ChemicalBook > CAS DataBase List > 1,8-Bis(dimethylamino)naphthalene

1,8-Bis(dimethylamino)naphthalene

Product Name
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
Formula Weight
214.31
MOL File
20734-58-1.mol
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1,8-Bis(dimethylamino)naphthalene Property

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)
NIST Chemistry Reference
1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-(20734-58-1)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
14795
Product name
N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine
Purity
purum, ≥99.0% (NT)
Packaging
10g
Price
$58.4
Updated
2024/03/01
Sigma-Aldrich
Product number
14795
Product name
N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine
Purity
purum, ≥99.0% (NT)
Packaging
50g
Price
$199
Updated
2024/03/01
TCI Chemical
Product number
B1018
Product name
1,8-Bis(dimethylamino)naphthalene [for Dehydrohalogenation]
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$42
Updated
2024/03/01
TCI Chemical
Product number
B1018
Product name
1,8-Bis(dimethylamino)naphthalene [for Dehydrohalogenation]
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$78
Updated
2024/03/01
Alfa Aesar
Product number
L00313
Product name
1,8-Bis(dimethylamino)naphthalene, 98+%
Packaging
10g
Price
$42.5
Updated
2024/03/01
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1,8-Bis(dimethylamino)naphthalene Chemical Properties,Usage,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

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 in organic synthesis and catalysis.

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

Raw materials

Preparation Products

Hexamethylene Diisocyanate
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1,8-Bis(dimethylamino)naphthalene Suppliers

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View Lastest Price from 1,8-Bis(dimethylamino)naphthalene manufacturers

Nanjing Fred Technology Co., Ltd
Product
1,8-Bis(dimethylamino)naphtalene 20734-58-1
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1 ton
Release date
2023-11-16
Shaanxi Dideu Medichem Co. Ltd
Product
1,8-Bis(dimethylamino)naphtalene 20734-58-1
Price
US $0.10/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
1000 tons
Release date
2020-01-06
Henan Fengda Chemical Co., Ltd
Product
1,8-Bis(dimethylamino)naphthalene 20734-58-1
Price
US $50.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-22

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  • PROTON-SPONGE (1,8-BIS-(DIMETHYLAMINO)NAPHTHALENE), 99%
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  • 1,8-Bis(dimethylamino)naphtalene ISO 9001：2015 REACH
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