Proton sponge (HCID 88675)

개요

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

이름 및 식별자

우선 이름: Proton sponge
IUPAC: 1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine
영어명: 1,8-Bis(dimethylamino)naphthalene
분자식: C14H18N2
분자량: 214.31

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 3.4
극성 표면적: 6.5 Å²
수소 결합 공여자 수: 0
수소 결합 수용자 수: 2
회전 가능 결합 수: 2
무거운 원자 수: 16
형식 전하: 0
복잡도: 203

실험 및 물리화학적 성질

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]

물리화학적 성질

녹는점: 49 · 49-51 °C(lit.)
끓는 점: 144 · 144-145°C (3.7505 mmHg)
밀도: 1.12 · 1.12
인화점: 230 °F · >230 °F
저장 조건: Keep in dark place,Inert atmosphere,Room temperature
용해도: 유기 용매에 용해됩니다.
물리적 상태: 결정성 분말
산도 계수 (pKa): 12.1 · 12.1(at 25℃)
색상: 옅은 갈색빛이 도는 핑크색
수용성: 불용성
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
NIST: 1 · 1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-(20734-58-1)

화학적 성질

1,8-Bis(dimethylamino)naphtalene is pale brownish-pink crystalline powder

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Regulatory Information · 2건

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%)

독성 정보

Adverse EffectsDermatotoxin - Skin burns.

안전 데이터

wgk: 3
ridadr: 3259
HS 번호: 29215900
risk_code: 22-36/37/38-34
hazard_code: Xn,C
safety_code: 26-45-36/37/39
위험 등급: 8
F 고인화성물질: 8-10-23
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
스토리지 클래스: 11 - Combustible Solids

화학 및 산업

용도 및 제조

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

응용 분야 · 3건

개요Significant 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.

용도1,8-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.

일반 설명Proton-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.