4-(Dimethylamino)pyridine

HCID 14284CAS 1122-58-3

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

4-Dimethylaminopyridine1122-58-3N,N-Dimethylpyridin-4-aminedmap4-(Dimethylamino)pyridine4-Pyridinamine, N,N-dimethyl-DTXSID0044369PFP1R6P0S84-DMAPDTXCID80243694-[dimethylamino]pyridineRefChem:98776
Show more names
4,4-dimethylaminopyridine4-(Dimethylamino)pyridine, 99%, prilled4-(N,N-dimethlyamino)pyridine26DCLPYAURORA KA-64954-DiMethylaMin
214-353-5p-DimethylaminopyridineN,N-DIMETHYL-4-PYRIDINAMINEN-(4-Pyridyl)dimethylamineN,N-Dimethyl-4-aminopyridinePyridine, 4-(dimethylamino)-MFCD00006418887925-31-7

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

Experimental & physicochemical properties

Vapor Pressure1.0 [mmHg]
Physical Description · 2 items

Large Crystals

Colorless solid; [Merck Index] Beige crystalline solid; [Sigma-Aldrich MSDS]

Collision Cross Section120.6 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID0044369];120.5 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0044369]

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 4 items

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

Hazards SummaryA skin and strong eye irritant; Toxic by ingestion; Highly toxic by skin absorption; [Sigma-Aldrich MSDS] See 4-Aminopyridine.
Hazard Classes and CategoriesAcute 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 · 6 items

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 · 4 items

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

Chemistry & industry

Uses & manufacturing

UsesA catalyst used in organic syntheses; [Merck Index]
U.S. Production2023: 50,000 - <250,000 lb;2022: 50,000 - <250,000 lb;2021: 50,000 - <250,000 lb;2020: 250,000 - <550,000 lb
Industry UsesCatalyst
General Manufacturing Information · 2 items

Pharmaceutical and Medicine Manufacturing

4-Pyridinamine, N,N-dimethyl-: ACTIVE

Applications · 6 items

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

Downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]

Additional notes

DefinitionChEBI: 4-Dimethylaminopyridine is a dialkylarylamine and a tertiary amino compound.

Related reactions

24,121 records

Linked notes

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