N,N-dimethylpyridin-4-amine

• ChemBase编号: 8556
• 分子式: C7H10N2
• 平均质量: 122.1677
• 单一同位素质量: 122.08439833
• SMILES: c1cc(ccn1)N(C)C
• Canonical SMILES: CN(c1ccncc1)C
• InChI: InChI=1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3
• InChIKey: VHYFNPMBLIVWCW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N,N-dimethylpyridin-4-amine
• IUPAC系统名: 4-(dimethylamino)azine; N,N-dimethyl-4-aminoazine; 4-(dimethylamino)azabenzene; N,N-dimethyl-4-aminoazabenzene
• IUPAC传统名: 4-dimethylaminopyridine
• 别名: ChemDose™，4-(二甲氨基)吡啶浸渍片剂; DMAP，ChemDose™ 浸渍片剂; 4-(二甲氨基)吡啶，ChemDose™ 片剂; DMAP 溶液; 4-(二甲氨基)吡啶 溶液; 4-(二甲氨基)吡啶; 4-二甲基氨基吡啶; 4-Dimethylaminopyridine; N,N-dimethylpyridin-4-amine; 4-(dimethylamino)pyridine; N,N-dimethyl-4-aminopyridine; 4-DIMETHYLAMINO PYRIDINE; N,N-Dimethylpyridin-4-amine; DMAP; 4-(Dimethylamino)pyridine; ChemDose™, 4-(Dimethylamino)pyridine impregnated tablets; DMAP, ChemDose™ impregnated tablets; 4-(Dimethylamino)pyridine, ChemDose™ tablets; DMAP solution; 4-(Dimethylamino)pyridine solution; 4-(Dimethylamino)pyridine

登记号

• CAS号: 1122-58-3
• EC号: 214-353-5
• MDL号: MFCD00006418
• Beilstein号: 3539759; 110354
• PubChem SID: 24846774; 24874123; 24874122; 160971863; 24864562
• PubChem CID: 14284
• Chemspider ID: 13646
• 维基百科标题: 4-Dimethylaminopyridine

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.11969553
• LogD (pH = 7.4): 0.008813705
• Log P: 0.86361724
• 摩尔折射率: 38.3297 cm^3
• 极化性: 14.25138 Å^3
• 极化表面积: 16.13 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: methanol: soluble0.1 g/mL, clear; methanol: soluble0.1 g/mL, clear, colorless to almost colorless
• 外观: prilled; white to off-white
• 熔点: 108-110 °C(lit.); 110-113 °C; 110-113°C; 110-113°C; 111-114 °C; 112°C; 112-114°C
• 沸点: 162 °C at 50 mmHg; 162°C/50mm; 162°C/50mm
• 闪点: 0 °F; 110 °C; 124°C; 124°C(255°F); -18 °C; 230 °F; 25 °F; -4 °C
• 密度: 0.884 g/mL at 25 °C; 0.906 g/mL at 25 °C
• 折射率: n20/D 1.384; n20/D 1.417

安全信息

• 保存注意事项: TOXIC; Very Toxic/Corrosive/Light Sensitive/Store under Argon
• RTECS编号: US9230000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 易燃性(Flammable) (F); 有毒(Toxic) (T); 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 1992; 2811; UN2928
• 德国WGK号: 3
• 联合国危险货物等级: 3; 6.1
• 联合国危险货物包装类别(PG): 1; 2; I
• 危险公开号: 11-22-27-36/37; 11-22-27-36-66-67; 22-27-34; 25-27-36/37/38; 25-27-36/37/38-40; R:22-27-34
• 安全公开号: 16-26-28.1; 16-26-28.1-29-33-36/37/39-45; 26-27/28-36/37/39-45-60; 26-28-36/37/39-45; 26-28-36/37-45; S:27/28-29-36/37/39-45
• TSCA收录: true; 是
• GHS危险品标识: GHS05; GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H310-H314-H318; H301-H310-H315-H319-H335; H302-H310-H315-H319-H335-H351
• GHS警示性声明: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P280-P301 + P310-P302 + P350-P305 + P351 + P338-P310; P261-P280-P302 + P350-P305 + P351 + P338-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1992 3/PG 2; UN 2811 6.1/PG 1

产品相关信息

• 纯度: ≥98.0% (NT); ≥99%; ≥99.0% (NT); 98%; 99%
• 浓度: 0.5 M in ethyl acetate; 0.5 M in THF
• 级别: puriss.; purum; ReagentPlus®
• Empirical Formula (Hill Notation): C7H10N2

详细说明

Sigma Aldrich - 39405

Application
酰化反应的高效催化剂
Other Notes
超强亲核酰化反应催化剂。综述1,2,3

Sigma Aldrich - 700169

Legal Information
ChemDose 是 Reaxa Ltd. 的注册商标。受国际专利申请号 PCT/DK05/000428 和相关专利申请（包括欧洲专利申请号05753717.7）保护。
法律信息
ChemDose 商标 Reaxa Ltd.

Sigma Aldrich - 714720

包装
100 mL in Sure/Seal™

Sigma Aldrich - 522821

Application
酰化反应的高效催化剂
包装
100, 500 g in glass bottle
Legal Information
Reilly Industries, Inc. 产品
Quality
低尘，自由流动

Sigma Aldrich - 107700

Application
与 TiCl4 共同用于硅烯酮缩醛和羧酸的 Claisen 缩合反应，生成 β-酮酸酯。
酰化反应的高效催化剂
包装
5, 25, 100 g in glass bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 714844

包装
100 mL in Sure/Seal™

Sigma Aldrich - 522805

Application
酰化反应的高效催化剂
包装
5 g in glass bottle

Sigma Aldrich - D5640

Application
酰化反应的高效催化剂

Sigma Aldrich - 29224

Application
酰化反应的高效催化剂

MP Biomedicals - 05222621

MP Biomedicals Rare Chemical collection

参考文献

• Hypernucleophilic catalyst. Greatly accelerates the acylation of hindered, including tertiary, alcohols; reviews: Angew. Chem. Int. Ed., 17, 569 (1978). Chem. Soc. Rev., 12, 129 (1983). Catalyst for acylation of alcohols using mixed anhydrides of hindered carboxylic acids with methanesulfonic acid: Synth. Commun., 12, 727 (1982), and with mixed carboxylic anhydrides: J. Org. Chem., 50, 560 (1985). In the Yamaguchi method of macrocyclic lactonization the mixed anhydride formed with 2,4,6-Trichlorobenzoyl chloride, L14159 is cyclized with 2 equiv. of DMAP; high dilution conditions are not required: Bull. Chem. Soc. Jpn., 52, 1989 (1979). For improved method in a high yield synthesis of erythronolide A, see: J. Org. Chem., 55, 7 (1990).
• Greatly increases the rate of ester and thio ester formation in the carbodiimide method of coupling (Steglich esterification): Angew. Chem. Int. Ed., 17, 522 (1978). For similar use in macrolactonizations, see: J. Org. Chem., 50, 2394 (1985), and in carbodiimide peptide coupling reactions: Int. J. Pept. Prot. Res., 18, 459 (1981). For peptide reagents, see Appendix 6.
• Effective catalyst for transesterification of ?-keto esters in toluene: J. Org. Chem., 50, 3618 (1985), and for smooth decarboalkoxylation of enolizable ?-keto esters in toluene containing a small amount of water: J. Org. Chem., 54, 3474 (1989). Under these conditions, other bases (N,N-dimethylaniline, pyridine, tetra-n-pentylammonium bromide) are ineffective.
• Also useful as a catalyst for various alkylations. For use in formation of trityl ethers, see: Tetrahedron Lett., 95, (1979); extension to mono- and di-methoxytrityl ethers: Tetrahedron Lett., 21, 3899 (1980); J. Org. Chem., 47, 571 (1982); Chem. Lett., 15 (1982); J. Am. Chem. Soc., 104, 1316 (1982). Useful in silylation of alcohols to give TBDMS ethers: Tetrahedron Lett., 99, (1979).
• Catalyst in a simple preparation of N-Boc-amides, using Di-tert-butyl dicarbonate, A14708: Acta Chem. Scand. B, 40, 745 (1986); and also of N-Boc-pyrroles: Org. Synth. Coll., 9, 121 (1998).
• Reacts with thionyl chloride to form the chlorosulfinyl chloride, an effective reagent for the conversion of acids to their acid chlorides: Synth. Commun., 12, 1139 (1982), and for the dehydration of aldoximes to nitriles: Synthesis, 472 (1983).
• For a brief feature on the uses of this reagent in synthesis, see: Synlett, 1568 (2003). Review of developments in the search for optimal reactivity and selectivity with 4-(dialkylamino)pyridines: Angew. Chem. Int. Ed., 43, 5436 (2004).