4,4'-ビス(ジメチルアミノ)ベンゾフェノン

4,4'-Bis(dimethylamino)benzophenone

HCID 7031CAS 90-94-8

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

Michler's ketone90-94-84,4'-BIS(DIMETHYLAMINO)BENZOPHENONEBis(4-(dimethylamino)phenyl)methanonebis[4-(dimethylamino)phenyl]methanoneMichler ketonep,p'-Michler's ketoneTetramethyldiaminobenzophenoneNCI-C02006p,p'-Bis(dimethylamino)benzophenoneMethanone, bis[4-(dimethylamino)phenyl]-DTXSID2020894
名称をさらに表示
4,4'-ビス(ジメチルアミノ)ベンゾフェノンp,p'-ミクレルズケトンミヒラーのケトンミチラーのケトンビス[4-(ジメチルアミノ)フェニル]ケトンミヒラーズケトンミヒラーケトンミクレルズケトンミッヒラーケトンミクレルケトンMichlerケトンp,p'-ミヒラーズケトン4,4'-カルボニルビス(N,N-ジメチルアニリン)ビス[4-(ジメチルアミノ)フェニル]メタノン4,4’-ビス(ジメチルアミノ)ベンゾフェノン4,4’ビス(ジメチルアミノ)ベンゾフェノン[[[4,4’-ビス(ジメチルアミノ)ベンゾフェノンN,N,N',N'-テトラメチル-4,4'-ジアミノベンゾフェノン4,4′‐ビス(ジメチルアミノ)ベンゾフェノンミヒラー・ケトンMICHLERS KETONEBIS-DIMETHYLAMINOPHENYLMETHANONE4,4'-Bis(Dimethylamino)Benzophenonemichler’s
Benzophenone, 4,4'-bis(dimethylamino)-NSC 9602N,N,N',N'-Tetramethyl-4,4'-diaminobenzophenonep,p'-Bis(N,N-dimethylamino)benzophenoneBis(p-(N,N-dimethylamino)phenyl)ketoneBis(p-(N,N-dimethylamino)phenyl) ketoneAI3-22412NSC9602

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

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Other Aromatics (Nitrogen)

Carcinogens

SpringerMaterials PropertiesAngular frequency
LogP3.87
Color/Form · 2 件

WHITE TO GREENISH LEAFLETS

LEAF IN ALCOHOL, NEEDLES IN BENZENE

Solubility · 3 件

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

Flash Point220 °C

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.

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 · 6 件

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 · 5 件

Chemical: Methanone, bis[4-(dimethylamino)phenyl]-

Hazard Traits - Carcinogenicity

Substance: 4,4'-bis(dimethylamino)benzophenone (Michler’s 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.)

Other Safety InformationIMAP assessments - CMR chemicals not registered under REACH: Human health tier II assessment
DOT LabelPoison
Fire HazardsLiterature sources indicate that this chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract.
Hazards Summary · 1 件

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]

安全と保護具

Fire FightingFires involving this chemical can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

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 · 1 件

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.

Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 件

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

Personal Protective Equipment (PPE) · 1 件

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

Adverse EffectsIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.
Ongoing Test Status · 1 件

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 · 6 件

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

Non-Human Toxicity ExcerptsBenzophenone /is/ non-irritating to animal eyes. /Benzophenone/
Evidence for CarcinogenicityMichler's Ketone (4,4'-bis(dimethylamino)benzophenone): reasonably anticipated to be a human carcinogen.
National Toxicology Program Studies · 1 件

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.

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

化学と産業

用途と製造

Uses · 4 件

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 · 2 件

(1972) 5.48X10+5 G (PRINCPL CUSTMS DISTS)

(1975) 2.00X10+7 G (PRINCPL CUSTMS DISTS)

U.S. Production · 2 件

(1972) PROBABLY GREATER THAN 1.36X10+6 G

(1975) PROBABLY GREATER THAN 9.08X10+5 G

Consumption PatternsESSENTIALLY 100% CHEM INT FOR DYES
Methods of Manufacturing · 2 件

CONDENSATION OF DIMETHYLANILINE WITH PHOSGENE IN THE PRESENCE OF ZINC CHLORIDE

... FROM DIMETHYLANILINE & PHOSGENE /OR/ FROM DIMETHYLANILINE, ALUMINUM CHLORIDE & CARBON TETRACHLORIDE.

General Manufacturing InformationMethanone, bis[4-(dimethylamino)phenyl]-: ACTIVE
応用分野 · 5 件

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 · 1 件

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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