メチルレッド

2-((4-(Dimethylamino)phenyl)diazenyl)benzoic acid

HCID 10303CAS 493-52-7

基本情報

標準SMILES
CN(C)c1ccc(N=Nc2ccccc2C(=O)O)cc1
InChIKey
CEQFOVLGLXCDCX-UHFFFAOYSA-N
分子式
C15H15N3O2
平均分子量
269.3 g/mol
単同位体質量
269.11642672

概要

Methyl red is an azo dye consisting of benzoic acid substituted at position 2 by a 4-[(dimethylamino)phenyl]diazenyl group. It has a role as a dye. It is a member of azobenzenes, a monocarboxylic acid and a tertiary amino compound. It is a conjugate acid of a methyl red(1-).

名称と識別子

優先名称
2-((4-(Dimethylamino)phenyl)diazenyl)benzoic acid
IUPAC
2-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid
現地名
メチルレッド
英語名
Methyl Red
分子式
C15H15N3O2
分子量
269.3

名称と別名

2-((4-(dimethylamino)phenyl)diazenyl)benzoic acid2-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid2-{[4-(dimethylamino)phenyl]diazenyl}benzoic acidDTXSID90859408RefChem:1060520DTXCID70809724Methyl red493-52-7O-METHYL REDC.I. Acid Red 2Acid Red 22-Carboxy-4'-(dimethylamino)azobenzene
名称をさらに表示
アシッドレッド2メチル レッドメチル レッド溶液メチルレッド (0.04%水溶液)メチルレッド (0.1%, 約95%エタノール溶液)C.I.アシッドレッド22-(4-ジメチルアミノフェニルアゾ)安息香酸2-[[4-(ジメチルアミノ)フェニル]アゾ]安息香酸o-メチルレッド4'-ジメチルアミノアゾベンゼン-2-カルボン酸2-カルボキシ-4'-(ジメチルアミノ)アゾベンゼン4-(ジメチルアミノ)アゾベンゼン-2'-カルボン酸4'-(ジメチルアミノ)アゾベンゼン-2-カルボン酸2-[4-(ジメチルアミノ)フェニルアゾ]安息香酸O-(P-ジメチルアミノフェニルアゾ)安息香酸P-ジメチルアミノアゾベンゼン-O-カルボン酸メチルレッド溶液4-ジメチルアミノアゾベンゼン-2'-カルボン酸メチルレッド - ブロモクレゾールグリーン 混合指示薬メチルレッド ACID-BASE INDICATOR,REAG. PH. EUR.ACID REDMETHYL RED INDICATORMETHYL RED ETHANOLMETHYL RED, NEUTRALMETHYL RED MIXED SOLUTIONMETHYL RED, WATER SOLUBLEMETHYL RED, SPIRIT SOLUBLEMETHYL RED MIXED SOLUTION RMETHYL RED SOLUTION R
4-Dimethylamino-2'-carboxylazobenzenep-(Dimethylamino)azobenzene-o-carboxylic acidCerven methylova2-(4-Dimethylaminophenylazo)benzoic acidCerven kysela 2o-((p-(Dimethylamino)phenyl)azo)benzoic acidBenzoic acid, 2-[[4-(dimethylamino)phenyl]azo]-2-((4-Dimethylamino)phenylazo)benzoic acid

データベース識別子

CAS
493-52-7
PubChem CID
10303
DTXSID
DTXSID90859408
ChEMBL
CHEMBL375971
ChEBI
CHEBI:49770
UNII
69083AX1ZX
Nikkaji
J1.557A

物性

構造計算による物性

XLogP
3.3
極性表面積
65.3 Ų
水素結合供与体数
1
水素結合受容体数
5
回転可能結合数
4
重原子数
20

実験および物理化学的性質

Collision Cross Section175.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1042154]

物理化学的性質

融点
179 · 179-182 °C (lit.)
沸点
412.44 °C · 412.44°C (rough estimate)
比重(密度)
0.839 g/mL · 0.839 g/mL at 25 °C
蒸気密度
9.3 · 9.3 (vs air)
屈折率
1.593 · 1.5930 (estimate)
闪点
11 °C · 11 °C

化学的性質

化学的特性dark red crystalline powder

安全と法規制

安全データ

wgk
1
tsca
TSCA listed
rtecs
DG8960000
ridadr
UN 1170 3/PG 2
hs_code
29270000
risk_code
10-20/21/22-68/20/21/22-68-36/38-23/25-11-36/37/38-34-51/53-39/23/24/25-23/24/25

化学と産業

応用分野 · 5 件

解説〘名〙 (methyl red) 赤~紫色の結晶。化学式は C15H15N3O2 酸塩基指示薬の一つ。酸性側で赤、塩基性側で黄色。変色域は pH4.4~6.2 塩素で酸化をうけ無色になるため、塩素検出にも用いられる。MR と略記される。精選版 日本国語大辞典 精選版

用途pH測定用、中和滴定用指示薬(弱塩基-強酸系)。

用途酸塩基中和滴定指示薬。

使用As indicator in 0.1% alcoholic solution; pH: 4.4 red, 6.2 yellow. Used for titrating NH3, weak organic bases, e.g., alkaloids; not suitable for organic acids, except oxalic and picric acid. Methyl red is easily reduced, thereby losing its color, and readings should be made promptly. It is gradually being replaced by sulfonphthalein indicators, such as bromcresol green, which are more stable and exhibit a sharper change in color.

一般的な説明Methyl red solution is an azo dye which turns to red when pH is below 4.4 (yellow pH < 6.2, orange pH 4.4-6.2). Some bacteria utilize glucose to form large amounts of acid with the result that the pH value of the medium falls distinct. Other species produce no or less free acid. This difference can be visualized by using methyl red. This test is used to differentiate enteric bacteria.

調製方法 · 2 件

製造方法2-Aminobenzoic aciddiazo, and N,N-dimethylaniline coupling.

純化方法The acid is extracted with boiling toluene using a Soxhlet apparatus. The crystals which separate on slow cooling to room temperature are filtered off, washed with a little toluene and recrystallised from glacial acetic acid, *benzene or toluene followed by pyridine/water. Alternatively, dissolve it in aqueous 5% NaHCO3 solution, and precipitate it from a hot solution by dropwise addition of aqueous HCl. Repeat this until the extinction coefficients do not increase. [Beilstein 16 IV 504.]

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補足説明 · 1 件

定義An acid–base indicator that is red in solutions below a pH of 4.2 and yellow above a pH of 6.3. It is often used for the same types of titration as methyl orange but the transition range of methyl red is nearer neutral (pH7) than that of methyl orange. The two molecules are structurally similar.

関連反応

1 件

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