基本信息
- 标准SMILES
CN(C)c1ccncc1- InChIKey
VHYFNPMBLIVWCW-UHFFFAOYSA-N- 分子式
- C7H10N2
- 平均分子量
- 122.17 g/mol
- 单同位素质量
- 122.08439833
名称与标识
- 首选名称
- 4-(Dimethylamino)pyridine
- IUPAC
- N,N-dimethylpyridin-4-amine
- 中文名
- 4-二甲氨基吡啶(DMAP)
- 英文名
- 4-Dimethylaminopyridine
- 分子式
- C7H10N2
- 分子量
- 122.17
名称与别名
展开更多名称
数据库标识
- 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
性质
结构计算性质
- XLogP
- 1.3
- 极性表面积
- 16.1 Ų
- 氢键供体
- 0
- 氢键受体
- 2
- 可旋转键
- 1
- 重原子
- 9
- 形式电荷
- 0
- 复杂度
- 75
实验与物化性质
Physical Description
Large Crystals
Colorless solid; [Merck Index] Beige crystalline solid; [Sigma-Aldrich MSDS]
物理化学性质
- 熔点
- 112 °C · 112 °C
- 沸点
- 162 °C · 162 °C
- 堆积密度
- 520 kg/m3 · 520kg/m3
- 密度
- 0.906 g/mL · 0.906 g/mL at 25 °C
- 蒸气压
- 0.169 hPa · 0.169 hPa at 20 °C
- 折射率
- 20 · n20/D 1.431
- 闪点
- 110 °C · 110 °C
- 储存条件
- 30 °C · Store below +30°C.
- 溶解度
- 50 mg/mL, · methanol: 50 mg/mL, clear
- 酸度系数(pKa)
- pKa (20°): 9.7
- 形态
- prilled
- 颜色
- off-white to yellow
- 气味 (Odor)
- characteristic odor
- PH值
- 11 · 11 (60g/l, H2O, 20℃)
- 酸碱指示剂变色ph值范围
- 9.7 · 9.7 (10% aq soln)
- 水溶解性
- 76 g/L · 76 g/L (25 ºC)
- Merck
- 14 · 14,3389
- BRN
- 110354 · 110354
- 稳定性
- 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 数据库
- 1122 · 1122-58-3(CAS DataBase Reference)
- NIST化学物质信息
- 4 · 4-Pyridinamine, N,N-dimethyl-(1122-58-3)
- EPA化学物质信息
- 4 · 4-(Dimethylamino)pyridine (1122-58-3)
化学性质
白色结晶粉末
安全与法规
GHS分类
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.
危害信息
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
法规信息
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
安全数据
- wgk
- 3
- tsca
- TSCA listed
- 毒性
- LD50 orally in Rabbit: 140 mg/kg LD50 dermal Rabbit 90 mg/kg
- RTECS号
- US8400000
- hazard_note
- Toxic/Corrosive
- 包装类别
- II
- 危险等级
- 8
- 存储类别
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- 安全说明
- 36/37/39-45-28A-26-28-36/37-53-27-22-16
- 海关编码
- 29333999
- 自燃温度
- 420 °C
- 危险品标志
- T,C,T+,Xn,F
- 危险性类别
- Acute Tox. 2 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Irrit. 2STOT SE 1
- 危险类别码
- 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
- 危险品运输编号
- UN 2811 6.1/PG 2
化学与工业
用途与制造
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
4-Pyridinamine, N,N-dimethyl-: ACTIVE
应用领域
简介4-二甲氨基吡啶,常用简称DMAP,是一种超强亲核的酰化作用催化剂。其结构上供电子的二甲氨基与母环(吡啶环)的共振,能强烈激活环上的氮原子进行亲核取代,显著地催化高位阻,低反应性的醇和胺/酸的酰化/酯化反应,其活性约为吡啶的104~106倍。 酰基转移是自然界和有机合成中常见的转化,其中手性DMAP是常见的不对称酰基转移催化剂。自1996年,Vedejs和Fu小组分别报道中心手性和面手性的DMAP催化剂以来,手性DMAP催化剂得到了极大的发展,各种中心手性、面手性、螺手性和中心手性的DMAP陆续报道,且在许多不对称酰基转移反应中得到了很好的应用。
应用4-二甲氨基吡啶是一种广泛应用于化学合成的新型高效催化剂,在有机合成、药物合成、农药、染料、香料等合成的酰化、烷基化、醚化等多种类型的反应中有较高的催化能力,对提高收率有极其明显的效果。
用途4-二甲氨基吡啶是一种广泛应用于化学合成的新型高效催化剂,在有机合成、药物合成、农药、染料、香料等合成的酰化、烷基化、醚化等多种类型的反应中有较高的催化能力,对提高收率有极其明显的效果。
用途用作超强亲核的酰化作用催化剂
用途酯化反应中的高效催化剂
用途广泛用于化学合成的催化剂,在有机药物合成、农药、染料、食品添加剂等合成的酰化、羰基化、醚化及酯化等。 4-二甲氨基吡啶是近年来广泛用于化学合成的新型高效催化剂,其结构上供电子的二甲氨基与母环(吡啶环)的共振,能强烈激活环上的氮原子进行亲核取代,显著地催化高位阻、低反应性的醇和胺的酰化(磷酰化、磺酰化、碳酰化)反应,其活性约为吡啶的104-6倍。在有机合成、药物合成、农药、医药、染料、香料、高分子化学、分析化学中的酰化、烷基化、醚化、酯化及酯交换等多种类型的反应中有较高的催化能力,对提高收率有极其明显的
用途一种用于酰化反应的高效催化剂
制备方法
生产方法将4-羟基吡啶、二甲胺盐酸盐和六甲基磷酰三胺在220℃加热4h。生成的固化反应物用水漂洗,加盐酸在100℃水解1h。冷至室温,搅拌下加入氢氧化钠水溶液,然后用氯仿提取。提取液在用硫酸镁干燥后蒸除溶剂,剩余物用沸腾的己烷提取,热滤,浓缩,结晶,得4-二甲氨基吡啶。收率约55%。
上下游产品信息
上游原料
下游产品
试剂价格
- HY-Y1089R · 25 mg
- 4-二甲氨基吡啶(DMAP)4-Dimethylaminopyridine (Standard) — 360元
- HY-Y1089R · 50 mg
- 4-二甲氨基吡啶(DMAP)4-Dimethylaminopyridine (Standard) — 530元
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