기본 정보
- 표준 SMILES
ON=C1CCCCC1- InChIKey
VEZUQRBDRNJBJY-UHFFFAOYSA-N- 분자식
- C6H11NO
- 평균 분자량
- 113.16 g/mol
- 단동위원소 질량
- 113.08406397
개요
Prisms, liquid or light tan crystalline solid. (NTP, 1992)
이름 및 식별자
- 우선 이름
- Cyclohexanone Oxime
- IUPAC
- N-cyclohexylidenehydroxylamine
- 현지명
- 사이클로헥사논옥심
- 영어명
- Cyclohexanone oxime
- 분자식
- C6H11NO
- 분자량
- 113.16
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
100-64-1- PubChem CID
- 7517
- DTXSID
DTXSID4021842- ChEMBL
CHEMBL137035- UNII
- 2U60L00CGF
- EC Number
- 202-874-0
- Nikkaji
- J45.666G
물성
구조 계산 물성
- XLogP
- 1.2
- 극성 표면적
- 32.6 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 8
- 형식 전하
- 0
- 복잡도
- 90.7
실험 및 물리화학적 성질
Solubility
less than 1 mg/mL at 68 °F (NTP, 1992)
SOL IN WATER, ALCOHOL, ETHER, METHYL ALCOHOL
Boiling Point
403 to 410 °F at 760 mmHg (NTP, 1992)
206-210 °C
Melting Point
192 to 196 °F (NTP, 1992)
89-90 °C
Physical Description
Prisms, liquid or light tan crystalline solid. (NTP, 1992)
Solid; [HSDB] Liquid or light tan solid; mp = 89-91 deg C; [CAMEO] White chunks or powder; [Alfa Aesar MSDS]
물리화학적 성질
- 녹는점
- 86 · 86-89 °C (lit.)
- 끓는 점
- 206 · 206-210 °C (lit.)
- 밀도
- 1.0125 · 1.0125 (rough estimate)
- 증기압
- 1.78 Pa · 1.78Pa at 20℃
- 굴절률
- 1.486 · 1.4860 (estimate)
- 인화점
- 90 °C · 90 °C
- 저장 조건
- 30 °C · Store below +30°C.
- 용해도
- 17.7 g/L · 17.7g/L
- 산도 계수 (pKa)
- 12.42 · 12.42±0.20(Predicted)
- 물리적 상태
- 결정질 분말, 결정 또는 덩어리
- 색상
- 황백색에서 베이지색 갈색까지
- 수용성
- 20 °C에서 · 20°C에서 <0.1g/100mL
- BRN
- 1616769 · 1616769
- Henry's Law Constant
- 4.3 · 4.3×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 3 · 3.0(89℃)
- 안정성
- 안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다. 고온에서 발연황산과 격렬하게 반응함.
- InChI
- 1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2
- InChIKey
- VEZUQRBDRNJBJY-UHFFFAOYSA-N
- SMILES
- O\N=C1/CCCCC1
- LogP
- 1.265 at · 1.265 at 25℃
- NIST
- Cyclohexanone, oxime(100-64-1)
- EPA
- Cyclohexanone oxime (100-64-1)
화학적 성질
Cyclohexanone oxime, a white crystalline solid, has a molecular weight of 113.16 and a melting point of 90 C. It is soluble in water and ethanol (Lide, 1992). This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer. Cyclohexanone oxime is produced by the condensation of cyclohexanone with hydroxylamine sulfate or hydroxylamine phosphate (Fisher and Cresentini, 1985).
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 1.9% (5 of 262) of reports.
Danger
H228 (55%): Flammable solid [Danger Flammable solids]
P210, P240, P241, P260, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P319, P330, P337+P317, P370+P378, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 262 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory Information
Chemical: Cyclohexanone, oxime
Status: Active Update: 27-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/7659
Cyclohexanone oxime: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Mixtures of cyclohexanone and oxime (varying ratios) produced anesthesia, conjunctivitis, and increased aggression in oral studies of rats; Emergency treatment: Methemoglobinemia; [HSDB] May peroxidize; [CAMEO] Increased methemoglobin levels observed in dermal lethal-dose study or rabbits; Progressive anemia with increased splenic hemosiderin deposition and hematopoiesis observed in 90-day gavage study of rats; No changes in sperm motility or vaginal cytological parameters seen; Limited evidence of mutagenicity in vitro and no evidence in vivo; A major metabolite, cyclohexanone (CAS # 108-94-1), caused reduced fetal body weight and increased frequency of retardation of ossification at levels maternally toxic in inhalation study of rats (LOAEL for maternal and developmental toxicity both equal 5,600 mg/m3/day); [EPA ChAMP: Screening Level Hazard Characterization] A strong eye irritant; Harmful by ingestion; Prolonged or repeated ingestion exposure may cause injury to the hematopoietic system; [ECHA REACH Registrations] An irritant; Toxic by ingestion; [Alfa Aesar MSDS]
Reactivity Profile
CYCLOHEXANONE OXIME reacts violently with fuming sulfuric acid at temperatures > 302 °F. (NTP, 1992). Several explosions or violent decompositions have occurred during distillation of aldoximes, which may be attributable to the formation of peroxides of various types. This is especially the case in the presence of acid, Chem. Eng. News, 1974, 52(35), 3. A nickel catalyzed aldoxime rearrangement to an amide, went out of control after changing the solvent employed, J. Loss Prev., 1993, 6(2), 69.
안전 및 보호
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
독성 정보
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=100-64-1]
TSCA Test Submissions
Cyclohexanone oxime was examined for mutagenic activity in Salmonella typhimurium tester strains TA98, TA100, TA1535, TA1537 and TA1538 in the presence and absence of metabolic activation provided by rat liver S9 fraction. The method used to induce liver enzyme activities was not reported. The test article was not mutagenic in the plate incorporation assay at concentrations of 5 to 5000 ug/plate with or without activation. The investigators observed toxicity at the high dose level, but did not report the degree of toxicity or in which strain(s) it was observed.
안전 데이터
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- GW1925000
- HS 번호
- 29280090
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 36/37/39
- Hazard Classifications
- Acute Tox. 4 Oral
- 스토리지 클래스
- 11 - Combustible Solids
- 유해 물질 데이터
- 100-64-1(Hazardous Substances Data)
화학 및 산업
약리 정보
Metabolism/Metabolites
CYCLOHEXYLAMINE WAS DEAMINATED TO CORRESPONDING KETONES BY RABBIT LIVER MICROSOMES IN PRESENCE OF NADPH & MOL OXYGEN. CYCLOHEXANONE OXIME, IDENTIFIED FROM INCUBATION MIXTURES, MAY BE AN INTERMEDIATE OF MICROSOMAL DEAMINATION OF ALICYCLIC PRIMARY AMINES.
용도 및 제조
Uses
Used to make caprolactam; [HSDB] A closed-system intermediate (CSI); [EPA ChAMP: Screening Level Hazard Characterization] Used in coatings; [ECHA REACH Registrations]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
IN PREPN OF CAPROLACTAM
응용 분야
용도Cyclohexanone oxime is used in a wide variety of industrial applications. Primarily, it is used as a captive intermediate in the synthesis of caprolactam, which is polymerized in the production of polycaprolactam (Nylon-6) fibers and plastics (Fisher and Cresentini, 1985; NCI, 1985). The annual U.S. caprolactam production is over 500,000 tons (NCI, 1985). Approximately 90% of the monomer is used to produce fibers for clothing, carpets, home furnishings, and tire cording. The remaining 10% is used to produce nylon resins for food packaging film, extrusion compounds for bristle filaments and wire coatings, and molded plastics for automobiles and appliances (NCI, 1985). Cyclohexanone oxime is also thought to be an intermediate in the oxidative metabolism of sodium cyclamate, an artificial sweetener (Unger and McMahon, 1981).
일반 설명Prisms, liquid or light tan crystalline solid.
상·하류 제품 정보
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