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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 75
実験および物理化学的性質
Physical Description
Large Crystals
Colorless solid; [Merck Index] Beige crystalline solid; [Sigma-Aldrich MSDS]
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
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 50 mg/mL、透明 · メタノール: 50 mg/mL、透明
- 外見
- プリルした
- 酸解離定数(Pka)
- pKa (20°): 9.7
- 色
- オフホワイトからイエロー
- PH
- 11 · 11 (60g/l, H2O, 20℃)
- 臭い (Odor)
- 特有の臭い
- 水溶解度
- 76 g/L · 76g/L(25℃)
- Merck
- 14 · 14,3389
- BRN
- 110354 · 110354
- 安定性
- 安定。酸、酸化剤と相容れない。
- 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 データベース
- 1122 · 1122-58-3(CAS DataBase Reference)
- NISTの化学物質情報
- 4 · 4-Pyridinamine, N,N-dimethyl-(1122-58-3)
- EPAの化学物質情報
- 4 · 4-(Dimethylamino)pyridine (1122-58-3)
化学的性質
化学的特性White solid
安全と法規制
GHS分類
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.
危険有害性情報
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
法規制情報
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
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
- 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
- 化審法
- (5)-5479
- 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
- packing_group
- II
- 自然発火温度
- 420 °C
- Hazard Classifications
- Acute Tox. 2 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2STOT SE 1
- ストレージクラス
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
化学と産業
用途と製造
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
4-Pyridinamine, N,N-dimethyl-: ACTIVE
応用分野
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.
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