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1,5-ジアミノナフタレン

1,5-Diaminonaphthalene

HCID 16720
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
2243-62-1
標準SMILES
Nc1cccc2c(N)cccc12
InChIKey
KQSABULTKYLFEV-UHFFFAOYSA-N
分子式
C10H10N2
平均分子量
158.2 g/mol
単同位体質量
158.08439833

概要

1,5-naphthalenediamine appears as colorless to pale purple crystals or lavender powder. (NTP, 1992)

名称と識別子

優先名称
1,5-Diaminonaphthalene
IUPAC
naphthalene-1,5-diamine
現地名
1,5-ジアミノナフタレン
英語名
1,5-Naphthalenediamine
分子式
C10H10N2
分子量
158.2

名称と別名

1,5-NAPHTHALENEDIAMINE2243-62-11,5-Diaminonaphthalene1,5-NaphthylenediamineNCI-C03021DTXSID302091613PD3J52LKNSC-401110DTXCID909161,5-DANRefChem:907019218-817-8
名称をさらに表示
1,5-ジアミノナフタレン1,5-ナフチレンジアミンナフタレン-1,5-ジアミン1,5-ナフタレンジアミンナフチレンジアミン-(1,5)1,5ジアミノナフタレン1,5ナフタレンジアミンナフタレン-1,5-ジイルジアミン1,5‐ナフタレンジアミン1,5-ジアミノナフタレン, 97%1,5- ナフタレンジアミン1,5-ジアミノナフタレン (昇華精製品)Diaminonaphthalene1,5-Diaminonapthalene1,5-diaminenaphthaleneC.I.76595NSC 401110
naphthalene-1,5-diamine1,5-Napthalenediamine1,5-diaminonaphtaleneMFCD000040291,5-naphthylendiamin1,5-diamino naphthalene1,5-Naphthalene-di-aminenaphthalene, 1,5-diamino-

データベース識別子

CAS
2243-62-1
PubChem CID
16720
DTXSID
DTXSID3020916
ChEMBL
CHEMBL538965
ChEBI
CHEBI:53003
UNII
13PD3J52LK
EC Number
218-817-8
Nikkaji
J40.472A

物性

構造計算による物性

XLogP
2.1
極性表面積
52 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
0
重原子数
12
形式電荷
0
複雑度
140

実験および物理化学的性質

Chemical ClassesOther Classes -> Naphthalenes
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 3 件

log Kow = 0.89

1.48

0.89

Density · 3 件

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

1.4 g/cu cm @ 25 °C

1.4 g/cm³

Color/FormColorless prisms
Solubility · 5 件

less than 1 mg/mL at 68.9 °F (NTP, 1992)

Soluble in benzene and ethanol

In water, 380 mg/l @ 25 °C

... It is soluble in alcohol, ether, and chloroform.

Solubility in water, g/100ml at 20 °C: 0.004

Flash Point · 2 件

226 °C

226 °C

Boiling Point · 3 件

Sublimes (NTP, 1992)

Boiling point: sublimes

sublimes

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxide/.
Melting Point

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H351: Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Warning

H302 (68.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory InformationREACH registered substance: 1,5-naphthylenediamine (EC: 218-817-8)
DOT LabelClass 9
Fire Hazards · 2 件

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsSYMPTOMS: This compound is an irritant.
Hazards SummaryDanger of cutaneous absorption; Danger of skin sensitization; [MAK] May cause skin sensitization; [ICSC] An irritant; [MSDSonline] See beta-Naphthylamine and alpha-Naphthylamine.
Reactive GroupAmines, Aromatic
EC ClassificationSymbol: Xn, N; R: 40-50/53; S: (2)-36/37-60-61
Special ReportsDHEW/NCI; Bioassay of 1,5-Naphthalenediamine for Possible Carcinogenicity (1978) Technical Rpt Series No. 143 DHEW Pub No. (NIH) 78-1398
Reactivity Profile · 1 件

化学と産業

用途と製造

Uses · 5 件

Used to make polyurethane elastomers, dyes, and pharmaceuticals; Not commercially produced in the US; [HSDB]

ORGANIC SYNTHESIS

CHEM INT FOR 1,5-NAPHTHALENE DIISOCYANATE, FOR DYES

The major use of the compound is for the manufacture of 1,5-naphthalene diisocyanate, in the production of polyurethane elastomers. It is also used in the synthesis of dyes and pharmaceuticals.

Synthetic Polymer MALDI Matrix Compounds

U.S. Exports · 2 件

(1977) No Data

(1979) No Data

U.S. Imports · 2 件

(1977) No Data

(1979) 2.00X10+6 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 2 件

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Methods of Manufacturing · 3 件

REDUCTION OF 1,5-DINITRONAPHTHALENE; AMMONOLYSIS OF 1,5-DIHYDROXYNAPHTHALENE

1-Nitronaphthalene can be nitrated further to give a 40:60 mixture of 1,5- and 1,8-dinitronaphthalenes. Similar results are obtained by direct nitration of naphthalene with H2SO4-HNO3 under careful control of temperature over the range 40-80 °C. Although separation of the isomers by fractional crystallization or solvent extraction is usually carried out at this stage, the mixed isomers can also be reduced and the resulting diamines separated. Reduction of the dinitronaphthalenes is achieved by treatment of a nonaqueous solution with iron or hydrogen in the presence of a catalyst.

... Amination of 1,5-dihydroxynaphthalene with ammonia and ammonium bisulfite. Although less efficient on a stage basis it offers an economical alternative to nitration and reduction if the 1,8-naphthalenediamine is not also required.

General Manufacturing InformationNOT PRODUCED COMMERCIALLY IN THE US
応用分野 · 4 件

関連反応

17 件
反応記録を作成
HRID 758 の反応式
HRID 758反応物としてuspto-grants-1998_03
HRID 22622 の反応式
HRID 22622反応物としてuspto-grants-2005_02
HRID 49657 の反応式
HRID 49657生成物としてuspto-grants-2004_03
HRID 479923 の反応式
HRID 479923反応物としてuspto-grants-2003_11
HRID 525980 の反応式
HRID 525980反応物としてuspto-grants-2016_05
HRID 702982 の反応式
HRID 702982生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 992196 の反応式
HRID 992196反応物としてuspto-grants-2002_10
HRID 1074310 の反応式
HRID 1074310生成物としてuspto-grants-1990_11
1 / 3 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
· 3 件

374 °F (NTP, 1992)

190 °C

187 °C

Vapor Pressure · 2 件

0.0000293 [mmHg]

Vapor pressure, Pa at 20 °C: 0.0000023

Physical Description · 3 件

1,5-naphthalenediamine appears as colorless to pale purple crystals or lavender powder. (NTP, 1992)

Colorless to light purple solid; [ICSC] Sensitive to prolonged exposure to air; [CAMEO] Powder; [MSDSonline]

COLOURLESS-TO-LIGHT-PURPLE CRYSTALS.

物理化学的性質

融点
185 · 185-187 °C(lit.)
沸点
200 · 200-210°C 5mm
比重(密度)
1.4 · 1.4
蒸気圧
0 Pa · 0Pa at 20℃
屈折率
1.6441 · 1.6441 (estimate)
闪点
200 · 200-210°C/5mm
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
溶解性
0.04 g/リットル · 0.04g/リットル
酸解離定数(Pka)
4.59 · 4.59±0.10(Predicted)
外見
粉
色
グレーからダークブラウン
水溶解度
0.1 g/100 · <0.1 g/100 mL で 20.5 ºC
BRN
907947 · 907947
Henry's Law Constant
1.5 · 1.5×105 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C10H10N2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6H,11-12H2
InChIKey
KQSABULTKYLFEV-UHFFFAOYSA-N
SMILES
Nc1cccc2c(N)cccc12
LogP
0.91 · 0.91
CAS データベース
2243 · 2243-62-1(CAS DataBase Reference)
NISTの化学物質情報
1 · 1,5-Naphthalenediamine(2243-62-1)
EPAの化学物質情報
1 · 1,5-Naphthalenediamine (2243-62-1)
化学的性質 · 1 件

化学的特性GREY TO DARK BROWN POWDER. 1,5-Naphthalenediamine [2243-62-1]. 1,5-diaminonaphthalene, Alphamin, C10H10N2, Mr 158.2: oxidation of 97 with iron (III) chloride in water produces a blue-violet color. Treatment with boiling aqueous sodium bisulfite followed by addition of alkali gives a mixture of 1-amino-5-hydroxynaphthalene and 1,5-dihydroxynaphthalene. Sulfonation (5 % oleum, 100℃) gives 1,5-diaminonaphthalene2-sulfonic acid, and nitration in acetic acid produces 2,4,6,8-tetranitro-1,5-diaminonaphthalene. Coupling with diazo compounds takes place in the 2-position; reduction of the resulting azo compound with SnCl2– HCl produces 1,2,5- triaminonaphthalene.

1,5-NAPHTHALENEDIAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Chemical DangersDecomposes on burning. This produces toxic fumes.
Air and Water ReactionsThis chemical is sensitive to prolonged exposure to air. Insoluble in water.
Hazard Classes and Categories · 5 件

Acute Tox. 4 (68.6%)

Carcinogenicity - category 2

Acute toxicity (Oral) - Category 4

Hazardous to the aquatic environment (Acute) - Category 2

Carc. 2

安全と保護具

Fire Fighting · 2 件

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rest. Refer for medical attention .

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.

Safe StorageWell closed.
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.

Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 件

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Eye PreventionWear safety spectacles.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves. Protective clothing.

毒性情報

Ecotoxicity Values · 5 件

EC50 Tetrahymena pyriformis /(unicellular, ciliated freshwater protozoa)/ 45 mg/L/60 hr

EC50 Scenedesmus subspicatus /(freshwater algae)/ 0.3 mg/L/72 hr (cell multiplication inhibition test)

EC50 Daphnia magna (Straus) 15 mg/L/24 hr

LC50 Brachydanio rerio /(Zebra fish)/ 17 mg/L/96 hr /Conditions of bioassay not specified/

LC50 Oryzias latipes /(Japanese medaka)/ 31 mg/L/48 hr /Conditions of bioassay not specified/

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5,000(SRC), determined from a structure estimation method(2), indicates that 1,5-naphthalenediamine is expected to have slight mobility in soil(SRC). 1,5-Naphthalenediamine is a weak base with a pKa of 4.44(3) indicating it will partially exist in the protonated form under acidic conditions. Volatilization from moist surfaces is not expected to be an important fate process because cations do not volatilize and the estimated Henry's Law constant of the free base is 6.6X10-11 atm-cu m/mole(SRC), calculated using a fragment constant estimation method(4). 1,5-Naphthalenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-5 mm Hg(SRC), determined from a fragment constant method(5). 1,5-Naphthalenediamine was not degraded in a single screening study using an activated sludge inoculum; however, no data were located regarding the biodegradation of 1,5-naphthalenediamine in soil(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5,000(SRC), determined from a structure estimation method(2), indicates that 1,5-naphthalenediamine is expected to adsorb to suspended solids and sediment(SRC). 1,5-Naphthalenediamine is a weak base with a pKa of 4.44(3) indicating it will partially exist in the protonated form under acidic conditions. Volatilization from water surfaces is not expected to be an important fate process because cations do not volatilize and the estimated Henry's Law constant of the free base is 6.6X10-11 atm-cu m/mole(SRC), calculated using a fragment constant estimation method(4). According to a classification scheme(5), a BCF of 1.5 measured in carp(6), suggests bioconcentration in aquatic organisms is low(SRC). 1,5-Naphthalenediamine was not degraded in a single screening study using an activated sludge inoculum(5); however, no data were located regarding the biodegradation of 1,5-naphthalenediamine in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,5-naphthalenediamine, which has an estimated vapor pressure of 2.9X10-5 mm Hg at 25 °C (SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,5-naphthalenediamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 2X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1,5-naphthalenediamine may be removed from the air by wet and dry deposition(SRC). Naphthalene and structurally related chemicals absorb light greater than 290 nm and may be susceptible to photolysis(4); however the rate of this potential reaction is not known for 1,5-naphthalenediamine(SRC).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
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=2243-62-1]

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1,5-naphthalenediamine can be estimated to be 5,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,5-naphthalenediamine is expected to have slight mobility in soil. The pKa of 1,5-naphthalenediamine is 4.44(3), indicating that this compound will partially exist in the protonated form in the environment under acidic conditions and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(4). Primary and secondary aromatic amines are also susceptible to strong irreversible binding to humic material due to the high reactivity of the aromatic amino group(5).

Artificial Pollution Sources1,5-Naphthalenediamine's production and use as an organic synthesis reagent(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

1,5-Naphthalenediamine, present at 100 mg/l, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1). No biodegradation data was located for 1,5-naphthalenediamine in soil or water(SRC).

Carcinogen Classification · 6 件

1,5-Naphthalenediamine

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 27: (1982) Some Aromatic Amines, Anthraquinones and Nitroso Compounds, and Inorganic Fluorides Used in Drinking-water and Dental Preparations

1987

1987

1,5-Naphthalene-diamine

Environmental BioconcentrationA BCF of 1.5 was measured for carp exposed to 0.02 mg/l of 1,5-naphthalenediamine for 6 weeks(1). According to a classification scheme(2), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil · 1 件

1,5-Naphthalenediamine is a weak base with a pKa of 4.44(1) indicating it will partially exist in the protonated form under acidic conditions. Volatilization from water and moist soil surfaces is not expected to be an important fate process because cations do not volatilize and the estimated Henry's Law constant of the free base is 6.6X10-11 atm-cu m/mole(SRC), calculated using a fragment constant estimation method(2). 1,5-Naphthalenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(3).

安全データ

wgk
2
rtecs
QJ3400000
ridadr
UN 3077 9/PG 3
hs_code
29215990
risk_code
40-50/53
化審法
(4)-323
hazard_code
Xn,N
safety_code
36/37-60-61
hazard_class
9
packing_group
III
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 2Skin Sens. 1
ストレージクラス
11 - Combustible Solids
有毒物質データの
2243-62-1(Hazardous Substances Data)

用途試薬、工業用原料

用途有機合成原料。

使用1,5-naphthalenediamine be used as intermediates for the synthesis of materials.

一般的な説明Colorless to pale purple crystals or lavender powder.

調製方法 · 2 件

1-Nitronaphthalene can be nitrated further to give a 40 : 60 mixture of 1,5- and 1,8-dinitronaphthalenes. Similar results are obtained by direct nitration of naphthalene with H2SO4– HNO3 under careful control of temperature over the range 40 – 80℃. Although separation of the isomers by fractional crystallization or solvent extraction is usually carried out at this stage, the mixed isomers can also be reduced and the resulting diamines separated. Reduction of the dinitronaphthalenes is achieved by treatment of a nonaqueous solution with iron or hydrogen in the presence of a catalyst. An alternative process for 1,5-naphthalenediamine involves amination of 1,5-dihydroxynaphthalene with ammonia and ammonium bisulfite. Although less efficient on a stage basis it offers an economical alternative to nitration and reduction if the 1,8-naphthalenediamine is not also required.

純化方法Recrystallise the amino-naphthalene from boiling H2O, but this is wasteful due to poor solubility. Boil it in chlorobenzene (charcoal), filter hot and cool the filtrate (preferably under N2). This gives colourless crystals. Dry it in a vacuum till free from chlorobenzene (odour), and store it in sealed ampoules under N2 away from light. [Beilstein 13 IV 340.]

上流・下流製品情報

上流原料

1,4,5-トリニトロナフタレンNaphthalene, 1,4,5,8-tetranitro-5-ニトロ-1-ナフタレンアミン1-ニトロナフタレン

下流製品

1,5-ジイソシアナトナフタレン5-アミノ-1-ナフトール

補足説明

定義ChEBI: A naphthalenediamine compound having amino substituents in the 1- and 5-positions.