4-ジメチルアミノピリジン

4-(Dimethylamino)pyridine

HCID 14284CAS 1122-58-3

基本情報

標準SMILES
CN(C)c1ccncc1
InChIKey
VHYFNPMBLIVWCW-UHFFFAOYSA-N
分子式
C7H10N2
平均分子量
122.17 g/mol
単同位体質量
122.08439833

名称と識別子

優先名称
4-(Dimethylamino)pyridine
IUPAC
N,N-dimethylpyridin-4-amine
現地名
4-ジメチルアミノピリジン
英語名
4-Dimethylaminopyridine
分子式
C7H10N2
分子量
122.17

名称と別名

4-Dimethylaminopyridine1122-58-3N,N-Dimethylpyridin-4-aminedmap4-(Dimethylamino)pyridine4-Pyridinamine, N,N-dimethyl-DTXSID0044369PFP1R6P0S84-DMAPDTXCID80243694-[dimethylamino]pyridineRefChem:98776
名称をさらに表示
4-ジメチルアミノピリジンN,N-ジメチル-4-ピリジンアミンN,N-ジメチルピリジン-4-アミンN,N-ジメチル(4-ピリジル)アミンジメチルアミノピリジン4-(ジメチルアミノ)ピリジンp-ジメチルアミノピリジン(4-ピリジル)ジメチルアミンN-(4-ピリジル)ジメチルアミン4‐ジメチルアミノピリジン4-(ジメチルアミノ)ピリジン 溶液4-(ジメチルアミノ)ピリジン、CHEMDOSE™タブレットジメチル(4-ピリジル)アミン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

データベース識別子

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

物性

構造計算による物性

XLogP
1.3
極性表面積
16.1 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
1
重原子数
9

実験および物理化学的性質

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

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]

物理化学的性質

融点
112 °C · 112 °C
沸点
162 °C · 162 °C
比重(密度)
0.906 g/mL · 0.906 g/mL at 25 °C
蒸気圧
0.169 hPa · 0.169 hPa at 20 °C
屈折率
20 · n20/D 1.431
闪点
110 °C · 110 °C

化学的性質

化学的特性White solid

安全と法規制

GHS分類

GHS Classification · 6 件

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.

危険有害性情報

Regulatory Information · 4 件

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 件

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

法規制情報

Regulatory Information · 4 件

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

安全データ

wgk
3
tsca
TSCA listed
rtecs
US8400000
ridadr
UN 2811 6.1/PG 2
毒性
LD50 orally in Rabbit: 140 mg/kg LD50 dermal Rabbit 90 mg/kg
hs_code
29333999

化学と産業

用途と製造

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 件

Pharmaceutical and Medicine Manufacturing

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

応用分野 · 5 件

解説4-ジメチルアミノピリジン,融点112~113 ℃.水,エタノール,ベンゼン,クロロホルムに易溶,エーテルに可溶.アルシル化やアルキル化の触媒に用いられる.酸無水物を用いた第三級アルコールのアシル化などで顕著な効果がみられる.森北出版「化学辞典(第2版)

用途ペプチド合成におけるカップリング反応用、有機合成原料。

用途N,N-ジメチル-4-アミノピリジン (N,N-dimethyl-4-aminopyridine) は様々な有機合成反応で触媒として用いられる求核剤、強塩基である。4-(ジメチルアミノ)ピリジン、4-ジメチルアミノピリジンとも呼ばれ、DMAP(ディーマップ)と略称される。利用例として酸無水物のエステル化、ベイリス?ヒルマン反応、シリル化、トリチル化、シュテークリヒ転位、シュタウディンガー反応などが挙げられる。

使用4-Dimethylaminopyridine (Valaciclovir EP Impurity G; Valacyclovir USP Related Compound G) is a highly efficient catalyst for acylation reactions.

一般的な説明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.

調製方法

純化方法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.

上流・下流製品情報

下流製品

1-[4-(Trifluoromethyl)pyrimid-2-yl]piperazine2-ヒドロキシ-4-(トリフルオロメチル)ピリミジン2-クロロ-4-(トリフルオロメチル)ピリミジンドセタキセル1-[2-(ピロリジン-1-イル)エチル]ピペラジン5-(Trifluoromethyl)-1-methyl-1H-pyrazole1-tert-Butyl-5-(trifluoromethyl)-1H-pyrazole-4-carbaldehydePiperazine-1,4-dicarboxylic acid tert-butyl ester methyl ester2-Hydrazinyl-1-morpholinoethanoneN-メチル-4-(トリフルオロメチル)アニリン1-メチル-3-トリフルオロメチル-1H-ピラゾール1-アセチル-5-ブロモインドリン

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