所有图片(1)
别名:
1,8-双二甲氨基萘, N,N,N′,N′-四甲基-1,8-萘二胺
线性分子式:
C10H6[N(CH3)2]2
CAS号:
分子量:
214.31
Beilstein:
396782
EC 号:
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22
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质量水平
检测方案
99%
形式
solid
mp
49-51 °C (lit.)
溶解性
chloroform: soluble 50 mg/mL, clear (faint yellow to dark yellow to dark red)
SMILES字符串
CN(C)c1cccc2cccc(N(C)C)c12
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
InChI key
GJFNRSDCSTVPCJ-UHFFFAOYSA-N
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一般描述
质子海绵（Proton-sponge ）是一种亲核碱，用于烷氧羰基化（alkoxycarbonylation）、脱氟化氢、芳基化和分子内环化反应。
质子海绵也称1,8-二甲氨基萘。因为空间位阻效应，它是一种有亲核性的强碱。它还参与蛛网形-6,9-C2B8H14和选择酰氯的反应。它还是一种有效的H+清除剂。
质子海绵也称1,8-二甲氨基萘。因为空间位阻效应，它是一种有亲核性的强碱。它还参与蛛网形-6,9-C2B8H14和选择酰氯的反应。它还是一种有效的H+清除剂。
应用
由于空间位阻效应而具有弱亲核性的强碱。
质子海绵可以用来合成C-取代t-BuNH-8,9-R,R′-nido-7,8,9-C3B8H9 (R,R′=H,H; MeH; Me,Me; Ph,H 和Ph,Ph)三碳内酯化合物。它还可以用来制备饱和铱氟烷基（氢化物）复合体。
法律信息
Proton-sponge is a registered trademark of Merck KGaA, Darmstadt, Germany
警示用语：
Warning
危险分类
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
靶器官
Respiratory system
WGK
WGK 3
闪点(°F)
closed cup
闪点(°C)
closed cup
个人防护装备
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Mario Bakardjiev et al.
Inorganic chemistry, 52(15), 9087-9093 (2013-07-28)
Reactions between arachno-6,9-C2B8H14 (1) and selected acyl chlorides, RCOCl, in the presence of PS (PS = "proton sponge", 1,8-dimethylamino naphthalene) in CH2Cl2 for 24 h at reflux, followed by in situ acidification with concentrated H2SO4 at 0 °C, generate a
1, 8-Bis (dimethylamino) naphthalene
Barner BA
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Mario Bakardjiev et al.
Dalton transactions (Cambridge, England : 2003), 39(17), 4186-4190 (2010-04-15)
Treatment of C-substituted nido dicarbadecaboranes 5,6-R',R-5,6-C(2)B(8)H(10) (1) (where R',R = H,H (1a); H,Me, (1b); Me,Me, (1c); H,Ph, (1d) and Ph,Ph, (1e) with 1,8-bis-(dimethylamino)naphthalene (proton sponge = PS) and t-BuNC in CH(2)Cl(2), followed by acidification, generated a series of pure neutral
Unusual Reactivity of ?Proton Sponge? as a Hydride Donor to Transition Metals: Synthesis and Structural Characterization of Fluoroalkyl (hydrido) Complexes of Iridium (III) and Rhodium (III).
Hughes RP, et al.
Organometallics, 20(14), 3190-3197 (2014)
J. Chem. Soc. Perkin Trans. II, 857-857 (1991)
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