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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 128
実験および物理化学的性質
Chemical Classes
Nitrogen Compounds -> Other Aromatics (Nitrogen)
Reactive agents - 1st degree
Density
1.145 (NTP, 1992) - Denser than water; will sink
1.145 @ 20 °C
Color/Form
GREEN PLATES OR LEAFLETS
GREENISH-YELLOW SOLID
Solubility
less than 0.1 mg/mL at 70 °F (NTP, 1992)
INSOL IN WATER; SOL IN ALC, ETHER
SOL IN FORMAMIDE
Melting Point
198.5 to 200.3 °F (NTP, 1992)
92.5-93.5 °C
Physical Description
P-nitrosodimethylaniline appears as a dark green crystalline solid. Insoluble in water. Harmful if ingested.
Green solid; [Merck Index] Green crystalline powder; [MSDSonline]
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
- 溶解性
- soluble in Chloroform, Methanol
- 外見
- powder to crystal
- 酸解離定数(Pka)
- -0.9 · -0.90±0.12(Predicted)
- 色
- Yellow to Brown to Dark green
- Merck
- 14 · 14,6638
- BRN
- 607293 · 607293
- 安定性
- 安定。強力な酸化剤、強力な還元剤、強酸、酢酸、無水酢酸とは相容れない。とても燃えやすい
- InChI
- 1S/C8H10N2O/c1-10(2)8-5-3-7(9-11)4-6-8/h3-6H,1-2H3
- InChIKey
- CMEWLCATCRTSGF-UHFFFAOYSA-N
- SMILES
- N(C)(C)c1ccc(cc1)N=O
- CAS データベース
- 138 · 138-89-6(CAS DataBase Reference)
- EPAの化学物質情報
- N,N-Dimethyl-p-nitrosoaniline (138-89-6)
化学的性質
化学的特性green crystalline powder
安全と法規制
GHS分類
GHS Classification
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
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.)
Fire Hazards
Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
· Flammable/combustible material.
Health Hazards
Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
· Fire will produce irritating, corrosive and/or toxic gases.
Hazards Summary
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]
DOT Hazard Classification
p-Nitrosodimethylaniline
UN1369
Div 4.2 Spontaneously combustible material (49 eCFR § 173.124)
PG II: the degree of danger presented by the material is medium
安全と保護具
Accidental Release Measures
· 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
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:
Isolation and Evacuation
Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
Immediate precautionary measure
毒性情報
Non-Human Toxicity Excerpts
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
- hs_code
- 2921 42 00
- risk_code
- 11-25-36/37/38-43
- 消防法
- 危-5-II
- hazard_code
- F,T
- safety_code
- 16-26-36/37-45
- hazard_class
- 4.2
- packing_group
- II
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Self-heat. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
- ストレージクラス
- 4.2 - Pyrophoric and self-heating hazardous materials
- 有毒物質データの
- 138-89-6(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
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.
用途と製造
Uses
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
(1972) No Data
(1975) No Data
U.S. Imports
(1972) No Data
(1975) No Data
U.S. Production
(1972) PROBABLY GREATER THAN 4.54X10+5 G
(1975) PROBABLY GREATER THAN 4.54X10+5 G
Methods of Manufacturing
REACTION OF NITROUS ACID WITH DIMETHYLANILINE
PREPD IN COLD FROM NANO2 & SOLN OF DIMETHYLANILINE IN HCL.
General Manufacturing Information
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
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
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー10 社
補足説明
定義ChEBI: The 4-nitroso derivative of N,N-dimethylaniline.
関連反応
化合物ノート
読み込み中…