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;PROTON-SPONGE(R);proton-sponge tm;LABOTEST-BB LT00453982;1, 8-dimethylaminonaphthalene;1,8-bis(dimethylamino)naphtalene;4,5-Bis(dimethylamino)naphthalene;1,8-Bis(Dimethylamino)naphthaline
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: $60.2
Updated: 2025/07/31

Sigma-Aldrich

Product number: 14795
Product name: N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine
Purity: purum, ≥99.0% (NT)
Packaging: 50g
Price: $205
Updated: 2025/07/31

TCI Chemical

Product number: B1018
Product name: 1,8-Bis(dimethylamino)naphthalene [for Dehydrohalogenation]
Purity: >98.0%(GC)(T)
Packaging: 1g
Price: $30
Updated: 2025/07/31

TCI Chemical

Product number: B1018
Product name: 1,8-Bis(dimethylamino)naphthalene [for Dehydrohalogenation]
Purity: >98.0%(GC)(T)
Packaging: 5g
Price: $56
Updated: 2025/07/31

Sigma-Aldrich

Product number: 158496
Product name: Proton-sponge?
Purity: 99%
Packaging: 10g
Price: $54.1
Updated: 2025/07/31

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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

1,8-Bis(dimethylamino)naphthalene can be used as a very strong base in organic synthesis and catalysis.

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-C₂B₈H₁₄and 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

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.]

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

Chongqing Chemdad Co., Ltd

Product: 1,8-Bis(dimethylamino)naphthalene 20734-58-1
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99
Supply Ability: 20tons
Release date: 2025-04-24

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

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tetramethyl-1,8-naphthalenediamine

LABOTEST-BB LT00453982

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proton-sponge tm

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1,8-Bis(dimethylamino)naphtalene ISO 9001：2015 REACH

20734-58-1 1,8-Bis(dimethylamino)naphtalene

1,8-Bis(Dimethylamino)naphthaline

1, 8-dimethylaminonaphthalene

N,N,N’,N’-Tetramethyl-1,8-naphthalenediamine

N,N,N',N'-tetramethyl-1,8-diaminonaphthalene

Proton-sponge<sup><sup>?</sup></sup>

N1,N1,N8,N8-Tetramethylphthalene-1,8-diamine

20734-58-1

C14H18N2

C10H6NCH322

Building Blocks

Polyamines

Organic Bases

Organic Building Blocks

Nitrogen Compounds

Synthetic Reagents

Amines and Anilines