1122-58-3
No Data 1 Kilogram 1-1000 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
1122-58-3 4-Dimethylaminopyridine
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4-Dimethylaminopyridine
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1122-58-3 Usage

Uses

In a wide variety of organic syntheses as a catalyst.

Reactions

DMAP reacts readily with electrophilic reagents. It is possible to quaternize DMAP in high yield with either methyl iodide or ethyl bromide, decomposes quantitatively in the presence of aqueous alkali to N-methy1-4-pyridone[17]. Addition of DMAP to S, S'-diethyl-S, S'-dimethyl-S, S-1, 2vinylenedisulfonium salts results in the smooth formation of the salt with concomitant generation of ethyl methyl sulfide[19]. Reaction of DMAP with acetylenedicarboxylic acid leads spontaneously to the bis-adduct in high yields[20]. On reaction with perbenzoic acid the strongly polar N-oxide is formed. Nitration of DMAP with HNO3/H2SO4 gives the 3-nitro derivatives in 81 % yield and, under forcing condition; the 3,5-dinitro compounds are obtained[16]. Reaction with O-(p-toluenesulfony1)hydroxylamine affords the N-amino compound in 67% yield which is isolated as the perchlorate. By treatment with D2O it is possible to selectively exchange the a-protons in DMAP, with DClO4 to exchange the P-protons to furnish and with D2O/NaOD to replace all aromatic protons by deuterium[18].

Chemical Properties

White solid

Chemical Properties

DMAP (m.p. 112-113°C) and PPY (m.p. 57-58°C)[4] are colorless, crystalline substances which are very soluble in methanol, ethyl acetate, chloroform, methylene chloride, 1,2-dichloroethane, acetone, and acetic acid and less soluble in cold hexane, cyclohexane, and water. DMAP can be recrystallized from ethyl acetate and PPY from pentane or hexane. The basicities of DMAP[5] and PPY in water as well as the dipole moment of DMAP[7-9] in benzene and dioxane have been determined by several groups. Of especial interest are the thermodynamic investigations concerned with the protonation of DMAP in water[11] and calculations whereby the influence of substituents on the basicity has been determined[6, 9, 10].

Uses

A highly efficient catalyst for acylation reactions.

Uses

4-Dimethylaminopyridine is a versatile hypernucleophilic acylation catalyst, it is used to improve the yield, reduce the reaction time, improving relaxation process conditions. Widely used in perfumes, dyes, pigments, pesticides, pharmaceuticals and polymer compounds and other fields. Also used as a catalyst for the synthesis of polyurethane, a curing agent and a blowing catalyst.

Uses

A highly fluorescent adenosine analogue, which in a dimethoxytrityl, phosphoramidite protected form, can be site-specifically inserted into oligonucleotides through a 3?5?phosphodiester linkage using an automated DNA synthesizer

References

Litvinenko, L. M.; Kirichenko, A. I. Dok. Akad. Nauk SSSR, Ser. Khim. 1967, 176, 97; Steglich, W.; H?fle, G. Angew. Chem. 1969, 81, 1001; Angew. Chem. Int. Ed. 1969, 8, 981. Scriven, E. F. V.; 4-Dialkylaminopyridines: Super Acylation and Alkylation Catalysts; Chem. Soc. Rev. H. Vorbriiggen, Angew. Chem. 84, 348 (1972); Angew. Chem. Int. Ed. Engl. 11, 305 (1972). L. Pentimalli, Gazz. Chim. Ital. 94, 902 (1964). R. W Taft, C. A. Grob, J . Am. Chem. SOC. 96, 1236 (1974). C. W N. Cumper, A. Singleton, J . Chem. SOC. B 1967, 1096. A. R. Katritzky, E. Fi! Randall, L. E. Sutton, J. Chem. SOC. 1957 1769. H. Lumbroso, J. Barassin, Bull. SOC. Chim. Fr. 1965, 3143. C. D. Johnson, I. Roberts, P. G. Taylor, J. Chem. SOC.C hem. Commun 1977, 897. M. R. Chakrabarty, C. S. Handloser, M. W Mosher, J. Chem. SOC. Perkin Trans. I1 1973, 938 Pyridine syntheses, 1st Communication.-2nd Communication: H. Vorbriiggen, J. Kottwitz, K. Krolikiewicz, Chem. Ber., in preparation. This publication gives a complete survey of the various syntheses of DMAP and PPY; H. Vorbriiggen, DOS 2517774 (1975), Schering AG; Chem. Abstr. 86, 55293d (1977). W Steglich, G. Hofle, Tetrahedron Lett. 1970, 4727. E. Koenigs, H. Friedrich, H. Jurany, Ber. Dtsch. Chem. Ges. 58, 2571 (1925). A. C. Satterthwait, W P. Jencks, J. Am. Chem. SOC. 96, 7031 (1974). A. G. Burton, R. D. Frampton, C. D. Johnson, A. R. Katritzky, J. Chem. SOC. Perkin Trans. 11 1972, 1940. G. B. Barlin, J. A. Benbow, J . Chem. SOC. Perkin Trans. I1 1975,1385. J. A. Zoltewicz, J. D. Meyer, Tetrahedron Lett. 1968, 421. H. Braun, A. Amann, M. Richter, Angew. Chem. 89,488 (1977); Angew. Chem. lnt. Ed. Engl. 16, 471 (1977). B. P. Schaffner, H. Wehrli, Helv. Chim. Acta 55, 2563 (1972). 4-Dialkylaminopyridines as acylation catalysts, 4th Communication.-3rd Communication: G. Hofle, W Steglich, Synthesis 1972, 619. W Steglich, G. Hofle, Angew. Chem. 81, 1001 (1969); Angew. Chem. Int. Ed. Engl. 8, 981 (1969). J. E. McMurry, J . H. Musser, M. S. Ahmad, L. C. Blaszczak, J. Org. Chem. 40, 1829 (1975). D. J. Zwanenburg, W A. P. Reynen, Synthesis 1976, 624. 1. S. Bindra, A. Grodski, J. Org. Chem. 42, 910 (1977). H. Paulsen, H. Hohne, Carhohydr. Res. 58, 484 (1977). W Steglich, G. Hiiye, Tetrahedron Lett. 1968, 1619. W Steglich, G. HoJe, Chem. Ber. 104, 3644 (1971). W Steglich, G. HoJe, Chem. Ber. 102, 1129 (1969). G. HiiJe, A. Prox, W Steglich, Chem. Ber. 105, 1718 (1972). P. W Henniger, J. K. Van der Drift, DOS 2235390 (1973), Koninklijke Nederlandsche Gist-en Spiritusfabriek N. V.; Chem. Abstr. 78, 124608j J. Maurer, DOS 180867O(US Pat. 3530093) (1967), Ciba-Geigy; Chem. Abstr. 71, 1032541 (1969). P . C . Sriuastaua, M, Pickering, L. B. Allen, D. G. Streeter, M . 7: Campbell, J. R. Witkowski, R. W Sidwell, R. K. Robins, J. Med. Chem. 20, 256 (1977). S. D. Larsen, S. A. Monti, J. Am. Chem. SOC. 99, 8015 (1977). M. Wakselman, E. Guibl-Jampel, Tetrahedron Lett. 1970, 1521.

Purification Methods

Recrystallise DMAP from toluene [Sadownik et al. J Am Chem Soc 108 7789 1986]. [Beilstein 22 V 112.] § A polystyrene supported version (PS-DMAP) is commercially available.

Application as acylation catalysts

Acylation of alcohol The high catalytic activity of DMAP and PPY can be used for acylating sterically hindered secondary or tertiary alcohols with carboxylic anhydrides or acyl halides when the pyridine method fails. In most cases, it is necessary to use only 0.05-0.2 mol of catalyst per mol of substance and the acid that is formed can be bound with an equivalent amount of trimethylamine[21, 22] or pyridine[20]. Such solvents as hexane, toluene, benzene, methylene chloride, chloroform, ethyl acetate, tetrahydrofuran, triethylamine, pyridine, or acetic anhydride are suitable for use with these catalysts. Among the tertiary alcohols which can be easily acylated with DMAP and PPY, mention should be made of l-methyl cyclohexanol, 1-ethynylcyclohexanol, 1,l-diphenylethanol, linalool, l, l-dimethoxy-2-methyl-3-buten-2-ol, 5,5-dimethoxy-2-methyI-3-pentyn-2-ol, and cis-4- (1-hydroxyisopropyl)-2-methylcyclohexanone. Acylation of phenols In the acylation of phenols, DMAP and PPY effect a similar increase in reaction rate as is found in the case of alcohols. Hence, the method is of interest for the acylation of sterically hindered phenols. For example, mesitol can be smoothly acetylated with acetic anhydride/DMAP to 2,5-ditert-butylphenol and analogous compounds can be transformed into acyl derivatives of the type in high yields[24]. 11,12-Dihydroglaziovine smoothly affords the acyl derivative[23, 25]. Acylation of amines DMAP and PPY have been seldom used for the acylation of amines. The kinetic investigations of Lituinenko and Kirichenko [26] have shown that an enormous increase in reaction rate is observed when acylations are carried out in aprotic solvents. These authors have determined the following relative rate constants (in parentheses) for the amine-catalyzed acylation of m-chloroaniline with benzoyl chloride in benzene: N, N-dimethylaniline (0.1); triethylamine (0.072); 2,6-dimethylpyridine (0.03); pyridine (1.80); 4-methylpyridine (10.0); and DMAP (10600). Acylation of enolates Acylations involving CH-acid compounds which can be performed with pyridine or triethylamine as catalyst are found to proceed at a much higher rate when DMAP or PPY is used. The Dakin-West reaction of N-acyl amino acids, in which a 2-oxazolin-5-one is acetylated at C-4 with a carboxylic anhydride in pyridine with formation of a new C-C bond, has been extensively investigated[27]. The combination products, consisting of the ambident oxazolin-5-one anions and N-acylpyridinium cations initially formed under kinetic control, are transformed via the ion pair into the thermodynamically most stable product[28]. Decarboxylative ring opening by the subsequently formed carboxylic acid yields the a-acyl amino ketone[29, 30]. Reactions of isocyanates Pyridine-catalyzed reactions of isocyanates with carboxylic acids to form amides are found to be strongly accelerated on replacement of pyridine by DMAP. Phenylacetic acid is found to react with phenyl isocyanate in 1,2-dichloroethane at 24°C to give the amide in 66 % yield in less than 5 min; whereas on using the same amount of pyridine only 53% could be isolated after 2h. With triethylamine, only very little is formed besides diphenylurea[31]. Miscellaneous Applications DMAP has been used in the hardening of epoxy resins with dicyanodiamine, in the transformation of nitriles into thionamides, and in the transfer of silyl groups to tertiary hydroxyl groups[32, 33]. Transfer of Functional Groups Dimethylarninopyridinium salts are interesting reagents for the transfer of acyl and also cyano and phosphono groups in aqueous medium[34, 35].

Uses

DMAP is a useful highly basic nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement.

Overview

4-Dimethylaminopyridine is highly powerful catalyst of organic synthesis. The treatment of substrates such as alcohols, phenols and amines with acetic anhydride (or acetyl chloride) in the presence of pyridine has provided a general acetylation method since the turn of the 20th century. However, this approach often proves to be unsatisfactory for the acetylation of deactivated substrates. It was not until the late 1960’s that certain 4-dialkylaminopyridines were found (independently by two research groups)[1, 2] to be much superior to pyridine as catalysts for difficult acetylations or acylations, in general. Figure 1 the chemical structure of DMAP 4-Dialkylaminopyridines were soon found to have general applicability for catalysis of a wide variety of reactions. 4-dimethylaminopyridine’s (DMAP) wide applicability has been frequently reviewed since the first review appeared in 1978. [3] The accelerating pace of reported applications for DMAP and the availability of DMAP in commercial quantities, at modest prices, have continued to stimulate great interest in its use as a catalyst in the fields of organic, polymer, analytical and biochemistry. Today there are thousands of examples of the use of DMAP in far ranging fields of chemistry in both patents and the research literature. Many full-scale production processes utilizing DMAP have been and are being operated. Several pharmaceutical and agricultural products that rely on DMAP’s superior catalytic properties in their synthetic sequences have been produced for years. Since 1976 more than 11,000 US patents have been granted which mention DMAP or dimethylaminopyridine. The functional groups and class of compounds that are involved in the reactions with DMAP include alcohols, amines, arenes, azides, carbenes, enols, epoxides, hydrazines, hydroxylamines, phenols, thiols, lipids, sugars, aminoacids, peptides, alkaloids, steroids, terpenes, and others. Reactions that have been published in the literature using DMAP fall into, but are not limited to, the following types of reactions: Acylation; Acetylation; Alkylation; Benzoylation; Bischler-Naperalski cyclization, Carbonylation; Carbo-diimidation; Cyclization; Dehydration; Esterificaton; Indole Synthesis; Nucleophilic Substitution; Rearrangement; Silylation; Sulfonamidation; Sulfonation; Tritylation; Formylation; Carbamoylation; Phosphorylation; Lactonization; Pivaloylation; Dakin-West Reaction; Baylis-Hillman Reaction.
InChI:InChI=1/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3/p+1

1122-58-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (D1450)  4-Dimethylaminopyridine  >99.0%(T) 1122-58-3 25g 90.00CNY Detail
TCI America (D1450)  4-Dimethylaminopyridine  >99.0%(T) 1122-58-3 100g 210.00CNY Detail
TCI America (D1450)  4-Dimethylaminopyridine  >99.0%(T) 1122-58-3 500g 720.00CNY Detail
Alfa Aesar (A13016)  4-(Dimethylamino)pyridine, 99%    1122-58-3 5g 96.0CNY Detail
Alfa Aesar (A13016)  4-(Dimethylamino)pyridine, 99%    1122-58-3 25g 288.0CNY Detail
Alfa Aesar (A13016)  4-(Dimethylamino)pyridine, 99%    1122-58-3 100g 846.0CNY Detail
Alfa Aesar (H51715)  4-(Dimethylamino)pyridine, 99%, prilled    1122-58-3 5g 160.0CNY Detail
Alfa Aesar (H51715)  4-(Dimethylamino)pyridine, 99%, prilled    1122-58-3 25g 478.0CNY Detail
Alfa Aesar (H51715)  4-(Dimethylamino)pyridine, 99%, prilled    1122-58-3 100g 1227.0CNY Detail
Aldrich (700169)  4-(Dimethylamino)pyridine,ChemDosetablets  Loading: 0.04 mmol tablet. 1122-58-3 700169-10TAB 822.51CNY Detail
Aldrich (700169)  4-(Dimethylamino)pyridine,ChemDosetablets  Loading: 0.04 mmol tablet. 1122-58-3 700169-100TAB 5,243.94CNY Detail
Sigma-Aldrich (Y0001099)  ValaciclovirimpurityG  European Pharmacopoeia (EP) Reference Standard 1122-58-3 Y0001099 1,880.19CNY Detail

1122-58-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Dimethylaminopyridine

1.2 Other means of identification

Product number -
Other names 4-Dimethylaminopyrid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Process regulators
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1122-58-3 SDS

1122-58-3Synthetic route

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

dimethyl amine
124-40-3

dimethyl amine

Conditions
ConditionsYield
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; acrylic acid at 90℃; for 1.5h; Inert atmosphere;
Stage #2: dimethyl amine at 70℃; for 2.5h; Inert atmosphere;
Stage #3: With sodium hydroxide at 70 - 90℃; for 3.5h; Temperature; Reagent/catalyst; Inert atmosphere;
99.4%
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; acrylic acid In water at 70℃; for 4h; Inert atmosphere;
Stage #2: dimethyl amine In water at 50℃; for 3h; Temperature; Inert atmosphere;
99%
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; hydroquinone; acrylic acid In water at 90℃; for 6h;
Stage #2: dimethyl amine In water for 3h; Temperature; Reflux;
98.6%
4-(dimethylamino)pyridine N-oxide
1005-31-8

4-(dimethylamino)pyridine N-oxide

Conditions
ConditionsYield
With bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt; potassium iodide In ethanol at 20℃; for 1h;95%
With phenylboronic acid In 1,2-dichloro-ethane at 120℃; for 10h;90%
With 1,1,1,2,2,2-hexamethyldisilane; tetrabutyl ammonium fluoride In tetrahydrofuran at 24 - 30℃; for 8h;84%
4-chlorpyridine hydrochloride
7379-35-3

4-chlorpyridine hydrochloride

dimethyl amine
124-40-3

dimethyl amine

Conditions
ConditionsYield
With sodium hydroxide; water In 1,4-dioxane at 70℃; under 6000480 Torr; for 20h; Substitution;93%
dimethyl amine

dimethyl amine

Conditions
ConditionsYield
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide In water at 25℃; for 24h; Inert atmosphere;90%
dimethyl amine
124-40-3

dimethyl amine

Conditions
ConditionsYield
In methanol at 40 - 45℃; for 4h; Autoclave;89.7%
lithium dimethylamide
3585-33-9

lithium dimethylamide

diisopropyl pyridin-4-ylphosphonate
58815-96-6

diisopropyl pyridin-4-ylphosphonate

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In toluene at -40 - 20℃; for 1.5h; Substitution;86%
methanol
67-56-1

methanol

4-nitropyridine
1122-61-8

4-nitropyridine

Conditions
ConditionsYield
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation;86%
With palladium 10% on activated carbon; potassium tert-butylate at 150℃; for 48h;
4-iodopyridine
15854-87-2

4-iodopyridine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;82%
4-chlorpyridine hydrochloride
7379-35-3

4-chlorpyridine hydrochloride

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With ammonia In water at 240℃; for 0.5h;78%
4-Chloropyridine
626-61-9

4-Chloropyridine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With potassium carbonate at 80℃; for 10h;75%
for 34h; Reflux; neat (no solvent);69%
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;21 %Spectr.
4-bromopyridin
1120-87-2

4-bromopyridin

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;73%
Conditions
ConditionsYield
Stage #1: C9H8N2O2; dimethyl amine In water at 45℃; for 0.25h;
Stage #2: With sodium hydroxide In water at 70℃; for 1 - 2h;
67.1%
4-(Methylamino)pyridine
1121-58-0

4-(Methylamino)pyridine

methanol
67-56-1

methanol

Conditions
ConditionsYield
With rhodium(III) chloride hydrate; potassium tert-butylate at 130℃; for 48h; Sealed tube; High pressure;66%
1-(4-pyridyl)pyridinium chloride hydrochloride
5421-92-1

1-(4-pyridyl)pyridinium chloride hydrochloride

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
Stage #1: 1-(4-pyridyl)pyridinium chloride hydrochloride; N,N-dimethyl-formamide at 150 - 155℃; for 2 - 3h;
Stage #2: With sodium hydroxide In water at 20℃; pH=10 - 12;
65.05%
Stage #1: 1-(4-pyridyl)pyridinium chloride hydrochloride; N,N-dimethyl-formamide at 150 - 155℃; for 2 - 3h;
Stage #2: With sodium hydroxide In water at 20℃; pH=10 - 12;
65.05%
Conditions
ConditionsYield
In water51%

A

B

N4,N4-dimethylpyridine-3,4-diamine
5028-28-4

N4,N4-dimethylpyridine-3,4-diamine

C

2-amino-5-bromo-4-dimethylaminopyridine
114474-08-7

2-amino-5-bromo-4-dimethylaminopyridine

Conditions
ConditionsYield
With potassium amide In diethyl ether; ammonia at -78 - -33℃; for 1.5h;A 40%
B 32%
C 10%
(3-bromopyridin-4-yl)-dimethyl-amine
84539-35-5

(3-bromopyridin-4-yl)-dimethyl-amine

A

dmap
1122-58-3

dmap

B

N4,N4-dimethylpyridine-3,4-diamine
5028-28-4

N4,N4-dimethylpyridine-3,4-diamine

Conditions
ConditionsYield
With potassium amide In diethyl ether; ammonia at -78℃; for 0.0833333h;A 4%
B 31%
N-(1-ethoxyvinyl)-N,N-dimethylamine
816-65-9

N-(1-ethoxyvinyl)-N,N-dimethylamine

1,2,4-triazine
290-38-0

1,2,4-triazine

Conditions
ConditionsYield
In 1,4-dioxane at 100℃; for 12h;27%
4-aminopyridine
504-24-5

4-aminopyridine

methanol
67-56-1

methanol

A

4-(Methylamino)pyridine
1121-58-0

4-(Methylamino)pyridine

B

dmap
1122-58-3

dmap

Conditions
ConditionsYield
With aluminum oxide at 300 - 369℃;
4-phenoxypyridine
4783-86-2

4-phenoxypyridine

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

Conditions
ConditionsYield
at 180℃;
Conditions
ConditionsYield
With phenol at 180 - 190℃;
4-(dimethylamino)pyridinium cation
55277-36-6

4-(dimethylamino)pyridinium cation

C14H13NO
114444-46-1

C14H13NO

A

dmap
1122-58-3

dmap

B

1-methyl-4-(phenylacetyl)pyridinium cation
124225-44-1

1-methyl-4-(phenylacetyl)pyridinium cation

Conditions
ConditionsYield
In water at 25℃; Equilibrium constant;
1-(2-Cyano-ethyl)-4-dimethylamino-pyridinium; bromide
130671-19-1

1-(2-Cyano-ethyl)-4-dimethylamino-pyridinium; bromide

A

dmap
1122-58-3

dmap

B

acrylonitrile
107-13-1

acrylonitrile

Conditions
ConditionsYield
With potassium hydroxide; potassium chloride In water at 25℃; Rate constant; var. basic media; pH dependence of the velocity const.;
1-(2-Cyano-ethyl)-4-dimethylamino-pyridinium

1-(2-Cyano-ethyl)-4-dimethylamino-pyridinium

A

dmap
1122-58-3

dmap

B

acrylonitrile
107-13-1

acrylonitrile

Conditions
ConditionsYield
With potassium chloride; hydroxide In water at 25℃; Equilibrium constant;
4-Dimethylamino-1-[2-(4-nitro-phenyl)-ethyl]-pyridinium; bromide
135041-86-0

4-Dimethylamino-1-[2-(4-nitro-phenyl)-ethyl]-pyridinium; bromide

A

dmap
1122-58-3

dmap

B

4-nitrostyrene
100-13-0

4-nitrostyrene

Conditions
ConditionsYield
With potassium hydroxide; potassium chloride at 25℃; Rate constant;
N-phenylbenzimidoyl-4-dimethylaminopyridinium chloride
96318-91-1

N-phenylbenzimidoyl-4-dimethylaminopyridinium chloride

A

N-phenyl benzoyl amide
93-98-1

N-phenyl benzoyl amide

B

dmap
1122-58-3

dmap

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 30℃;
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 25℃; Rate constant;
4-Dimethylamino-1-{[(Z)-phenylimino]-m-tolyl-methyl}-pyridinium; chloride
101476-38-4

4-Dimethylamino-1-{[(Z)-phenylimino]-m-tolyl-methyl}-pyridinium; chloride

A

dmap
1122-58-3

dmap

B

3-methyl-N-phenylbenzamide
23099-05-0

3-methyl-N-phenylbenzamide

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 30℃;
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 25℃; Rate constant;
1-{(3-Bromo-phenyl)-[(Z)-phenylimino]-methyl}-4-dimethylamino-pyridinium; chloride
113399-37-4

1-{(3-Bromo-phenyl)-[(Z)-phenylimino]-methyl}-4-dimethylamino-pyridinium; chloride

A

B

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 30℃;
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 25℃; Rate constant;

A

dmap
1122-58-3

dmap

B

3-methoxy-N-phenylbenzamide
6833-23-4

3-methoxy-N-phenylbenzamide

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 30℃;
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 25℃; Rate constant;
1-iodo-2,4-dinitrobenzene
709-49-9

1-iodo-2,4-dinitrobenzene

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; iodide
111055-10-8

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; iodide

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
2,4,6-trinitrochlorobenzene
88-88-0

2,4,6-trinitrochlorobenzene

4-Dimethylamino-1-(2,4,6-trinitro-phenyl)-pyridinium; chloride
111055-14-2

4-Dimethylamino-1-(2,4,6-trinitro-phenyl)-pyridinium; chloride

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
2,4-bis(trifluoromethylsulfonyl)chlorobenzene
4975-09-1

2,4-bis(trifluoromethylsulfonyl)chlorobenzene

1-(2,4-Bis-trifluoromethanesulfonyl-phenyl)-4-dimethylamino-pyridinium; chloride
111055-13-1

1-(2,4-Bis-trifluoromethanesulfonyl-phenyl)-4-dimethylamino-pyridinium; chloride

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
2,4-dinitrophenyl benzenesulfonate
970-88-7

2,4-dinitrophenyl benzenesulfonate

Benzenesulfonate4-dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium;
111055-12-0

Benzenesulfonate4-dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium;

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
N-Pentafluorophenyl(C-pentafluorophenyl)imidoyl chloride
71153-92-9

N-Pentafluorophenyl(C-pentafluorophenyl)imidoyl chloride

4-Dimethylamino-1-{pentafluorophenyl-[(Z)-pentafluorophenylimino]-methyl}-pyridinium; chloride

4-Dimethylamino-1-{pentafluorophenyl-[(Z)-pentafluorophenylimino]-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism;100%
4-Nitrophenacyl bromide
99-81-0

4-Nitrophenacyl bromide

1-[2-(4-nitrophenyl)-2-oxoethyl]-4-(dimethylamino)pyridinium bromide

1-[2-(4-nitrophenyl)-2-oxoethyl]-4-(dimethylamino)pyridinium bromide

Conditions
ConditionsYield
In benzene for 0.166667h; Ambient temperature;100%
In acetone for 0.5h; Heating;90%
2,4-Dinitrofluorobenzene
70-34-8

2,4-Dinitrofluorobenzene

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; fluoride
111055-09-5

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; fluoride

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
N-(pentafluorophenyl)-benzimidoyl chloride
87228-28-2

N-(pentafluorophenyl)-benzimidoyl chloride

4-Dimethylamino-1-{[(Z)-pentafluorophenylimino]-phenyl-methyl}-pyridinium; chloride
120703-73-3

4-Dimethylamino-1-{[(Z)-pentafluorophenylimino]-phenyl-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism; presence of tetraethylammonium salts;100%
2,3,4,5,6-Pentafluoro-N-phenyl-benzimidoyl chloride
120703-72-2

2,3,4,5,6-Pentafluoro-N-phenyl-benzimidoyl chloride

4-Dimethylamino-1-{pentafluorophenyl-[(Z)-phenylimino]-methyl}-pyridinium; chloride
120703-76-6

4-Dimethylamino-1-{pentafluorophenyl-[(Z)-phenylimino]-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism; presence of tetraethylammonium chloride;100%
4-Methyl-N-(2,3,4,5,6-pentafluoro-phenyl)-benzimidoyl chloride
120703-70-0

4-Methyl-N-(2,3,4,5,6-pentafluoro-phenyl)-benzimidoyl chloride

4-Dimethylamino-1-{[(Z)-pentafluorophenylimino]-p-tolyl-methyl}-pyridinium; chloride
120703-74-4

4-Dimethylamino-1-{[(Z)-pentafluorophenylimino]-p-tolyl-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism;100%
4-Nitro-N-(2,3,4,5,6-pentafluoro-phenyl)-benzimidoyl chloride
120703-71-1

4-Nitro-N-(2,3,4,5,6-pentafluoro-phenyl)-benzimidoyl chloride

4-Dimethylamino-1-{(4-nitro-phenyl)-[(Z)-pentafluorophenylimino]-methyl}-pyridinium; chloride
120703-75-5

4-Dimethylamino-1-{(4-nitro-phenyl)-[(Z)-pentafluorophenylimino]-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism;100%
1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; chloride
110465-52-6

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; chloride

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
2,4,6-trichloropyrimidine
3764-01-0

2,4,6-trichloropyrimidine

sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

1,1',1''-(pyrimidin-2,4,6-triyl)-tris-4-dimethylaminopyridinium tris(tetraphenylborate)

1,1',1''-(pyrimidin-2,4,6-triyl)-tris-4-dimethylaminopyridinium tris(tetraphenylborate)

Conditions
ConditionsYield
In ethyl acetate Ambient temperature;100%
In ethyl acetate100%
2,3,4,5,6-pentachloropyridine
2176-62-7

2,3,4,5,6-pentachloropyridine

1-(4-dimethylamino)-[2,3,5,6-tetrachloro-pyridin-4-yl]pyridinium chloride

1-(4-dimethylamino)-[2,3,5,6-tetrachloro-pyridin-4-yl]pyridinium chloride

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 80℃; for 3h;100%
In 1,2-dichloro-benzene at 60℃;87%
In 1,2-dichloro-benzene at 80 - 90℃;
2,3,4,5,6-pentachloropyridine
2176-62-7

2,3,4,5,6-pentachloropyridine

(3,5-dichloropyridine-2,4,6-triyl)-1,1',1''-tris[4-(dimethylamino)pyridinium] trichloride

(3,5-dichloropyridine-2,4,6-triyl)-1,1',1''-tris[4-(dimethylamino)pyridinium] trichloride

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 120℃; for 3h;100%
In 1,2-dichloro-benzene Heating;
Heating;
1-bromo-octane
111-83-1

1-bromo-octane

4-(dimethylamino)-1-octylpyridinium bromide

4-(dimethylamino)-1-octylpyridinium bromide

Conditions
ConditionsYield
In acetonitrile for 15h; Heating;100%
In acetone for 9h; Heating;50%
In ethyl acetate at 70℃; for 48h;
C58H72N10(2+)*2Cl(1-)

C58H72N10(2+)*2Cl(1-)

Conditions
ConditionsYield
In methanol for 24h; Heating;100%
methanesulfonic acid 3-(2-phenylethynyl-phenyl)-prop-2-ynyl ester
864950-69-6

methanesulfonic acid 3-(2-phenylethynyl-phenyl)-prop-2-ynyl ester

4-dimethylamino-1-[3-(2-phenylethynyl-phenyl)-prop-2-ynyl]-pyridinium; methanesulfonate

4-dimethylamino-1-[3-(2-phenylethynyl-phenyl)-prop-2-ynyl]-pyridinium; methanesulfonate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;100%
2,4-dinitrophenyl benzoate

2,4-dinitrophenyl benzoate

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 25℃; Kinetics;100%
4-dimethylaminophenylazopentakis[4-(dimethylamino)-1-pyridinio]benzene pentakis(iodide)

4-dimethylaminophenylazopentakis[4-(dimethylamino)-1-pyridinio]benzene pentakis(iodide)

Conditions
ConditionsYield
In chlorobenzene for 24h; Heating;100%
2,4-dihydroxyphenylazopentafluorobenzene

2,4-dihydroxyphenylazopentafluorobenzene

trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

2,4-dihydroxyphenylazopentakis[4-(dimethylamino)-1-pyridinio]benzene pentakis(triflate)

2,4-dihydroxyphenylazopentakis[4-(dimethylamino)-1-pyridinio]benzene pentakis(triflate)

Conditions
ConditionsYield
In chlorobenzene for 24h; Heating;100%
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

N-[4-(dimethylamino)phenyl]-1-(2',3',4',5',6'-pentafluorophenyl)methanimine

N-[4-(dimethylamino)phenyl]-1-(2',3',4',5',6'-pentafluorophenyl)methanimine

4-dimethylaminobenzaldehyde pentakis[4-(dimethylamino)-1-pyridinio]phenylimine pentakis(triflate)

4-dimethylaminobenzaldehyde pentakis[4-(dimethylamino)-1-pyridinio]phenylimine pentakis(triflate)

Conditions
ConditionsYield
In chlorobenzene for 48h; Heating;100%

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The one-pot three-component reaction for the synthesis of pyrido[2,3-d]pyrimidine derivatives has been reported via initial Knoevenagel, subsequent addition and final heterocyclization of substituted aromatic aldehydes, cyanoacetamide and 6-aminouracil in N,N-dimethylformamide (DMF) solvent usin...detailed

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Non-covalent bonded 2D–3D supramolecular architectures based on 4-Dimethylaminopyridine (cas 1122-58-3) and organic acids09/25/2019

Studies concentrating on non-covalent weak interactions between the organic base of 4-dimethylaminopyridine, and acidic derivatives have led to an increased understanding of the role 4-dimethylaminopyridine has in binding with the organic acid derivatives. Here anhydrous and hydrous multicompone...detailed

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