N,N-ジメチル-4-ニトロソアニリン

N,N-dimethyl-4-nitrosoaniline

HCID 8749

基本情報

CAS
138-89-6
標準SMILES
CN(C)c1ccc(N=O)cc1
InChIKey
CMEWLCATCRTSGF-UHFFFAOYSA-N
分子式
C8H10N2O
平均分子量
150.18 g/mol
単同位体質量
150.07931295

概要

P-nitrosodimethylaniline appears as a dark green crystalline solid. Insoluble in water. Harmful if ingested.

名称と識別子

優先名称
N,N-dimethyl-4-nitrosoaniline
IUPAC
N,N-dimethyl-4-nitrosoaniline
現地名
N,N-ジメチル-4-ニトロソアニリン
英語名
N,N-Dimethyl-4-nitrosoaniline
分子式
C8H10N2O
分子量
150.18

名称と別名

N,N-Dimethyl-4-nitrosoaniline138-89-6Accelerinep-Nitroso-N,N-dimethylaniline4-Nitrosodimethylanilinep-(Dimethylamino)nitrosobenzeneN,N-DIMETHYL-P-NITROSOANILINEp-NitrosodimethylanilideParanitrosodimethylanilideBenzenamine, N,N-dimethyl-4-nitroso-p-NitrosodimethylanilineUltra Brilliant Blue P
名称をさらに表示
N,N-ジメチル-4-ニトロソアニリンp-ニトロソ-N,N-ジメチルアニリンN,N-ジメチル-4-ニトロソベンゼンアミンウルトラブリリアントブルーPアクセレリンNDMA【ジメチルニトロソアニリン】N,N-ジメチル-p-ニトロソアニリン4-ニトロソ-N,N-ジメチルアニリン1-ニトロソ-4-(ジメチルアミノ)ベンゼンN,NジメチルpニトロソアニリンパラニトロソジメチルアニリンN,N-ジメチル-4-ニトロソアニリン, 98%SKL297Nitro baseAccelereneVulcanilineultrabrilliantbluep
Dimethyl(p-nitrosophenyl)amine4-(Dimethylamino)nitrosobenzenep-(N,N-Dimethylamino)nitrosobenzeneN,N-Dimethyl-4-nitrosobenzenamineNCI-C01821Aniline, N,N-dimethyl-p-nitroso-Dimethyl-p-nitrosoanilineDTXSID7025138

データベース識別子

CAS
138-89-6
PubChem CID
8749
DTXSID
DTXSID7025138
ChEMBL
CHEMBL1569493
ChEBI
CHEBI:59990
UNII
726V2ETM9E
EC Number
205-343-1
Nikkaji
J3.628E

物性

構造計算による物性

XLogP
1.8
極性表面積
32.7 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
1
重原子数
11

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Other Aromatics (Nitrogen)

Reactive agents - 1st degree

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
Density · 2 件

1.145 (NTP, 1992) - Denser than water; will sink

1.145 @ 20 °C

Color/Form · 2 件

GREEN PLATES OR LEAFLETS

GREENISH-YELLOW SOLID

Solubility · 3 件

less than 0.1 mg/mL at 70 °F (NTP, 1992)

INSOL IN WATER; SOL IN ALC, ETHER

SOL IN FORMAMIDE

Melting Point · 2 件

198.5 to 200.3 °F (NTP, 1992)

92.5-93.5 °C

物理化学的性質

融点
85 · 85-87 °C(lit.)
沸点
271.72 °C · 271.72°C (rough estimate)
比重(密度)
1 · 1,15 g/cm3
屈折率
1.618 · 1.6180 (estimate)
貯蔵温度
30 °C · Store below +30°C.
水溶解度
Insoluble in water

化学的性質

化学的特性green crystalline powder

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 2.2% (1 of 45) of reports.

Danger

H251 (97.8%): Self-heating; may catch fire [Danger Self-heating substances and mixtures]

P235, P261, P264, P264+P265, P270, P271, P272, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, P407, P410, P413, P420, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 3 件

Chemical: Benzenamine, N,N-dimethyl-4-nitroso-

N,N-Dimethyl-4-nitrosoaniline: 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.)

DOT LabelSpontaneously Combustible
Fire Hazards · 2 件

Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:

· Flammable/combustible material.

Fire PotentialMODERATE, WHEN EXPOSED TO HEAT OR FLAME
Health Hazards · 2 件

Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:

· Fire will produce irritating, corrosive and/or toxic gases.

Hazards Summary · 1 件

An irritant and sensitizing agent, but not known to cause methemoglobinemia; [HSDB] Oral LD50 (mammals) = 650 mg/kg; Effects after feeding rats lethal doses include somnolence, convulsions, and hematuria; [RTECS] May spontaneously combust on contact with air; [CAMEO] An irritant; Toxic if swallowed; May cause skin sensitization; [Aldrich MSDS]

安全と保護具

Fire FightingExcerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 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.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Storage Conditions...KEEP ALL FLAMMABLES AWAY FROM AREA WHERE OXIDIZING AGENTS ARE STORED. STORAGE AREA SHOULD BE KEPT COOL & VENTILATED, & SHOULD BE FIREPROOF.
Nonfire Spill ResponseExcerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:

毒性情報

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Human Toxicity Excerpts...APPARENTLY NOT METHEMOGLOBIN FORMER, BUT IS HIGHLY IRRITATING TO SKIN BOTH AS PRIMARY IRRITANT & SENSITIZING AGENT.
Non-Human Toxicity Excerpts · 4 件

P-NITROSODIMETHYLANILINE ADMIN TO NZR RATS & NZO MICE @ 300 MG/L DRINKING WATER OVER 1ST HALVES OF LIFESPAN, AVG AMT ACTUALLY CONSUMED 1.2 G/RAT & 262 MG/MOUSE. SIGNIFICANT INCREASES OCCURRED IN TUMORS OF LUNGS, KIDNEY & MALIGNANT LYMPHOMA IN RATS, & IN TUMORS OF LUNGS, DUODENUM & MALIGNANT LYMPHOMA IN MICE.

THE EFFECTS OF A SINGLE SC INJECTION OF P-NITROSODIMETHYLANILINE (I) ON MALE RATS WERE STUDIED BY THE USE OF URINARY ENZYME MEASUREMENTS. ALKALINE PHOSPHATASE IN URINE WAS ELEVATED 48 HOURS AFTER I. ACID PHOSPHATASE AND MURAMIDASE ACTIVITIES IN URINE WERE SIGNIFICANTLY ELEVATED SOON AFTER THE ADMIN OF I AND REMAINED ABOVE THE NORMAL LEVELS LESS THAN OR EQUAL TO 120 HOURS AFTER I. URINE VOLUME AND PROTEIN LEVELS WERE MARKEDLY REDUCED. PROTEIN IN SERUM WAS REDUCED WHILE KIDNEY AND LIVER PROTEINS WERE RAISED. THE SIGNIFICANCE OF INTERACTION OF THE BIOTRANSFORMATION PRODUCTS OF I WITH THE RENAL SYSTEM IS DISCUSSED.

AFTER THE APPLICATION OF 25 GAMMA P-NITROSODIMETHYLANILINE (I) TO EPILATED GUINEA PIG SKIN, THE ANIMAL INITIALLY BECAME MILDLY SENSITIVE TO THE COMPOUND, BUT 1-2 WEEKS LATER THE GUINEA PIG BECAME INSENSITIVE TO SC INJECTED I 500 GAMMA IN COMPLETE ADJUVANT. THE SHORTER THE INTERVAL BETWEEN THE TOPICAL APPLICATION OF I AND ITS INJECTION IN ADJUVANT, THE GREATER THE SENSITIVE REACTION, INDICATED BY THE DEGREE OF ERYTHEMA. ONE DAY AFTER A SENSITIZING INJECTION, SOME MEASURE OF INSENSITIVITY WAS INDUCED BY TOPICAL APPLICATION OF THE SENSITIZER. THEREFORE, UNRESPONSIVENESS AND SENSITIZATION DEVELOPED OVER THE SAME PERIOD OF TIME AFTER THE INITIAL TOPICAL APPLICATION OF SENSITIZER.

N,N-Dimethyl-p-nitrosoaniline was found to be positive when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). N,N-Dimethyl-p-nitrosoaniline was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 1.000, 3.300, 5.000, 8.000,l 10.000, 33.000, 50.000, 100.000, 200.000, and 333.000 ug/plate. The compound was positive in strains TA100 and TA98 with and without activation. The lowest positive dose tested was 8.000 ug/plate in strain TA100 without activation.

安全データ

F
4.7-8-9
wgk
3
tsca
TSCA listed
rtecs
BX7175000
ridadr
UN 1369
毒性
LD50 orally in Rabbit: 65 mg/kg

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

THE NITROSOARENES STUDIED REACTED WITH THE THIOLS IN A 2ND-ORDER REACTION. THE REACTION VELOCITIES WITH GLUTATHIONE INCREASED WITH INCREASING HAMMET CONSTANT OF THE SUBSTITUENT. THIOLYTIC CLEAVAGE OF THE LABILE INTERMEDIATE WAS FAVORED BY INCREASING THE THIOL CONCENTRATION AT THE EXPENSE OF SULFINAMIDE ISOMERIZATION. LOWERING THE PH FAVORED SULFINAMIDE ISOMERIZATION AND DECREASED PHENYLHYDROXYLAMINE FORMATION. THE GLUTATHIONE CONCENTRATION IN THE RED BLOOD CELLS RESULTED IN THE ALTERATION OF FERRIHEMOGLOBINEMIA AND COVALENT BINDING OF NITROSOARENES WITH NEGATIVE HAMMET CONSTANTS. THE EFFLUX OF GLUTATHIONE DISULFIDE INCREASED MARKEDLY IN THE BILE AND VENOUS EFFUSATE.

PARTIALLY PURIFIED, UNTREATED RAT LIVER CYTOSOL CONTAINS AT LEAST 2 ENZYMES WHICH RAPIDLY REDUCE THE C-NITROSO CARCINOGEN P-NITROSO-N,N-DIMETHYLANILINE (I) IN THE PRESENCE OF NADPH OR NADH AT PH 6-7. TWO MOLES OF NADPH ARE REQUIRED FOR EACH MOLE OF I, CORRESPONDING TO THE REDUCTION OF THE NITROSO GROUP TO THE AMINE. I WAS NOT REDUCED BY RAT KIDNEY OR BRAIN CYTOSOL, PLASMA, OR HEMOGLOBIN.

Absorption, Distribution and ExcretionMOST AROMATIC AMINES ARE LIPID-SOL TO VARIABLE EXTENT & ARE READILY ABSORBED THROUGH SKIN. /AROMATIC AMINES/

用途と製造

Uses · 6 件

Used in printing fabrics; Also use as an intermediate for dyestuffs, an accelerator for rubber vulcanization, and a seed disinfectant; [HSDB]

Farming (Pesticides) [Category: Industry]

IN PRINTING FABRICS

AS DYESTUFFS INTERMEDIATE

CHEM INT FOR ORG COMPOUNDS (N,N-DIMETHYL-P-PHENYLENEDIAMINE); ACCELERATOR FOR RUBBER VULCANIZATION

5% BY WT WAS USED WITH OTHER CHEMICALS FOR DISINFECTING SEEDS

U.S. Exports · 2 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production · 2 件

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Methods of Manufacturing · 2 件

REACTION OF NITROUS ACID WITH DIMETHYLANILINE

PREPD IN COLD FROM NANO2 & SOLN OF DIMETHYLANILINE IN HCL.

General Manufacturing Information · 2 件

Benzenamine, N,N-dimethyl-4-nitroso-: ACTIVE

P-NITROSODIMETHYLANILINE (I) IS A SEED-DRESSING FUNGICIDE. THUS, TREATMENT OF WHEAT SEEDS WITH 5% (I) COMPLETELY CONTROLLED TILLETIA CARIES.

応用分野 · 3 件

用途有機化合物製造、加硫促進剤

使用manufacture of organic Compounds; accelerator in vulcanizing; in printing fabrics.

一般的な説明A dark green crystalline solid. Insoluble in water. Harmful if ingested.

調製方法 · 1 件

純化方法Recrystallise the nitroso-aniline from pet ether or CHCl3/CCl4 and dry it in air. Alternatively suspend it in H2O, heat to boiling and add HCl until it dissolves. Filter, cool and collect the hydrochloride [42344-05-8] with m 177o after recrystallisation from H2O containing a small amount of HCl. The hydrochloride (e.g. 30g) is made into a paste with H2O (100mL) in a separating funnel. Add cold aqueous 2.5 NaOH or Na2CO3 to a pH of ~ 8.0 (green color due to the free base) and extract with toluene, CHCl3 or Et2O. Dry the extract (K2CO3), filter, distil off the solvent, cool the residue and collect the crystalline free base. Recrystallise it as above and dry it in air. [Beilstein 12 IV 1558.]

サプライヤー10 社

江苏艾康生物医药研发有限公司025-5885952 15955137747 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
Anhuyan (Hainan) Biotechnology Co., LTD+86-18163349544 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]

補足説明

定義ChEBI: The 4-nitroso derivative of N,N-dimethylaniline.

関連反応

9 件

化合物ノート

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