4-니트로톨루엔

4-나이트로톨루엔 · 4-니트로톨루엔 · p-나이트로톨루엔(p-니트로톨루엔) · p-니트로톨루엔 · 1-메틸-4-니트로-벤젠 · p-메틸니트로벤젠 · 1-METHYL-4-NITROBENZENE · PNT

식별자 및 물리적 특성

CAS No.	99-99-0
분자식	C7H7NO2
평균 분자량	137.14 g/mol
단동위원소 질량	137.04767846 g/mol
SMILES	Cc1ccc([N+](=O)[O-])cc1
InChIKey	ZPTVNYMJQHSSEA-UHFFFAOYSA-N
PubChem CID	7473
ChEMBL	CHEMBL155320
ChEBI	CHEBI:35227
EC No.	202-808-0
DTXSID	DTXSID5023792
현지명	4-니트로톨루엔

화학 및 물리적 성질

XLogP	2.4
극성 표면적	45.8
수소 결합 공여자 수	0
수소 결합 수용자 수	2
회전 가능 결합 수	0
무거운 원자 수	10
형식 전하	0
복잡도	122
물질 분류	Nitrogen Compounds -> Nitros, AromaticReactive agents - 1st degree
SpringerMaterials Properties	13C nuclear magnetic resonance spectrum
LogP(분배 계수)	log Kow = 2.372.41
냄새	Bitter almondWeak aromatic odor
밀도	1.286 at 68 °F (USCG, 1999) - Denser than waterwill sink1.1038 at 75 deg/4 °C1.29 g/cm³1.1038 @ 75°C1.121.392 g/mL at 25 °C (lit.)
Viscosity	1.2 mPa (= cP) at 60 °C
Color/Form	Yellowish crystalsColorless rhombic needlesOrthorhombic crystals from alcohol and etherCrystalline solid
용해도	less than 1 mg/mL at 68.9 °F (NTP, 1992)Soluble in alcohol, benzene, ether, chloroform, acetoneSoluble in ethanolvery soluble in ethyl ether, acetone, benzene, carbon tetrachloride, chloroform, pyridine, toluene, carbon disulfide.In water, 442 mg/L at 30 °CIn water, 361 mg/L at 25 °CIn water, 242 mg/L at 20 °C0.26g/L
인화점	223 °F (NTP, 1992)106 °C223 °F (Closed cup)103 °C c.c.
Endocrine Disruptors	Potential endocrine disrupting compound
끓는 점	460.9 °F at 760 mmHg (NTP, 1992)238.3 °CBoiling point: 105 °C at 9 mm Hg238 °C238.3 °C @760 [mm Hg]460 °F238 °C (lit.)
Decomposition	The substance decomposes on heating producing toxic fumes /of/ (nitrogen oxides).Energy of decomposition ( in range 300-420 C) was measured as 1.74 kJ/g by differential scanning calorimetry, and temperature of adiabatic storage which gives an induction time to exothermic decomposition of 24 hours was determined as 232 C by adiabatic Dewar tests, with an apparent energy of activation of 162 kJ/mol. Energy of decomposition of pure 4-nitrotoluene in the range 240-460 C was determined by micro differential scanning calorimetry as 3.52 kJ/g, peaking at 409 C.Decomposes violently at 279 °C and will burn even in absence of air.
녹는점	52-54 °C (lit.)
증기 밀도	4.7 (vs air)
증기압	5 mm Hg ( 85 °C)
굴절률	1.5382
저장 조건	2-8°C
물리적 상태	결정질 고체
pKa(산도 계수)	11.27 (Perrin, 1972)
비중	1.392
색상	노란색
폭발한계	1.6%(V)
용해도	0.35g/L(20℃)
비열	Cp(crystal): 1.26 J/(g·K), at 25℃
Merck	14,6650
BRN	1906911
헨리 상수	5.64 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
유전율	22.2(58.0℃)
안정성	안정성 충격에 민감할 수 있습니다. 황산, 강염기, 환원제, 강산화제와 호환되지 않습니다.
InChI	1S/C7H7NO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3
InChIKey	ZPTVNYMJQHSSEA-UHFFFAOYSA-N
SMILES	Cc1ccc(cc1)[N+]([O-])=O
LogP(분배 계수)	2.37 at 25℃
NIST	Benzene, 1-methyl-4-nitro-(99-99-0)
EPA	p-Nitrotoluene (99-99-0)

화학적 성질

light yellow crystals

안전 및 규제

GHS 분류	DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]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)H301+H311+H331 (33.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]
규제 정보	Chemical: Benzene, 1-methyl-4-nitro-Status: Active Update: 22-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13893Benzene, 1-methyl-4-nitro-: HSNO Approval: HSR002789 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
운송 라벨(DOT)	Poison
화재 위험	Special Hazards of Combustion Products: Yields toxic oxides of nitrogen when burning. (USCG, 1999)Combustible. Risk of fire and explosion on contact with acids or oxidizing agents.
화재 가능성	Combustible when exposed to heat or flame.... Contact with strong oxidizers or sulfuric acid may cause fires ... /Nitrotoluene/
건강 유해성	INHALATION, INGESTION, OR SKIN: Headache, flushed face, dizziness, dyspnea (difficult breathing), cyanosis, nausea, vomiting, muscular weakness, rapid pulse and respiration, irritability, and convulsions. (USCG, 1999)
유해성 요약	Nitrotoluenes (all isomers) have the potential to induce methemoglobinemia in the same manner as aniline and nitrobenzene. [ACGIH] Irritating to the eyesCan induce methemoglobinemia[ICSC]The major hazards encountered in the use and handling of 4-nitrotoluene stem from its toxicologic properties and explosivity. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this bitter-almond-smelling, white-to-yellowish, crystalline substance may occur from its manufacture and use in the synthesis of dinitrotoluene, trinitrotoluene, and various azo and sulfur dye intermediates such as p-toluidine, p-nitrobenzaldehyde and 4-nitro-2-chlorotoluene. Effects from exposure may include contact burns to the skin and eyes, headache, weakness, dizziness, nausea, shortness-of-breath, tachycardia, and methemoglobinemia. The onset of symptoms may be delayed up to 4 hours. OSHA has set a time-weighted-average (TWA) limit of 2 ppm as a final rule to become effective December 31, 1992. Local exhaust ventilation should be applied to control airborne 4-nitrotoluene to permissible limits. In activities and situations where over-exposure may occur, wear a positive pressure self-contained breathing apparatus and chemical protective clothing which is specifically recommended by the shipper or manufacturer. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated clothing should be removed and left at the site for cleaning. While 4-nitrotoluene does not ignite easily, it may burn with the production of irritating or poisonous gases. Also, containers of this substance may explode violently in the heat of a fire. For fires involving 4-nitrotoluene, extinguish with dry chemical, CO2, water spray, fog, or standard foam. Fight fire from as far a distance as possible, and if fire is advanced, evacuate the area. Dike fire control water. 4-Nitrotoluene should be stored away from sources of ignition, heat, strong oxidizers, and sulfuric acid. Small spills of 4-nitrotoluene should be carefully shovelled into a clean, dry container and covered loosely (liquid solutions are taken up with vermiculite, dry sand, or earth). Large dry spills on land should be covered with a plastic sheet to prevent dissolving in the rain or firefighting water, until removal is possible. Large liquid solution spills on land should be diked far ahead of the spill and not allowed to enter water sources or sewers. Spills into bodies of water should be trapped at the bottom with sand bag barriers and removed with suction hoses, or treated with activated carbon and the resulting immobilized masses removed with mechanical dredges or lifts.

용도

4-Nitrotoluene is an explosive material.

일반 설명

A yellow liquid with a weak aromatic odor. Toxic. Insoluble in water. Combustible but may take some effort to ignite. Produces toxic oxides of nitrogen when burned. In a spill, immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater or nearby streams. Used to make other chemicals.

제조 및 합성 방법

생산 방법

After distillation of the meta fraction from the isomer mixture, the still residues are cooled in a crystallizer to separate technical quality 4-nitrotoluene. Further distillation of nitrotoluene residues and fractions should be implemented with great care because this has been reported to cause explosions.