1,8-Bis(dimethylamino)naphthalene
- CAS No.
- 20734-58-1
- Chemical Name:
- 1,8-Bis(dimethylamino)naphthalene
- Synonyms
- PROTON SPONGE;1,8-BIS(DIMETHYLAMINO)NAPHTHALENE;N1,N1,N8,N8-TETRAMETHYLNAPHTHALENE-1,8-DIAMINE;N,N,N',N'-TETRAMETHYL-1,8-DIAMINONAPHTHALENE;PROTON-SPONGE(R);proton-sponge tm;LABOTEST-BB LT00453982;1, 8-dimethylaminonaphthalene;1,8-bis(dimethylamino)naphtalene;4,5-Bis(dimethylamino)naphthalene
- CBNumber:
- CB4163778
- Molecular Formula:
- C14H18N2
- Molecular Weight:
- 214.31
- MDL Number:
- MFCD00003920
- MOL File:
- 20734-58-1.mol
- MSDS File:
- SDS
Melting point | 49-51 °C(lit.) |
---|---|
Boiling point | 144-145°C (3.7505 mmHg) |
Density | 1.12 |
Flash point | >230 °F |
storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
solubility | Soluble in organic solvents. |
form | Crystalline Powder |
pka | 12.1(at 25℃) |
color | Pale brownish-pink |
Water Solubility | insoluble |
Sensitive | Light Sensitive |
Merck | 14,3388 |
BRN | 396782 |
InChIKey | GJFNRSDCSTVPCJ-UHFFFAOYSA-N |
CAS DataBase Reference | 20734-58-1(CAS DataBase Reference) |
FDA UNII | 6S79D2P9H8 |
NIST Chemistry Reference | 1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-(20734-58-1) |
SAFETY
Risk and Safety Statements
Symbol(GHS) | GHS07 |
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Signal word | Warning | |||||||||
Hazard statements | H315-H319-H335 | |||||||||
Precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 | |||||||||
Hazard Codes | Xn,C | |||||||||
Risk Statements | 22-36/37/38-34 | |||||||||
Safety Statements | 26-45-36/37/39 | |||||||||
RIDADR | 3259 | |||||||||
WGK Germany | 3 | |||||||||
F | 8-10-23 | |||||||||
HazardClass | 8 | |||||||||
HS Code | 29215900 | |||||||||
NFPA 704 |
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1,8-Bis(dimethylamino)naphthalene price More Price(41)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | 14795 | N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine purum, ≥99.0% (NT) | 20734-58-1 | 10g | $58.4 | 2024-03-01 | Buy |
Sigma-Aldrich | 14795 | N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine purum, ≥99.0% (NT) | 20734-58-1 | 50g | $199 | 2024-03-01 | Buy |
TCI Chemical | B1018 | 1,8-Bis(dimethylamino)naphthalene [for Dehydrohalogenation] >98.0%(GC)(T) | 20734-58-1 | 1g | $42 | 2024-03-01 | Buy |
TCI Chemical | B1018 | 1,8-Bis(dimethylamino)naphthalene [for Dehydrohalogenation] >98.0%(GC)(T) | 20734-58-1 | 5g | $78 | 2024-03-01 | Buy |
Alfa Aesar | L00313 | 1,8-Bis(dimethylamino)naphthalene, 98+% | 20734-58-1 | 10g | $42.5 | 2024-03-01 | Buy |
1,8-Bis(dimethylamino)naphthalene Chemical Properties,Uses,Production
Description
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.
Chemical Properties
1,8-Bis(dimethylamino)naphtalene is pale brownish-pink crystalline powder
Uses
Very strong base in organic synthesis and catalysis.
Uses
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.
Uses
Very strong base with weak nucleophilic character due to steric effects.
Definition
ChEBI: N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine is a member of naphthalenes.
General Description
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.
Mechanism of action
A possibility of non-conventional two-step protonation of 1,8-bis(dimethylamino)naphthalene (proton sponge) is discussed. Unlike the generally accepted mechanism, involving relatively slow direct penetration of a proton into the cleft between the peri-NMe2 groups, it consists of the rapid addition of a proton to the out-inverted NMe2 group with the subsequent slower rotational transfer of the proton into the inter-nitrogen space to produce a stable chelated cation. The conclusion is that both pathways of proton sponge protonation, traditional and non-conventional, contribute in parallel with a still undefined ratio. The estimated out-basicity of the proton sponge is at least 5.5 orders of magnitude lower than the directly measured in-basicity[2].
Solubility in organics
Soluble in most organic solvents, such as methanol and chloroform.
Purification Methods
It 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.]
References
[1] Utsab Bhattacharyya, Ralph Puchta, Renjith Thomas . “The proton sponge 1,8-bis(dimethylamino)naphthalene: The quicker-picker-upper also for s-block metal cations?” Chemical Physics Letters 777 (2021): Article 138735.
[2] Ozeryanskii, Valery A. et al. “Out-Basicity of 1,8-bis(dimethylamino)naphthalene: the experimental and theoretical challenge??.” Organic & Biomolecular Chemistry 15 (2013): 2360–2369.
1,8-Bis(dimethylamino)naphthalene Preparation Products And Raw materials
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
Nanjing Fred Technology Co., Ltd | +86-25-84696168 +86-15380713688 | Austin@fredbio.com | China | 2427 | 58 |
Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | sales@chemdad.com | China | 39916 | 58 |
Henan Fengda Chemical Co., Ltd | +86-371-86557731 +86-13613820652 | info@fdachem.com | China | 20291 | 58 |
Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29798 | 60 |
Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21663 | 55 |
Nanjing ChemLin Chemical Industry Co., Ltd. | 025-83697070 | product@chemlin.com.cn | CHINA | 3012 | 60 |
ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32836 | 60 |
Changzhou Ansciep Chemical Co., Ltd. | +86 519 86305871 | sales@ansciepchem.com | CHINA | 4242 | 58 |
Shenzhen Nexconn Pharmatechs Ltd | +86-755-89396905 +86-15013857715 | admin@nexconn.com | China | 10311 | 58 |
Accela ChemBio Inc. | +1-858-6993322 | info@accelachem.com | United States | 19563 | 58 |
View Lastest Price from 1,8-Bis(dimethylamino)naphthalene manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
---|---|---|---|---|---|---|---|---|
2024-09-27 | 1,8-Bis(dimethylamino)naphtalene
20734-58-1
|
US $1.00 / kg | 1kg | 99% | 1 ton | Nanjing Fred Technology Co., Ltd | ||
2023-12-23 | 1,8-Bis(dimethylamino)naphthalene
20734-58-1
|
US $50.00-1.00 / KG | 1KG | 99% | g-kg-tons, free sample is available | Henan Fengda Chemical Co., Ltd | ||
2022-09-03 | 1,8-Bis(dimethylamino)naphtalene
20734-58-1
|
US $0.00 / KG | 25KG | 97% | 1tons | Henan Aochuang Chemical Co.,Ltd. |
- 1,8-Bis(dimethylamino)naphtalene
20734-58-1
- US $1.00 / kg
- 99%
- Nanjing Fred Technology Co., Ltd
- 1,8-Bis(dimethylamino)naphthalene
20734-58-1
- US $50.00-1.00 / KG
- 99%
- Henan Fengda Chemical Co., Ltd
- 1,8-Bis(dimethylamino)naphtalene
20734-58-1
- US $0.00 / KG
- 97%
- Henan Aochuang Chemical Co.,Ltd.
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