Basic information
- Standard SMILES
CN(C)c1ccncc1- InChIKey
VHYFNPMBLIVWCW-UHFFFAOYSA-N- Molecular formula
- C7H10N2
- Average molar mass
- 122.17 g/mol
- Monoisotopic mass
- 122.08439833
Names & identifiers
- Preferred name
- 4-(Dimethylamino)pyridine
- IUPAC
- N,N-dimethylpyridin-4-amine
- English name
- 4-Dimethylaminopyridine
- Molecular formula
- C7H10N2
- Molecular weight
- 122.17
Names & synonyms
Show more names
Database identifiers
- CAS
1122-58-3- PubChem CID
- 14284
- DTXSID
DTXSID0044369- ChEMBL
CHEMBL3561645- ChEBI
CHEBI:182593- UNII
- PFP1R6P0S8
- EC Number
- 214-353-5
- Nikkaji
- J1.582.952D、J31.394G
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 16.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 75
Experimental & physicochemical properties
Physical Description
Large Crystals
Colorless solid; [Merck Index] Beige crystalline solid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 112 °C · 112 °C
- Boiling point
- 162 °C · 162 °C
- Density
- 0.906 g/mL · 0.906 g/mL at 25 °C
- bulk density
- 520 kg/m3 · 520kg/m3
- vapor pressure
- 0.169 hPa · 0.169 hPa at 20 °C
- refractive index
- 20 · n20/D 1.431
- Flash point
- 110 °C · 110 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 50 mg/mL, · methanol: 50 mg/mL, clear
- form
- prilled
- pka
- pKa (20°): 9.7
- color
- off-white to yellow
- PH
- 11 · 11 (60g/l, H2O, 20℃)
- Odor
- characteristic odor
- PH Range
- 9.7 · 9.7 (10% aq soln)
- Water Solubility
- 76 g/L · 76 g/L (25 ºC)
- Merck
- 14 · 14,3389
- BRN
- 110354 · 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
- 1.34 at · 1.34 at 25℃
- CAS DataBase Reference
- 1122 · 1122-58-3(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 R6P0S8 · PFP1R6P0S8
- NIST Chemistry Reference
- 4 · 4-Pyridinamine, N,N-dimethyl-(1122-58-3)
- EPA Substance Registry System
- 4 · 4-(Dimethylamino)pyridine (1122-58-3)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS06,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 301 · H301+H331-H310-H315-H318-H370-H411
- Precautionary statements
- 262 · P262-P273-P280-P301+P310-P302+P352+P310-P305+P351+P338
- target organs
- Nervous system
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- T,C,T+,Xn,F
- Risk Statements
- 25 · 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
- 36 · 36/37/39-45-28A-26-28-36/37-53-27-22-16
- RIDADR
- 2811 · UN 2811 6.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 8400000 · US8400000
- Autoignition Temperature
- 420 °C · 420 °C
- Hazard Note
- Toxic/Corrosive
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29333999 · 29333999
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 DermalAcute · Acute Tox. 2 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2STOT SE 1
- Toxicity
- 50 orally · LD50 orally in Rabbit: 140 mg/kg LD50 dermal Rabbit 90 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 100 ml · 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.1% (6 of 522) of reports.
Danger
H301 (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 exposure; Respiratory 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.
Hazard information
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/17217;Status: Active Update: 19-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25538
4-(Dimethylamino) pyridine: Does not have an individual approval but may be used under an appropriate group standard
CSL Reaction Information
CSL00204
2-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,Pyrophoric
Not Available
10.1021/cen-v071n032.p002
Regulatory information
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/17217;Status: Active Update: 19-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25538
4-(Dimethylamino) pyridine: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- US8400000
- ridadr
- UN 2811 6.1/PG 2
- hs_code
- 29333999
- Toxicity
- LD50 orally in Rabbit: 140 mg/kg LD50 dermal Rabbit 90 mg/kg
- risk_code
- 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
- Symbol(GHS)
- GHS05,GHS06,GHS08,GHS09
- hazard_code
- T,C,T+,Xn,F
- hazard_note
- Toxic/Corrosive
- safety_code
- 36/37/39-45-28A-26-28-36/37-53-27-22-16
- hazard_class
- 8
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- target organs
- Nervous system
- 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
- Hazard Classifications
- Acute Tox. 2 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2STOT SE 1
- Autoignition Temperature
- 420 °C
- Precautionary statements
- P262-P273-P280-P301+P310-P302+P352+P310-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
4-Pyridinamine, N,N-dimethyl-: ACTIVE
Applications
Uses4-Dimethylaminopyridine (Valaciclovir EP Impurity G; Valacyclovir USP Related Compound G) is a highly efficient catalyst for acylation reactions.
Uses4-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.
UsesDMAP 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.
UsesIn a wide variety of organic syntheses as a catalyst.
UsesA 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 DescriptionValacyclovir 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: 4-Dimethylaminopyridine is a dialkylarylamine and a tertiary amino compound.
Related reactions
Linked notes
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