Proton sponge (HCID 88675)

概要

N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine is a member of naphthalenes.

名称と識別子

優先名称: Proton sponge
IUPAC: 1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine
現地名: 1,8-ビス(ジメチルアミノ)ナフタレン
英語名: 1,8-Bis(dimethylamino)naphthalene
分子式: C14H18N2
分子量: 214.31

名称と別名

20734-58-11,8-Bis(dimethylamino)naphthaleneProton spongeDMAN cpd6S79D2P9H8DTXSID10174807RefChem:73727DTXCID5097298244-001-6N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine1,8-Bis(dimethylamino)naphtaleneN,N,N',N'-Tetramethyl-1,8-naphthalenediamine

名称をさらに表示

1,8-ビス(ジメチルアミノ)ナフタレンプロトンスポンジ4,5-ビス(ジメチルアミノ)ナフタレンN,N,N',N'-テトラメチル-1,8-ナフタレンジアミンN,N,N',N'-テトラメチルナフタレン-1,8-ジアミンN,N,N',N'-テトラメチル-1,8-ジアミノナフタレンN，N，N’，N’-テトラメチルナフタレン-1，8-ジアミン1,8‐ビス(ジメチルアミノ)ナフタレン1,8-ビス(ジメチルアミノ)ナフタレン, 98+%N1,N1,N8,N8-テトラメチルナフタレン-1,8-ジアミンN, N, N ', N ' -テトラメチル-1,8-ナフタレンジアミンN,N,N′,N′-テトラメチル-1,8-ナフタレンジアミンプロトンスポンジN,N,N′,N′-テトラメチルナフタレン-1,8-ジアミンN,N,N',N'-tetramethyl-1,8-diaminonaphthalenePROTON-SPONGE(R)proton-sponge tmLABOTEST-BB LT004539821, 8-dimethylaminonaphthalene

1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-Proton-spongeMFCD00003920N,N,N',N'-Tetramethylnaphthalene-1,8-diamine1,8-Naphthalenediamine, N1,N1,N8,N8-tetramethyl-Maybridge1_002116N,N,N',N'-Tetramethyl-1,8-naphthalene diamine

データベース識別子

CAS: 20734-58-1
PubChem CID: 88675
DTXSID: DTXSID10174807
ChEMBL: CHEMBL1574733
ChEBI: CHEBI:194986
UNII: 6S79D2P9H8
EC Number: 244-001-6
Nikkaji: J83.008I

物性

構造計算による物性

XLogP: 3.4
極性表面積: 6.5 Å²
水素結合供与体数: 0
水素結合受容体数: 2
回転可能結合数: 2
重原子数: 16
形式電荷: 0
複雑度: 203

実験および物理化学的性質

PolymersNitrogen Compounds -> Amines, Polyaromatic

SpringerMaterials Properties13C nuclear magnetic resonance spectrum

Solubility31.2 [ug/mL] (The mean of the results at pH 7.4)

Physical DescriptionPale cream crystalline powder; [Alfa Aesar MSDS]

物理化学的性質

融点: 49 · 49-51 °C(lit.)
沸点: 144 · 144-145°C (3.7505 mmHg)
比重(密度): 1.12 · 1.12
闪点: 230 °F · >230 °F
貯蔵温度: Keep in dark place,Inert atmosphere,Room temperature
溶解性: 有機溶剤に可溶。
外見: 結晶性粉末
酸解離定数(Pka): 12.1 · 12.1(at 25℃)
色: 淡い茶色がかったピンク
水溶解度: 不溶性
Merck: 14 · 14,3388
BRN: 396782 · 396782
InChI: 1S/C14H18N2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10H,1-4H3
InChIKey: GJFNRSDCSTVPCJ-UHFFFAOYSA-N
SMILES: CN(C)c1cccc2cccc(N(C)C)c12
CAS データベース: 20734 · 20734-58-1(CAS DataBase Reference)
NISTの化学物質情報: 1 · 1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-(20734-58-1)

化学的性質

化学的特性1,8-Bis(dimethylamino)naphtalene is pale brownish-pink crystalline powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

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

Aggregated GHS information provided per 95 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

Chemical: 1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-

1,8-Bis(dimethylamino)-naphthalene: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses burns; [Alfa Aesar MSDS]

Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Adverse EffectsDermatotoxin - Skin burns.

安全データ

F: 8-10-23
wgk: 3
ridadr: 3259
hs_code: 29215900
risk_code: 22-36/37/38-34
hazard_code: Xn,C
safety_code: 26-45-36/37/39
hazard_class: 8
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 11 - Combustible Solids

化学と産業

用途と製造

UsesPrototype of a group of very high alkalinity aromatic diamines known as proton sponges; Used in organic synthesis and catalysis; [Merck Index]

応用分野 · 5 件

用途有機合成において、微量のプロトン源によって反応が妨害される場合、プロトンスポンジの添加が効果的な場合がある。

用途有機合成原料。

説明Significant attention in organic chemistry has been given to the so-called proton sponges, which are bi-center nitrogen bases that show spectacularly high basicity and very low nucleophilic character. The first member of this class of compounds 1,8-bis(dimethylamino)naphthalene or DMAN dragged attention due to its unexpectedly high basicity (pKa: DMAN 12.1; 1,8-diaminonaphthalene: 4.6) after its discovery in 1941[1]. It is prepared with an 82% yield from 1,8-diaminonaphthalene, dimethyl sulfate, and sodium hydride.

使用1,8-Bis(dimethylamino)naphthalene, also referred to as protone sponge, is a lipophilic proton trapping agent. 1,8-Bis(dimethylamino)naphthalene is used in the matrix for mass spectroscopy analysis of lipids and fatty acids.

一般的な説明Proton-sponge is also referred as 1,8-dimethylamino naphthalene. It is very strong base with weak nucleophilic character due to steric effects. It also participates in the reactions between arachno-6,9-C2B8H14 and selected acyl chlorides. It has been tested as an effective H+ scavenger.

調製方法 · 1 件

純化方法1,8-Bis(dimethylamino)naphthalene is prepared by methylating 1,8-diaminonaphthalene, and likely impurities are methylated products. The tetramethyl compound is a stronger base than the unmethylated, di and trimethylated derivatives. The pKa values are: 1,8-(NH2)2 = 4.61, 1,8-(NHMe)2 = 5.61, 1-NHMe-8-NHMe2 = 6.43 and 1,8-(NMe2)2 = 12.34. The mixture is then treated with H2O at pH 8 (where all but the required base are protonated) and extracted with Et2O or CHCl3. The dried extract (K2CO3) yields the tetramethyldiamine on evaporation which can be distilled. It is a strong base with weak nucleophilic properties, e.g. it could not be alkylated by refluxing with EtI in MeCN for 4 days; and on treatment with methyl fluorosulfonate only the fluorosulfonate salt of the base is obtained. [NMR: Adler et al. J Chem Soc, Chem Commun 723 1968, Brown & Letang J Am Chem Soc 63 358 1941, Brzezinski et al. J Chem Soc Perkin Trans 2 857 1991.] Alternatively, crystallise proton sponge from EtOH and dry it in a vacuum oven. Store it in the dark in a CO2-free atmosphere. [Benoit et al. Can J Chem 65 996 1987, Beilstein 13 IV 344.]