基本情報
- 標準SMILES
CN(C)c1ccc(C(=O)c2ccc(N(C)C)cc2)cc1- InChIKey
VVBLNCFGVYUYGU-UHFFFAOYSA-N- 分子式
- C17H20N2O
- 平均分子量
- 268.35 g/mol
- 単同位体質量
- 268.15756326
概要
Michler's Ketone can cause cancer according to an independent committee of scientific and health experts.
名称と識別子
- 優先名称
- 4,4'-Bis(dimethylamino)benzophenone
- IUPAC
- bis[4-(dimethylamino)phenyl]methanone
- 現地名
- 4,4'-ビス(ジメチルアミノ)ベンゾフェノン
- 英語名
- Michler's ketone
- 分子式
- C17H20N2O
- 分子量
- 268.35
名称と別名
名称をさらに表示
データベース識別子
- CAS
90-94-8- PubChem CID
- 7031
- DTXSID
DTXSID2020894- ChEMBL
CHEMBL15137- ChEBI
CHEBI:82347- UNII
- 3Z2SN6B347
- EC Number
- 202-027-5
- Nikkaji
- J4.330C
物性
構造計算による物性
- XLogP
- 3.9
- 極性表面積
- 23.6 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 4
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 281
実験および物理化学的性質
Chemical Classes
Nitrogen Compounds -> Other Aromatics (Nitrogen)
Carcinogens
Color/Form
WHITE TO GREENISH LEAFLETS
LEAF IN ALCOHOL, NEEDLES IN BENZENE
Solubility
less than 0.1 mg/mL at 64 °F (NTP, 1992)
PRACTICALLY INSOL IN WATER; SOL IN ALCOHOL, WARM BENZENE, VERY SLIGHTLY SOL IN ETHER
VERY SOL IN PYRIMIDINE
Boiling Point
greater than 680 °F at 760 mmHg (decomposes) (NTP, 1992)
ABOVE 360 °C WITH DECOMP
Melting Point
342 °F (NTP, 1992)
172 °C
179 °C
Physical Description
Michler's ketone appears as white to greenish crystalline leaflets or blue powder. (NTP, 1992)
White to greenish solid; [Merck Index] May also be in the form of a blue solid; [CHEMINFO] Light blue powder; [MSDSonline]
物理化学的性質
- 融点
- 174 · 174 -176 °C(lit.)
- 沸点
- 360 °C · 360 °C
- 比重(密度)
- 1.0208 · 1.0208 (rough estimate)
- 屈折率
- 1.5486 · 1.5486 (estimate)
- 闪点
- 220 °C · 220 °C
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 5 mg/mL、透明 · エタノール: 5 mg/mL、透明
- 外見
- 粉
- 酸解離定数(Pka)
- 2.55 · 2.55±0.12(Predicted)
- 色
- ブルーからダークブルーまたはグレー
- 水溶解度
- 400 mg/L · 400mg/L(20℃)
- Merck
- 14 · 14,6177
- BRN
- 790733 · 790733
- 安定性
- 安定。可燃性。強力な酸化剤、強力な還元剤とは相容れない。
- InChI
- 1S/C17H20N2O/c1-18(2)15-9-5-13(6-10-15)17(20)14-7-11-16(12-8-14)19(3)4/h5-12H,1-4H3
- InChIKey
- VVBLNCFGVYUYGU-UHFFFAOYSA-N
- SMILES
- CN(C)c1ccc(cc1)C(=O)c2ccc(cc2)N(C)C
- CAS データベース
- 90 · 90-94-8(CAS DataBase Reference)
- NISTの化学物質情報
- 4 · Methanone, bis[4-(dimethylamino)phenyl]-(90-94-8)
- EPAの化学物質情報
- Michler's ketone (90-94-8)
化学的性質
化学的特性white to light greenish crystals
安全と法規制
GHS分類
GHS Classification
Danger
H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]
P203, P264+P265, P280, P305+P354+P338, P317, P318, P405, and P501 (click each P-code to see the statement)
Danger
H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P203, P264+P265, P280, P305+P354+P338, P317, P318, P405, and P501 (click each P-code to see the statement)
危険有害性情報
Regulatory Information
Chemical: Methanone, bis[4-(dimethylamino)phenyl]-
Hazard Traits - Carcinogenicity
Substance: 4,4'-bis(dimethylamino)benzophenone (Michlerâs ketone)
4,4'-Bis(dimethylamino)benzophenone: Does not have an individual approval but may be used under an appropriate group standard
The 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.)
Hazards Summary
MAK-2 (considered to be carcinogenic for man because sufficient data from long-term animal studies or limited evidence from animal studies substantiated by evidence from epidemiological studies indicate that it can make a significant contribution to cancer risk); [MAK] A skin, eye, mucous membrane, and respiratory tract irritant; [CAMEO] An irritant; [MSDSonline]
Special Reports
DHEW/NCI; Bioassay of Michler's Ketone for Possible Carcinogenicity (1979) Technical Rpt Series No. 181 DHEW Pub No. (NIH) 79-1737
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. Michler's Ketone (4,4'-Bis(dimethylamino)benzophenone) (90-94-8) 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/s113mich.pdf]
Hazard Classes and Categories
Eye Dam. 1 (100%)
Carcinogenicity - category 1B
Germ cell mutagenicity - Category 2
Carcinogenicity - Category 1B
Carcinogenicity - Category 1B
Carcinogens
安全と保護具
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: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.
Protective Action Criteria (PAC)
1.2 [mg/m3]
13 [mg/m3]
79 [mg/m3]
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
毒性情報
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=90-94-8]
Carcinogen Classification
Michler’s ketone [4,4´-Bis(dimethylamino)benzophenone]
Group 2B: Possibly carcinogenic to humans
Volume 99: (2010) Some Aromatic Amines, Organic Dyes, and Related Exposures
2010
2008
Michler's ketone
National Toxicology Program Studies
A bioassay for the possible carcinogenicity of technical grade Michler's ketone was administered in the feed, at either of two concentrations, the groups of 50 male and 50 female animals of each species. Twenty animals of each sex and species were placed on test as controls. The high and low dietary concentrations of Michler's ketone were respectively, 500 and 250 ppm for male rats, 1000 and 500 ppm for female rats, and 2500 and 1250 ppm for mice of both sexes. The compound was administered to rats and mice for 78 weeks. There were significant positive associations between the concentrations of Michler's ketone administered and mortality in rats and mice of both sexes ... and /in/ the incidences of hepatocellular carcinomas in both sexes of rats and in female mice and hemangiosarcomas in male mice. In all of these cases the high dose to control Fischer exact comparison was also significant. Under the conditions of this bioassay, dietary administration of Michler's ketone was carcinogenic to male and female Fischer 344 rats and female B6C3F1 mice, causing hepatocellular carcinomas, and to male B6C3F1 mice, causing hemangiosarcomas.
RAIS Toxicity Values
0.00025
CALEPA
0.86
CALEPA
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DJ0250000
- ridadr
- 2811
- 毒性
- LD50 orally in Rabbit: > 6400 mg/kg
- hs_code
- 29223990
- risk_code
- 45-41-68-36/37/38
- 化審法
- (4)-892
- hazard_code
- T,Xi
- safety_code
- 53-45-36-26
- hazard_class
- 6.1
- packing_group
- III
- 自然発火温度
- 480 °C
- Hazard Classifications
- Carc. 1BEye Dam. 1Muta. 2
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 有毒物質データの
- 90-94-8(Hazardous Substances Data)
化学と産業
用途と製造
Uses
Used to make dyes and pigments; [Merck Index] Used to dye paper, textiles, and leather; Also used in printing inks and photosensitizer formulations; [CHEMINFO]
Pulp and Paper Processing [Category: Industry]
SYNTHESIS OF AURAMINE DERIVATIVES
Used in the manufacture of at least 13 dyes and pigments: C.I. (Colour Index) Acid Blue 34; C.I. Acid Blue 86; C.I. Acid Blue 88; C.I. Acid Violet 15; C.I. Acid Violet 38; Acid Violet 2B; C.I. Basic Orange 23; C.I. Basic Violet 3; C.I. Basic Yellow 2; Ceres Blue I; Fanal Blue 3B supra; C.I. Solvent Violet 9; and C.I. Solvent Yellow 34.
U.S. Imports
(1972) 5.48X10+5 G (PRINCPL CUSTMS DISTS)
(1975) 2.00X10+7 G (PRINCPL CUSTMS DISTS)
U.S. Production
(1972) PROBABLY GREATER THAN 1.36X10+6 G
(1975) PROBABLY GREATER THAN 9.08X10+5 G
Methods of Manufacturing
CONDENSATION OF DIMETHYLANILINE WITH PHOSGENE IN THE PRESENCE OF ZINC CHLORIDE
... FROM DIMETHYLANILINE & PHOSGENE /OR/ FROM DIMETHYLANILINE, ALUMINUM CHLORIDE & CARBON TETRACHLORIDE.
応用分野
解説4,4’‐ビス(ジメチルアミノ)ベンゾフェノンの別名。融点179℃,沸点360℃以上(わずかに分解),板状結晶。芳香族ケトンの一つ。染料を合成する際の中間体として重要な化合物。ドイツのミヒラーWilhelm Traugott Michler(1846―1889)が発見したのでこの名がある。ジメチルアニリンとホスゲンを塩化亜鉛の存在で反応させ合成する。(化学式) クリスタルバイオレット,オーラミンなどの染料合成に用いられる。ビス(ジメチルアミノ)ベンゾフェノンは,トリフェニルメタン系染料の合成中間体としてしばしば用いられ、マラカイトグリーン、メチルバイオレットなどの染料や感熱紙用色素のクリスタルバイオレットラクトンはいずれもミヒラーケトンから合成されている(図)。またグリニャール試薬,アルキルリチウムなどの有機金属試薬の定性分析に使われる(ギルマンテスト)。ベンゾフェノンと同様,アルカリ金属の作用により暗青色のラジカルを生成する。株式会社平凡社 世界大百科事典 第2版について 情報
用途染料、顔料の添加物、究用途
用途染料、顔料
使用In manufacture of dyes and pigments.
一般的な説明White to greenish crystalline leaflets or blue powder.
調製方法
純化方法Dissolve the ketone in dilute HCl, filter and precipitate it by adding ammonia (to remove water-insoluble impurities such as benzophenone). Then crystallise it from EtOH or pet ether. [Suppan J Chem Soc, Faraday Trans1 71 539 1975.] It is also purified by dissolving in *benzene, then washing with water until the aqueous phase is colourless. The *benzene is evaporated off, and the residue is recrystallised three times from *benzene and EtOH [Hoshino & Kogure J Phys Chem 72 417 1988]. [Beilstein 14 IV 255.]
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