基本信息
- 标准SMILES
COc1ccc(CC(=O)O)cc1- InChIKey
NRPFNQUDKRYCNX-UHFFFAOYSA-N- 分子式
- C9H10O3
- 平均分子量
- 166.17 g/mol
- 单同位素质量
- 166.06299418
概述
4-methoxyphenylacetic acid appears as pale yellow or off white colored flakes. Severely irritates skin and eyes. May be toxic by ingestion.
名称与标识
- 首选名称
- 4-Methoxyphenylacetic Acid
- IUPAC
- 2-(4-methoxyphenyl)acetic acid
- 中文名
- 对甲氧基苯乙酸
- 英文名
- 4-Methoxyphenylacetic acid
- 分子式
- C9H10O3
- 分子量
- 166.17
名称与别名
展开更多名称
数据库标识
- CAS
104-01-8- PubChem CID
- 7690
- DTXSID
DTXSID1059288- ChEMBL
CHEMBL1760597- ChEBI
CHEBI:55501- UNII
- AJP2V8U5K6
- EC Number
- 203-166-4
- Nikkaji
- J10.116H
性质
结构计算性质
- XLogP
- 1.4
- 极性表面积
- 46.5 Ų
- 氢键供体
- 1
- 氢键受体
- 3
- 可旋转键
- 3
- 重原子
- 12
- 形式电荷
- 0
- 复杂度
- 148
实验与物化性质
LogP
1.42
1.48
Physical Description
4-methoxyphenylacetic acid appears as pale yellow or off white colored flakes. Severely irritates skin and eyes. May be toxic by ingestion.
Solid
Collision Cross Section
122.84 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
137.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
物理化学性质
- 熔点
- 84 · 84-86 °C(lit.)
- 沸点
- 140 °C3 · 140 °C3 mm Hg(lit.)
- 堆积密度
- 440 kg/m3 · 440kg/m3
- 密度
- 1.1708 · 1.1708 (rough estimate)
- 蒸气压
- 0.071 Pa · 0.071Pa at 25℃
- 折射率
- 1.5101 · 1.5101 (estimate)
- 闪点
- 193 °C · 193°C
- 储存条件
- 30 °C · Store below +30°C.
- 溶解度
- 6 g/l · 6g/l
- 酸度系数(pKa)
- 1 · pK1:4.358 (25°C)
- 形态
- Crystalline Powder and Chunks
- 颜色
- White to light yellow
- 水溶解性
- 6 g/L · 6 g/L (20 ºC)
- BRN
- 1101737 · 1101737
- InChI
- 1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
- InChIKey
- NRPFNQUDKRYCNX-UHFFFAOYSA-N
- SMILES
- COc1ccc(CC(O)=O)cc1
- LogP
- 1.295 at · 1.295 at 25℃
- CAS 数据库
- 104 · 104-01-8(CAS DataBase Reference)
- NIST化学物质信息
- 4 · Benzeneacetic acid, 4-methoxy-(104-01-8)
- EPA化学物质信息
- 4 · Benzeneacetic acid, 4-methoxy- (104-01-8)
化学性质
白色片状结晶体。熔点为86-88.5℃,沸点140℃(0.4kPa)。溶于乙醇和乙醚。
安全与法规
GHS分类
GHS Classification
Warning
H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1334 reports by companies from 8 notifications to the ECHA C&L Inventory.
危害信息
Regulatory Information
Chemical: Benzeneacetic acid, 4-methoxy-
Status: Cease Manufacture Update: 30-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18981
4-Methoxphenylacetic Acid: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
安全与防护
安全数据
- wgk
- 3
- tsca
- TSCA listed
- RTECS号
- AI8960000
- hazard_note
- Irritant
- 存储类别
- 11 - Combustible Solids
- 安全说明
- 26-36
- 海关编码
- 29189090
- 危险品标志
- Xn,Xi
- 危险性类别
- Eye Dam. 1
- 危险类别码
- 22-36/37/38-20/21/22
化学与工业
用途与制造
应用领域
简介对甲氧基苯乙酸(4-methoxyphenylacetic acid),通常为白色片状晶体,熔点为84-86℃,易溶于热水、乙酸乙酯、乙醇、乙醚等,可溶于冷水。对甲氧基苯乙酸是合成新一代抗抑郁药文发拉新(Venlafaxine)的中间体,也是合成葛根素、异黄酮类等多种心血管药物的关键性中间体。
用途对甲氧基苯乙酸是一种重要的医药中间体,广泛地应用于医药、染料等方面。
用途用于有机合成,用作葛根素的中间体。
制备方法
合成方法关于对甲氧基苯乙酸的合成方法,国内外的报道主要有以下几种: a)氰化法,一般用对甲氧基苄氯和氰化钠反应生成对甲氧基苯乙腈,后者经水解得到对甲氧基苯乙酸,这种方法要使用剧毒的氰化物,因而存在严重的安全隐患; b)苯乙酮重排法,该法常以对甲氧基苯乙酮原料,与硫磺和六水哌嗪反应,经过重排及水解得到对甲氧基苯乙酸,但该法生成的硫化氢剧毒奇臭,收率也不高; c)羰基合成法,该法以对甲氧基氯苄为原料,在催化剂作用下,与CO 反应生成对甲氧基苯乙酸,这种方法的缺点是所使用的催化剂价格昂贵,CO 危害性也较大。
生产方法由对甲氧基苯乙酮为原料制得。将乙醇、硫磺及六水哌嗪加入反应锅中回流4h,然后蒸出乙醇。将所得硫化哌嗪与对甲氧基苯乙酮在135-140℃反应20h,再加入氢氧化钠回流20h。反应结束后,冷至35℃以下,用盐酸调整pH值至8-9。用离心机分出硫磺后,再中和至pH值为3-4,冷却,离心脱水,将所得粗品精制即得对甲氧基苯乙酸。
上下游产品信息
上游原料
下游产品
试剂价格
- A14399 · 100g
- 4-甲氧基苯乙酸, 98+%4-Methoxyphenylacetic acid, 98+% — 221元
- 12602 · 250g
- 4-甲氧基苯乙酸4-Methoxyphenylacetic acid, 99%, Thermo Scientific™ — 730元
供应商50 家
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