1122-58-3

1122-58-3 - Names and Identifiers

Name	4-Dimethylaminopyridine
Synonyms	DMAP 26DCLPY AURORA KA-6495 AKOS BBS-00004314 4-dimethylamiopryidine 4dimethylaminopyridine 4-Dimethylaminopyridine 4-Dimethylaminepyridine p-Dimethylaminopyridine 4 dimethylamino pyridine 4-dimethylamino pyridine 4-(dimethylamino)-pyridin 4-(Dimethylamino)pyridine 4-Dimethyl amino pyridine n,n-dimethyl-4-pyridinamin N-(4-Pyridyl)dimethylamine N,N-dimethylpyridin-4-amine N,N-Dimethyl-4-pyridinamine 4-N,N-Dimethylaminopyridine N,N-dimethylpyridin-2-amine Dimethyl-pyridin-4-yl-amine 4-(dimethylamino)pyridinium Pyridine, 4-(dimethylamino)- N,N'-DIMEHTYL-4-PYRIDINAMINE N,N-Dimethyl-4-aminopyridine gamma-(Dimethylamino)pyridine Dimethyl-pyridin-4-yl-amine(DMAP) 4-(DIMETHYLAMINO)PYRIDINE SOLUTION 4-(Dimethylamino)PyridineForSynthesis 4-(Dimethylamino) PyridineForSynthesis 4-(Dimethylamino)pyridine, ReagentPlus
CAS	1122-58-3
EINECS	214-353-5
InChI	InChI=1/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3/p+1

1122-58-3 - Physico-chemical Properties

Molecular Formula	C7H10N2
Molar Mass	122.17
Density	0.906 g/mL at 25 °C
Melting Point	112 °C
Boling Point	162 °C
Flash Point	110 °C
Water Solubility	76 g/L (25 ºC)
Solubility	Soluble in water, ethanol, acetone, benzene, toluene, xylene, dichloroethane, chloroform, acetic acid, acetic anhydride, ethyl acetate, hexane, tetrahydrofuran, triethylamine, pyridine, DMF and other solvents.
Vapor Presure	0.169 hPa at 20 °C
Appearance	White crystal
Color	off-white to yellow
Odor	characteristic odor
Merck	14,3389
BRN	110354
pKa	pKa (20°): 9.7
PH	11 (60g/l, H2O, 20℃)
Storage Condition	Store below +30°C.
Stability	Stable. Incompatible with acids, oxidizing agents.
Refractive Index	n20/D 1.431
MDL	MFCD00006418
Physical and Chemical Properties	trait light yellow or white crystal
Use	4-dimethylaminopyridine is a new type of efficient catalyst widely used in chemical synthesis, in organic synthesis, drug synthesis, pesticides, dyes, spices and other synthetic acylation, alkylation, etherification and other types of reactions have high catalytic ability, and have an extremely obvious effect on improving the yield.

1122-58-3 - Risk and Safety

Risk Codes	R25 - Toxic if swallowed R34 - Causes burns R24/25 - R36/37/38 - Irritating to eyes, respiratory system and skin. R27 - Very Toxic in contact with skin R36 - Irritating to the eyes R24 - Toxic in contact with skin R20 - Harmful by inhalation R61 - May cause harm to the unborn child R40 - Limited evidence of a carcinogenic effect R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R67 - Vapors may cause drowsiness and dizziness R66 - Repeated exposure may cause skin dryness or cracking R21/22 - Harmful in contact with skin and if swallowed. R11 - Highly Flammable R36/37 - Irritating to eyes and respiratory system. R22 - Harmful if swallowed R19 - May form explosive peroxides
Safety Description	S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S28A - S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. S53 - Avoid exposure - obtain special instructions before use. S27 - Take off immediately all contaminated clothing. S22 - Do not breathe dust. S16 - Keep away from sources of ignition.
UN IDs	UN 2811 6.1/PG 2
WGK Germany	3
RTECS	US8400000
TSCA	T
HS Code	29333999
Hazard Note	Toxic/Corrosive
Hazard Class	8
Packing Group	II
Toxicity	LD50 orally in Rabbit: 140 mg/kg LD50 dermal Rabbit 90 mg/kg

1122-58-3 - Upstream Downstream Industry

Raw Materials

Pyridine

1122-58-3 - Reference

Reference

1. Tao Xuefen. Synthesis of propionate and malonate [J]. Guangzhou Chemical 2016 44(02):42-43 68.
2. Du Xu, Wang Qin, Liu Yang, Ma Lixia, Zhu Aichen, Wang Xianpeng, Wang Chuandong. Synthesis and Properties of Four-arm Star Biotinylated Polyethylene Glycol-Lactide [J]. Chemistry and Bioengineering, 2015,32(03):36-39.
3. Liu Tianjiao, Liu Fuqiang, Wang Yanping, et al. Study on Hydrophobic Modification of Blemilum Polysaccharide [J]. Chinese patent medicine, 2015, 37(002):423-426.
4. [IF = 3.591] Guichen Li et al."Poly(HPMA)-chlorambucil conjugate nanoparticles: facebook fabrication and in vitro anti-cancer activity." New J Chem. 2021 Oct;45(39):18544-18551
5. [IF = 2.457] Yongkai Yuan et al."Synthesis of polyunsaturated fatty boronic esters and their in vitro inhibition to HCT116   cell lines." Tetrahedron. 2019 Oct;75:130578
6. [IF = 5.582] Xiaowei Xu et al."Recyclable silicone elastic light-triggered actuator with a reconfigurable Janus structure and self-healable performance." Polym Chem-Uk. 2021 Dec;:

1122-58-3 - Nature

Open Data Verified Data

white crystalline powder. The melting point was 108-113 °c. Boiling point of 162 deg C (6. 6kPa). Flash point 230 °c. Water soluble 76g/L (25 degrees C). Insoluble in water, hexane, cyclohexane, soluble in ethanol, benzene, chloroform, methanol, ethyl acetate, acetone, acetic acid and dichloroethane.

Last Update：2025-06-10 22:55:16

1122-58-3 - Preparation Method

Open Data Verified Data

4 chloropyridine and dimethyl amine reaction.

Last Update：2022-01-01 10:53:13

1122-58-3 - Introduction

Soluble in water, ethanol, acetone, benzene, toluene, xylene, dichloroethane, chloroform, acetic acid, acetic anhydride, ethyl acetate, hexane, tetrahydrofuran, triethylamine, pyridine, DMF and other solvents, water solubility: 76g/l (25°C).

Last Update：2022-10-16 17:12:16

1122-58-3 - Application

Open Data Verified Data

4-methylaminopyridine is a new type of efficient catalyst widely used in chemical synthesis, in organic synthesis, drug synthesis, pesticides, dyes, fragrances and other synthetic acylation, alkylation, etherification and other types of reactions have high catalytic ability, and have an extremely obvious effect on improving the yield.

Last Update：2025-08-19 16:24:40

1122-58-3 - Safety

Open Data Verified Data

toxicity LD50(mg/kg): Rat oral 230.

Last Update：2022-01-01 10:53:14

1122-58-3 - Reference Information

pH indicator color change ph range	9.7 (10% aq soln)
LogP	1.34 at 25℃
NIST chemical information	Information provided by: webbook.nist.gov (external link)
EPA chemical information	Information provided by: ofmpub.epa.gov (external link)
Introduction	4-dimethylaminopyridine, commonly referred to as DMAP, is a super nucleophilic acylation catalyst. The resonance of the electron-donating dimethylamino group in its structure and the parent ring (pyridine ring) can strongly activate the nitrogen atom on the ring to undergo nucleophilic substitution, which significantly catalyzes high resistance, low-reactive alcohols and amines/acids The activity of the acylation/esterification reaction is about 104~106 times that of pyridine. Acyl transfer is a common transformation in nature and organic synthesis, in which chiral DMAP is a common asymmetric acyl transfer catalyst. Since 1996, Vedejs and Fu team reported the central chiral and planar chiral DMAP catalysts respectively, chiral DMAP catalysts have been greatly developed. Various central chiral, planar chiral, spiro chiral and central chiral DMAP have been reported one after another, and have been well applied in many asymmetric acyl transfer reactions.
Properties	4-dimethylaminopyridine (DMAP) is a colorless solid, soluble in most organic solvents, such as: methanol, dichloromethane, tetrahydrofuran, Ethyl acetate, etc., slightly soluble in water. Domestic and foreign reagent companies have sales. The reagent is relatively stable and can be stored at room temperature. It is irritating and corrosive to the skin. The laboratory prepared by 4-substituted (Cl, OPh, SO3H, OSiMe3) pyridine co-heating with dimethylamine.
application	4-dimethylaminopyridine is a new type of high-efficiency catalyst widely used in chemical synthesis. it has high catalytic ability in acylation, alkylation, etherification and other types of reactions synthesized by organic synthesis, drug synthesis, pesticides, dyes, spices, etc., and has extremely obvious effect on improving the yield.
"One-pot method" synthesis of 4-dimethylaminopyridine	Using 4-cyanopyridine, 2-vinylpyridine and dimethylamine as the main raw materials, 4-dimethylaminopyridine was synthesized in one pot method. The optimal process conditions are as follows: reactant ingredient ratio m(4-cyanopyridine)/m(2-vinylpyridine) = 1.5, refluxing the intermediate for 2h using aqueous solution (NaOH)= 40%, and the reaction yield reaches 87.4%. The target compound was confirmed by IR, ^ 1HNMR and MS. [Author] Chen Guoguang, Zhao Xin, Zhang Dayong [Organization] School of Pharmacy and Life Sciences, Nanjing University of Technology, 210009 of Chemistry and Environmental Sciences, Nanjing Normal University, Jiangsu, Nanjing 210097, Jiangsu
esterification catalyst	4-dimethylaminopyridine is a new type of high-efficiency catalyst widely used in chemical synthesis. It is used in organic synthesis, drug synthesis, pesticides, dyes, etc. It has high catalytic ability in various types of reactions such as acylation, alkylation, etherification and esterification, and has obvious effects on improving efficiency. When it is a catalyst, the acylating agent is preferably an acid anhydride, and it is in an organic base environment. The esterification of succinic acid and lower alcohols can be carried out in excess alcohols, which can be catalyzed by sulfuric acid or strongly acidic cation exchange resin, but if water is not separated, the conversion rate will be affected.
Super nucleophilic acylation catalyst-4-dimethylaminopyridine	4-dimethylaminopyridine is a new type of high-efficiency catalyst widely used in chemical synthesis in recent years. The resonance of the electron-donating dimethylamino group in its structure and the parent ring (pyridine ring) can strongly activate the nitrogen atom on the ring for nucleophilic substitution, significantly catalyzed the acylation (phosphorylation, sulfonylation, carbonylation) reaction of high-resistance, low-reactivity alcohols and amines, and its activity is about 104-6 times that of pyridine. In organic synthesis, drug synthesis, pesticides, medicine, dyes, spices, polymer chemistry, analytical chemistry, acylation, alkylation, etherification, esterification and transesterification and other types of reactions have a high catalytic ability, to improve the yield has a very obvious effect, in addition, can also be used as a phase transfer catalyst for interfacial reactions. Its advantages are: the amount of catalyst is small, usually only 0.01-5% of the moles of the reaction substrate is required, and the acid produced by the reaction can be neutralized with organic or inorganic bases; the reaction conditions are mild, and the reaction can be carried out at room temperature. Save energy; the choice of solvent is wide, and it can be carried out in polar and non-polar organic solvents; the reaction time is short, and pyridine is used for a long time, the reaction is completed in a few minutes with DMAP, which greatly improves labor productivity; the yield is high, such as the sterically hindered hydroxyl compound with almost no reaction of pyridine, the yield of DMAP can reach 80-90%, which can improve The reaction yield and product quality and simplify the process; less side reactions, small odor, and less three wastes; due to the excellent catalytic performance of DMAP, it is called a "super catalyst", it has become one of the most commonly used catalysts for organic synthesis workers. The domestic chemical pharmaceutical industry has successfully applied it to the production of B (propionyl) spiramycin, artemisinin succinate, statins and other raw materials, improving the process conditions and achieving good economic and social benefits. In addition, it is also widely used in the complete (semi) synthesis of complex natural products, such as: acetylation in the total synthesis of PRAVASTATIN, trifluoroacetylation in the total synthesis of TUBERCIDIN, acetylation in the total synthesis of MUGINEIC ACID and benzoylation in the total synthesis of TERPESTACIN, and acylation in the total synthesis of sildenafil (VIAGAR). In the production of pesticides, DMAP is used to improve the yield and product purity in the synthesis of methrin, it also has obvious catalytic activity in the reaction of isocyanate to carbamate and chrysanthemum chloride to pyrethroid. In the synthesis of organophosphorus in phosphorylation reaction, the effect is quite significant.
use	4-dimethylaminopyridine is a new type of high-efficiency catalyst widely used in chemical synthesis. it has high catalytic ability in acylation, alkylation, etherification and other types of reactions synthesized by organic synthesis, drug synthesis, pesticides, dyes, spices, etc., and has extremely obvious effect on improving the yield. as a super nucleophilic acylation catalyst high-efficiency catalyst in esterification reaction widely used as a catalyst for chemical synthesis, acylation, carbonylation, etherification and esterification in organic drug synthesis, pesticides, dyes, food additives, etc. 4-dimethylaminopyridine is a new type of high-efficiency catalyst widely used in chemical synthesis in recent years. The resonance of the electron-donating dimethylamino group in its structure and the parent ring (pyridine ring) can strongly activate the nitrogen atom on the ring to perform nucleophilic substitution, It significantly catalyzes the acylation (phosphorylation, sulfonylation, carbonylation) reaction of alcohols and amines with high resistance and low reactivity, and its activity is about 104-6 times that of pyridine. It has high catalytic ability in various types of reactions such as acylation, alkylation, etherification, esterification and transesterification in organic synthesis, drug synthesis, pesticides, medicine, dyes, fragrances, polymer chemistry, and analytical chemistry. It has extremely obvious ability to improve the yield. An efficient catalyst for acylation reactions
Production method	4-hydroxypyridine, dimethylamine hydrochloride and hexamethylphosphide triamine are heated at 220 ℃ for 4h. The cured reactant was rinsed with water and hydrolyzed at 100 ℃ for 1h with hydrochloric acid. Cold to room temperature, add sodium hydroxide aqueous solution under stirring, and then extract with chloroform. The extract is dried with magnesium sulfate and then evaporated to remove the solvent, and the remaining is extracted with boiling hexane, thermally filtered, concentrated, and crystallized to obtain 4-dimethylaminopyridine. The yield is about 55%.
spontaneous combustion temperature	420°C

Last Update：2024-07-11 16:52:08

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