HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(Dimethylamino)pyridine
DMAP · N,N-Dimethylpyridin-4-amine · N,N-Dimethyl-4-aminopyridine · p-Dimethylaminopyridine · 4,4-dimethylaminopyridine · 4-(Dimethylamino)pyridine, 99%, prilled · 4-(N,N-dimethlyamino)pyridine · 26DCLPY
Identifiers & Physical Properties
| CAS No. | 1122-58-3 |
|---|---|
| Molecular formula | C7H10N2 |
| Average molar mass | 122.17 g/mol |
| Monoisotopic mass | 122.08439833 g/mol |
| SMILES | CN(C)c1ccncc1 |
| InChIKey | VHYFNPMBLIVWCW-UHFFFAOYSA-N |
| PubChem CID | 14284 |
| ChEMBL | CHEMBL3561645 |
| ChEBI | CHEBI:182593 |
| EC No. | 214-353-5 |
| DTXSID | DTXSID0044369 |
Chemical & Physical Properties
| XLogP | 1.3 |
|---|---|
| Topological polar surface area | 16.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 75 |
| Vapor pressure | 1.0 [mmHg]0.169 hPa at 20 °C |
| Physical Description | Large CrystalsColorless solid[Merck Index] Beige crystalline solid[Sigma-Aldrich MSDS] |
| Collision Cross Section | 120.6 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID0044369]120.5 Ų [M+H]+ [CCS Type: DTIonization: ESI+ |
| Melting point | 112 °C |
| Boiling point | 162 °C |
| Density | 0.906 g/mL at 25 °C |
| Bulk density | 520kg/m3 |
| Refractive index | n20/D 1.431 |
| Flash point | 110 °C |
| Storage conditions | Store below +30°C. |
| Solubility | methanol: 50 mg/mL, clear76 g/L (25 ºC) |
| Physical state | prilled |
| pKa (acidity coefficient) | pKa (20°): 9.7 |
| Color | off-white to yellow |
| pH | 11 (60g/l, H2O, 20℃) |
| Odor | characteristic odor |
| PH Range | 9.7 (10% aq soln) |
| Merck | 14,3389 |
| BRN | 110354 |
| Stability | Stable. Incompatible with acids, oxidizing agents. |
| InChI | 1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3 |
| InChIKey | VHYFNPMBLIVWCW-UHFFFAOYSA-N |
| SMILES | CN(C)c1ccncc1 |
| LogP (partition coefficient) | 1.34 at 25℃ |
| CAS DataBase Reference | 1122-58-3(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | PFP1R6P0S8 |
| NIST Chemistry Reference | 4-Pyridinamine, N,N-dimethyl-(1122-58-3) |
| EPA Substance Registry System | 4-(Dimethylamino)pyridine (1122-58-3) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS05,GHS06,GHS08,GHS09 |
| Signal word | Danger |
| GHS hazard statements | H301+H331-H310-H315-H318-H370-H411 |
| GHS precautionary statements | P262-P273-P280-P301+P310-P302+P352+P310-P305+P351+P338 |
| Target organs | Nervous system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | T,C,T+,Xn,F |
| Risk statements (R) | 25-34-24/25-36/37/38-27-36-24-20-61-40-23/24/25-67-66-21/22-11-36/37-22-19 |
| Safety statements (S) | 36/37/39-45-28A-26-28-36/37-53-27-22-16 |
| UN transport number | UN 2811 6.1/PG 2 |
| Water hazard class (WGK) | 3 |
| RTECS number | US8400000 |
| Autoignition temperature | 420 °C |
| Hazard Note | Toxic/Corrosive |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Acute Tox. 2 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2STOT SE 1 |
| Packing group | II |
| Customs code | 29333999 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Toxicity | LD50 orally in Rabbit: 140 mg/kg LD50 dermal Rabbit 90 mg/kg |
| REACH registrations | Active |
| Limited quantities | 100ml (liquid) or 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 1.1% (6 of 522) of reports.DangerH301 (98.9%): Toxic if swallowed [Danger Acute toxicity, oral]H310 (70.3%): Fatal in contact with skin [Danger Acute toxicity, dermal]H314 (32.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H315 (59.4%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (32.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (49.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H331 (36%): Toxic if inhaled [Danger Acute toxicity, inhalation]H335 (37.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H370 (17%): Causes damage to organs [Danger Specific target organ toxicity, single exposure]H411 (36%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P308+P316, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 522 reports by companies from 53 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 6 of 522 reports by companies.There are 52 notifications provided by 516 of 522 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: 4-Pyridinamine, N,N-dimethyl-4-Pyridinamine, N,N-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 4-Pyridinamine, N,N-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 15-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17217Status: Active Update: 19-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/255384-(Dimethylamino) pyridine: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A skin and strong eye irritantToxic by ingestionHighly toxic by skin absorption[Sigma-Aldrich MSDS] See 4-Aminopyridine. |
| Hazard Classes and Categories | Acute Tox. 3 (98.9%)Acute Tox. 2 (70.3%)Skin Corr. 1 (32.2%)Skin Irrit. 2 (59.4%)Eye Dam. 1 (32.8%)Eye Irrit. 2 (49.4%)Acute Tox. 3 (36%)STOT SE 3 (37.9%)STOT SE 1 (17%)Aquatic Chronic 2 (36%) |
| CSL Reaction Information | CSL002042-Methoxyprop-2-yl Hydroperoxide + Dicyclohexylcarbodiimide + 4-(Dimethylamino)pyridine + Dichloromethane + Cesium hydroxide + Dimethylformamide"We would like to draw attention to a potential hazard associated with a procedure reported from our laboratories, "2-Methoxyprop-2-yl Hydroperoxide: A Convenient Reagent for the Synthesis of Hydroperoxides and Peracids," P. H. Dussault and A. Sahli [J. Org. Chem., 57, 1009 (1992). DOI: 10.1021/jo00029a043]. The procedure, which calls for room-temperature concentration of the ozonolysis-derived reagent before redissolution in an appropriate solvent, has been performed uneventfully on numerous occasions. Recently, however, several concentrated samples were observed to undergo rapid exothermic decomposition. In one case, an open vial containing a 2-g sample emitted a pillar of flame several feet high. We are currently investigating alternative procedures, including concentration of the reagent at 0 C. Extreme caution, including the rigorous use of safety shields, is warranted. The reagent should not be stored, but should be generated only as needed. Dilute solutions of excess reagent can be safely quenched with dimethyl sulfide, triphenylphosphine, or aqueous sodium sulfite." (reprint of full text)Flammable,PyrophoricNot Available10.1021/cen-v071n032.p002 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | US8400000 |
| UN transport number | UN 2811 6.1/PG 2 |
| Customs code | 29333999 |
| Toxicity | LD50 orally in Rabbit: 140 mg/kg LD50 dermal Rabbit 90 mg/kg |
| Risk statements (R) | 25-34-24/25-36/37/38-27-36-24-20-61-40-23/24/25-67-66-21/22-11-36/37-22-19 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS06,GHS08,GHS09 |
| Hazard symbols | T,C,T+,Xn,F |
| hazard_note | Toxic/Corrosive |
| Safety statements (S) | 36/37/39-45-28A-26-28-36/37-53-27-22-16 |
| Hazard class | 8Acute Tox. 2 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2STOT SE 1 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Packing group | II |
| Target organs | Nervous system |
| GHS hazard statements | H301+H331-H310-H315-H318-H370-H411 |
| Limited quantities | 100ml (liquid) or 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| Autoignition temperature | 420 °C |
| GHS precautionary statements | P262-P273-P280-P301+P310-P302+P352+P310-P305+P351+P338 |
Applications & Uses
Uses
4-Dimethylaminopyridine (Valaciclovir EP Impurity G; Valacyclovir USP Related Compound G) is 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
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.
Uses
In a wide variety of organic syntheses as a catalyst.
Uses
A highly fluorescent adenosine analogue, which in a dimethoxytrityl, phosphoramidite protected form, can be site-specifically inserted into oligonucleotides through a 35phosphodiester linkage using an automated DNA synthesizer
General Description
Valacyclovir Related Compound G, also called as 4-(Dimethylamino)pyridine (DMAP) is an excellent catalyst for acylation of hindered alcohols and in chemical transformations. It is highly nucleophilic in nature.