니트로아니솔

2-니트로아니솔 · 니트로아니솔 · 2-나이트로아니솔 · O-나이트로아니솔 · 1-METHOXY-2-NITROBENZENE · NCI-C60388 · 2-NITROANISOL · 2-NITROANISOLE

식별자 및 물리적 특성

CAS No.	29191-53-5
분자식	NO2C6H4OCH3
평균 분자량	153.14 g/mol
단동위원소 질량	153.04259308 g/mol
SMILES	COc1ccccc1[N+](=O)[O-]
InChIKey	CFBYEGUGFPZCNF-UHFFFAOYSA-N
PubChem CID	7048
ChEMBL	CHEMBL166415
ChEBI	CHEBI:48722
EC No.	202-052-1
DTXSID	DTXSID3020962
현지명	니트로아니솔

화학 및 물리적 성질

XLogP	1.7
극성 표면적	55.1
수소 결합 공여자 수	0
수소 결합 수용자 수	3
회전 가능 결합 수	1
무거운 원자 수	11
형식 전하	0
복잡도	143
물질 분류	Nitrogen Compounds -> Other Aromatics (Nitrogen)Carcinogens
SpringerMaterials Properties	13C nuclear magnetic resonance spectrum
LogP(분배 계수)	log Kow = 1.732.0
밀도	1.2540 g/cu cm at 20 °CRelative density (water = 1): 1.25 (20 °C)1.254 g/mL at 25 °C (lit.)
Viscosity	Liquid viscosity = 3.9768X10-3 at melting point
Color/Form	Colorless to yellowish liquidLight reddish or amber liquid
용해도	Miscible with ethanol, ethyl ethersoluble in carbon tetrachlorideIn water, 1.69X10+3 mg/L at 30 °CSolubility in water, g/l at 30 °C: 1.69 (slightly soluble)알코올에 용해됨(lit.)
인화점	124 °C142 °C closed cup142 °C c.c.>230 °F
끓는 점	277 °C144 °C at 4 mm HgBoiling point range: 268-271 °C273 °C (lit.)
Decomposition	When heated to decomposition it emits toxic fumes of /nitrogen oxide/.
녹는점	10.5 °C9-12 °C (lit.)
증기 밀도	Relative vapor density (air = 1): 5.29
굴절률	n20/D 1.561(lit.)
저장 조건	Refrigerator, Under Inert Atmosphere
물리적 상태	기름
색상	옅은 노랑
비중	1.254
용해도	1.45g/L(20℃)
Merck	14,6584
BRN	1868032
헨리 상수	2.3×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
유전율	43.0
안정성	안정적인. 강한 산화제와 호환되지 않습니다.
InChI	1S/C7H7NO3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3
InChIKey	CFBYEGUGFPZCNF-UHFFFAOYSA-N
SMILES	COc1ccccc1[N+]([O-])=O
NIST	Benzene, 1-methoxy-2-nitro-(91-23-6)
EPA	o-Nitroanisole (91-23-6)

화학적 성질

2-Nitroanisole is a yellowish or light-red to amber liquid. May be transported in molten form.

안전 및 규제

GHS 분류	DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
규제 정보	Hazard Traits - Carcinogenicity2-Nitroanisole: 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.)
화재 위험	Combustible.
유해성 요약	Inhalation of high concentrations can cause methemoglobinemiaThe substance may have effects on the blood, resulting in anaemia. [ICSC] An irritantEffects in high-dose animal studies include methemoglobinemia[MSDSonline] See 2021 (Volume 127) monograph at IARC.
UN 분류	UN Hazard Class: 6.1UN Pack Group: III
Special Reports	DHHS/NTPToxicology & Carcinogenesis Studies of o-Nitroanisole in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 416 (1993) NIH Publication No. 93-3147IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, vol 65, p. 376 (1998)[Available at: http://monographs.iarc.fr/index.php]Advisory Committee on Existing Chemicals of Environmental Relevance (BUA). o-Nitroanisole (1-methoxy-2-nitrobenzene). S. Hirzel Verlag, Stuttgart Germany 1993. This document reviews the currently available data on the environmental behavior of o-nitroanisole along with ecotoxic effects and toxicological data. ...National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. o-Nitroanisole (91-23-6) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s120onit.pdf]

용도

2-Nitroanisole is an intermediate in the synthesis of various potential therapeutic compounds.

일반 설명

2-Nitroanisole (2-methoxynitrobenzene is an industrial and environmental pollutant causing tumors of the urinary bladder in rats and mice. Tumorigenic potential of 2-nitroanisole has been evaluated by host-mediated in vitro and in vivo assay.

제조 및 합성 방법

생산 방법

Methanolic sodium hydroxide is added slowly to a solution of 2- chloronitrobenzene in methanol at 70 ℃; the mixture is then heated gradually to 95 ℃ under pressure to complete the reaction. After dilution with water the product 2-Nitroanisole is separated as an oil, in 90 % yield, and methanol is recovered from the aqueous layer.