M-디니트로벤젠

1,3-다이나이트로벤젠 · 1,3-디니트로벤젠 · M-디니트로벤젠 · m-Dinitro벤젠 · M-DINITROBENZENE · m-dnb · meta-dinitrobenzene · 2,4-Dinitrobenzene

https://huagongshe.com/ko/chemical/7452

식별자 및 물리적 특성

CAS No.	99-65-0
분자식	C6H4N2O4
평균 분자량	168.11 g/mol
단동위원소 질량	168.01710661 g/mol
SMILES	O=[N+]([O-])c1cccc([N+](=O)[O-])c1
InChIKey	WDCYWAQPCXBPJA-UHFFFAOYSA-N
PubChem CID	7452
ChEMBL	CHEMBL114070
ChEBI	CHEBI:51397
EC No.	202-776-8
DTXSID	DTXSID9024065
현지명	M-디니트로벤젠

화학 및 물리적 성질

XLogP	1.5
극성 표면적	91.6
수소 결합 공여자 수	0
수소 결합 수용자 수	4
회전 가능 결합 수	0
무거운 원자 수	12
형식 전하	0
복잡도	175
물질 분류	Nitrogen Compounds -> Nitros, AromaticReactive agents - 4th degree
의약품	Pharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties	13C nuclear magnetic resonance spectrum
농약	Pesticide -> EPA IRIS
LogP(분배 계수)	log Kow= 1.49
밀도	1.58 at 64.4 °F (USCG, 1999) - Denser than waterwill sink1.575 @ 18 °C/4 °C1.6 g/cm³1.5751 @ 18°C
Color/Form	Yellowish crystalsColorless to yellow, rhombic needles or platesPale white or yellow, crystalline solid.
용해도	0.02 % (NIOSH, 2024)1 g dissolves in 2000 ml cold water, 320 ml boiling water1 g dissolves in 37 ml alcohol, 20 ml boiling alcoholfreely sol in chloroform, ethyl acetateVery soluble in acetone and ethanolsoluble in etherIn water, 533 mg/l @ 25 °CSolubility in water: very poor0.02%클로로포름(약간 용해됨), DMSO(약간 용해됨), 메탄올(아주 약간)
Corrosivity	Liquid dinitrobenzene will attack some forms of plastics, rubber, and coatings. /Dinitrobenzene, all isomers/
인화점	302 °F (NIOSH, 2024)302 °F (CLOSED CUP)149 °C150 °C
끓는 점	556 °F at 756 mmHg (NTP, 1992)302.8 °C @ 770 mm Hg300-303 °C291 °C @760 [mm Hg]572 °F297 °C(lit.)
Decomposition	When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
녹는점	86 °C
증기압	8.15 x 10-4 mmHg at 35 °C (Hine et al., 1963)
굴절률	1.4660 (estimate)
저장 조건	2-8°C
물리적 상태	고체
비중	1.368
색상	흰색에서 황색을 띠는 결정
용해도	500mg/L(20℃)
비열	Cp(crystal): 1.17 J/(g·K), at 25℃
Merck	14,3273
BRN	1105654
헨리 상수	1.8×102 mol/(m3Pa) at 25℃, Chao et al. (2017)
유전율	2.8(20.0℃)
안정성	안정적인. 환원제, 산화제, 강염기와 호환되지 않습니다. 가열하면 폭발할 수 있음.
주요 응용	환경
InChI	1S/C6H4N2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H
InChIKey	WDCYWAQPCXBPJA-UHFFFAOYSA-N
SMILES	[O-][N+](=O)c1cccc(c1)[N+]([O-])=O
NIST	Benzene, 1,3-dinitro-(99-65-0)
EPA	m-Dinitrobenzene (99-65-0)

화학적 성질

orange to yellow crystalline powder. Freely soluble in benzene, chloroform, ethyl acetate, soluble in alcohol, slightly soluble in water. Can evaporate with water vapour.

안전 및 규제

GHS 분류	DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
규제 정보	Chemical: Benzene, 1,3-dinitro-Hazard Traits - NeurotoxicityReproductive Toxicity1,3-Dinitrobenzene: Does not have an individual approval but may be used under an appropriate group standardThe 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	Behavior in Fire: May explode (USCG, 1999)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
화재 가능성	Combustible
건강 유해성	Inhalation or ingestion causes loss of color, nausea, headache, dizziness, drowsiness, and collapse. Eyes are irritated by liquid. Stains skin yellowif contact is prolonged, can be absorbed into blood and cause same symptoms as for inhalation. (USCG, 1999)
유해성 요약	Methemoglobinemia, liver injury, and visual impairment (central scotomas) have been reported in exposed workers. Listed in table of Industrial Chemicals for Which Methemoglobin Formation is the Principal Cause of Toxicity[ACGIH] m-Dinitrobenzene was eliminated from in vitro testing after little response was detected, even at high concentrations. [French CL et al. Potency ranking of methemoglobin-forming agents. J Appl Toxicol. 15(3):167-74 (1995).]An eye and respiratory tract irritantCan induce methemoglobinemia and have effects on the liver[ICSC]The major hazards encountered in the use and handling of 1,3-dinitrobenzene stem from its toxicologic properties and explosivity. Toxic by all routes (ie, inhalation, ingestion, dermal absorption), exposure to this yellowish, crystalline substance may occur from its use in the production of analine, dyes, explosives, industrial solvents, and pesticides. Effects from exposure mayinclude contact burns to the skin and eyes, headache, nausea, lethargy, heart palpitations, methemoglobinemia, jaundice, and respiratory failure. Effects may be delayed up to 1-4 hours. OSHA has established an 8 hour, Time Weighted Average (TWA) limit of 1 mg/cu m, with a skin designation for this substance. 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 discarded or left at the site for cleaning before being reworn. 1,3-Dinitrobenzene is a severe explosion hazard when exposed to friction, mechanical shock, localized thermal shock, or contamination. For fires involving 1,3-dinitrobenzene, extinguish with dry chemical, CO2, water spray, fog, or standard foam. Fight the fire from as far a distance as possible in an explosion-resistant location. If fire is massive, back off, protect surroundings, and let burn. 1,3-Dinitrobenzene may be transported via air, rail, road, and water, in containers bearing the label, "Poison." 1,3-Dinitrobenzene should be stored in a permanent magazine, away from heat, sources of ignition, sources of physical damage, oxidizers, combustibles, caustics, and metals such as tin and zinc. For small spills of 1,3-dinitrobenzene, use a clean shovel to place material into clean, dry, covered containers for later disposal (liquid solutions are taken up with sand or other noncombustible absorbent). Dike far ahead of large liquid spills to prevent runoff. Large dry spills should be covered with plastic sheeting. Large spills into bodies of water should be trapped at the bottom with sand bag barriers, apply activated carbon, and use mechanical dredges or lifts to remove immobilized masses.

용도

개요

1,3-Dinitrobenzene (1,3-DNB) is an impurity present in the manufacture of 2,4,6-trinitrotoluene. Workers in munitions plants are at risk of exposure. While it does not bioaccumulate, it persists in the environments (air, water, and soil) with slow rates of degradation. Metabolism in animals (rabbits) results in reduction of the nitro functionalities to amine functionalities to produce 2,4-diaminophenol, m-nitroaniline, m-phenylenediamine, and 2-amino-4-nitrophenol. Human exposure is generally dermal contact or inhalation of vapor.

용도

1,3-Dinitrobenzene (1,3-DNB) is an impurity present in the manufacture of 2,4,6-trinitrotoluene. Dinitrobenzene (as a mixture of 1,2-dinitro- 1,3-dinitro- and 1,4-dinitro-isomers) is used in the manufacture of dyes and explosives, and in organic syntheses.

일반 설명

1,3-Dinitrobenzene is a yellow solid with a slight odor. Sinks in water. (USCG, 1999)

제조 및 합성 방법

제조 방법

1,3-Dinitrobenzene is accessible by nitration of nitrobenzene. The reaction proceeds under acid catalysis using sulfuric acid. The directing effect of the nitro group of nitrobenzene leads to 93% of the product resulting from nitration at the meta-position. The ortho- and para-products occur in only 6% and 1%, respectively.