2,5-ジメチルアニリン

2,5-ジメチルアニリン · 2,5-キシリジン · p-キシリジン · 2,5-ジメチルベンゼンアミン · 2，5キシリジン · ２，５ジメチルアニリン · 2,5‐キシリジン · 2,5-XYLIDINE

識別子と物理属性

CAS No.	95-78-3
分子式	C8H11N
平均分子量	121.18 g/mol
単同位体質量	121.08914935 g/mol
SMILES	Cc1ccc(C)c(N)c1
InChIKey	VOWZNBNDMFLQGM-UHFFFAOYSA-N
PubChem CID	7259
ChEMBL	CHEMBL249120
ChEBI	CHEBI:518305
EC No.	202-451-0
DTXSID	DTXSID3026306
現地名	2,5-ジメチルアニリン

化学・物理的性質

XLogP	1.8
極性表面積	26
水素結合供与体数	1
水素結合受容体数	1
回転可能結合数	0
重原子数	9
形式電荷	0
複雑度	90.6
医薬品	Pharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties	13C nuclear magnetic resonance spectrum
LogP（分配係数）	log Kow = 1.83 at pH 7.4
密度	0.979 at 70 °F (NTP, 1992) - Less dense than waterwill float0.9790 @ 21 °C/4 °CRelative density (water = 1): 0.980.973 g/mL at 25 °C(lit.)
Color/Form	YELLOW LEAF FROM PETROLEUM ETHERColorless to yellow oilYellow liquid or solid
溶解度	less than 1 mg/mL at 64 °F (NTP, 1992)Sol in ether, carbon tetrachlorideSLIGHTLY SOL IN ETHANOLSoluble in oxygenated solvents.5600 mg/l at 12 °C in waterChloroform (Slightly), Dichloromethane (Slightly), DMSO (Sparingly)<0.1 g/100 mL で 18 ºC
引火点	201 °F (NTP, 1992)93 °C
沸点	417 °F at 760 mmHg (NTP, 1992)214 °C @ 760 MM HG218 °C218 °C(lit.)
Decomposition	When heated to decomp, xylidines emit highly toxic fumes. /Xylidines/
融点	59.9 °F (NTP, 1992)15.5 °C11.5 °C(lit.)
蒸気密度	4.18 (NTP, 1992) - Heavier than airwill sink (Relative to Air)Relative vapor density (air = 1): 4.19
臭気閾値	Odor threshold in air= 1.00X10+12 molecules/cc. /Xylidine/Threshold for xylidine is 0.0240 mg/cu m /Xylidine/
蒸気圧	20Pa
屈折率	n20/D 1.559(lit.)
貯蔵条件	Store below +30°C.
外観・状態	液体
pKa（酸解離定数）	pK1:4.53(+1) (25°C)
色	澄んだ黄色から赤褐色
Merck	14,10084
BRN	2205178
ヘンリー定数	2.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
InChI	1S/C8H11N/c1-6-3-4-7(2)8(9)5-6/h3-5H,9H2,1-2H3
InChIKey	VOWZNBNDMFLQGM-UHFFFAOYSA-N
SMILES	Cc1ccc(C)c(N)c1
LogP（分配係数）	1.83
CAS データベース	95-78-3(CAS DataBase Reference)
NISTの化学物質情報	Benzenamine, 2,5-dimethyl-(95-78-3)
EPAの化学物質情報	2,5-Dimethylaniline (95-78-3)

化学的特性

clear yellow to red-brown liquid

安全性と法規制

GHS 分類	DangerH301+H311+H331 (37.6%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 101 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
規制情報	Chemical: Benzenamine, 2,5-dimethyl-Status: Active Update: 24-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/108612,5-Dimethylaniline: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報	IMAP assessments - Xylidines: Human health tier II assessment
輸送ラベル（DOT）	Poison
火災危険	This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 93 °C explosive vapour/air mixtures may be formed.
健康有害性	SYMPTOMS: Symptoms of exposure to this compound may include headaches, drowsiness, cyanosis, mental confusion, anorexia, convulsions, nervous system and blood effects, fatigue, loss of appetite, dizziness and damage to the lungs, liver and kidneys.
有害性の概要	The major hazards encountered in the use and handling of 2,5-xylidine stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this colorless to yellow oil or leaf may occur from its use as a chemical intermediate for the production of dyes. Contact with 2,5-xylidine may cause burns to the skin and eyes. Death is also a possible outcome from exposure. While the OSHA PEL is set at a TWA of 5 ppm, the ACGIH lists xylidine (mixed isomers) on its 1988-1989 Notice of Intended Changes with a proposed TLV of 0.5 ppm, and a designation of "suspected human carcinogen". In activities or situations where over-exposure may occur, wear a self-contained breathing apparatus, and full chemical protective clothing which is specifically recommended by the shipper or manufacturer to prevent skin contact with xylidine. If contact should occur, immediately flush the affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. Do not eat or smoke in xylidine work areas. While xylidine does not ignite easily, it can burn with the production of irritating or poisonous gases. Also, containers may explode violently in the heat of a fire. Fires involving xylidine may be extinguished with dry chemical, CO2, Halon, or standard foam. Water spray if used, should be applied with caution because it may cause frothing. Fight the fire from a maximum distance and dike runoff from fire control water. Xylidine should be stored away from heat, strong oxidizers, and hypochlorite bleaches. Shipping regulations and other DOT regulatory requirements should be consulted before transport. If xylidine should spill, dike far ahead, then take up with sand or other noncombustible absorbent and place into containers for later disposal. Incineration is a possible form of disposal for xylidine. Before implementing land disposal of waste 2,5-xylidine, consult with environmental regulatory agencies for guidance.

用途

有機合成原料。

使用

2,5-Dimethylaniline is widely used as raw materials to produce imaging chemicals like organic dyes and pigments. It is also used in the production of antioxidants, pharmaceutical, agricultural, rubber chemicals and other target organic molecules. 2,5-Dimethylaniline was also used in the synthesis of nanocomposite of multi-walled carbon nanotubes embedded in poly(2,5-dimethylaniline). 2,5-Dimethylaniline was used to study the effect of metabolites formed from 2,5-xylidine by fungi on laccase activity. The Fourier transform infrared (FTIR) and Raman spectra of 2,5-dimethylaniline was studied5. It induced transcription of lccIV.

一般的な説明

Dark brown liquid.

製法・合成法

純化方法

Convert p-xylidine to a derivative (see below) which, after recrystallisation, is decomposed with alkali to give the free base. Dry over KOH and fractionally distil. The acetyl derivative has m 142o (from H2O or toluene), and the benzoyl derivative has m 140o (from EtOH). [Beilstein 12 H 1135, 12 IV 2567.]