CAS 39269-10-8 1,3-Adamantanedicarboxylic acid (HCID 64339)

名称と識別子

優先名称: 1,3-Adamantanedicarboxylic acid
IUPAC: adamantane-1,3-dicarboxylic acid
現地名: 1,3-アダマンタンジカルボン酸
英語名: 1,3-Adamantanedicarboxylic acid
分子式: C12H16O4
分子量: 224.25

名称と別名

1,3-Adamantanedicarboxylic acid39269-10-8Tricyclo(3.3.1.1(sup 3,7))decane-1,3-dicarboxylic acidDTXSID40192519RefChem:899322DTXCID30115010254-395-1Adamantane-1,3-dicarboxylic acid1,3-Dicarboxyadamantane(1s,3s,5r,7r)-adamantane-1,3-dicarboxylic acid1,3-Adamantane dicarboxylic acidMFCD00167790

名称をさらに表示

1,3-アダマンタンジカルボン酸アダマンタン-1,3-ジカルボン酸トリシクロ[3.3.1.13,7]デカン-1,3-ジカルボン酸1,3-ジカルボキシアダマンタン1,3‐アダマンタンジカルボン酸アダマンタン-1,3-ジカルボン酸, 98%アダマンタン-3,5-ジカルボン酸アダマンタン-1,5-ジカルボン酸(1r)-アダマンタン-1,3-ジカルボン酸AKOS BC-0656adamantane-1,3-dicarboxylate1,3-Adamantanedicarboxylic Acid,97%1,3-Adamantanedicarboxylic Acid >1,3-Adamantanedicarboxylic acid 98%

Tricyclo[3.3.1.13,7]decane-1,3-dicarboxylic acidSTK803091Tricyclo(3.3.1.13,7)decane-1,3-dicarboxylic acidAKOS000569192tricyclo[3.3.1.1~3,7~]decane-1,3-dicarboxylic acidAS-12338EU-0045639EN300-11878

データベース識別子

CAS: 39269-10-8
PubChem CID: 64339
DTXSID: DTXSID40192519
EC Number: 254-395-1
Nikkaji: J261.364F

物性

構造計算による物性

XLogP: 1.1
極性表面積: 74.6 Å²
水素結合供与体数: 2
水素結合受容体数: 4
回転可能結合数: 2
重原子数: 16
形式電荷: 0
複雑度: 327

物理化学的性質

融点: 276 · 276-278 °C (lit.)
沸点: 380.6 · 380.6±15.0 °C(Predicted)
比重(密度): 1.461 · 1.461±0.06 g/cm3(Predicted)
貯蔵温度: Sealed in dry,Room Temperature
溶解性: DMSO（少量）、メタノール（微量、加温）
外見: 個体
酸解離定数(Pka): 4.24 · 4.24±0.40(Predicted)
色: ホワイトからオフホワイト
InChI: InChI=1S/C12H16O4/c13-9(14)11-2-7-1-8(4-11)5-12(3-7,6-11)10(15)16/h7-8H,1-6H2,(H,13,14)(H,15,16)
InChIKey: PAVQGHWQOQZQEH-UHFFFAOYSA-N
SMILES: C12(C(O)=O)CC3CC(CC(C(O)=O)(C3)C1)C2
CAS データベース: 39269 · 39269-10-8(CAS DataBase Reference)

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (33.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.；There are 2 notifications provided by 2 of 3 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)；Eye Irrit. 2A (66.7%)；STOT SE 3 (33.3%)

安全データ

wgk: 3
rtecs: YD1994000
hs_code: 29172090
risk_code: 36/37/38
safety_code: 26-36/37/39
ストレージクラス: 11 - Combustible Solids

化学と産業

応用分野 · 2 件

用途有機合成原料。

使用1,3-Adamantanedicarboxylic acid is a carboxylic acid derivative of adamantane. It is widely used in drug industry, polymer synthesis and fine chemicals as key intermediates. It is also used as antidepressants or antiparkinsonic drugs in clinical practice.

調製方法 · 2 件

製造方法1,3-Adamantanedicarboxylic acid was synthesized from 1-adamantane carboxylic acid by one-pot method. In this process, the ratio of mixed acid (nitric acid and sulfuric acid) have important effect on the yield, the role of sulfuric acid not only is solvent, but also can improve the oxidate ability of nitric acid.Efficient Synthesis of 1,3-Adamantanedicarboxylic Acid and 1,3-DiaminoadamantaneReaction: 1-Adamantane carboxylic acid (20 g), nitric acid (65 %, 20 mL) and sulfuric acid (98 %, 160 mL) were placed in a three-necked roundbottom flask fitted with an efficient magnetic stirrer and a thermometer. Cooled to 0 oC and held at 0 oC, anhydrous formic acid (80 %, 70 mL) was added dropwise in 5 h and reacted for 1 h. poured to crushed ice, filtered and then washed the precipitate several times with water to give a white solid. Then the white solid was dissolved in aqueous NaOH solution and the upper clear solution was separated and acidified by HCl to pH = 3. Filtered, washed with water, dried in vacuum, recrystallized from ethanol. White solid, yield 22.9 g (92 %). m.p.: 275- 276 oC1H NMR (DMSO-d6, 400 MHz) δ: 1.616 (m, 2H), 1.691-1.727 (m, 4H), 1.759-1.791 (m, 4H), 1.850-1.882 (m, 2H), 2.059 (m, 1H), 12.062 (br, s, 2H, COOH); 13C NMR (100 MHz, DMSO-d6) δ 27.37 (C-5, C-7), 34.98 (C-6), 37.66 (C-4, C-8, C-9, C-10), 39.78 (C-2), 39.89 (C-2, C-3), 177.76 (COOH). IR (KBr, νmax, cm-1) : 2913, 2851, 2636, 1691, 1451, 1410, 1344, 1249, 1103, 1084, 952, 743, 670, 528; Anal. calcd for C12H16O4: C 64.29, H 7.14; found C 64.55, H 7.22.

純化方法Dissolve the acid in aqueous NaOH, treat with charcoal, filter and acidify with dilute HCl. It crystallises from MeOH. [Stetter & Wulff Chem Ber 93 1366 1960, Beilstein 9 III 4066, 9 IV 2997.]