4-二甲氨基吡啶(DMAP)

4-(Dimethylamino)pyridine

HCID 14284CAS 1122-58-3

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

4-Dimethylaminopyridine1122-58-3N,N-Dimethylpyridin-4-aminedmap4-(Dimethylamino)pyridine4-Pyridinamine, N,N-dimethyl-DTXSID0044369PFP1R6P0S84-DMAPDTXCID80243694-[dimethylamino]pyridineRefChem:98776
展开更多名称
二甲氨基吡啶4-二甲胺吡啶匹杉琼杂质144-二甲氨基吡DMAP 溶液伐昔洛韦杂质3盐酸伐昔洛韦G4-二甲胺基吡啶4-二甲氨基吡啶4-二甲基氨砒啶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

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

实验与物化性质

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

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

化学性质

白色结晶粉末

安全与法规

GHS分类

GHS Classification · 6 条

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 · 4 条

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 条

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 · 4 条

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

化学与工业

用途与制造

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 条

Pharmaceutical and Medicine Manufacturing

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

应用领域 · 7 条

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%。

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

供应商50 家

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]

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